Author's Note: My Health Cleanse: Becoming a Sissy for my own Board


In front of the Cleanse Company corporate board in our modest country retreat, 50 acres, standing at the head of the solid oak table with the other ten members, I continue "and that is how I brought our highest profits ever!" in my confident, strong, happy voice. As founder, president and CEO I do more than anyone else. Everyone is happy with my results. "This is the best investment I ever made!" Sarah smiles buttressing my domination over the company. We leave the meeting together on a high note as I offer "Feel free to observe any of our customers in their healthy weight loss fantasies. You can't hurt them and they won't know you were there." Joan and several other board members take me up on my offer, going up to the observation deck. She smiles "I always like the unique ones... you should try it sometime, Brandon." as she playfully taps my modest gut. I just smile in response as the room empties. Ten successful years of profitable business.

Cleanse Company (CC) is my health spa. People pay us about five thousand dollars a week for life changes: health, longevity, weight loss, addiction recovery. All our customers water fast the whole time they are with us. Most of our customers sign up for additional life altering services, besides the time away from electronics and work. We really help our clients.

Most people think water fasting is hard or impossible: your friends haven't done it and your mind begs for food in the abject boredom. Try replacing three hours of eating daily with chanting to yourself "Why can't I have pizza", "I want beer", let alone watching your coworker go for "One drink after work" or take their long lunch breaks. Water fasting is beneficial for anyone who is overweight. Let the body heal cancers and rejuvenate its immune system. CC gives people freedom, letting them play out their fantasies while medically monitoring their healthy water fasting.

Most peoples' fantasies involve sex, consensual or non- consensual, kidnapping, or forced changes to their sexual orientation. Clients can live impossible fantasizes safely in our health spa. Water fasting and deep isolation from society, friends and social networks allows true fantasy. Everyone is monitored by doctors. The health spa is the best decision you could make for your future, the most responsible way to cleanse your body and enjoy a fetish without hurting anyone. Water fasting for a week can clear your gut, and for two weeks your whole immune system regenerates itself, doubling its vigor. Some clients even attempt the religious recommendation of 40 days water fasting.

Sarah and I leave the meeting together, we are friends and I'd like to get to know her intimately but working together makes that difficult. And I'm married anyhow. "Brandon, any interesting new clients?" she asks indicating with her body language we should go to the observation deck. "Well... Alisa is the cutest little thing, she wanted to imagine she was trapped in the bottom of a well, and that teenage boys would come talk to her, make fun of her, and do some other stuff, until an adult came to rescue her with food in exchange for certain services."

"That sounds interesting." Sarah suggests, her cute feminine voice hiding her decisive, competent managerial style. "Yes, Alisa said she wanted one to two weeks, depending on her willpower. She was very explicit that at the end she would have sex with a hunk in exchange for her freedom and for her first bits of food after the water fast." Sarah nods, knowing it is best to start with soup broth or fruit after a long fast.

"And then there is Aaron, he wanted to conflate fasting to lose weight with feminizing himself. Overweight, but his weeks here have improved his appearance in several ways." Smiling I continue shyly "Sometimes I think about weight and sissification" quietly drumming by gut. At about 230 pounds my fat is affecting my health. And I'm not getting any younger. Sarah smiles "Well you should do it!" She giggles in girly fashion. "'You're not just the president of CC- you're also a client!'." she mouths, repeating a well-known ad slogan, and making me blush.

As we go through the door to the mezzanine, I steer us toward Alisa's stage. We make the fantasy believable and use hypnosis to suppress the idea it is fake. Our doctors monitor clients preventing fatal escape attempts or suicides.

"Show me your breasts, and I'll give you this candy bar!" John taunts, leaning over the well, as three other teenagers laugh and walk around. Alisa is water fasting to avoid food for weight loss and to rest her digestive system, but she is contemplating the offer. The stage has a brick well surrounded with green grass on a slight hill, and a fake ceiling that uses a projector to show the sky- sun and birds; night and stars. The stage has built in radiant heating and air conditioning to make it warm during the day so Alisa feels the sun and cold at night. This is her third day.

"What if I don't want to eat?" Alisa yells back, annoyed, but secretly happy for the attention of young men. Sarah and I are looking through a large glass window at the whole stage. I divert my attention to several video feeds from the stage. "See the water in the bottom of the well?" I ask Sarah. She smiles. The well has mossy, smooth bricks on all sides and Alisa is 8 feet down- probably a skilled climber could get out and the teenagers can reach down and touch her hands. She is so close to freedom. "I just want to get out of here!" Alisa yells. Another teenager holds a large climbing rope just above her hands, laughing, "Maybe you should jump!"

Alisa's clothes were normal jogging wear, but she got them dirty laying in the water and mud at the bottom of the well. Only about two feet across, she can sit with her legs crossed, or lay in a kind of ball. "Looks cold." Sarah commented, and I smile, "Yes, and Alisa wanted wolves to howl at night, and for the teenagers to get meaner as the days go, to eventually bribe her to take her clothes off and later dump gross things into the well." Sarah stares at me amazed and I smile, shaking my head. I motion to the left, toward Aaron.

As we move across the upper level towards Aaron's stage, one of the teenagers yells, "You almost got it! Too bad... let's try again. I'll put a knot on the bottom of the rope for you this time." and the rest laugh. "You just have to reach a little higher and we'll save you!"

Aaron's fantasy is being a female personal assistant to a strong male CEO. Nothing rough nor actual sex. Looking at the stage, a man in a business suit is dictating to Aaron, who is dressed as a 1950's secretary, and pecking away at a typewriter. "His fantasy involves working for Mr. Big here in the stage where you see him. At night he goes to his 'house' where a dominatrix helps encourage him to fast (for healthy weight loss) and to practice typing lines- reinforcing that he is feminine. And in his sleep he is required to listen to hypnotic tracks, to reinforce the whole program."

We watch a little bit, as 'Mr. Big' gets up and walks close to Aaron. "Well, that's it for today, Sharron. Work on your typing." He says authoritatively, as Aaron shyly nods and says "Okay, good night Mr. Big." The man's penis is clearly hard, and he stands shamelessly right next to Aaron before he leaves. "How does he 'get home'?" Sarah asks. "VR treadmill" I respond happily. Outside the office stage, Aaron walks up to a treadmill tunnel simulator. "He has to walk in his heels 'through the city', with men."

"Men?" Sarah asks. "It is just video, but they cat-call him, and the men are big and tough." I pause. "Once in a while one will threaten him, as if to mug or rape him, and the treadmill stops, making her literally stop in her tracks." Sarah squirms.

"Eventually the treadmill will stop so he can walk off and get to the door to his second stage, where his strong 'wife' will continue re-enforcing how important it is to be healthy, to water fast, and to be girly." I smile. "He has to kneel outside his 'house' and wait for her."

Sarah turns to me, "And he paid extra for the second stage?" "Of course. He paid for two weeks, maybe 15 grand total, including the stages and the VT transition room." "Wow. Is this what you want, Brandon?"

Looking at Sarah I confess "I was just thinking since business is going so well, maybe I should enjoy some of the luxuries I produce." She smiles reassuringly asking "Did you fill out the pre-survey?" "No, but maybe I should." I move the conversation by pointing out that Aaron's house door opened and he is facing his 'wife', a tall, strong dominatrix in riding clothes looking down at him mad. "Sharron, your makeup is all a mess. Did you redo it once you got to our porch in like I said?" she asks in a strong voice. Sharron responds timidly, "No, I was tired from walking and I" as the wife Megan slaps his cheek, and grabs his head and forces him to look into her eyes. "Now, little sissy, you have to stay sexy if strong men like Mr. Big are going to like you." Crying a little, Sharron nods, and goes inside with his 'wife'.

We walk back toward the offices as Sarah plays with me a little more. "Maybe you just want to not be in charge for a few days, Brandon, and be the submissive one. And you could stand to lose some weight." "Whatever" I respond trying to act cool. But I fill out the forms. Dealing with the board over the last year has been too stressful and it made me fat. The company should help me lose the weight it made me gain.

The surveys are mainly free response. People's fantasies are varied and misguided so out artists make them practical one- or two-week vacations, depending on the customer's time and budget constraints. Many fantasies aren't thought out and can only exist a short while, don't make sense in reality, or cause too much physical harm or cost too much. The artists can take an idea like 'Have sex with the King of England' and draw it out into a week-long adventure for our clients.

I print out a copy and start filling it in. The first section is personal and medical - age, sex, no health problems, overweight, high blood pressure. Then the time commitment- explaining normally clients do not stop short of the 'vacation time', a whole week of water fasting. We let our clients stop if they need to and discuss it with a doctor, but we never refund their time and it's not our fault if they are still fat, even if they quit the first day. We never force anyone to do anything, not even become healthy, against their own free will. It's one of the core founding principles I built my business on, and it'll never change.

The next questions are brainstorming my fantasy. "Do you want to be dominant or submissive?" "Along with fasting, are there other major changes you want to enact?" "List bad habits you want to break." "Will there be other people in the fantasy?" There really are a lot of variables, I forgot how long it takes to fill the forms out. Sixty percent of customer complaints are about the forms. But they are the reason only 10% of complaints are about the fantasy world itself. I try to be truthful and honest in every way possible, discovering I have a deep fetish for submission and to be feminized, and a need to relinquish the reigns of control, even if just for a short while.


My Vacation

All the logistics are done. The company is going to pay for my week long water fast. I spent time with our artists on the details. At first I was considering something like what Aaron was doing, a transvestite fantasy with a strong wife and boss, I decided against that. I want to be an unsure sissy who is being encouraged to train herself in a dungeon by women, and I don't particularly want men involved. I'm not gay, and I made it clear there will be no male sexual acts.

Still fear and uncertainty are needed: the stress of being the president and always having the right answer makes the luxury of being unsure and inactive, of leaving a choice for later and being scared, seem tantalizing. What better time to do it then when my body itself is scared- when I withhold all the food and alcohol I am used to? I also requested "high-tech video game skills and scores". Shaking hands with the artists, they all agreed "This is great, Brandon. We'll discuss the final details amongst ourselves and start ordering the materials for your stage. Hope you have a wonderful stay at our spa!"

At 2AM sharp Monday morning, the kidnapers wake me up with deep voices, mocking "Sissy, sissy! Wakey wakey!" "Time to go to sissy school!", ripping me out from under my covers. I had stayed in a hotel room away from my family to start my vacation (I lied to my wife and two daughters about going to Cancún for a week). I was never really asleep in the hotel waiting to be 'kidnapped'. I had initiated the agreement this hotel about five years ago myself to support the business. "Certain CC clients expect good, but large, friends to come pick them up very late at night. Give all CC personnel full access to our clients' room keys and proper discretion. They may want to act out, but this is normal and to be expected." Amazing how far a great bottle of aged wine for the GM and a 'corporate rate' 50% higher and a minimum number of monthly stays for the owners can go.

I shake as the strong men quickly have my wrists zip-tied behind my back. "Joan is taking over CC, Brandon." one threatens. Both strong, tall black men are in dark professionally tailored suits. "She is going to convert you into a skinny, submissive sissy pawn and you are going to give her the company in a few weeks." I sort of laugh, knowing this is the line the artists had helped me pick. The other adds "Then your wife Molly will threaten to leave you, offer you a way to keep your children." He pauses briefly for effect. "In the end you'll probably be a shell of a person in some remote vacation home, a docile faggot serving a real man who helped you get started on your journey." The other man's vile smile proves he is considering having a docile servant.

I fight a little as they force me down the hallway, in the elevator; I fake trying to punch the 'emergency' button as they laugh easily defeating my efforts. Fighting makes the fantasy insanely plausible in my mind and I feel adrenaline rush through me. In my underwear, no shoes, no pajamas- protruding stomach and man boobs visible for all to see. The bell dings and they shove me out first like a boy into the lobby.

Sneaking a peek at the cute young night auditor, I recognize Julia. For fun I yell "Help! They're taking me!" She was our favorite and loves playing along. Her red hair and twinkling eyes make the conservative, drab hotel uniform look sexy and domineering as she responds in her youthful innocent tone. Her makeup suggests she was expecting some fun tonight and she was staring at the elevator the instant the door opened.

"Brandon, you'll look so much sexier once you are a skinny sissy, instead of a fat alcoholic wimp," she laughs, "then maybe we can go find boys together!" The two large men stop- taken aback - but slowly realize the joke and play along, laughing. One turns me toward her and shoves me up to the reception desk, man-boobs up front. "I.. please" I beg as she continues "Maybe when you get back we'll go on a double date with two hot men like these fine gentlemen." Looking closely at one's face for the first time in the bright lobby, his powerful grin grows. "Come on sissy," the other man taunts pushing me around, "time to meet Teacher."

The fantasy has to be plausible, and Sarah recommended I get Joan involved. "She is probably next in line to head the company anyhow." Sarah had suggested. The huge men push me around and take me out to their van. The van drives me to our facility, obviously we all knew what was happening so no blindfolds or anything like that. After a short drive the van halts and the big men force me around a little, bringing me to my own stage at CC. The artists insist clients never their stages beforehand because the effect is so much better, and as the two men shove me down the set of dirty concrete stairs in a cheaply improvised dark alley, one of yells "The sissy is here." After a long pause the door opens slowly to reveal my beautiful dominatrix.

I didn't pick her, I let the artists do their work. They chose well. Her amazing looks draw me toward her, and her power has me standing tall and paying attention like a young soldier, as my misbehaving dick rises. She simply states: "Hi sissy, I understand you are going to lose some weight and become a more submissive manager." "Yes, Miss." I respond and start walking in. She holds the door and points to a school desk. "Sit, Brandon." she says in a calm tone. I do staring at her black corset I smile ear to ear.

Her long black hair, European looks and black platform heels with strong rubber grips like boots are offset by a faux leather red miniskirt that goes beyond her knees. Large breasts held up by the black leather corset, dark red lipstick playing on the color of the skirt outlined to perfection, large format knuckle-to-knuckle gold snake rings on each ring finger, sharp straight silver earrings similar to the medial caduceus. Immaculate makeup and proud, strong posture that comes with long-term leadership and confidence. She walks up to the desk, a short, small school desk with a bright pink table, and smiles "Stare all you want. Now repeat to me why you are here again" (she smiles) "for the record."

"I am going to lose some weight and become a more submissive manager. To be healthy for my family, to live longer, to be more reasonable as the president of CC." "Good, that is right, and how is that going to happen?" she asks in a coy voice. We both know but me saying it solidifies things in my mind as I sit in my male underwear in front of this perfectly made up dominatrix, me half sleep and her in total control.

"I will water fast, and you will help me." "Perfect. And how will you avoid getting bored and succumbing to the temptation to eat over the next month?" she asks. Of course, this was a mistake: I only was fasting for one week. Anyhow I respond calmly "By becoming a sissy, a silly lady with no cares or duties." She stifles any emotion, but her awkward pause proves it was hard.

"But how will that help you become healthy?" she asks in the innocent voice of a twelve year old. "Because, Misses, it is one of my biggest taboos, and because I know there are endless fetishes to stave off the boredom of fasting." She smiles, satisfied, backs up and lightens her mood and demeanor indicating I passed the first hurdle.

"You will call me Miss, Mistress, Dominatrix, or at times Teacher. You need to trust me and do what I say to learn. First and obviously you will not be given any food or alcohol. Maybe later we'll let you eat cum, but for now, just healthy zero calorie water fasting for cleaning and weight loss." She takes a short crop and plays with my right man-boob, picking it up, letting it fall, and slapping it lightly. My hands are still zip-tied behind me, and over the back of the desk they hold me rigid.

"You wanted to be forced to be submissive, so I will help. You are going to become a sissy, scared to initiate talk with strangers, yet willing to think about sucking their cocks. You'll think about buying clothes and jewelry, but you won't consider money or cost. It will be so relaxing, just like being a young woman in high school."

Smiling I know this is the fantasy I want; sissification hypnosis videos always got me rock hard, and living the fantasy for just a week will keep my mind off the not eating. Everything is going according to plan.

"Yes, Teacher." "That's a good student, my little sissy." The dominatrix stands back a little, and changes to a serious tone. "If you play your cards right, you'll be healthy, you'll have a fun taboo fetish session, and you'll go back to your loving family with less stress and more happiness. The female mindset we'll teach you will let you calm down, enjoy life, lower your blood pressure, and do so much more for you. Girls will love how you will be able to relate with them, and men will be jealous of your commanding ability to focus on anything you set your mind on."

She sighs. "But if you fail- Joan is really considering taking your company, and Molly could be turned off by a half-attempt. She doesn't even know you are here right now, but we plan to tell her." This is just part of the game. Smiling I offer "I'll try my best, Mistress." She is not happy at all with the answer, but after a pause decides to move on, using her body to point in another direction and walking a few paces before turning her domineering countenance to me.

"We'll pick your sissy faggot name now." I'm surprised at the strong language as the Dominatrix pulls out her phone and turns the huge chalkboard in front of me into a computer screen. She shows a name selection website. "Hmm" she mumbles, checking 'Sex: Female' and 'Zodiac: Libra'. Then she taps 'random' several times and narrows the list down to three possible names.

"Sissy Brandon, are you Alisa, Sherry or Sally?" she asks sweetly, walking behind me with her crop whipping air occasionally. "Choose carefully, it will be your name for your whole time here" (she can't help but crow) "or maybe longer." I seriously think about it. "Can't I be Kali?" I ask. She looks and thinks for a bit. "Let's test it... sissy Kali. Who are you?" "I am Kali." She shakes her head and I try "Sissy Kali" annoyed. She seems to accept that, and repeats: "What is your name?" "My name is Kali." Smiling she acquiesces.

Mistress punches Kali into the website and briefly reads some inflections and common personalities. Smiling a bit too much as she reads "shakti" she turns the computer screen off converting it back to an electronic chalkboard with natural-looking grains and imperfections.

"Write your name." I get up and turn my back to her and indicating my hands. She sighs "Some people would make you use your mouth! Don't worry your little head, darling." and grabs my hands, cuts the zip-tie and roughly massages my wrists before allowing me to pull them in front of my stomach. Walking forward I look cluelessly at the large screen. Her sigh is much louder as Mistress reaches to the chalk board's mini-shelf and gets the stylus, putting it in my hand like I am a two year old, "It comes out when you press the release at the bottom. Be sure to return the stylus when you are done."

I write 'Kali' big, in the middle of the board. "No, sissy, write it like a girl!" she complains. I write it with some pretty flourishes, and I put a heart for the dot of the 'i' in Kali, under the first one. Smiling, she says "Good. Now do that one hundred times, sissy." I sigh. Mistress gets paper and a pen and sets it on my desk. "Sissy, you will write your name on the chalkboard fifty times, and then write it on paper fifty times. If you make a mistake on the paper, start over on the next piece of paper." She pauses, behind me, leaning toward my ear. "I suggest you practice on the chalkboard first, since you can make mistakes with less punishment and erase them like they never happened."

Her voice is eerie, like she is warning me and almost getting herself in trouble by doing so. She stands straight, walks past me, and turns smiling, like she is getting ready to go. "Remember, all or nothing, everything is at stake." she says in a voice that can't be talking just about a pretty heart above the straight short line of the letter 'i'.

"Enjoy your first day, sissy." she smiles as she leaves. I finally take in the situation now that Teacher is going. I'm in my underwear, no socks, no shoes. The chalkboard is on the front wall of this dungeon/classroom, and even though the board is black, the lighting makes it inviting, bright and warm. It has several styluses and an eraser built into the board, and releasing the eraser use it on my first large renditions of my name. Fifty of anything is hard to write on a chalkboard, but I imagine 5 columns and 10 rows to get started.

My fantasy name was in my mind for the last ten years, after I learned that men sometimes want to be girls, and after I realized I could get off thinking about that and watching and reading and thinking about sissification. I start writing, writing and writing, up on the board. It is silent, and after a while I count out loud. Twenty Kalis-less than half done with the first half of this task, but two thirds of the board is full. And now I am really feeling the lack of sleep. Everything is shadows: I only see the front chalkboard and my school girl desk. The darkness leads to tiredness. I could probably feel around to explore, but it is so late and I think Mistress wants me to finish before I fall asleep. My sleepiness is making things strange as two soft nightlights tick on: one over a small, unfurnished military-style cot, and another over a nice, comfy poster bed with nice throw pillows and a thick comforter.

I shake, feeling the room's chill. Slowly I perceive a soft voice in the background. My voice. Somehow with me thinking and writing my new name, the quiet "I am sissy Kali" and "Kali is my name" mix with my own thoughts. By the time I notice the hypnotic voice- my voice- I am already half-done with the paper writing. I embrace it, this is my vacation after all. You have to enjoy your vacation. At least you can and should enjoy it. The lady said "All or nothing".

My first page is perfect so I don't re-write anything. Tired I sigh and get up and start heading toward the poster bed. As I get close, bright lights turn on scaring me back. A booming alpha male voice startles me again commanding "Sissies don't get to sleep here unless they are entertaining a real man." I shake in my shadows but smile broadly. This is exactly the kind of thing I want, and I knew a comfortable bed was a ruse anyhow.

The lights turn off and I head for the small cot without blankets nor pillows. Surrounded by profound shadows I lay in my underwear shivering and fall asleep. The place must have climate controls to keep the chalkboard and schoolgirl desk warmer than this tiny prison cot.

In a few hours, she- the Dominatrix- is back, dressed very differently, standing over me and softly shaking me awake. "Kali, Kali." she says sweetly, getting me up. I sigh and sit in bed feet on the chill ground. "Silly girl, why didn't put on your pajamas?" She indicates toward a neatly folded pile of warm, fuzzy pink clothes with white highlights and a cute pink panty on top, next to super comfortable slippers, blatantly obvious now that the lights ore on. My incredulous stare at potential comfort and warmth makes the strong lady laugh, her perfect lined deep red lips tempting fate with a smear. "You must be such a poor, tired little thing. Too bad you didn't put on your sissy clothes, you must have been so cold."

Tired I shake it off and look at her. "It must have been uncomfortable sleeping in those gross man underwear." Her long black hair is in a loose ponytail. Her blue sweater top and black denim pants look very natural and family oriented. Only her voice and posture hint at power, her half inch heels and calm makeup suggest she teaches bible school. Sighing at my indecision Teacher commands "Put them on Kali." Her strong eyes make my imagination run, seeing her commanding legions of lawyers or pushing men to die for their nation using only her voice and eyes.

Jumping ahead, I grab the pajamas and start to put them on. She shakes her head, plainly annoyed. "Kali, your underwear have to go first!" I knew that too but was hoping she would forget. Taking them off I put on the simple pink pair of panties. Then I put the pajamas on and pick up my man underwear.

"You are going to cut those up and throw them away, sissy." Teacher says plainly handing me a pair of scissors holding the handle out to me. I willingly follow her instructions, cutting my "man underwear" and dropping them into a trash can near the chalkboard. Teacher hands me a matchbook stoically continuing "Burn them" and I immediately lite the last man clothes I would ever wear ablaze.

"That's a good sissy." She smiles, making me feel happy even though I am so tired. "Now sleep tight. Because you behaved so well, I am giving you a nice pillow." Teacher walks over to a hidden cupboard and enters a keycode, much too quickly for me to see, and pulls out a king-size pink pillow that has ruffles and sets it on the cot, where it looks out of place because it sticks past on both sides.

"Be ready for school when you get up, sissy. You may sleep in because I know this evening was so busy." Teacher mouths in a neat, polished voice. "Don't let the bedbugs bite." she jokes as she leaves. I lay back down and she lets me sleep until I am rested, easing me into my first day of water fasting. Really the goal is to let time pass as my body cleanses and heals itsel. The fetish is just a fun distraction. I need to get healthy. I want to be youthful.

I know as I close my eyes there are hypnotic suggestions playing in the background, but I am so tired I let them in. Already I agree with most- Kali is my name. I am sleeping on a cot. I have a cute pair of very comfortable, warm, pretty pajamas, and a fluffy little pink pillow. Both are huge upgrades from sleeping nearly naked on a pillow cot. Teacher gave me the nice pillow. The pajamas were always there available for me. Maybe I should have been more... I fall asleep ignoring the obvious logic of my situation.

When I wake, the hypnotic sounds are gone, and looking around more of the room I see a standard school wall clock with black hands indicating 1 PM: skipping breakfast and lunch was no problem. Shaking myself awake, the door opens and Teacher walks in before I get my feet on the floor.

"Good morning, sleepy head! What is your name?" she asks in her sweetest voice. "Kali." I respond instantly without thinking. Smiling, she runs up in a girliest way and lightly touches my shoulder and cooing "Good girl. Time to get dressed for school." She walks to the dungeon closet, with its own code entry keypad. She sets the uniform out for me before leaving.


School

Today is my first day of vacation. I am getting ready for school, hoping the hot dominatrix from this morning will keep me entertained as I water fast for health.

Dressing quickly in the white bra, white silk dress shirt and conservative plaid skirt I consider the school girl desk. It is heavier that it should be, and the pink table part is well-worn, with penned graffiti. Tucking in my shirt I feel clean and cool. The white frilled socks seem silly but I put them on, and step into short black patent leather shoes that scream 'religious school uniform' as the door opens.

"And use your deodorant." Teacher admonishes, handing me a feminine antiperspirant. "There, all set. Now get into your chair and we'll start." Teacher moves me to the small schoolgirl desk, built for a 13-year-old. The ridiculously small hard plastic seatback is joined by strangely solid metal to its light-pink foldable phenolic writing surface with various dark stains and lots of chewing gum deposited on the undersize. I barely fit sucking my gut in and let it relax setting on top of the "desk", and the motion reminds me I could use the bathroom and am very thirsty.

Teacher stands in front, in charge, and knowingly hands me a large half gallon bottle of water, smiling and coyly avoiding the subject of potty. "Drink it all, it is healthy for you, Kali!" she suggests. After a couple awkward I chug several large gulps. Even her thoughts seem to command me and I smile thinking about how great this vacation is going to be. My taboos, fetishes, fantasies... even the idea of not knowing where the bathroom is, and only having this hot girl to ask, makes me horny.

Her clothes are the same as when she woke me up to show my me pajamas. She is just a school teacher, common-place in any elementary school. Her black hair is in a long demure ponytail, the light blue sweater is padded de-emphasizing her large breasts and hiding the nipples; dark, simple pants. Her light-colored pumps have short heels and closed toes making it unclear if her toes share the deep blue shade of her short manicured fingernails.

"Kali, today we are going to do some training to help you be a nice, sweet girl that thinks about others, and not a stinky self-absorbed boy. Won't that be good?" she explains in a voice that implies the answer. "Yes, I am looking forward to it." I respond in a manly voice. She smiles, irritated, and continues "Okay, but you have to quit talking like that. You should have said 'That sounds good, Teacher' or 'Yes, please'. And be musical when you talk, just imagine you don't know the right words so you are forced to use emotion to express your idea. Raise your voice at the end like you are asking a question, even if you are sure of yourself."

Her instructions are clearly not a question, and even with this comfortable family look her voice is commanding preventing any second guesses about her meaning. I stare off into the middle distance as she sighs loudly and continues, making me blush.

"Sometimes it helps to imagine you are talking to your priest, your doctor, a police officer, a lawyer, a judge- always assume they are right, assume you ignorant. You are asking a deferent question because you are afraid it isn't even good question. Asking about algebra in calculus class. Defending your daughter's actions in front of a school principle even though you aren't sure what happened. Coming up for excuses for what happened when you were drunk a couple nights ago." I don't know all that implies but my mind latches on to it: I can relax, embrace the now, and be wrong or dumb without real punishment when I say things like I'm not sure they are true.

"Or imagine you are lying, only pretending to know. If you want to say 'ten plus five is fifteen' you should seriously consider that it might actually be fourteen or sixteen"- and she giggles- "or one hundred and five. That way your voice will have healthy feminine feel to it, a submissive insecurity to avoid gross manly ego. Whenever you state a fact, consider the opposite in your mind like it is a real possibility. That'll bleed into your voice and people will notice the difference."

"I think that is a good idea, Teacher." I mouth in a neutral tone, seriously considering this isn't a good idea as I say it. Somehow the insecurity lends a strong girlish aspect to my voice that even I recognize as I say it in front of this beautiful woman.

Her facial response reinforces my fear it sounded terrible, but she says "That wasn't terrible. You used the right words and the right inflections. Don't worry, Kali, during the next week your voice will improve so much. But for now: your writing. I reviewed your paper and I can see the chalkboard." Teacher stands directly over me and takes the moment to look down at me over her glasses, adding power as I sit cowering in my pink schoolgirl desk wearing a well-tucked white shirt. "What do you think of your handwriting?" she interrogates.

Knowing damn well my writing was sloppy, I lie "It looks just like any girl's." while trying to raise my voice like the whole sentence was a question even knowing statement is false. Shaking her head, her powerful voice corrects "Sissy Kali, you (emphasis) can't lie when you are in school. You know that your lettering was rushed and you were tired, and while I like the hearts you kept missing the cross-over where the shape closes itself. You will be practicing much more, and you earned a demerit for lying."

"Teacher, what is a demerit?" I ask innocently with a submissive attitude. She smiles at the insecurity I deliver in my voice, and the proper address. "Well, sissy, there are a few things that you probably don't know yet." Her smile fades reminding me I am her hostage and was kidnapped last night. Teacher presses a button on the phone, erasing the whole chalkboard, and sets down more paper on my desk.

Frightened I ask "Like what Teacher?" in a too-masculine tone. "Kali, Kali. Even if you really want to know something, you can't just blurt it out. For instance, I bet you are ready to use the bathroom." I nod, drinking some more water now that my throat is dry and the bathroom trip seems imminent. "Okay, Kali. Follow me and I'll show you the hidden door." She lets me enter the small bathroom alone and patiently waits as I relieve myself and calm down. "Don't forget to wipe" she admonishes from outside the door after my urine stream stops. I sort of laugh, standing over the toilet, but follow her instruction. There is a medicine cabinet, small mirror, good lighting; a bath tub for soaking and a nice commercial toilet. Also enema bags and a small array of accompanying butt plugs.

Coming out, I looking anxiously around the dungeon to assess my situation. There is an exit door. I am not bound, but I am wearing schoolgirl clothes. My short beard is still there (I feel it with my right hand drawing a disapproving facial gesture from Teacher) and I haven't done any kind of makeup or anything like that. But there are cameras and the observation deck. Probably Sarah is watching and laughing. It is Monday morning and most of the employees would recognize me, tell others, and stop to ogle from the observation deck. Everyone knows what I am doing for vacation. I can't quit without being a hypocrite.

Serious, Teacher continues about the details I don't know: "Well, sissy, I don't know how to tell you this, but Joan is hoping things go... maybe a little too well for you. She personally bought you an extra week of vacation." I kind of smile, they doubled my relaxation time from a single week up to two. That seems good, at my weight two weeks of water fasting would be so healthy. I'd go from 'obese' to overweight' using the medical BMI terminology. Teacher smiles seductively, "More time for me to keep you safe and sound while you lose weight and remove toxins by water fasting." I smile back, lulled in, but her smiles fades and in a sober voice she continues "We- us trainers and artists and actors- are concerned about you, Brandon."

It is the only time she ever spoke the old boy name to me. Surprised I pay attention. "Joan's added terms include an extension per demerit, a free extra day of training." How could CC afford to let me extend my vacation indefinitely? I'm the CEO! How can I afford to fantasize forever? My thoughts go back to my wife Molly for a split second.

I blurt "I don't know about that" insecurely. Concerned, she seems to check that I understand the gravity of the situation before continuing. "Kali, this could be great. If you embrace this, play along, and follow the rules-you're going to come out well rounded, healthy, safe and fit. It is my job to make sure you are as healthy as you can be, and by lying to yourself and second guessing the plan you came up with, you will only waste the best opportunities. You have to trust me and follow the program." I sullenly agree by nodding like a chastised child. "I don't know about Joan's additions, we stage workers aren't sure, but right now I think it is in your best interests, Kali, to immerse yourself in the fantasy and allow your body the stress-free ease it needs to properly cleanse and heal itself." She is on my side, behaving as my advocate, building trust and rapport. I wonder what I ever did to Joan.

As she leads I go sit back at the desk, looking down and thinking. The whole point of this vacation is so I can understand my employees, while I let my body cleanse itself and purge toxins. Sitting reminds me of the gut that bulges over the pink folding desk.

"Over the next few days you learn the basics of makeup. You are going to get a lot of practice making yourself pretty so strong men will notice you." I shake a little, trying to maintain the smile. As her smile evils I notice even though she is dressed as a school teacher her makeup is perfect. "Tell me what you see sissy." Teacher orders casually.

"Well, your lipstick is dark, which seems powerful. And your eyes are outlined in black." I don't really know anything about makeup. Some girls wear so much they look 'caked on', but Teacher looks like a natural movie star. "Well, Kali, that's good for a new sissy. You don't know what you don't know about beauty, and you only rely on instinct when you see other girls." I begrudgingly agree.

"For now you are going to aim to have a calm, cool style, more every-day than mine. You will be using lighter, softer shades of red and not the darker power colors I enjoy."

Using her tablet, the front screen comes alive with a long video for "helping to transition". Intro credits start and Teacher hands me a piece of paper with 10 blanks. "Pay attention, Kali. The movie has challenge images." I look up unsure. "Each has a word describing you." I nod slowly, not understanding. "They appear without warning, so you have to pay attention to the whole movie or you will miss them."

She smiles as I look down at the paper. "It is a demerit to miss one word, Kali. Just be sure you keep your eyes open the whole time and pay attention to the video. It gets worse the more you miss." She smiles down and touches my shoulder like a helpful bigger sister really concerned I do not fail. "After the movie finishes, go to the bathroom, brush your teeth, shower and shave everything below the eyebrows. The movie has some pointers about problem areas and things to watch out for. In your medicine cabinet you'll find all the tools you need." She smiles warmly "For now, you can't pause the movie. But that'll change soon. I'll be back in a couple hours, Kali."

The movie is boring. First it goes over shaving, with details about unusual areas like armpits, the anus and back. Then makeup types, colors, techniques, health, skin care; all a dull monotonic way. The challenge images appear without warning and disappear quickly. "Soft" is the first, pink text with glittering gems and a happy woman smiling seductively under the slanted letters. After, a smiling transvestite in nice makeup with an all red outfit (red short-sleeve shirt, red skirt to the knees, red high heels) cutely asks "Did you write down how you are like a good girl? Or do you want another day of free sissy training?" before smiling and fading back to the instructional monolog. "Quiet", "Shy", "Happy" are the next words as the movie starts defining terms like mascara, blush, eyeliner.

The movie is boring and technical. Thirty minutes in, I close my eyes, listening. "Be sure to avoid applying the liner" the sound drones on, boring as hell, hinting at how the shadow might smudge if applied in the wrong way. Eyes still closed I hear "Did you write down how you want to be like a good girl?" and my heart skips a beat. The transvestite's familiar voice continues differently: "I know! You want another day of training!" and as I open my eyes her deep red lips smile as she fades away.

The video resumes 5 minutes back, making me re-watch it and pay attention to get the rest of the words (Slut, Whore, Cocksucker, Plaything, Bimbo). Finally, it finishes, and I get up to go to the bathroom, armed with knowledge and techniques to comply with Teacher's demand I shave. I touch my beard for the last time, its thin, brownish-blonde hair, well-kept and short but full, I trim it daily.

I shave as required: arms, legs, pits; belly hair, crotch, anus. I make a mess in the shower but use some toilet paper to pick up most so the drain won't clog. After I brush my teeth, use the toilet, take a shower and put my schoolgirl uniform back on. Leaving the bathroom, my clothes feel even nicer on my smooth skin, and I wonder why I never tried this before- even just for a weekend. It feels amazing. I walk around a bit, then go sit down.

So here I am of my own free will and desire. Water fasting, dressed like a girl, no interruptions, no pain, only boredom to torture me. I get up and go to the chalkboard- writing is a nice distraction as I get better and better at writing my name and the little heart. Finishing the chalkboard, I return to my desk to sit and my feet feel better. As I start filling in the whole page with my nice, neat handwriting, calmly perfecting my style. Sighing, I lean back as the door opens and Teacher comes in smiling broadly.

"Kali! You look so much better!" Teacher reinforces, walking to the school girl desk and smiling down as I look up at her. "How does it feel?" I smile back "Teacher, I wish I would have shaved myself before- just once- this feels so nice!" She smiles and looks up at the chalkboard, walking toward, "Good work, sissy! You are really learning how to focus on your tasks and how engaging it is to become proficient at a core skill, even one that seems banal." I smile dumbly "Thank you, Teacher!"

Looking back at the new 'Kali' sheet of paper I am working on, Teacher warns, "These three are a little sloppy- you should probably start over." No erasers here, just sharp, fine pens. Then her demeanor changes entirely, as she asks in a very serious voice: "Kali, how did the intro movie go?" "It went good..." I respond uncertainly. Teacher shakes her head, clearly annoyed. "Lying again! Is that a good plan for a little girl like you?" She moves over me as I bend down in my schoolgirl desk and submissively fold feet under, pouting "No... No Teacher, I know it was not a good idea".

"Kali, you missed 'Fashionable' entirely, and your handwriting is nearly illegible." Frightened I look at her to beg for mercy. Teacher shakes her head, clearly in charge as I try to not actually cry. "You earned one demerit, and maybe you deserved two." Turning my 'challenge word' paper toward herself, Teacher crosses out two of my words with the worst handwriting. "Well, maybe you just want a longer vacation!" she smiles mischievously. "You can just ask for more days, sissy." She smiles broadly, backing up, "In fact, you can always ask for any punishment, and I will give it to you. If you want a longer vacation, just ask. Don't act out like a child." I nod feeling the need to agree "Yes, I will be sure to let you know, thank you Teacher." She smiles even more and turns and walks to the board, as if to lecture.

"One demerit. At least you know a little about makeup." Teacher paces adding a large pause. "Shawnda, my friend, will help you put makeup on yourself for the next few days. You will put it on, look at yourself in the mirror on a treadmill for about twenty minutes, and clean it off to re-apply again. That way you'll get lots of practice and lots of feedback!" Teacher nears and leans down to hug me, letting me feel her breasts, smiling. And at this moment the room's hypnotic speakers start churning again: "I want to learn how to do makeup", "I need to be passible", "If I don't learn I might look like a cross dresser", "I can look like a real lady"

Teacher backs off and opens the door, introducing Shawnda to my dungeon, and working her tablet computer turns on bright, open-air light bulbs that surround the oval-shaped mirror of a large, dark oak vanity. It is obviously well stocked and has a long bench in front, for two ladies to sit side by side. "Kali, this is Shawnda, be nice and say hello."

Shawnda is a somewhat overweight white woman, about 40 years old, with blonde, long, flowing hair in a ponytail and deep, dark red lips; her eyes are decorated but nothing whorish. Her clothes are simpler than her makeup, as if she was getting ready for date night with the husband, and still needs to change: jeans and a t-shirt with the words 'Love Boys' bedazzled across, both somewhat worn.

"Hi Miss, good to meet you." I reply hoping this is what Teacher wants. Teacher looks at me and asks, "What would you like to learn?" as it happens that the quiet hypnotic audio mouths "Sissies need to be skilled to have passable makeup"and dumbly I blurt "I am a sissy but I don't want people to think I am a crossdresser." to Shawnda's stifled laughter (Teacher looks on stoically). "I doubt there will be any problem there, Kali" Shawnda responds with a touch of malevolence.

"Tomorrow do what Shawnda says, Kali." Teacher turns. "Make sure Kali follows the treadmill program we laid out." "I will Jen, this whole thing is just too good to miss out on." Shawnda replies happily. Teacher pauses irritated slightly, then hides it and smiles and leaves. Well, at least now I know her name, Jen- not that I can call her that. Madam and Teacher are the only safe terms I can think of for Teacher when she is in her comfortable school teacher's clothes.

Shawnda leaves as Teacher looks at me and smiles. "You are going to love it here." she idly comments, not wanting a response. She gives me the key for the ankle cuffs, and I unlock them, putting them in a neat pile on my desk. Looking around, Teacher smiles, "It is fairly late, 7PM on a Monday. Kali, you know where the bathroom is and your pajamas are." "Yes, Teacher." "Tomorrow Shawnda will guide you- get clean and ready for her in your school clothes before 9AM." "I will, Miss" Teacher leaves me alone, bored. My stomach growls a little and I really miss food. The boredom makes my mind wander to thoughts of pizza and beer.

I go try the handle on the exit door. Locked, obviously. Several red lights shine on me and the door, and the strong male voice from the 4-poster bed laughs "Sissies need strong men to protect them when they leave the house" as clear footsteps come down the stairs behind the door. Mistress appears immediately- angry and annoyed. "Kali, sissy, why did you touch the door? Never do that again, I wanted to leave it unlocked because you used to be the president and I thought you were responsible and knew better! Now get back in your room, and try to entertain yourself until bed!"

Embarrassed I turn and half-run toward my school girl desk, hearing a stifled giggle from Mistress. The door slams and a loud deadlock slides into place. But I am still curious so I look around the dungeon. The light keeps it mostly shadows. The cupboard and closet are on the opposite wall from the exit door, but they are basically hidden and all locked up. The 4-post bed is lit up invitingly to the right with my back towards the door. My little cot with its small pink "pillow", which I go sit on in a huff, is to the left; the girl's school desk is in the center.

Bored I play with myself, but avoid orgasm knowing it would displease Teacher. Was this a vacation a good idea? Maybe I should have just moderated my diet. Sighing, I think about food too much. Drinking water and peeing in the bathroom is so boring: who could spend days water fasting, let alone weeks? Even though I am not really hungry, I just want to chew and swallow- the boredom is so invasive, so unending, and the habit of night snacking seems like enough to make me call off the whole vacation. Thoughts of coffee, pizza, cookies, beer, hamburgers keep torturing my mind. I am so bored! This is dull like watching water boil, paint dry, grass grow. I almost want a punishment.

Even the hypnotic audio seems to know I am thinking about food and beer: sometimes it suggests "I wish I had something to take my mind off the delicious lobster bisque from Thursday" "Beautiful, ripe blueberries with ice cream", "Pizza and beer are your friends". Gentle reader, I suspect they are trying to get me to commit even more to being a sissy, by showing my how torturous it would be if I were left to my own devices. The hypnos do have general feminization phrases as well- "I can't wait for makeup training" and "I wonder if a boy will come say hi to me as a woman".

Finally I fall asleep in my cute pajamas on the cot, again playing with myself a little and feeling the smooth skin that even my quick razor shaving produced for the first time against the soft, fuzzy pajamas.

The next day I get up early and shower, switching to my schoolgirl clothes. Putting them on is the most interesting thing since I talked to Teacher last. I want to misbehave so she will come pay attention to me, last night was so boring. I finish the handwriting paperwork and around 8:45AM and wait idly.

Thankfully around 9AM Shawnda comes in smiling "Hi, sissy!" in an upbeat voice. I smile back: someone is here to do something with me. "Hi Shawnda, how was your evening?" She smiles secretively "Well, my boyfriend took me out to dinner, and after we..." and her face turns red. "But let's get started! I know you want to tell stories, not just hear them!" Now I turn red as she giggles. "To get men, you really need to put your best face forward." and I submissively nod.

Shawnda has me sit at the vanity, and shows me the basics of foundation and blush, applying both to my surprisingly hairless face. Then, she says "Treadmill" and goes out the exit door. Left alone, I look around an in another dark section of the dungeon new lights turns on. Sure enough- small pitch-black walls delineate a room with a treadmill. It has a short dog door that I have to get on my hands and knees to crawl through. Inside, the walls are mirrors. There is a treadmill with a touchscreen that reads '20 minutes - 2 mph - no incline - 2" business pumps'. Dutifully, I press the treadmill's built-in green Start button, dial the incline down, and up the speed from 1 mph (barely moving) to 2mph (slow walk).

The touchscreen responds simply by turning each setting green as I get it right, and once all are green, the 20 minutes starts counting down- 19:58, 19:55, so on. Sighing, I realize there is nothing to do but look at myself in the mirrors. They wrap around so I can see my whole body without turning. I see my face the best, but even my shoes are plainly visible depending on which section of the mirrors I look at. Once I almost trip, but I am getting use to my new heels as the miles go by.

As time wears on, the hypnotic audio and me watching myself- dressed in the conservative school girl outfit, with some foundation and blush- starts messing with my mind. Part of me wants to say "this is silly" but part of me really starts thinking "I wish I looked just a little more sexy, if only I had lipstick on boys would..." - I cut off he thought off right away as the timer finally expires. Shaking my head I know walking in heels took a lot of concentration and let the hypnotic effects of seeing myself really set in.

The treadmill keeps going, but the touchscreen proclaims "Done" with a happy green checkmark and a pink heart. Finally I press the red Stop button and the treadmill slows and halts. Getting back down on my knees I exit the treadmill room humiliatingly crawling backwards and go sit in my desk. Five minutes later, Shawnda comes back. She looks at me, and annoyed says "Kali, after the treadmill, you have to go get cleaned up dear. If you are sweaty you'll need to take a quick shower. But this time, just use the makeup removing tissues. Go do it now, sweetie." And she makes an impatient waiting gesture crossing her arms and leaning on the wall.

The exercises and training go on that way- I crawl to my 'evaluation chamber' staring at my handiwork in the mirrors and crawling back to Shawnda for more advice- for three whole days. Jen never showed her face during worst part of the water fasting. My body took its sweet time switching from food energy to using my fat reserves, and the lightheadedness made me more irritable, arguing finer points with Shawnda, who always won.

Eventually, like hypnotist's willing patient, it became easier to just agree with whatever Shawnda said. Shawnda wouldn't have been able to convince me how important it was to get my makeup perfect if I had a full stomach and was expecting a beer later. But in this stage, isolated from all social contact, and wanting to be a girl all help me accept her suggestions. And focusing on my hygiene and makeup is the only way I can avoid the torture of thinking about wine and vodka, pasta and pie, delicious sugary frappes and huge, soft Bavarian pretzels with beer cheese.

Three days of practice went by in a flash, along with the hunger pains. "I'll miss you, Kali!" Shawnda coos, pushing our guts together in a supportive hug. I had made up my face 50 times in three days, in all different styles and fashions, but mainly down-to-earth, or for a nice dinner. We did 'whore' makeup a couple times, 'clown' makeup, 'geisha' and a couple other specialty styles. These were more fun to watch when I walked in the mirrored treadmill room, more visually interesting, but less passable and less useful.

Meanwhile Joan was turning my friends in the board against me. I know she told the kidnappers to suggest I was going to lose my company, but I never suspected she meant it. Engrossed in my sissification I ignore the risk she poses. Certainly my good friend Sarah would warn me if things were going that way. Or maybe one of the other board members, or a stage worker like Sally or Jen.

But gentle reader, things were much worse. Sarah begs "But Joan, he is making us so much money as president!" as Joan scoffs pointing down at my stage from the observation deck and turning back towards Sarah. "How can he ever make any major decision again? And how do you expect any employee at CC to respect him after he has spent weeks as a sissy here? Even future employees will see the recordings!" "He did it for his health" Sarah weakly suggests as Joan shakes her head. "No, tomorrow the board is going to meet, and we will vote him out of his position." Sarah is deep in guilt as Joan continues "We don't even need you, Sarah."

"There are only a couple other board members that are even considering voting no on a call for no confidence against Brandon." Joan waits long seconds for Sarah to compose herself. Sarah finally brings herself to look into Joan's eyes. Sarah is deeply hurt by the possibility she harmed me with her ruse. She really wanted me to laugh, and say something like "Yeah right, I don't use my own goods" or "Maybe you could take care of me for a week". As it happened, Sarah was single, and in love with the power I had over the board, the company, and in her eyes the world. Joan interrupts: "You should vote to relieve him." Sarah looks deep in Joan's eyes to check her intentions before nodding heartily. "Yes, Brandon is done, he never should have taken a vacation here as a sissy, and you are right to help the shareholders by removing a broken man from control." Smugly smiling Joan encourages Sarah's new attitude: "It is for the best."

Gentle reader, Joan's tentacles reached beyond my life's work, the company I built from scratch. She started being very friendly with Molly. Too friendly. But I knew nothing of this, only Jen's idle, fantasy-world threats.


Piercings

I was 'kidnapped' late at night, and that morning Jen (she dresses as Teacher and Mistress) taught me my new sissy name, Kali, and introduced me to Shawnda for makeup training. Then she left me bored for a half day, which was torture. Becoming a sissy, if nothing else, passes the time as I get healthy and lose weight water fasting. Shawnda showed me the basics of many makeup styles- 50 faces in the last 3 days. I got years of practice making up my face under her expert tutelage.

Friday I wake up relaxed and at ease. The hard part of the water fast is over: my body is using my fat and expecting me to fast. I just need to avoid getting bored and thinking about food. If I avoid strenuous labor I'll be fine for weeks. I get up, put on the schoolgirl outfit I am used to, feminine deodorant, and go do my makeup, mainly out of boredom.

Just a normal day, a little eyeliner, foundation, blush; simple red lipstick. At first it seems much easier without having Shawnda pick on every minor detail, each small mistake, but I realize I am self-correcting as I wipe off a small segment of my lip liner. About ten minutes later I happily go sit in the schoolgirl desk. It's strange my facial hair isn't back yet, but I see no reason to focus on that.

As I sit down, the door opens, and Jen walks in wearing Teacher clothes, beaming. "Good work, Kali! I am so happy for you." she beams coming over to hug me. She specifically avoids messing up my makeup. Backing up a little Jen stands over me and smiles again. "Today is going to be a big day for you!" Her smile is contagious.

"I hope so Jen." I say proudly, smiling.

"What?" Jen shouts, her face hardening and her height growing as she shoves herself up over me in my little schoolgirl desk. "What did you call me, you little sissy?" As I realize my mistake I start "Umm- I am sorry Teacher, it won't happen again, Madam." "Two demerits for addressing me like an equal. Today was going to be fun for you, but now you forced me to change the whole thing just because of your own stupidity!"

I look down at my desk and cry a little, shaken up because she was so happy and now so mad. "Never do that again, Kali. I am your Teacher." She scoffs "Today we were going to pick out a nice pair of earrings for you to wear for the first time. But now things are going to be very different." Teacher is so annoyed she paces and sighs "I guess it wasn't unexpected" and moves over to the locked cupboard to pull out a few things. I feel my eyeliner and mascara run as I try to compose myself enough to look up and to see what Teacher is doing.

She sets down a pink box, ordering "When I get back, you need to be wearing this outfit, and I want your makeup to be slutty. You have 30 minutes, sissy." Angry she leaves as I sit quietly crying in my schoolgirl desk. I can't even look up until the door closes.

After a bit, disgusted with myself, I get up and see she set out for me. Sexier panties, nylons, a red bra and an oversized, comfortable white shirt that was faded and said "Love" in large pink letters on the front. Putting that stuff on took no time. Then, like I had over the last three days, I clean my face to start my makeup. I naturally put on two inch heels. The t-shirt is long so I decide she wants my skirt left off. Doing my makeup takes most of the half hour as I contour and highlight, finishing by filling in my outlined lips with the standard, bright red. My guilt for misbehaving feeds into the sluttiness of my makeup producing an astounding result.

Satisfied with my new look, purple eye shadow and deep red blush making the perfect red lips look outright conservative, I go back and sit again at the desk. Maybe perfect makeup will counterbalance my four demerits. I lock on the ankle cuffs, securing the double lock, and put the key on the pink desk in the center for Teacher. Four demerits mean an extra week of vacation! My Cancún excuse won't convince anyone. I just shake my head, unsure how to proceed.

The Dominatrix Jen walks in angrily, but she smiles as she sees my face. "Shawnda is really good at training, isn't she sissy Kali?" "Yes, Mistress." She smiles "That's a good girl. Now remember this was going to be a fun experience for you today. Young girlfriends getting our first piercings. But..." she pauses making me look down.

"But because of your major mistake earlier, you earned two demerits." I blush. "Demerits mean an extra day plus a punishment. For two demerits, your punishment today is being forced to have the piercings and tattoos the artist thinks your makeup suggests. Kali, do you understand?" "Yes, Mistress." I agree. "This is your fault, Kali." I start to cry as I pout "Yes, Mistress." Joan's 'extra week' and my own demerits mean over three weeks of water fasting.

Afraid I look up as Mistress continues "Johnny and Ronda will be taking care of everything. Do exactly what they say, Kali." Mistress looks down at me seductively. "We wouldn't want to add (emphasis) too many more days to your vacation, now would we?" "No, Mistress." She leaves, happier but still annoyed with me. Silently the door shuts silently, and fifteen minutes re-opens.

Johnny enters, a burly tattoo artist carrying a large toolbox. As he holds the door for Ronda, he looks in and proclaims "Here is the faggot in training." I look up, feeling the red bra shine through the oversized white shirt and remembering my slutty makeup as the strawberry sweet lipstick touches my tongue. Ronda is an overweight black woman, and she has almost every piercing I can imagine, lots of jewelry and loud, gaudy metal bracelets. She walks in on her yellow-strapped, light tan mules with her flowing, black ruffled skirt and smiles "Oh, Johnny-- Kali is just letting her submissive feminine side come out during her short health spa trip. Why do you always take things out of context?" in a false caring voice as Jonny laughs.

He bangs his hardcase down on my schoolgirl desk making me jump. Slowly he opens it to the left, smiling with ill intent as I eye the contents. Several tattoo guns, a large array of piercing devices, ink and disinfectant, towels and bandages. "Have any tattoos, sissy?" "No, sir." I say in this timid defeated voice. Johnny loves the power role and pushes, picking up one of the needles and holding up it near my eye. "It has to be perfectly sharp, or else it hurts the girls like the dickens. Imagine being in prison getting a tattoo with a dull, rusty nail." I shudder as Ronda throatily laughs. Unexpectedly Mistress comes in.

"Jen, we didn't expect to see you here today!" Ronda practically yells as Johnny stands down, setting the needle down and backing away from me a little. The ladies hug each other deeply. Mistress is in her dominatrix outfit, all dark leather and she has the tool belt with whips, cuffs and rope. Her hair is in a tight braid and held up. Ignoring me she explains to the artists "Sissy Kali was a naughty girl this morning. Because of her misbehavior, I am not going to limit your creativity." Mistress pauses. "You probably noticed her distinctive look." Ronda breaks in, "I was wondering. You said Kali was going to just get simple ear piercings. Kali looks so..."

"Well, she is getting much more done now!" Mistress confirms, looking toward me to explain. "I... I misbehaved, Ronda, so..." I stutter feeling Mistress's demand. She takes over "Kali sinned and this is her fault and her punishment. Let's talk about her body in private." They move toward the treadmill to talk amongst themselves. The artists are agreeing and nodding toward Mistress as she stands tall and does most of the talking. Ronda especially laughs and can't contain herself, stifling her voice as she says "strapped down" and laughs. Johnny and Mistress seem to just think her reaction is funny.

"Sissy, we're going to put you on an X-table for the next few hours while the artists do their job. Go to the bathroom now so you won't have to interrupt their work." I get up and use the facilities before willingly laying down on a red padded table that has straps to secure my body, arms and legs separated. Mistress slowly straps me in, locking my limbs and torso down, while Johnny menacingly prepares his tools near my head so I can see his every action, and Ronda walks around me, laughing and shaking her head, as if evaluating my body. I am overweight and wearing girl clothes, silent and blushing more and more as they continue.

Ronda has at least 5 ear piercings on each side, a large nose ring, several eyebrow piercings, and stones in her cheek and lips; her dress hides her nipples and crotch from my view. Johnny moves away from my head and Ronda puts her hand on my chest and leans over so her face is right above mine. Her breath invades my body, greasy deep-fried chicken and biscuits mixed with coffee, and she smiles down "Jen had asked for conservative ear piercings and let you pick one dime-sized tattoo. Many men have that much. I guess you wanted more, didn't you sissy Kali?" Her pause makes it clear she expects an answer as her unbrushed mouth reminds me of food and I think I can feel a little piece on my face. "Yes, I do want more, Misses."

Ronda laughs hard at being called 'Misses'. Thankfully she pushes herself up using my chest as she realizes how much of her spittle is hitting my face. Smiling down she taunts "Now we are going have more artistic freedom. And Jen wanted you to smile and thank us the whole time, so she is" - Mistress cuts the black woman off as she submissively halts.

Mistress's commanding voice pierces "Kali, if you aren't convincingly happy and thankful for each tattoo and piercing, I'll help encourage you until you show me you are." as she holds up a short leather paddle. Smiling, she leans over me and kisses Ronda above my face, and after they part she leans over me and drops a large amount of spit over my mouth. "Be nice, little slut. I noticed you were squirming when Ronda was laughing, you need more experience with saliva." I sort of cough "Thank you Mistress, thank you Misses" as Ronda and Johnny laugh together, and Ronda gets a book to point out pictures to Mistress.

Mistress backs up and mentions, "Ronda has some interesting ideas to help your body keep up with your slutty makeup, Kali." I shudder as she continues "Aren't you excited to be a blank canvas for these nice people?" During the long second I think of a response she maneuvers the paddle in her hand. "Yes Mistress, I can't wait to get a piercing or two." I offer as Johnny laughs even harder and Ronda continues pointing to images in the tattoo book.

"First thank Johnny and Ronda for the four ear piercings in each lobe you will receive." "Thank you for piercing my ears, Johnny and Ronda." I meekly respond. Johnny stands near me, his warm crotch next to my face, and looks down "No problem sissy- you need nice earrings to be passable." I didn't even notice he had the piercing gun, and he quickly pops it twice. Painlessly I have my first ear piercings. I smile a little and say "Thank you Johnny", which brings a big smile to Mistress's face. "That's a good sissy, keep behaving like that and everything will be just fine." she says stowing her paddle on the tool belt. The next ear piercings were done by hand with special needles, and they hurt.

Mistress whipped me dozens of times and as my hypnotic music suggests "I can't wait to try different earrings out", "My cheek piercings look so hot", "I love this tattoo" and I crying while smiling and thanking. Next were straight bars in my nipples, a nose piercing with a small, hidable horseshoe, and another on the right side of my nose; an eyebrow piercing on the right, and a piercing in my penis, not a prince albert, but a new ring is down there.

And the tattoos. Johnny really liked me to beg for him to start each one, asking Mistress if "The sissy really wants it" so she'd whip me into begging. On my cheek, a small circle. On my upper right thigh, normally hidden, the words "Sissy Slut" with a decorative 3-inch heart. On the left breast, kind of to the side and normally hidden, a large star and two smaller ones. On my ankle, a key and a lock. And they made me turn over, so on my ass, they could put "Loves Fun" entangled with a unicorn's long, spiraled horn. They also pierce my tongue twice and put a black ring into my left lower lip.

Mistress moves close to me to unbuckle my head and neck seductively. "Now I know you already thanked our artists, but maybe you noticed the bulge forming in Johnny's pants, sissy." I am too out of it to think much. "Yes, Mistress, Johnny has a nice bulge" I respond on auto pilot. Smiling, she nods to Johnny, and he walks to me suggesting "Kiss it through my pants, Kali." I meekly comply, breathing on his manhood, thinking about my makeup and all the sore piercings.

Luckily that is all he wants, and the artists pack up, leaving Mistress health supplies and care instructions. "See you later, sissy!" they both say as they leave with Mistress. It must have been fun for them, me constantly smiling and begging for more, and getting paddled whenever I wasn't eager enough for my next improvement. Still strapped down my makeup is messy from Johnny's jeans, my tears and Ronda and Jen's spit, as I consider my cut off shirt, panties and bra, and my bladder starts to complain.

Thirty minutes later Teacher reenters with a different set of clothes for me. She wears a yellow sweater, jeans; school-teacher clothes, smiles and stands directly over my head, looking down at me, her face upside down to me. "Well, now that was an exciting morning, wasn't it, Kali?" eyeing my makeup. "Yes, I enjoyed it" I lie. "Now, Kali, remember what I told you about lying? I'll let it slide this time, but girl, you really need to tell the truth." I mope and she shakes her head. "It's okay, baby... this was a punishment after all. You just need to behave a little better and learn a little more, and you will be a good girl." "Yes, I want to Teacher." I respond submissively really wanting to please her. Even as Teacher, Jen is scary to me.

Suppressing a mean smile and slowly releasing me, she asks "Tell the truth- which is your favorite tattoo?" I sigh, considering, and respond "I like the stars on my breast, Teacher." This brings a big smile and a painful hug as she helps me stand up. She calmly orders "Go wash that slutty makeup off and put on your new clothes." "I will, Teacher." "Later we'll talk about some of the hygiene for your new adornments." She smiles and leaves through the door, shutting it silently.

They left my nylons on but tore them, so I throw them away. I go get cleaned up and get the new set of clothes. Three inch light brown mules, a pair of white shorts, black bra, and a yellow shirt with a big undercut. Putting on the new panties I delicately handle the skin around the penis piercing. Then I remove the makeup and redo it in a more appropriate fashion. Noticing the hypnotic voices again I hear: "I love my star tattoo", "I wonder if I should get something tattooed on my shoulder", "I need to buy some large earrings". Some of the thoughts are familiar ones I already considered as I was doing my makeup. As I go to my desk Teacher comes in.

"That's better, Kali. Now you can't spend all day looking at your piercings, you need to keep learning too." I agree "Yes, Madam." She smiles "Your next school project will be clothing fashion. Just like last time, you need to watch a video. But this time, sissy, you will have to take a test afterward on some of the fashion rules, in addition to catching all of the challenge words." I sigh loudly, but she seems to have expected- even wanted- that.

"The video is about two hours, so this time you can pause it if you want." I try not to show my relief but she knows and smiles. "Pay attention to the video because the test will be hard. It is better to re-watch the video than to fail the test."

Teacher reaches into a large purse hanging over her shoulder and fishes out a tablet that she carefully hands me. "This is for the screen. Pretty soon it will do a lot more." I look curiously at the medium-sized tablet. "For now it has Start and Pause so you don't lose focus on your movie and end up missing anything." Another smile, this one much too sugary. "Don't get distracted by your piercings or your tattoos either, sissy. If you want to look at them pause the video first. You can even go use the mirrors in the treadmill room if you want."

I acknowledge "Thank you Teacher, that is all good. How many days do I have to finish the test?"

She laughs and considers. "Let's not put a time it, probably a few days." "Oh, I see. Thank you, Teacher." "Have fun, Kali. Remember, fashion is important, but it is also fun." And she leaves, never having started the video. The room slowly begins its hypnotic chant again, this time, cooing "I wonder how a white skirt would look on me", "I love scarves", "Maybe it would be better if I wore larger earrings".

Getting up, I rush to the treadmill room to explore my new body. I get on my knees, crawl through disturbing some of my sore parts, get up on the treadmill and start it slowly walking out of habit. Anyhow I look sexier walking forward than dumbly standing still.

Everything looks attractive, and all of my male body hair is still gone- which is strange. I never shaved my legs before, maybe they grow slowly. Looking myself over I seem a little less bloated and even a little more youthful. Water fasting definitely works, and the dungeon will lighten my skin quickly because there is no harmful UV sunlight.

After about a half hour walk, looking at myself and hearing the hypnos, I am too horny to watch any video. Looking about the dungeon, I start walking around carefully in the dark recesses. There are normal dungeon things around, from whips and paddles to vibrators and dildos. No fleshlight or love doll, other than some gay male 'love dolls' just the crotch area with an anus, dick and balls. And there is some other bondage furniture. No cloth or towels to jack off into, and the dildos could be fun but I just want to masturbate. Light and shadow are used to hide and show areas in the dungeon, and the only areas with good lighting are the locked entrance door and the main chalkboard/electronic screen in front of the school girl desk.

Horny, I find a dark corner and jerk off to my new look onto the floor. The piercing hurts but the volume proves I was ready to masturbate. Tucking my penis back away, I see the last little drips are staining my panties. Oh well, nothing to do about that, so I go sit at the desk and start the video.

It is long, boring, technical, and historic. The 'hidden images' pop up as usual, there are about 15 total, and I write down the stylized words that come up describing me and my goals- "Sexy", "Horny", "Bimbo", "Airhead", and so on.

Around 6PM Teacher comes back to check on me. I had finished the movie, so she asks, "Do you want to try the test?". "Sure, I will." She looks at me a little annoyed. "Yes Teacher, I would like to try the test." Smiling, she half-hugs me, standing near, and continues "Great, Sally will come help you take it tomorrow. Maybe you can re-watch the video, Sally is very thorough." Teacher almost walks to the door.

But then Teacher stops, turns, smiles meanly and takes out a flashlight. She flicks it on, and I see it is a blacklight, used to see all the bodily fluids in trashy hotel rooms. I feel my face blushing and I try to keep from looking into the corner where my wet cum is puddled. She smiles, walking with the beam playing around my feet on the perfectly clean floor. And she sort of points it around the room, happily, before setting it on my desk. Everything is spotless. The whole stage was just built last week, after all.

"Do you have something you want to tell me?" she asks kindly. As I squirm she moves right in front of me and leans over my small, quivering form. "Well, sissy? Is there a place in my clean dungeon where it would be interesting to shine this blacklight?"


The Test and the Tablet

I'm Brandon and Monday I was kidnapped to become a sissy. Today it's Saturday, and I'm sore. Yesterday I got new tattoos and piercings that would make any girl blush. I'm here at Cleanse Company to fix my health and feel younger by water fasting. That's what I keep telling myself as I wake and dress in my schoolgirl clothes, apply makeup, and wait around.

Sally came in around 10AM, as I was getting desperate with boredom and solitude, smiling with Teacher. Sally is in a nice 'job-interview' business suit with pants. Maybe 23 years old, she is young and happy, her hair up and her makeup business casual, nothing powerful or strong in her makeup. "Hi sissy, Teacher says you think you are ready to talk fashion." I agree, silently nodding. She continues, taking lead: "I am Sally. What is your name, sissy?" My wry smile displeases Teacher. Wiping it off my face I say "Kali, Miss Sally." Teacher still seems annoyed from yesterday, but her body language shows approval

Sally continues "We are going to talk for about an hour, but each time you make a mistake, you'll get an ongoing punishment, and there is an increasing random chance you'll fail the test." Teacher interjects speaking for the first time today: "Failing a test is a demerit. So be careful if you start making mistakes." Her outfit is a simple, light blue sundress with white strappy sandals, and her long black hair is tied together with a leather rope, folded around her neck and draped over the front of her chest in a primitive style. I look at her face consider her makeup in the most platonic way possible, noting her eye liner is wider than mine and looks great. She looks a little too made-up to be a schoolteacher, and as I realize she knowingly smiles staring into my eyes.

Sally warns "I have to give you a fair test, no matter what." Teacher smiles ominously "So don't make mistakes. You watched the video, right? Failing means a demerit: a special punishment like last night, and another day of vacation." She pauses demanding acknowledgement. "I understand, Teacher." Teacher continues "We'll explain soon, but there is an ongoing consequence for each question you answer incorrectly." Both ladies seem very serious.

Teacher asks "Do you want to postpone the test?" Her tone suggests I probably should, and Sally's body language seems to agree. "No..." my ridiculously unsure tone makes the ladies giggle, as I put subconsciously raise my right arm to cover my clothed breasts.

Sally stifles her chuckle "Okay. If you want we can stop at any time and you won't get any new punishments." (she pauses) "Let's start the Fashion Test, sissy Kali." Teacher stands tall and gets ready to leave, but she asks "Sissy, is everything okay? Do you want me to do anything for you?" I smile looking forward to passing this first test and start my fantasy "No thankyou Teacher. I am so happy here." She looks down for some reason, but then nods and leaves satisfied. I stare at her backside as she sways her hips specifically for me, and silently closes the door- doubtless unlocked so Sally can leave.

Sally pulls out a cellphone and taps for a while to change my chalkboard to a photo from an Emmy nomination. A beautiful, well dressed lady with too much side boob exposed. "Kali, would you ever dress like that?" "No, of course not!" "And why not?" "Her breast is too exposed, but also the dress has a slit that is in the wrong area." "Good, Kali. Now do you remember her name and when this photo was taken?" I look at the screen dumbfounded. Fashion sense, not history!

"Kali? Be sure to answer right, those were two questions and both need an answer, or else you'll take have to engage in two new ongoing skills." I just don't have a clue. "The first two questions." Sally complains as she realizes how right Teacher was about my ignorance. Linda... in.. 2018? It might have been in the video... Sally is annoyed now and warns "I thought you paid attention to the movie. Maybe you should just quit the test and take two punishments. If you're going to waste my time, we can just give you ongoing punishments to let you explore your sick sissification fetish."

I gulp silently as Sally tirades "This is important sissy. If you can't even get the first thing about fashion right maybe you just aren't cut out for elegant life." Her inflections implied any whore can find cheap, slutty clothes from a secondhand store and put on some matching slutty makeup. I look down and feel tears starting to form. I am a man just fantasizing! I muzzle the thought silently.

"I.. I am sorry for wasting your time, yes Sally, I would like to stop the test." Sally shakes her head tapping buttons on her tablet. Assessing the situation she explains "Sissy Kali, you should use better language. 'Misses Sally, may I please stop this test? I am sorry but I am not ready.' It might bite you if you speak too masculine with Teacher or another facilitator." My front screen shows the fashion movie fast forwarding to two minutes thirty seconds and playing, making my failure obvious. "Linda Crawfort made this disastrous appearance down the red carpet in 2015, as a ploy to get back at her then husband Stan, by embarrassing him at the reception..." Sally stops the video and returns the electronic screen to a chalkboard appearance.

"I don't know how I.." I blubber as Sally stops me and holds my shoulder while she stands over my desk. "Oh, sissy, don't worry, you'll get it! This is a major life change for you." She looks deeply into my eyes. "You are happy, right? Is this what you want, faggot cocksucker?" Taken aback, I nod and indicate she should continue. "I'm so happy for you! So let's get Jen"- she stops, thinking and corrects herself- "-Teacher- back to help introduce you to the full features of your training tablet." She looks dumbly at my blank, black tablet and then toward the apparently unlocked entry door to the dungeon, in a rare awkward silence.

Luckily Teacher walks in smiling "Kali, I'm sorry you didn't get my warnings about taking the test too early. Most people get at least fifteen minutes in on their first try." Sally giggles as Teacher ignores her "Now you'll have to pay the price." I look into her eyes, empowered by her admission of partial guilt, and ask "Are you going to teach me a lesson?" She laughs heartily and turns away, her stomach rolling, as Sally whispers something to her. The laughs taper off and she offers "I'm sorry you stopped your first test. Most of this fantasy will be test based, and I know cutting a test short is a low point. Are you okay to keep going, Kali?" Embarrassed I immediately agree "I want to do well, Teacher. Please help me train." She pauses, staring at nothing. Looking up she straightens and walks to my schoolgirl desk.

Teacher powers on my tablet, enters some code and holds it up for me. "Kali I enabled your tablet's full functionality. It will entertain you and let you run the main screen, the ninety-inch electronic chalkboard up front." Teacher and Sally both get behind me to see what I am doing as see it enabled for the first time.

The tablet starts with a happy animation with roses and hearts, cute girly intro music and the title "Kali's Sissy Training Tablet". I shake in response but both ladies support me. A simple menu system letting me pick 'Areas of Study', 'Ongoing Skills' flashing red 'Unassigned: 2', 'Videos', and 'Pornography'. After that, the last two options 'Tests' and 'Hypnosis' are disabled. Teacher quietly instructs "Tap 'Areas of Study', sissy Kali."

'Areas of Study' starts with an animation introducing a complex leveling-up system of like Role Playing Video Game. Like the tablet's street maps, you can pan around and zoom in and out using your fingers. Lines connect small dull white spheres to each other ending at the very center: a large pink ball throbs like a heartbeat. Everything moves dynamically and shifts around, slowing. Grouped areas of intricate webbing have highlighted pink descriptions above them: Feminine, Social, Spiritual, Pain Slut, Whore, and Nursing.

A sparkling indicator at the top shows I have 100 Experience Points. Sally comments "We start most sissies with one or two hundred points. You'll get more when you pass tests, and at our discretion for meritorious acts." I confirm "So by gaining XP I can alter my training goals." to their smiles.

Teacher chimes in happily "Yes, XP lets you pick more new Areas of Study to become a better sissy." Sally contrasts "On the other hand, Ongoing Skills are fun tasks to help train your body and soul as a sissy. Depending on the areas of study you are in, better and better ongoing skills will become available. Based on your choices, your training videos and tests are chosen." The ladies seem to be sugar coating the situation, but Teacher is more stoic as Sally has a hard time containing her smirks.

Teacher's helpful voice offers "Next you will pick two Ongoing Skills. But first pick your Areas of Study so the list of Ongoing Skills will have more options- there wouldn't be many options there right now."

Sally plays with the interface zooming into the 'Feminine' sphere cluster and panning the web around. The cluster's background fades in, a rounded heart with pink shiny skin like a dew-soaked apple slowly rotating decorated with little diamond piercings that are dull. The center ball has links to skills grouped within the 'Feminine' cluster, each to their own smaller group of intricate webbing and orbs: 'Posture/Demeanor', 'Emote', 'Boys', 'Day-to-Day', and 'Toys'. Smiling Sally explains "Each has specialized topics for you to study. As you gain Experience Points your options will expand and the web will light up."

She sighs/smiles "And the animations will improve, like here the diamonds will shine, and in other areas unique changes will happen, to keep the interface fun for our clients." Teacher amends "The animations link to how many skills you purchase in each area. It is like a 'grow' video game where everything gets better and better as you play, flowers bloom, trees get tall, cities form."

Sally zooms in farther as the tiny dark grey balls near Posture/Demeanor get big enough to read their names: 'Sitting', 'Walking', 'Standing', 'Being Submissive'. Sally taps one explaining "Each has a price in XP. Passing tests from the Area of Study or related Ongoing Skills will give you more XP to open more areas and become more of a sissy." Inside the grouping 'Walking', she taps a sphere at random, and the details come up- 'Basic ladylike walking, 50XP'. Then she zooms out, out, out and eventually the interface returns all the way back to the Main Menu. "Go ahead, try it out and pick Areas of Study to use up your XP Kali." I look toward Teacher, who nods agreeing with Sally's suggestion.

I enter 'Areas of Study' and consider the major areas: Feminine, Social, Spiritual, Pain Slut, Whore, and Nursing. Wow, a lot of options, a lot of corporate expense for Cleanse Company. Noticing my look, Sally explains "Most of the content will be custom generated for your specific situation and mental mood after you pick what areas you are most interested in, Kali." I zoom in on 'Feminine' and the pink heart appears in the background, while I zoom in more toward 'Toys'.

The dull, dark web goes on and on with future skills to learn. I tap a sphere at random: 'Play with Dolls, 50XP'. Clicking others, I see 'Adult Toys, 75XP', 'Name your Animals, 50XP', 'Pony Play, 25XP'. I pick 'Name your Animals, 50XP' and I confirm. Zooming out to the top view, I zoom toward Pain Slut on a whim. Teacher and Sally both kind of giggle but are supportive, one putting a hand on my upper back. The Pain Slut area has an animated woman in the throes of pleasure tied down on an X-Cross as its moving background with various dull welts on her body.

Within this area of the skill map web clusters read 'Whips', 'Electric', 'Hot/Cold/Tactile', 'Sensory Dep', 'Bondage'. Sally comments off-handedly "There is always some overlap, but we try to organize things in a logical way." I quickly zoom to the 'Electric' cluster of glowing balls and select 'Beginner Nipple Excitement, 50XP' Teacher comments "That uses up your Experience Points, so now let's pick new Ongoing Training Skills. Each wrong answer from a test will require an Ongoing Skill as penance, but you can also decide to start additional Ongoing Skills if you like." as I zoom out to the main menu.

Teacher drones "Ongoing Skills can lead to XP too, Kali. You really should embrace them. But failing to perform the work of the Ongoing Skill- not doing the training that is required- Is much worse. You will have to find a balance based on your abilities, and your dedication." as Sally looks on bored.

Taking over Sally explains: "For now the last two options Testing and Hypnotics are disabled. But once you pass Fashion everything will be at your fingertips to learn as quickly or slowly as you desire, along with certain other privileges and rights." During the short interlude Teacher asks "Is everything okay so far, Kali? Is there anything you need or want?" "No, Teacher, I am happy here" I submissively respond, fascinated by the sheer number of orbs that enable ever-increasing levels of Areas of Study. I wonder if they can all be enabled, and how many there are. Just reading through some of the detailed descriptions soon became a turn-on. Teach politely orders, "Okay, Kali. So tap on the Ongoing Skills so we can set you up."

The Ongoing Skills screen has an upper display: Unallocated Skills- 2, Demerits- 4, Days Remain- 14, Days Water Fasted- 4 and Weight Lost- 15 pounds with a smiley face that encouraging sparkles. The rest of the screen is a simpler, scrollable list of tasks that can be enabled, each with a cute anime-styled icon that fills half the screen with a detailed description when clicked. The descriptions and images are interesting and sexy, again a source of horniness as I consider the possibilities.

"Wear an Electric Bra" has a happy cartoon girl smiling even with little lightning bolts coming out of a leather bra from her nipples, "Name your Animals" shows a cartoon of a young toddler happily playing with stuffed toys, "Tea Time with your Toys" shows an older girl sitting properly at a small table with dolls, with a very formal expression of seriousness on her face. Other options are 'Play with Electric Shock Gloves', 'Get into Electro Porn', 'Sissy Orgasms' and 'Daily Porn Requirement'.

I press "Name your Animals" and the tablet shows a more in-depth description along with the rest of the image, there are actually four happy toddlers playing with an array of stuffed toys as their bigger sister looks on: "As a sissy you just must have a collection of cute stuffed toys that all need names and personalities. You will add one animal a day until you have four total and spend at least fifteen minutes per animal talking with it and playing. Test: let Sally play with your animals and check your imagination (100XP Reward). Next Level: Spend only 20 minutes total playing with all your stuffed animals daily".

Teacher gets in front of me and smiles "You have to assign all Unallocated Skills daily or else they'll change to demerits, adding special punishments and more time to your little sissy vacation." I agree "I understand, Teacher" confirming 'Name your Animals' and it turns green 'In Progress'.

Teacher continues explaining the details: "Once you start and ongoing skill, you must comply with the daily requirements. For instance, that one will mean playing with toys every day. But, after you pass the test, the ongoing skill will 'level up'." Sally confirms "Sometimes the next level is harder or takes more time, but at the end of the progression only a small maintenance effort is required."

Scrolling I see an interesting item: 'Sissy Orgasm'. I tap it and Sally smiles from my left. "Yes, I figured after last night you might fixate on that." The badge is a cute sissy producing copious amounts of cum. Zooming in the anime image shows three happy sissies, in panties, each egging the next on as one can't help herself and is cumming. 'New sissies will be allowed to orgasm at any time, but they must be wearing slut clothes, slut makeup, and the orgasm must be done in the mirror room looking at their bodies. Sissies must not spill a drop. Test: four orgasms in one day, Next Level: Mirror Room requirement will be removed'. Teacher orders "Based on last night's events, you should pick Sissy Orgasm." as I am already confirming. She continues "You can always pick extra Ongoing Skills to train to earn more Experience Points. The other way to earn XP is by passing tests like Fashion." as I also turn on the 'Wear an Electric Bra' skill. I exit to the main menu, hoping I understand everything well enough.

Teacher looks to me deeply, drawing in my eyes. "Is there something you would like to tell me, Sissy Kali?" She sees I am silent and suggests "Kali, is anything wrong?" I finally respond "No, I am happy here, Teacher." Despondently Teacher looks down. She hides the awkward pause by re-confirming the rules: "So now, to orgasm, you must be in slutty clothes and makeup, like when you got your tattoos, and you must orgasm in the mirrored treadmill room into your hand. Catch all your seed in your hand, and then do what you want with it without making a mess."

She navigates my tablet herself entering 'Videos'. "Here you can watch your training videos to prepare for- and to pass- your sissy tests." Sally smiles as Teacher continues "There are also some other videos in here you may like to see." She scrolls down a bit to 'Kali getting ready to be a sissy' and hits play. The front screen shows me with a red face checking into the discrete hotel, using an alias. Then it shows me anxiously trying to sleep, with night vision. I keep tossing and turning, but at least I didn't masturbate.

The video stops and Teacher jumps out of Videos and down to the Pornography section. "Pick one, Kali."

One called 'Kali's Story' is also greyed out. I pick one I think might be good, 'Joanne Meets the Quarterback', and hit play. It is a nice scene and I get hard quickly, even with both women watching. The porno is just normal straight stuff, where a cheerleader is letting a big man play with her in the locker room.

I look away, and the screen and music stop: 'focus on the movie, sissy' is shown with a dreamy girl staring into space. I look at the movie's run time. It lasts 40 minutes. Sally and Teacher laugh as Teacher explains: "Pornography is meant to be focused on and watched in its entirety, Kali! You aren't allowed to cum to it because you have to be looking at yourself in the mirror room, but over time the rules will change. For now just remember the computer knows if you are focusing on the screen. Every minute you are not paying attention to your training porn, the movie rewinds at double speed."

So starting a porno means finishing it, no matter what. I sigh, unsure if that is awesome or terrible. Sally understanding says "If you don't know if something is good or bad, maybe you should accept it with open arms." Teacher agrees and continues "Sissy, if you start a porno and go to bed before it is finished, you will receive a full demerit. You should also know if you orgasm against the rules, from now on that will merely add two ongoing skill assignments. Better to cum if you must than stop pornography before it finishes." Sally laughs first, and both break into loud cackles as they start for the door: a sissy worried about correctly watching a porno. As the door closes silently I focus on the screen, which automatically resumes at 0:00.

I edge to the porno, it is pretty good, but it is strange how two girls told me to watch it, I'm not allowed to look away, and shouldn't cum. Normally I watch pornos away from my wife and daughters, without their knowledge, and turn them off the instant I manage to cum. It doesn't help that I know they are watching me, maybe with other people from work, edge wearing my schoolgirl clothes sitting at my cute pink school girl desk.

The ending is climatic, a blowjob from two other players that came back because they 'forgot their wallets while celebrating the big win' after the quarterback surreptitiously sent a pic on his phone of the girl. Smiling, the cheerleader offered, "If I see a cock, I have to touch it." She smiled "And if I touch it, I need to feel it in my mouth."

I run to the treadmill, forgetting the slut clothes rule, drop-roll through the humiliating door, jump up looking at the mirrors- only to remember. Sighing, I back out, get out, and rip off the conservative school clothing. Putting on a red nightie that happened to be on my makeup desk, I rush some bright red 'fuck me' lipstick and deep blue eyeshadow, before going back to the treadmill and jacking off into my hand.

Finally relaxing after so much edging, I make sure not to spill the cum. Going to the bathroom is an idea but I merely lift my hand up to my face, sucking all the cum and finally wiping my hand dry on my own thigh (not the lingerie). As I calm down and head toward my bed cot, keeping the clothes and makeup, I hear the hypnotic audio plainly: "That cheerleader really enjoyed the taste of cum" "Touch a dick... need it in your mouth" "People could be watching me"


Toy Learning

Yesterday I got full access to my tablet: Areas of Study, Ongoing Skills, and unlimited videos. I'm Brandon, CEO of Cleanse Company, and this week I'm taking my vacation in my own sissification fantasy to become healthier water fasting under supervision.

I wake to Teacher standing over my cot with a heavy, leather bra. "Kali, here is the bra you will wear for this electric punishment." I wake slowly, but put on the bra quickly enough for her to be satisfied. It has rounded metal spikes all around, but especially near my nipples. "How does it work, Teacher?" I ask in a submissive voice as I finish. She turns me around, and I hear two clicks as she locks my bra on. "The bra has a set of batteries and can give you electric shocks. For now, the system will slowly build up to a very light level of shocking, similar to mosquito bites, and run for five minutes; then it'll slowly ramp down and stay off for 55 minutes." That doesn't seem too bad. Teacher's shoes are pink trainers, and she is wearing sweats with two vertical pink stripes on the legs, overall grey, and a loose matching top that reads 'Train Hard'.

"Now, your toys. Let's see... today you can have a bear, a tiger or a rabbit. Which stuffed animal would you like, Kali?" "The bear, please." "Okay, and what are you going to call it?" I think for a few seconds, then blurt "Rupert". "Sounds good, sissy. As an ongoing skill you'll spend 15 minutes a day with Rupert, playing out loud and coming up with back story. Eventually Sally will test you on him. She'll be fact checking your recordings for the test so you better not contradict yourself!" Her smile is very kindergarten as she reaches into the oversized teacher's bag to reveal Rupert, an 8" tall stuffed animal.

I sigh, the video recorders will make any lapse obvious. Her smile fades slightly at my sigh, but Teacher continues "Feel free to keep learning fashion and enjoy the rest of your day. Sally and I are hoping you'll pass the fashion test soon so we can move on to more interesting subjects!" before leaving.

The challenge of water fasting is the eternal boredom. I'm not tired- if anything I have a light, happy energy. If not from the lack of food maybe this feeling is from wearing girl clothes and avoiding the stress from being head of the Cleanse Company board.

I watch the fashion video twice, orgasm in my slutty outfit to myself in the treadmill room, wash in the sink (getting my cum to the bathroom without spilling was more work that it was worth! I'll just eat it from now on) and watch a shorter porno called "Sissies loving dicks". Eventually I 'play' with Rupert, talking to it and letting him be silent: "Yes, Rupert, it is a lot of fun to play tic-tac-toe!" "I like coffee too, but I can't have it today, because I am water fasting." "It's not that kind of water fast, silly, this is a real water fast." ... "Rupert, I need to go to bed now."

In the background, the hypnotic speakers are pumping sweet messages like "Rupert has soft fur" and "I like stuffed animals" into my mind, and while I am bored it is relaxing to really just sit and play with a toy. I am wearing my school girl outfit, and my makeup is very respectable.

The door bursts open unexpectedly and my bra turns on with agonizing continuous shocks that take the wind out of me making it hard to stay sitting and somehow make me clench my arms around Rupert, as a large group of people enter. I am tightly hugging Rupert and sitting cross-legged in the center of the room, as bright lights turn on illuminating everything I've known over the last week- my cot, the treadmill, the large bed, the fetish and bondage gear. Teacher and Sally lead, Teacher loudly commanding "Kali, stay where you are and be quiet." as the ongoing electricity knocks the wind out of me. Both wear business-professional attire, Teacher's makeup done to the nines but super conservative, and Sally made up well but not to the extent Teacher is. Sally's grey suite with pants is ultra conservative, she wears flats; Teacher is wearing short black pumps, and a long black skirt.

As I stutter and gasp still dazed and move Rupert into the most girly, feminine hug as if he will defend me from whatever is happening, I realize this is going to be bad and people from my life form a line in front, looking down at me.

Everyone is eyeing me in my girly clothes with tattoos and piercings, well-done makeup, with my smooth shaven legs and face! The whole Cleanse Company board- Joan, Sarah, and six other people I trust my business and career with. My family- Molly my wife and my three beautiful frightened daughters are here. My two best friends, Ted and Adam, round out the humiliation as both try to laugh while pretending to ignore me. My friends are hoping this is a trick but everyone else is stoic and stern. Teacher is clearly in charge and commanding the situation, and my daughters starting to cry in fear, as I sit uselessly hugging my friend Rupert.

Teacher nods toward Joan who talks first as in a daze I finally start to set Rupert down cutely on the ground near me, sitting him up looking toward the crowd, to focus.

"Brandon, things are changing quickly for you, aren't they?" Joan smiles with terrible evil in her face. Most of the others are merely disgusted, and my wife won't look me in the eyes once I finally muster courage to try. My youngest daughter is confused beyond belief and is crying. "I am now the CEO of the company. We can't have some pervert like you representing us!" Her demeanor changes from evil villainess to poor estranged widow in an instant, clearly playing politics with the board, as she continues in a mock abused voice, "How could you Brandon? We trusted you!" Sarah in seems to agree, looking toward me for answers I don't have.

I shudder and try to stand up- only to have the bra shock me so hard I fall back into my sitting position on the floor, as if I hadn't even tried to move. My mouth opens and closes stupidly as I try to ask Sarah for help by staring at her, only to start considering a small flaw about her attire. I try to shake the thought without shaking my head as they continue talking: her pants should never, ever be worn with such a wide white belt.

Teacher takes the floor "Your wife is going to explain the new rules for your marriage, but before that I wanted the whole board to agree in front of you that you are no longer owner. Then we'll let the board and your poor children leave." Joan's evil smile continues as Teacher voices steadily "Are all board members in favor of Joan's generous offer to supersede Brandon as CEO of Cleansing Company?" Everyone agrees, Sarah last and reluctantly. Teacher continues "I see all members except one agree to the measure. May a board member other than Brandon or Sarah second to confirm the vote." "Second" Judy confirms, distraught. As I look toward my friend Sarah she shakes her head in disgust and I realize everyone can probably see between my legs because of how I am sitting so I fold my hands over my crotch in another amazingly girly gesture and Sally can't suppress a short, quiet giggle.

Joan hammers the last nails with gusto: "If any board member has a question for Brandon, a doubt about my new position, or concerns over his leaving the company, now is the time. Brandon's vacation is planned to last another two weeks and as you know he will not be available for outside contact during that time." A couple board members open and close their mouths, but Sarah is the only one to speak: "How could you? I thought you knew I was kidding, Brandon. This is serious now. Don't try to explain. I just want to go. You renigged all your responsibilities."

The board files out as Teacher and Sally comfort my family, Molly and the ladies focusing on my daughters, and my friends walk over to stand above me as I sit on the floor scared. Sally coaches my wife as the kids calm, and Adam comments "He really did it." Ted laughs "It's just an intricate joke, right, Brandon? You had your company set up a stage... no, you re-used a client's stage... to pull our legs?" I look up and tear up, "I just wanted to get healthy" as they both turn hard against me. "What!? You really took your own medicine, 'Kali'."

Shaking their heads each looks down in total disgust and they joke "Maybe she gives good blowjobs" "I don't know, man, I'm not gay". I try to interject, "Guys, I'm just" but Ted cuts me off "Maybe when you are done fantasizing we can go to a bar or play video games or something. But we have families, and neither of us is going to talk to you if you are a transvestite!" Adam offers "Well, if your going to live a once-in-a-lifetime faggot fantasy, you better enjoy it! Lord knows it cost you enough." Ted sort of smiles toward Adam "Nothing to do but edge and orgasm all day" and they leave with "Brandon, turn straight when you get back." "I will" I whimper in the voice of a ten-year-old as they each shake their heads and ignore me to leave, avoiding the ladies and my daughters.

Seeing the men leave, Teacher politely turns my wife Molly towards me. In her best Sunday dress, black and white with a large ribbon bow in back, Molly looks amazing. Her teary eyes challenge my own tear ducts: "Brandon, how can I ever trust you when you left us all on our own without telling us where you really were? When were you planning on coming back? Did you really set up your vacation to be endless? What about us? Who was going to care for the kids and me?" and she starts crying for real, as my oldest daughter tries to hug and comfort her somehow, even after she herself was obviously just crying. Molly yells "Did you even ask about us!?" in a desperate tone as Teacher lowers her chin, clearly agreeing and sorry for the trouble the company caused our family.

Sally arranges for my children to leave, so only Teacher and I are here alone with my wife. "Shannon... Kelly, Cindy" I try calling my daughter's names, but I am still sitting and Teacher and Sally motion for them to leave before anything worse happens. Sally walks with them toward the door. "Molly" I start, but bite my tongue.

Teacher takes charge as usual "Kali, stand up and come at least give your wife a hug." I slowly do so, scared I will be shocked, but the bra is only giving me the mosquito-like shocks I am used to. My wife reluctantly lets me hug her, but feeling my bra and girly outfit only seems to solidify her distrust. Teacher nods to her, and my wife explains the new arrangement as Sally comes back.

"Brandon, or Kali," (Molly shakes her head at my new name) "Teacher and I are going to monitor your progress and give you up to three weeks to earn 5,000 of your 'experience points'." She sobs a little, and Teacher continues for her: "If you fail to get 5k XP in time she will divorce you and take your children. After you get 5k, you'll need to finish out any days left from demerits before you can leave. Once you do all of that, we'll have a meeting to decide how to proceed." Now I start to sob.

My wife reiterates- "Brandon, we're leaving you unless you live out this stupid fantasy to its end to get it out of your system. And even though Joan took the company, she gave me a healthy 'founder's bonus'. She left me enough to take care of the girls, move and change my whole identity if I want. If you don't perform, we are leaving you." I try to hug her again, but she shrugs me off.

"But if you do this, get out of your little fantasy, and switch back to being a real man- then maybe I'll let you back into our life." She pauses. "We can share what Joan gave me, and live happily ever after, maybe even have some fetish fun of our own once in a while." Molly blushes as she suggests fetish while I am dressed like this. That would be amazing!

Teacher seems pleased and offers "Maybe you two should kiss? It will be the last time for a few weeks." My wife reluctantly brings her face toward mind, embracing my thick leather electric bra straps with the integrated batteries, and tasting my strawberry flavored red lipstick, as her silk-smooth facial skin rubs against my smooth hairless chin, and one hand wanders toward my shaved leg, feeling up slowly toward my crotch, as if to verify I still have something down there.

She feels my embarrassingly shriveled penis and her hands move up and down feeling the hairlessness of my body. We kiss of a bit, then spend a long time hugging before she finally breaks the teary embrace, crying and turning to leave. She runs out banging the door behind her, although I think it wasn't on purpose, as Teacher stands straight and reinforces her authority over me and Sally shakes her head "You could have been more reassuring to your old wife."

"Kali, Joan wasn't joking when she had the kidnappers from the hotel room tell you what was going to happen. Your wife was hoping you would at least ask me one time if it was real- or at least talk to someone else, like Sally, about your company, about her, about the kids. It's like you didn't even care." I look down ashamed beyond ashamed.

"I think most of the board was hoping too. At first most of them laughed Joan off, but as time went on... you ignored all your worldly responsibilities. Your wife was deadly scared that she would be destitute and forced to give her children to an orphanage."

After a long pause, my bra gives me a medium shock and I look up into Teacher's eyes. "You have to do your best to make this right. Be a good sissy, do what we say, pass the tests and maybe your wife will believe you want to fight for your old life. 5,000 experience points is a lot, but it is possible to reach in a couple weeks. Sally and I are here to help you fix your mistakes, help you make the consequences of your bad decisions go away. Do what we suggest and maybe your wife will take you back into your loving family. It will never be the same, but imagine what will happen if you don't reach your goal- she will leave you forever, and take your three beautiful daughters to another man."

Sally laughs, "I don't know if Ted or Adam will ever look at you the same, but maybe some night when they really want some" but Teacher cuts her off. With that, Teacher leaves the room, Sally in tow, and it falls back into timid darkness as my bra resumes its low stinging. I head to my cot for sleep even though it is still early and I know I should be working for Experience Points.

If I lose my wife and kids, I might go crazy and do something rash- turn gay, stay a girl, kill myself, I don't know. Teacher said Molly's goal of 5k is reachable. I can pass her test, play out my own fantasies. And then I can become the virile male head of the household I truly am.


Three Weeks: Passing Fashion, Finally

I am Brandon, and I signed up for my health spa retreat (water fasting for a week to regain years of youth) at Cleaning Company, my own startup business. But Joan got to everyone and took the company. And, she got wife Molly to threaten to leave me unless I earn 5,000 'Experience Points' playing my own sissification games!

As I lazily lay in my pajamas on my cot, I daydream about a lesbian orgy with Molly and another bisexual girl. Did Joan ever want me to have a fair chance? It is hot to think about Molly and me passing as lesbians and maybe even letting guys hit on us. My daydream moves toward Teacher, her perfect body and tied-back, long, straight black hair; her perfect breasts and tone, fit build.

The door opens to Teacher's commanding voice: "Kali, today I want you to focus on the fashion video and actually pass the test today, you really need to get a move-on to reach your goals." Teacher exhorts. Wearing a red blazer, like a real estate agent, with a conservative long black skirt, her hair is up, and her makeup is playful. She smiles as she knows I am considering her clothes in the girliest way possible. She is right: I need to pass the first mandatory test to gain the first of 5,000 experience points! Teacher looks at me for a few seconds, and comments, "You know, Kali, maybe I could help you stay engaged. Would you like that? It could shave a days off your learning time, and that might make the whole difference for keeping Molly..." I agree much too quickly and Teacher smiles. "Start the video, and I'll come back to help keep you focused."

I agree curtly and she leaves. Getting up, I use the little lady's room, change to the normal schoolgirl uniform noting again all my body hair- even the beard- is still strangely gone, sit down start to use my tablet to start the boring fashion video, after my basic day-to-day makeup. The video is boring as ever. Sure, I write down challenge words, but it is so dull. Just as I am about to shut my eyes the door bursts open and Mistress appears, jerking me awake.

"Sissy, I see you are already fading, and they haven't even got past the second world war!" Jen was right- the video includes historical details that are so boring and old I don't understand why I need them, but according to the narrator "fashion trend sets fashion future" and "all respectable ladies respect their elders". I sigh drawing a stern look from the Dominatrix.

Mistress pauses the video and commands "Give me your wrists", chaining them to hooks I hadn't noticed on the front of the pink schoolgirl desk. The chain makes me reach one hand far forward to give the other enough slack to scratch my nose. "Stop fidgeting!" she continues pulling my thighs down tight to the chair with a wide leather strap.

Taking a short rubber whip with a pink heart on the punishment end and a black fake leather wrapped handle, Mistress explains "Along with this little toy, remember I control your bra's electronics too. Please watch the video, and repeat the key points the narrator mentions." The video resumes as Mistress stands over me from behind, pacing and holding her remote control.

The video is monotonic: "White is a special color. It is only proper to wear white clothing after Labor Day, unless you are traveling on safari or in some tropical banana republic." The stereotypical racism of the 90's always makes me laugh, even though this is the fourth time I've heard the narrator say that line with a straight face. Mistress reminds me "Repeat the key point Kali" and I mouth "White only after Labor Day". "Red shows daring and power, but purple is a masculine force that is off limits." I stare into the middle distance as the narrator drones on.

This time Mistress shocks me hard after I am silent for too long. Trying to curl up, the new locks on my arms and thighs resist and Mistress says "Kali" like I'm a misbehaved dog. After a quick, quiet and rushed sigh I respond "Red is daring so I have to be in a special mood to wear it. Purple is off limits for nice girls like me." Mistress touches my shoulder in a reassuring way as I hear her tapping the whip on the back of the plastic schoolgirl desk's chair. I repeat the key points, and write the challenge words as they come up.

The whole video goes quickly with Mistress's constant ministrations. At the end she suggests, "Kali I think you might be okay to take the test today, but you should watch the video one more time beforehand." I look up at her, as Mistress unlocks my wrists and thighs, releasing me from the seat for a well-deserved stretch. "I think I want to try, Mistress." "Okay. From now on you can sign up for tests using the tablet, just tap on 'Test' and pick what you want to try."

Mistress stands back and I smile at her amazing looks. The black leather, the military boots, the toolbelt with her whip and bra remote control, her hair tied into a weaved, tight ponytail; her makeup almost hellish, focusing on 'red' and 'tired', powerful but morbid. "Sissy, remember, passing tests earns XP so you can do more interesting things and reach your real goals. Some tests might even make sense to try before you train for them. But remember, failing a test is a demerit, and making any mistake during a test will cost you: you'll need to pick another ongoing training obligation. Don't get click-happy on your tablet, Kali."

She backs off and asks again: "Is everything okay, Kali? Do you need anything? Do you want anything?" I smile but politely shake my head, and Mistress lowers her head and exposes her wrists in a yielding posture that suggests I am correct and she was wrong to ask. I proudly focus on my tablet.

After Mistress leaves, I feel like I made a mistake, but my tablet dings "Task Reminders: Play with Rupert, Start the Electric Bra Training for Today". I click on the bra training button, and it comes to life, giving me shocks like before, maybe stronger, pulsing on and off without the slow ramp-up I was used to in its hourly pattern. And since I just watched the stupid, boring fashion video, I get up and find Rupert, still sitting where I left him from the last time I saw Molly. Somehow, moving Rupert to the other corner of the dungeon helps shake the terrible feels associated with the place where my company, wife and daughters were all taken away from me. A rare urge to eat and drink alcohol hits, but when I start playing with Rupert it goes away so I embrace him.

The dungeon door opens and Teacher comes in, this time dressed like a kindergarten teacher, smiling and pulling a toy red wagon behind, her hair in a loose, comfortable ponytail and a light green sweater, tan pants, with a large red belt buckle; flat athletic shoes. Smiling, she proclaims: "Sissy Kali! I'm glad you remembered to play with your girly toys! Be sure to make real stories with them since there will be a test for this task just like any other." I sigh, embarrassed at how willingly I fell into using the fantasy of Rupert the Bear to take my mind off things. We were just talking about buying a nice car to go to the beach in for a morning picnic.

Teacher laughs a little, continuing "It is super healthy for a girl like you to have a big imagination and to enjoy herself. For your 'Name your Animals' task let's pick your next furry friend." She indicates the toy wagon containing a unicorn, a horse with a pink stripe in her mane, two zebras with different patterns and a rabbit. Grudgingly I pick up one of the zebras, and Teacher smiles "You know, horses, ponies, zebras and unicorns are by far the most feminine animals. They are almost... dreamy, mythical creatures, and so smart in real life too." I sigh but knowing how this will go I offer "Teacher, may I call her Elsie?"

Teacher smiles brightly and nods. Strangely the electric bra is off the whole time I play, so I end up playing for over an hour even though I only needed to for 30 minutes. My hypnos run in line: "Kali loves playing with toys" "Sissy girls just love cute, soft animals" "No real man plays with his daughter's toy stuffed animals." It turns out Elsie is snotty and makes Rupert and me annoyed or jealous. The bra gives me a little shock, and I get up, realizing how much time passed. But even so, this is an enjoyable, easy task and I kind of smile. Maybe this won't be so hard after all.

Unexpectedly the door opens and Sally walks in, smiling. She has a light, loose red summer dress on and short red pumps, very simple day-to-day makeup, hair down. "Time for the fashion test, sissy." Realizing I never re-watched the training video, I get up anxiously and follow Sally's lead.

Sally quizzes me and I do well, only missing two questions. Mistress's training helped me to internalize the details. The test goes on, and finally her phone dings and she smiles down at me, "You passed, Kali! 100 XP!" I get up and we share a very girly hug, as she continues, "This is great! You made two mistakes, but those will help you with your training so it is easier to pass future tests. Do you want to try any other tests right now?"

"May I do the Name Your Animals test?" "Well, you only have two animals, Kali. But... if you want, I'll give the test right now, and we'll see how you do." I smile as we sit, she grabs an adult office chair from the darkness (wish I could sit in that!). "Kali, tell me about the furry toys you love so much." "Sally, well, Rupert is a nice bear and he is pretty much like me. We both don't like Elsie the zebra, she is kind of mean." "How so?" Sally asks sweetly. "Well, Rupert and I thought we had a nice car, but Elsie said it was small and ugly, and that it doesn't go fast." I sigh, confiding, "She said her boyfriend has a nicer car and she wouldn't be with a guy that drove something so small." Sally laughs, "Okay, sissy, I think you just earned 50 Experience Points!" We both smile as I get my tablet and start picking new skills to train using my 100XP and 2 Unassigned Ongoing Skills.

Sally points me toward a large oversided, dark wood double-door that was locked on the far wall. "This is your sissy wardrobe! Help yourself to any clothes in there, now that you passed Fashion, you have full access to the clothes we sized perfectly for you!" Getting up, I go look at the huge walk-in closet's contents. "Wow" is all I know to say as Sally comes in with me, giving me a big bear hug, somehow getting her face next to mine so we are both looking forward into the closet. "This is going to be so much fun!" she encourages, as I look at rows of high heels, closet rods burgeoning with dresses and skirts of all description, and a large dresser with drawers full of panties, bras and lingerie. There are two glass cases displaying items for special events- a magnificent white wedding dress and a black high school prom dress, among other, folded items. "Isn't it exciting?" Sally asks as my hypnotic messages start "I wonder how the red dress would look on me" "When can I wear the prom dress?" "Look at all those shoes!" My own curiosity agrees with the hypnotic suggestions, burning the implications deep into my mind, as I stare smiling.

We go back to my desk and using the tablet's menus I pick 'Areas of Study' - 'Feminine' - 'Day-to-Day,' - 'Hygiene' and several choices pop up: 'Taking care of your Hair- 75 XP', 'Nails and Cuticles- 80XP', 'Face Masks and Skin- 20XP', 'Cycle- 50 XP'. I click 'Cycle' as Sally smiles inwardly, and then 'Social'-'Girl Talk'-'Fashion' to use the last of my XP.

Switching to 'Ongoing Skills' I pick 'Random Intense Bra Shocks' and 'Sissy Orgasm 2'. The descriptions are 'up to three times and hour, thirty seconds of painful, pleasurable nipple torture' and 'Sissies can orgasm anywhere, but they need to play with their nipples, catch all their cum in their hands, swallow all their cummies'. The bra skill's cartoon artwork emphasizes the girl's fear as she sits, waiting for and scared of another shock. Sally smiles "Nice choice for shocks, Kali. Accepting random shocks will train your body to know, experience and live with pain." She smiles in a naughty way. "Soon you'll really enjoy it, even need pain for stimulation." Smiling nicer, Sally continues "If I were you, I'd watch all the new training videos that unlocked, and sign up for some tests if you think you are ready. You really need to gain some Experience Points, Kali! Five thousand points in just a few short weeks will take dedication."

"Okay, thank you Sally." "Also, at 10AM tomorrow, a new friend will come to talk to you about fashion to help you become used to talking like a girl with a girl. Your clothes closet is yours since you passed the fashion test, and you should dress yourself how you feel- not school girl uniform- for when Ann comes to talk. I think you two will probably watch TV or something, so I'll talk to teacher about getting a couch in here for you ladies to sit next to each other."

I smile and Sally gets serious. "Kali, are you okay here? Do you need anything?" (she emphasizes this last) "Are you worried about anything?" I shake my head, imagining time with Ann, pretending to be a lesbian or at least a girl gossiping with another girl. Sally waits several seconds before supportively smiling, and starts out.

After she goes I decide to watch a porno so I open the tablet's sparkling menus and pick Pornography, then scroll through the longish list, idly reading names. Some seem too close to home for right now- 'Molly fucks her first black man' and 'Sissy Kali playing with herself.' But I settle on 'Sissy meets Daddy for Tea' and hit play. The videos just have titles- no description, no length. I hope it is short because I always pay attention to the whole thing. The video starts with a sissy- it is obvious because the camera is looking between her legs as the metal chastity on her penis shines when she not-so-sophisticatedly uncrosses and re-crosses her legs. Slowly panning up to her face I see she is anxiously waiting for her date. When the man finally arrives, she smiles broadly, getting up for a big kiss. The coffee shop is oddly empty and they are around a corner from the cashier. Soon the blue-dressed, olive-skinned sissy is under the table, playing with Mr. Big's cock. The video finishes with them leaving together out the front door, the girl with a little cum on her face being guided by the strong man. I get super hard, but quit diddling whenever orgasm approaches, trying to draw out my orgasm as I play with my nipples as well.

As I play with myself during the car scene where the sissy is on her knees as Mr. Big drives, the door opens to two large men. "Where do you want it?" the one asks, as the other looks at me in shock. Shaking his head, the lead man explains "It is just a sissy, come on Karl. Let's bring the couch in while she thinks." In shock I cover myself up, hiding my small penis and pulling the bra back into place using the most feminine of gestures. The strong men return bringing a couch to an area I point out near the screen, to the right of my school girl desk. "Wow, you really are a real-life sissy, aren't you?" "Yes, sir" I say softly. Both men laugh but leave quickly as I remember the porno is still visible and rewinding at double speed. I rush back to my desk to re-watch the blowjob scene, sighing and slowly playing with myself, trying not to think about the men.

The ending is good, the sissy getting fucked in the large man's bed, and I couldn't help but look over toward the nice comfortable bed that is off limits at the beginning. As the camera pans into the girl's face, she makes an expression of pleasure that I can't imagine, and I cum into my hand jealous and wanting to feel like she did in that moment. The movers seemed nice, maybe... I don't know, but my hypnotic audios read my mind playing "Strong men have nice, comfortable beds" "I could just sleep next to him" "I miss having someone to sleep by" as I slowly clean my hand with my tongue. And there sixty minutes went by like nothing.

Spent, I watch dull training videos, learning about periods, toxic shock syndrome, and social norms for girls talking with girls. Finally I go to sleep on my cold cot in my girly pajamas, putting my smooth face against the pink, ruffled pillow.


Three Weeks: More Dedication

Time fades as I become more and more girly. I always have a tampon in, unless an Ongoing Skill requires a butt plug. My nails are typically a bright orange or pink, and I work the cuticles daily. Now I only orgasm with a dildo in my mouth while watching sissy porn. The hypnotics are always pertinent: "I wish I could have a man", "I want someone to fuck me", "Stupid plastic-I want dick". Ann, the young girl that comes to talk most days, smiles "It's natural to want some men to experiment with, Kali. Especially if you haven't ever given a blowjob to strong, throbbing penis."

Sometimes when I'm horny, instead of pornography I switch to the 'Hypnosis' menu on my tablet. A draggable ball changes the focus between three extremes: 'Spirit', 'Slut', 'Transition'. Below lists of possible message previews automatically scroll by. As I move the control ball the scripts change- "You are a slut", "I just want men to see me", "Maybe this skirt is too short". But it is complex because the control moves on three dimensions- the feminine spirit (macho or girly), sluttiness (conservative or whore) and progression (doing what I do now, or bettering myself). I can enable 'Visual Mode' to show images onscreen: sissy captions and short videos that support the hypnotic suggestions, and the audio volume increases so I hear every word.

I turn that off for now, time to work. I'm in my normal day-to-day makeup, wearing jean shorts with an electric buttplug and my penis pulled back between my butt cheeks, tucking and hiding my small balls. I have a tight blue shirt with lots of exposed cleavage. Studying sissification for my beautiful wife Molly, I watch a training video 'Pleasing your man- wake him up with your mouth'. I pay total attention because the computer shocks my buttplug if I look away. Smiling is also becoming a requirement for more videos, along with staring/focusing, and the computer knows if I am just pretending.

After I use the nail stripper and re-color my nails. Looking at the tablet, the requirement for today is "Revlon 270", a sparkly red; also, the two ring fingers are to be blue. As I carefully apply the last touches, Ann walks in unannounced as usual, and laughs at my concentration. "Kali, you really are vain, aren't you?" I try to laugh it off- girls don't 'sigh'- and smile at her. "Ann, what a cute outfit!" She smiles and tells me "So you remember Dillan? He fucked me so hard last night-baby, you have to meet him! Such a cutie!"

Our chats moved from fashion to discussing romance plots in TV soaps to gossiping about boys. "Chad is so hunky, don't you think Kali?" "I really like how Vince told that Karl off, Ann! He really overstepped!"

My Ongoing Skills include practice blowjobs on dildos and cleansing daily enemas, but I need to get more experience points! Complaining a bit to Ann "I really wish I had more experience points", she recommends "Girl, just get Mistress in here and ask to do more Ongoing Skills!" before smiling in her cheery way and talking about a recent fashion show in New York that was live on TV. "You can watch it- I'll get them to put it in your video list!"

As she left, Ann promised to ask Mistress in. I await her excited- she was the focus of my sexual attention before but now she is just a facilitator that could get me more sissy experiences.

Mistress comes soon, very happy to see me sitting in my school girl desk, arms folded and legs crossed. My stomach is noticeably smaller now, although strangely my breasts (man boobs) are the same size. Maybe just my bowls finally emptying made the difference. She walks in and smiles broadly, "Ann tells me you have an XP problem, sissy Kali." I sort of blush "Yes, Mistress, May I pick additional tasks?"

She smiles down, "Kali, ongoing training is always healthy! Do you know you need 4,500 more experiences points to meet your personal goals?" "Yes, Mistress." She thinks for a second, then continues in a somber voice "You have been averaging 50 XP per day. So, you are looking at three months."

I cringe as she continues "So I am glad you finally asked for help. Did Ann spark this?" "Kind of, Mistress... I was complaining about XP and then she said." Her encouraging smile, tightly laced long black hair, and leather outfit seem at odds: she is acting more like Teacher. "How quickly would you like to earn your XP, Kali?"

We agree to aim at 200 XP per day- a rate four times faster than what I've been able to do so far- and Mistress works her phone. "So you'll want to take about 5 extra ongoing tasks right now, and try to pass several tests daily." I trust Mistress's calculations implicitly and hope to do as she says.

My tablet shows "Ongoing Skills-5 Unassigned" and I start going through the lists. Most of the easy stuff is done, areas like kid's toys are all finished. I pick some task under 'Adult Toys': 'Improved Butt Plugs', 'Sex Dildo Pleasure'; and the balance are other areas: 'Sleep in Bondage', 'Talk with a Man', 'Draft Coming Out Letters'.

Satisfied, Mistress continues "You know, by growing, you have access to better tests to prove yourself." She smiles to herself. "Sissy, some of the best are nonverbal- short and physical, worth much more XP."

The next day Saul, a handsome gentleman in a dark grey suit, came in with Ann and talked with us. Ann started "The company said we should spend time with Saul." Leaning in toward me she whispers "He's cute, isn't he?" as we all sit in the couch, with me in the middle, and Saul starts talking about sports and his job.

He is a nice guy, and both Ann and I are impressed, but he "Never saw a real transvestite before" and was "open to experimentation". So when he left, Ann turned to me, smiling: "He likes you, and he even knows your little secret!"

Sighing (Ann admonished "Ladies don't make gross boy sounds, Kali") I nod my head. Saul is a really nice guy. After Ann leaves, I do some of the harder training tasks- taking stronger electric shocks for longer and using the lubricant, fucking myself with the dildo while I watch sissy porn. The dildo doesn't really turn me on, but after days of the butt plug, it is easy enough to insert- and water fasting has my insides the cleanest they've ever been, so now is the time. My nighttime porno, 'Jessy and Justin', has the sissy stranded without gas on a rural road hours away from any city, and Justin notices her car is just out of gas- but convinces Jessy the engine is ruined.

Crying, she realizes there is no-where for her to go, and confides she has no money. Justin suggests, "come live with me for a while- you can save some money and eventually go where you want" with an evil grin.

The next scene has him fucking her anally, as I play with my dildo. Cumming is allowed if I catch and eat it, and as the movie climaxes so do I- with the dildo far in me, just like Jessy has Justin. My hypnotic audios capitalize on the situation- "I want to get fucked", "I wonder what size penis Saul has", "The dildo felt nice in me".


Three Weeks: My Last Vacation Days

I tried so hard and really wanted to please Molly, Jen, Sally. Mistress told me the grim news: "Sissy, you only have three days left before the time your former wife Molly gave you to fantasize is up. She warned you, and I did too. If you're going to get 2,000 more experience points in the next few days, you'll need to take responsibility and pass some serious tests!" Even as a sissy I am a failure, on top of losing my company and risking my wife. I wonder if I can I do it as I look down in shame.

My voice squeaks hoping against hope "Mistress, is that even possible?" "Well, normally no, but I'm rooting for you. I'll enable some quick tests that you can probably pass if you put your mind to it, sissy." She clicks on her phone, then looks to me with that somber face. "I've always said you need to avoid failing tests." I respond properly "Yes, you have Mistress."

"Now things are different. Sure, we'll punish you for failing, but you really need the XP. So I recommend taking more tests than you need to reach your sissy goals, and assuming you'll fail some. That way, you can cover every eventuality." "That makes sense" I absently agree as I start reviewing the various new options in the 'Test' menu. Many are truly quick and easy: "Post yourself as Kali on FaceSpace", "Send out three of your draft 'coming out of the closet' letters", "Sleep with Saul in the comfy bed", "Make a short porno with another sissy".

There are about twenty options, each dirtier than the last, as I stare silently. Mistress quips "Don't they all look so delicious? A growing sissy like you is probably excited for all the fun opportunities!" smiling a bit too much as I can't help but look up and mirror her grin.

Swallowing, I pick about six tests to attempt today. No more training videos, and Mistress seems pleased with my choices and explains, "Ann and Saul will be coming by soon. I'm going to leave for now and get some supplies ready. Kali, this is really exciting- if you put your mind to it, you can reach Molly's goal! You might even see your daughters again. I really wish the best for you, Kali." She smiles and leaves, revealing the back of her neck, unusually her hair is up in a tight circular braid. Her tonality and facial expressions were clear: I can win, and she hopes I do. Jen was always supportive, even when I ignored her.

My tablet dings "The first test is in 15 minutes- recommend Slutty Clothes and Makeup". I obey, putting on a red 'fuck me' dress and matching 4" heels, horrible blue eye shadow, generally slutty makeup, bright red lipstick. The test is 'Get phone numbers from an online GregsList posting'. Sally comes in smiling. "Kali, I'm so proud- finally finding a real life man!" I shudder and notice her suburban 'mommy clothes' are the polar opposite of mine as she starts having me pose and taking photos.

She helps me write the post- short and sweet, "Brand new virgin sissy wants a good fuck", and after she gets everything ready I push 'Publish' to put myself out. She attached three pictures- my ass, my body and a head shot featuring my perfectly made up blue eyes and seemingly thick, long lashes.

"That's a pass, Kali! 50XP! What other tests did Mistress get you to sign up for?" I gulp "I need to send out three of the letters I wrote about me actually being a gay sissy to three other friends..." (Ted, Adam, and everyone that saw me here are off limits).

"That's fun, I'm glad we wrote those letters! You should know we already sent them all out." I stare incredulously as Sally slowly smiles, and starts laughing in a friendly way. "Don't worry, sissy faggot, I would never rob you of the right to hit 'send' for your own girly letters." she says plainly annoyed I didn't enjoy the joke. She pulls out a small web-only laptop computer, setting it on my desk. "You have five minutes to send three emails. I've already set up the attachments so everyone will get your FaceCraig link and attached copies of those pictures in lower resolution. Be sure to get them all out in time or you'll fail this test and earn a demerit, sissy." Walking away, Sally continues in closing "I forget if Saul or the other sissy is coming to meet you next. And I don't know what you want to look like for either- hmmm. Good luck, Kali, time is ticking!" and I look down at a count-down timer: 4:25, 4:24 as the door shuts quietly.

Shit, shit. The post was somewhat anonymous. Now I need to link it in an email to three people that know me but don't know about my vacation- people I haven't spoken to them for a month. Crap. Jony, Kyle and Devon will get their emails. I could just hit 'send' but I want to re-read them.

"Jony, you are my favorite receptionist, and I love how you always greet me and other guests. I wanted to tell you I am going through a major change. I realized I really don't want to control anything, and I want to be so much more submissive. So I wanted to let you know that I have changed. Now I am a girl called Kali. I want to date men and I know you have a lot of contacts. Please give them my number, I really want to enjoy my new life. It is 555-555-2731 if you forgot. Best wishes and I hope we can still be friends. I don't know if I'll still work at the same company but maybe I'll stop by your place to say hi in a few weeks. Best, Kali (you knew me as a man called Brandon)"

"Kyle, sorry man, I haven't been in touch. Things changed. Maybe you can come over to my place sometime and see. I always wondered about your... member. Now I'm not gay, but I am a hot cross-dressing passable sissy. I just got overwhelmed with being CEO, and tired of being fat. Now I am skinny and hot, and people are going to look at me instead of look away or down in disgust or sorrow." (I grab my left boob with my right hand, surprised it is so big, even though my belly fat is all gone. Even my thighs and ass seem out of proportion, they have too much fat) "I guess I mean I want to taste you. Call me, let's talk. Kali (hot, cute Brandon)"

The computer beeps like a car running out of fuel. The timer reads 1:30 as I press on.

"Dr. Devon Schloss, M.D.- I was once Brandon you are my primary care family doctor. I feel I need to inform you of certain life changes, and offer you a chance to have me in an intimate setting. No, I'm not gay. But you need to know as my doctor and maybe we could become something more. I am a girl, and I love anal and giving blowjobs. So I think I need more specific attention on anal health, and certain important vaccines for the sexually active, and I want to get monthly STD testing. But doctor, I always loved the way you command your office- and I always wondered about you. The real you. Call me after work sometime, 555-555-2731. Please don't cut me as a patient from your practice. I'll be arriving as a girl from now on, I am very passible and please update my records to reflect my right name Kali. I always wondered. Kisses, Kali. (formerly Brandon)"

I stare, ready to adjust the closing valediction to something more formal, but the low-gas buzzer goes off again and I hit 'Send'. The timer had 30 seconds left, erg. I could have said "Best"... well, it's done, I'll need to find a new doctor. He'll probably call Molly tonight, concerned.

All three will probably call me too, since I haven't been available for so long. Luckily my voicemail is simple: "Hi, this is Brandon, CEO of Cleanse Company. Please contact Joan" (I sigh irritated knowing what I know now) "my trusted associate for business needs. Otherwise, leave a message. I should be back in a couple weeks." Then they'll probably call Molly or Adam (Ted doesn't know any of them).

I only have a few minutes to think about changing before the door opens again. A stereotypical producer barges in carrying his director's chair followed by two laborers- one with a large video recorder, the other a boom mike with a Go-Pro mobile camera. The director folds my small computer with one hand and laughs eyeing me, "First time, sissy? I think we might have a business future... tell me your phone number." I stare at his gaudy gold chain and exposed thick, black, expansive chest hair. His thin white tank-top undershirt ('wife beater') with food stains and loose jeans, and sandals. Maybe he is 45, he's fat and balding in the front, grey unshaven beard, looking like a piece of shit. Somehow I want to volunteer "555-555-2731" and my choking voice makes the video guy laugh out loud.

Both the helpers are in blue dress shirts, jeans, nice belts; good haircuts, young, almost religious or at least ready for boarding school. The video guy starts "Sissy, go lay in your bed so we can do the intro shots and get lighting, your" (he sighs and shakes his head) "new friend Molly will be here soon."

Molly- my wife Molly? I smile and all three men laugh, the director loudly plopping his chair down at the foot of my bed. He yells "Places!" as I rush into the comfy bed for the first time. Molly. This is my reward- Teacher is compensating me for her little lies over the last month; Sally felt bad about failing me on those tests and wanted my fantasy to come true. They both know Molly suggested "lesbian fun" the last time we saw each other. My cock is growing too as the director laughs and the two boys look away embarrassed. "Look at the sissy getting ready for a fucking!" the gross old man laughs and the microphone guy can't help giggling.

I pose following his requests, still dressed as a total slut and not in night clothes. "Sit up on the bed" "Lean on your side like you are reading a book" "Lay across the bed, so your feet are hanging off the side, and hold your head up in your hands, elbows on the other edge." "Now smile, make your eyes big, pretend to cry."

The door has been open the whole time, and when the director stops ordering me, he already has his arm around Molly's back, his hand up on her right shoulder, as the short, slender girl stands next to his chair staring at me. I look straight at her for the first time, done posing, and the director blurts "Sissy, this is Molly. Molly, this is..."

"Kali" I interject in the highest, girliest pitch I've ever heard. The director immediately continues "She met you at a bar, but since you two drove separately she got home first. I think she changed her makeup while she was waiting for you, Molly." His dumb smile makes me feel like street trash, wishing I'd at least washed off my face. "Hi, Kali" the diminutive sissy mouths in a reasonable tone as I stare in disbelief.

She walks up to me and caresses my face, trying to encourage me. "Do you like bottoming?" she asks honestly as I stare. The director gives us a few seconds, but quickly orders: "Up, both up. Go to the right of the bed, hold hands and walk toward the bed. You'll switch to kissing, before Kali will sit on the bed first and lure Molly to sit next to her. Then kiss a little more and we'll end the scene."

I passed the test, barely. At the very end, as Molly was fucking me, after I gave her two blowjobs, Sally came in smiling. "Kali, I'm glad you are enjoying your lesbian fetish!" she said loud enough to make the director yell at her. Anyhow Sally continued quieter "Cum without touching your penis and you'll pass this test." I did, playing with my nipples as Molly fucked me and licked my ear, whispering "You can let go. Relax."

The director nodded, "Offer still stands, sissy. I'll call you once your vacation is done. I'm Ron Pack. You could do good in this industry." The video and microphone laborers seem guilty and disgusted, but they willingly follow Ron and leave, both avoiding Molly's and my eyes. Sally runs in and hugs me, ignoring a little cum on my face, while Molly hangs out smiling. "This is a big step, Kali! Do you want me to forward links of the porno to your..." I finally put my foot down, "No." She smiles "Not yet, okay sissy. I am still proud." as my body shakes. Molly waits a bit, then comes in closer and hugs me- the most paternal, platonic, nonsexual hug- and speaks close to my face "You did great. We have to stick together in this world, some people are very mean to us."

He (well, she, Molly) smiles supportively before backing off and leaving. His hair was short, eyes blue, cock larger than mine- 7 inches (18cm) and wide, but skinny, scrawny, little muscle tone. But he was able to fuck, he pumped... my thoughts trail off as I consider my next test. Sally smiles seeing my gears turn, and suggests, "Saul seemed like a nice guy... maybe a long sleeve maxi dress in dark, deep blue? But take off your whore makeup!" She looks for a laugh, but I am too out. "It's okay Kali. Just go get cleaned up, and to pass you'll need to give yourself an enema before, and make Saul cum in your anus. But he isn't expecting that so you'll have to ask."

She giggles a bit. "I think he likes you more than Ann! Just be assertive and firm, let him know what you want. He definitely wants it, but he is scared you do not." Another firm hug, and Sally leans back, then forward to kiss me lightly on my crotch-stained lips. She just pecks, and quickly turns and leaves.

As I start seriously considering sex with Saul the hypnotics come back- the director had the off- "Can I get him?" "I liked Molly's cock" "Maybe Saul has a bigger dick then that sissy" "Saul likes when I rub his chest" "I wonder if Saul will wear a suit"

I rush with a girly run to the bathroom, showering and washing most of the slutty makeup off. The makeup desk is next, I put on comfortable, warm makeup and then outline my eyes to add some edginess. Wardrobe: I do pick a deep blue dress like Sally suggested, but I go to the lengths of wearing a garter, forming corset and some hair ornaments. My earrings are short but expensive, just like the two rings I decide to wear. The door opens after two shy, quiet knocks.

Saul walks in tall, wearing a black suit with very light, almost indistinguishable, white stripes that run up and down. "Hi, Kali." he mouths authoritatively. "Sally said you needed a friend to talk to because the hunger from water fasting is driving you crazy."

I turn my head down to the right, and sigh against my best training. "Food!? I just had cum!" screams from my subconscious as I try to smile and look back up. Food is the last thing on my mind as my throat pushes words out: "Saul, I was really wondering if you would want to..."

He smiles, then laughs slowly. With his hand, he sort of gestures to his crotch, and I am drawn in and down. I rush forward, almost tripping and sink to my knees on the concrete at his crotch. He smiles broadly and laughs "You didn't think it would be hard to convince me, did you?" He is big, and strong. After I finish him off on my knees, Saul uses one hand to lift me up to the comfy bed.

He fucks me for an insane amount of time- thirty minutes? Forty five? I lose track of time completely, as orgasm after orgasm rocks my sissy body and I moan louder than I want. I get the best sleep I've had all vacation. Saul massaged me and spooned me, keeping his strong, warm breath with the slightest beautifully intoxicating scent of booze right on my ear all night long. I sleep well enjoying lucid dreams.

Mistress wakes me. "Kali, was Saul a good fuck?" she mocks. I try to shake the sleepy fuzz out of my head as she continues "Remember to pick new tests! You got 500 XP yesterday, but you need 1500 more or you know what will happen." She walks away a bit, then turns back. "Kali, you didn't do the last test you signed up for. It is Electro-Hypno-Cock Desire Reinforcement."

I nod, knowing she is right-Saul had me busy all night. "You should get a demerit for failing, but I want to give you a running chance." Her makeup is strong, but grayscale- black, white, grey, maybe a little shininess in the very corners of her eyes near her nose. "Finish that first, then you may pick additional tests. Godspeed, little faggot." She leaves as I seriously consider sleeping for another hour. Saul's disappearance makes me feel like I earned some remuneration, just a few minutes.

Two hours later, I wake. Happily walking to my schoolgirl desk, I see my tablet is a quietly beeping and blinking red. "Electro-Hypno-Cock Desire Reinforcement" comes up in bright white letters every flash.

Shaking my head, Teacher walks in all smiles. "Kali! You got Saul!" and hugs me congratulating my first fuck with a real man. "Isn't it so nice? The feeling of a live, beating penis deep in you?"

She laughs uncontrollably, clearly messing up her character, but recovers "Here, wear this bra and get in your desk." I shake again but with my messy panties, I sit in the desk after the bra is on. "Pay attention! When there is a cock or penis in frame, look at it! Otherwise the bra will deliver increasing shocks- so powerful you might end up on the floor, unable to see the screen, locked in the punishment until I come back."

I look up wondering if that was a joke but she leaves immediately without looking back. Her long ponytail is held with multiple short brown leather ties, and it swishes back and forth as my large screen powers on with a white background and a happy cartoon sissy looking at a cartoon TV, wearing large headphones.

My tablet blinks faster (2Hz) and I okay the "Start Sissification Reinforcement" option to shut it up. The tablet goes black as the eye-tracking cameras activate as the ninety-inch display proclaims "Sissies stare at cock" in a bold pink, curvy-font. The pornos and vids go. Like an animal being trained, I am shocked whenever I don't obey. Big, black penises are good to stare at. Breasts really, really hurt. Girl-faces are mildly painful. Boy-faces are not painful, but their cocks- I shake as I hear an audio hypno "Maybe Kali could work a gloryhole" and my mind agrees.

Mouth open, I stare, amazed and scared. Molly- for the real Molly- I cry openly as the hypno dies down. My breasts are so sore from the shocks I can't touch them.

I pass, barely, and Sally and Teacher rush in, Sally hugging me deeply and painfully. "It's okay, sissy... it's okay." Teacher, in command, holds her head above both of us and reminds me in the friendliest manner: "Kali, that makes 500. But you need 1500 more in the next two days." (she pauses) "I gave you full marks for your last test."

Still I bawl. I can't, I won't go to a dirty room to suck nameless cocks. My face is red in tears as Teacher kneels before me and hints "Do you want Molly?" My mind considers synonyms: the drug called Molly (ecstasy), my wife, or the small sissy? Concerned Teacher leans down touching her cashmere sweater to my exposed hairless chest to look into my eyes. Realizing she pushed too far, she comforts me "Kali, go ahead and sleep in the comfy bed. We woke you up too soon, you earned some rest after you got fucked by Saul. We'll come back after you pick some more tests."

I cry more, lost. "Let me pick some more now" I try, and she smiles, leaning back, like a smart lady humoring a dumb child. She takes the tablet, not to leave with it, but to usher me to bed for now. Sally seems to agree, but she is worried. I lay down, exhausted, as they leave the tablet on the schoolgirl desk and leave bickering amongst themselves.

The water fasting, the recent fucking, the long hypno- I am physically and mentally exhausted, and sleep gives my brain a chance to run through the mental consequences in vivid dreams. They focus on Molly, not the sissy but my beautiful real wife, and my worries about experience points.

My wife Molly was up in the observation deck at that moment, with Teacher and Sally, and Joan. "Why is he doing this?" she asks crying openly as Sally hugs her and Teacher and Joan try to comfort her. Teacher suggests "You sort of asked him to, Molly. You gave him a reasonable goal." Joan agrees "Most people just learn how to clean tables, cook turkeys and sort laundry, and they get well over 7,000 experience points. He was too complacent at the beginning, and now he feels like he has to make up for lost time." Molly shakes, still ready to cry, as she looks down at a replay of Saul's visit on one of the many monitors.

Backing up, she looks at some of the other adventurers- a lady being held in a literal fairy tail tower of ivory, her hair growing magically long as she sleeps; a man commanding a large virtual army in a valiant war effort in Scotland; even a romantic one where a woman was trying to convince a strong knight to stay home with her rather than go to battle. "Why didn't Brandon pick a normal fantasy?" she cries as Teacher and Sally both move to comfort her, and Joan turns away hiding an evil smile to look at me lying in bed, with makeup running and a foot exposed, showing the long, bright red nails. What a sissy, Joan thinks, considering my future. In a few days Molly will have to decide, even though Brandon probably won't meet her goal, a very reasonable goal at that, she'll have to decide what to do with him.

Waking up peacefully, I jump into action: only two days left! The tablet is alive with choices, and I browse like an excited child, trying to find the best. I hurriedly click away: 'Meet the larger Friends of Saul', 'Meet a Sissy that speaks only Spanish', 'Shocking Plug', 'Urine Acceptance', 'Silence in the Face of Pain', and 'Booster Shots'. 'Make a trailer for your next Porno', 'Spend time with Sissy Molly', 'Thank Saul with a Meal', on and on- dozens of choices. Unsure, the door opens to Mistress.

Walking in with tall posture and a stern face, her perfect makeup and braided hair along with the polished leather put my lazy makeup and comfortable sweater and jeans to shame. Something is wrong, and she walks up to me in disgust. "Kali, take off your clothes NOW."- her voice assumes obedience and I comply before any doubt raises in my mind. I pull off the jeans and fold them, setting them on the desk; my bra and panties come off without a pause as she continues to lord over me, and I quiver like a little child that knows she did something naughty.

Naked, Mistress points: "Sissy, go to the wall and raise your arms up into the straps." I obey immediately and she whispers standing over my ear as she latches the leather belt buckles, keeping my arms up: "Good sissy". Backing up, as I stand facing the wall, she whisks a leather flogger through the air. The soft leather is cut into four independent tails that she dances over my shoulder, giving me a perfect view.

"You didn't play fair. You fucked up bigtime, we're taking away 100 XP you didn't earn, and giving you two demerits. And I'm going to make your back red to make the rest of your time here even harder. Do you know what you did wrong, sissy? Remember, never lie, little girl."

I am silent, and Mistress breaths angry steam into my right ear as Sally appears from no-where on my left side with a sad face. "You faked two of the emails." Mistress stands even taller and leans over my right shoulder to stare me in the face. "You let Sally send fake emails? You wrote letters to people who do not exist?" I cower, naked, arms held up by the simple leather straps.

Sally backs up to read: "Devon-address unknown. Kyle-address unknown. Stupid 404 errors, faggot!" as her volume rises in girly indignation, cracking in a way Mistress's never would, and turns to raw anger. "Lose three hundred XP and gain three demerits, by order of Joan!!" She is truly angry: "I thought we were doing good! You were getting exposure, and trulying learning about yourself! But now we can't trust you, even to be honest about your own friends!? What kind of a..."

Mistress takes Sally out, and I wait for ten minutes. She returns, her military boots' clangs reinforcing her determination and leadership, and immediately starts whipping me. "Kali," she mouths between strokes in a calm voice, "Sally was out of line and you only earned two demerits." "And we aren't", she braces and whips me particularly has on my butt, "going to take away any XP but the 100 points you got by cheating." The whipping continues, no longer sharp stinging, transmutating into a warm burning, as the soft leather disperses her softer-than-they-feel blows. She avoids my crotch and stays mainly on my back, continuing to whip me. "But, you disappointed us. So, I am counting 100 strokes- one for each ill-gotten experience point- and"

Her last volley left Mistress a little out of breath, so she stops and backs up, regaining her solid voice: "And, you can take as many tests as you want from now on, just pick them on the tablet, but we are not letting you do the easy ones anymore. Just sending a fucking email and you screwed it up so royally!" as she leans in and restarts her efforts, slashing back and forth over me with the soft leather. "50." she announces, pausing for me to consider my mistake. "Stand up straight, take it like a real woman!" she yells bursting into another fast volley, before slowing and enjoying the rest of my punishment.

I hurt. I expect blood but of course Mistress is careful and skillful; I was safe the whole time. She pulls my arms down, tells me to go lay on the cot on my stomach, and leaves briefly, returning as Teacher with a cooling, non-oily cream that she applies all over the sore spots. Teacher is silent, and leaves without a word, as I re-consider my situation.

The throbbing that I caused. How I am now farther behind, and it is already noon, and I am so sore I don't think I can physically do many of the tests. How can I get 1600 XP in just a couple days? Not even two full days. I want to get up, but it is just too much. I am failing Molly. All I needed to do is run through a couple gay fantasies, and I could go back to her loving arms. I fall asleep, exhausted, wondering if the cream also had something to calm my nerves and mellow my mind.

When I come to, it is 4PM. Shaking myself up, I know I have to get busy. I run to the bathroom, clean up, throw on blue panties and a simple yellow tube top to avoid a bra. Quick and dirty makeup, then to the school girl desk for almost the last time. Flipping through the tablet's pages of options, my butt complaining almost enough for me to stand, I calculate: 1600XP. I should try to get 1000 today, but how? Obviously the tasks are ranked for difficulty, and some would probably be all-nighters.

I choose just three to attempt: 'Sissy Molly tests your Toy Capacities- 300XP', 'Make Saul dinner and ask him to fuck you- 500XP', 'Learn to enjoy the taste of Urine- 200XP'. There, it's done. Sighing, I get up and consider watching a video. But Teacher is immediately present with several other men- I remember the people who brought in the couch- with large roll-around carts.

They bring in a small round table, like a romantic French Bistro might have, and an array of hosting stuff- tablecloth, candlesticks, silverware, flowers. "You aren't allowed to eat, and even tasting will result in the same kind of punishment you got this morning, Kali." Teacher warns as my mouth salivates. "Your first job is to get ready for Saul. We've already made most of the meal, but you will chop and toss the salad, slice the meat, and put everything in serving bowls after you set the table properly."

She smiles wryly. "This is your chance to thank him for fucking you so well, and to pass the test, you need to honestly ask him to sleep with you again, and do whatever he says." Everyone leaves, Teacher parting with "I hope you do well, Kali. Saul will be here around 7PM."

I rush around, setting the table. Should I set myself a place? I'm still water fasting, but I decide to set myself a whole setting so he isn't self conscious. I make up the salad, chopping celery, carrots and red cabbage for some color, combine with a nice romaine lettuce head and plate in a large glass bowl with a blue cheese dressing in its own small server.

They supplied mashed potatoes, pre-cut ham, freshly baked rolls; I get everything on the table and light the romantic candle. Force of habit almost makes me eat one of the olives, but I realize what I am doing and leave it. Looking at the clock, I rush to the bathroom, clean myself, and put on a dark red shift dress with a low-cut neck - still avoiding a bra- and do my makeup for a formal dinner party.

Saul arrives a few minutes early letting himself in without knocking. "Wow, Kali, you look gorgeous!" he compliments me as he walks over and gives me a big hug, making me flinch. "What's wrong, Kali?" he asks concerned. "I... Mistress had to give me a lesson.", I admit. "Well, let's eat!" Saul says excitedly.

As we sit, he asks "Aren't you going to eat?" "No, I'm on a water fast, silly!" "Wow, it must have been hard preparing all this knowing you couldn't eat it. Well, I'm starving, so I'm going to just dig right in." "That's fine, Saul. I had such a good time with you that I wanted to thank you before I finish up my vacation and go back to real life." Saul looked up at me, considering. I wonder how much he knows.

"When are you leaving?" he asks as he opens the red wine, a merlot, and fills his glass higher than a bartender normally would. "Tomorrow should be my last day, Saul." Thinking, he suggests, "Then... to celebrate, why don't you have some wine? Teacher said if the mood is right you can." I smile, so thankful that Saul understands. "Yes, please" I respond trying to not sound over-eager.

As I sip my wine, Saul pigs out on all the food. I couldn't eat like that if I wanted, my stomach has been empty for far too long and I'll need to ease in with some light broth or maybe a vegetable smoothie. But the wine goes down nicely and takes the edge off everything, and while Saul has three of his behemoth glasses, I drink quite a bit too. After, we decide to go cuddle on the couch and watch some TV, before bed.

Saul drinks another glass of wine, and I have some more. Feeling more and more feminine, Saul always knows the right thing to say and treats me l am a proper lady. It makes me feel special and as we remove each other's clothes to get ready, he kisses me deeply, "I love you, Kali."

We have sex again, of course: I give a blowjob, he fucks me, we're both sweaty and disgusting but he still spoons me properly and falls asleep with me between his huge arms. The wine really hit me since I've been fasting for so long, and I fall fast asleep, still buzzed drunk, with only the slightest concern about experience points and the other tests I signed up for tonight.

In the morning, Saul wakes me by carefully playing with my nipples, and comments "Wow, Kali, those are some nice breasts." I wonder how I kept body fat in just the right places, but I am proud of them. "I- I have to get up, Saul. I need to do a few things today since it is my last day here." He sighs, "Can't we just lounge around a bit?" as I shift out from his embrace, my head pounding from all the wine last night, and suggest with my body language a quick shower together. He smiles, his morning wood at full staff, as he follows me into the bathroom shower.

I give him another blowjob kneeling in the shower, thank him for all his help, and lather him up really feeling his body. Then I wash myself, and we dress as I politely tell him to get out. Teacher and Sally come in while we are just finishing getting dressed. They both smile knowingly, and Teacher asks "How was it?" Saul smiles broadly and I respond "I really enjoyed all my time with Saul, Teacher, but I told him I am busy today." Teacher and Sally both laugh, but nod, and talking me aside Sally whispers "You could just spend the rest of the day with Saul." But I don't, I want him to get going so I say another polite goodbye and Saul leaves like a proper gentleman, carrying a small rucksack with his dirty clothes, and a happy smile on his face.

"Well, you've really done it now, Kali." Teacher's tone changes dramatically once Saul is gone. Sally breaks in "How was he? Is he big?" like a gossiping teen. I can't help but smile, "8 inches" and both ladies laugh a laugh that could be supportive, fun, or mocking- "Well, they're plenty more like him, for a little sissy like you sex won't ever be a problem again."

Sighing, Teacher takes charge "Kali, you definitely earned your 500XP, which is much more than you have been averaging and made up the majority of the tests you wanted to do yesterday." She smiles, but then turns very serious. "You needed 1600 to reach your wife's goal, so now you still need 1100XP. You aren't even half-way there. And, worse, look what time it is." The wine must have had a bigger impact than I thought, because it is already 11AM! Saul really was a gentleman staying with me for so long, my subconscious filters up as I try to ignore the feminine thought.

"What can I do, Teacher?" I ask hoping for forgiveness, or maybe some free XP for effort. She shakes her head sadly as Sally sighs. "I don't think there is anything to do. Just enjoy the rest of your day, and beg Molly for forgiveness." "But.. but" I stammer, and Sally offers, "Well, at least do the other two tests you said you'd do yesterday. Then maybe we can make an argument for you, that you were trying but ran out of time..." She seems genuine and honest as Teacher's body language supports the idea.

I latch onto it. Hope against hope, maybe I can make it... I grab the tablet as both ladies smile evil, seductive smiles. "I mise as well pick enough extra tests so I could possibly reach my goal." I flip through, remembering the other ones I signed up for yesterday- 'Sissy Molly tests your Toy Capacities' and 'Learn to enjoy the taste of Urine'- add up to a total of 500XP. Going back to Areas of Study I use my new XP from my time with Saul to increase my options.

Back in the Test area, I pick enough to just reach my goal of 5,000 XP- selecting 'Gloryhole', 'Get Hit On', 'Flirt with a Stranger', and 'Caged Sissy Orgasm'. No-one thinks I'll have time to complete them all, but at least I can say I tried. "Molly will be back to play with you in about thirty minutes. Put on your red dress and for heaven's sake, wear a bra! Use one of the wireless cloth ones with the wider bands and non-scratching hooks." Teacher goes to a wall to open and display the large shelf with a vast array of dildos and sexual toys. "Do what Molly says, stay open to new experiences, and you can't fail!" They both laugh, not in a mean way, and leave me to get dressed and made up.

When Molly finally arrives, she too has some wine for us to share. It is barely noon, but she smiles "It'll make our time together more enjoyable, Kali! Come on!" and no-one complained about me drinking last night. It is a girly chardonnay, but we both enjoy some in cute, tall stemmed glasses as we sit on the couch, fondling each other and watching gay porn. I want this to go well, so I try to butter her up even more: "This is going to be some much fun!" She smiles "You're going to learn so much!" as one of the men cums onto another's face. Molly smiles, "I remember my first time getting an orgasm centered right on me... so much attention, he was so happy." I smile back, but somehow the memory of putting my face up to Johnny's pants after he tattooed me as Ronda watched sours the moment for me.

"You're thinking about him, right?" Molly asks innocently. I laugh, trained not to sigh, and smile. "I'm thinking of a man, sure, but not Saul." I pause as she seems apologetic, and press "We should start the test, Molly. I need to" - she cuts me off, smiling understandingly. "We need to enjoy each other." My body shakes but I nod, and a big part of me wants to just suck her cock.

"Kali? Kali?" she asks nicely as she wakes me up. Looking at the clock, I realize it is 4PM! "What" I start, laying in the comfy bed, my mouth tastes like her and my anus feels used. Molly smiles down and suggests "Let's start the test. You already made your proctor like you." As the memory of our brief sexual encounter comes back, I agree, and Molly passes me a nice 1" dildo. "Just show me how you like to play with it, relax, and enjoy, honey." I smile back as she helps me with the comforter to expose my naked body.

I insert the pink ridged toy, getting it close to my prostate from experience, and diddle myself as she watches. After a few minutes, Molly smiles "All good so far. Now, use this larger vibrator." I switch, picking up the bigger toy and turning it on slow, then inserting and fucking myself. Quickly enough I feel the need to turn it to maximum vibrate, and I manage a pleasant sissy orgasm into my hand which I immediately eat.

Molly smiles, "Perfect- a handless orgasm, you ate your sissy cum, all good. But you should savor the cum in your mouth, and in the future try to draw the event out by switching the vibrations on and off when you get close. Okay, the final part of the test is two-fold. First, you'll have to insert this large enema butt plug. Then, you'll have to keep a medium-sided enema inside for a half hour."

I shake my head but start to comply anyhow, glad my hole was just stretched by the smaller toys. The plug is hard to get in, even with a lot of lubricant, but I manage sort of pushing against the floor and a small block. With that part complete, I go to the bathroom for my enema bag. Just a normal water enema, little bit of salt to help balance the electrolytes, maybe three cups of water. Nodding her approval, I hook the hose into my plug and wait as the water flows.

After disconnecting everything, I look at the clock. 5:30PM. So, around 6 the first test of the day should be all set. Molly follows my eyes, understanding. "Kali, you know..."

She smirks naughtily "You might possibly pass one more test today, if you really worked on it. But wouldn't it be so much fun to spend your last night here playing with me?" The wine is wearing off and I could really use some more. Obviously I have to spend the evening with Molly for that.

Working the consequences in my head, I have a hard time explaining why it would be better to avoid wine, anger Molly and instead spend time trying to pass pointless tests that will have no meaning whatsoever tomorrow, except how depraved I got myself. A little voice warns "Teacher, Sally and my wife will be disappointed" but I realize the louder audio from the hypnotics in the room has been reinforcing "I like lesbian fun with Sissy Molly", "Molly has a cute cock", "Will she let me suck it again?"

Holding the enema is draining my willpower as Molly uses her feminine wiles to make her wishes known. She thrusts her hips about, smiling, and asks "What would you rather do?" in a playful, feminine voice. She is shorter than me, wearing a comfortable but revealing shirt that exposes her pierced belly button. The hair is short and dyed an unnatural shade of blonde, closer to white, with deep black roots. She has large breasts, and her short t-shirt ("Girls spread the love") is white; her fingernails are short suggesting anal play and polished a perfect, neutral red. On her feet, black strappy sandals with a short 1" heel; her crotch and penis hidden by tight, short shorts in faded blue denim that have useless small pockets which stick past.

She is in shape, her cock is not visible in any way, her legs are long and perfectly smooth; her makeup is comfortable, girl-next-door, and Molly is beyond 'passable'. I am lucky, in my own much less passable body, to be near her- even cuddling and kissing. Really I have no choice. I need her.

Responding to a particularly harsh cramp, I buck up and blurt "Screw these tests, I want to spend time with you, Molly!" She smiles broadly as I continue "I have half a mind to just let this enema out! It is really starting to cramp." Molly gets a little concerned and suggests "But it is hot when a girl tries to hold things in. Let your emotions out, moan and turn off the filters you are using to trap everything inside." Realizing that was a bit abstract she suggests "If you make 30 minutes we'll celebrate with some wine and I'll give you a fabulous send-off." As the next round of cramps come, I contort my face, resign the last bits of control I was pretending to have. I start moaning and complaining to Molly. Supportively, she giggles back, but I only have five more minutes to hold this, and everything will be done.

Molly leaves the bathroom "Go ahead and release your stinkiness, then clean all the toys properly, and take a nice warm shower. I'm going to pick some clothes for you and put them outside. I like looking through your wardrobe, and (girly giggle) Cleanse Company said I can pick some clothes to keep for myself."

Relieved I passed, I go to the toilet, deflate and carefully work the large plug out of my anus. Even though I've held the enema this long, I manage to slide the plug out without releasing any on my hand and still holding the enema fast as I ease down onto the toilet seat. Careful, I let a small stream, trying to draw out and expel as much gross gunk as I can, before finally resigning to open wide. Knowing the situation, I realize I should probably take another quick enema. All the equipment is ready so I quickly fill up with another two cups, using the normal enema attachment and not the large plug. I feel great as I release it, rightfully pleased the water is clean and my abdomen cramps are slowing.

Quick shower, then I open the door and grab the clothes Molly left- in a sort of shy way, just peaking out, but she must be in my wardrobe picking her new free clothes- and throw them on. Finally, to the makeup counter, where I put on playful evening style makeup, ready for a major date. Molly picked a simple, short yellow sundress with smooth ruffles so I put in practical diamond stud earrings. Re-checking my look, I realize the makeup is too formal for the outfit. Even the diamond studs are out of place.

I am about to use a makeup remover to start over when I feel Molly's hand on my should. "Kali, come on. You look great. Let's go relax and have a couple more wines before bed." My face changes from annoyed and irritated to reassured and happy as I realize she really wants to spend time with me.

The next morning was appalling, the consummation of all my efforts, total and profound defeat. I would only warn the weaker, gentler reads to stop here, and merely imagine the possibilities, as I did that night.

I lay with Molly, giggling and touching her face, playing with her hair. As she smiles, I hear the door open. Teacher, Sally, Molly my wife. They walk in, Teacher leading, irritated and obviously disappointed. Molly has been crying, and didn't redo her makeup, unsure if she should be mad or sorry. Sally is trying to be the glue that keeps them calm and grounded; I suspect Molly was hugging Sally for support before.

Teacher speaks first as Sissy Molly and I part and shimmy back, verifying the sheets cover us appropriately. There probably is cum on both of our faces, long dried; I use my hands to pull my hair into a presentable form and comb my face before hiding them submissively under the covers. Sissy Molly is less bashful but seems to know we made a mistake and is quiet and respectful. Both of us need to use the bathroom and are hung over, but neither dares leave the bed with these three strong real ladies present.

"Kali, we explained the situation to your former wife, and our recommendation was that she leave you." I look down, ashamed, without offering any defense. My belly fat is gone, but my breasts and hips are huge, way out of proportion for a man. All my body hair is gone, revealing bright, light, shimmering skin. "You only got 4500 XP out of the reasonable goal we set of five thousand. But worse, even after we gave you chance after chance to redeem yourself, you kept ignoring your duties. Sally?" Teacher's voice is starting to crack. It is clear she thinks of her student's failure as somehow personal, no matter how angry a face she tries to put on.

"Kali, two days ago you had a good chance to pass some simple tests and reach your goal. But instead, you went to be with your male lover." Molly looks at me, somewhat jealous, but obviously she knew that was a likely. "And yesterday, we made it so you could have (emphasis) still"- she pauses and uses her body to really emphasize this- "reached the reasonable goal your former wife gave you." As she shakes her head I try to butt in but Sally overpowers my voice handily. "You didn't even sign up for enough tests to pass, and you spent all your time with Sissy Molly just ignoring most of them." Looking up, Teacher notes: "I think she 'thought' she did, Sally, but Kali only signed up for enough tests to get a total of 4900 XP. I think the sissy forgot about the 100XP we took back for lying." She scoffs "Faggots always lie." as I look down in tears.

Sally resumes "But really, the bigger failing is that you never once used your safe word or asked to leave or requested help from anyone, Kali. You willingly spent your whole vacation being a sissy, albeit a half-assed cross-dressing non-passable sissy. Now what do you expect us to do? What else can we tell your wife? You didn't even attempt to be a man, even after we tripled your vacation time!"

Silence. Sissy Molly's breathing is louder than anyone else and she feels the need to suggest, "Molly," (referring to my wife) "he really didn't mean any harm. Let him back into your life, and I'm sure he will..." as I continue looking down, feeling like I need to speak. Sissy Molly continues as my previous wife looks on incredulously "will be the man you knew, and maybe even get his old job back."

Teacher and Sally laugh at the idea of restoring my job, Teacher cutting Sissy Molly off "No, that won't happen. Everyone turned against her; Kali will never lead Cleanse Company ever again. But" (she turns to my former wife) "really the choice is yours now, Molly. Maybe you should talk with the sissies before you choose. Remember, the company will enforce today's decision for all of our lifetimes."

The lady I was married to knows the gravity of the situation and is taking this very seriously. Angry but near tears, she offers her first question as Sally folds her arms. "Brandon, did you fuck that sissy? Or did... he fuck you?" Sissy Molly giggles too loudly at this, and I shove her under the blankets, giving a disapproving look that makes me feel even more guilty. It is the kind of connected interaction only lovers can make.

Molly the real lady looks down and shakes her head in disgust. "Obviously, you both fucked each other! Did you use your mouth on her? You never touched my pussy with your tongue the whole time we were married!" Sissy Molly's broad smile makes the answer obvious as I get more and more withdrawn, my throat closing up making it impossible to even squeak let alone plot some round-about argument in my own defense.

Teacher suggests "Do you think he'll want to dress up and have sex with men after he leaves?" Molly thinks for a second before questioning me directly- "Did you let men fuck you here?" I respond, defeated, "Just Saul..." and her harsh interrogation continues "Did you like it!?" Now this is the most embarrassing moment of the whole story, where a stupid, hypnotically motivated, incriminating and happy smile came on my silent lips. I feel the guilt building like a burning fire inside my stomach as seconds pass without making a noise, and I can't even wipe this damn smile off my face. Saul was so good, and even with the ladies here, I can't help but flash back to my last mind-blowing orgasm with the strong, respectful gentleman.

Molly had it. "Fuck you! Fucking faggot, sissy Kali, you are never going to see me or the kids again. Maybe you can call up some of your old friends for a blowjob- I saw your damn FaceSpace advertisements and your little photo shoot, you fucking piece of shit!" Turning to Teacher, my former wife yells- even at Teacher, yells- "Fucking throw the book at the sissy! I never want to see it again!"

Turning back to me, her voice reaching the limits of its vocal potential, she said the last things I ever heard from her. "You had every chance! You could have just not gone on this little fantasy! You could have told me your fucking plan! I could have participated, or at least known! Why did you make Joan come tell me instead of being honest?" Her voice is losing the angry edge, and becoming quieter, sadder. "The children. The company. You lost it all, and you didn't even ask for it back. Even today, you haven't said two words in your own defense. I think you'd prefer if we all left so you could enjoy breakfast with that-that thing." Sissy Molly is quiet now, seeing the gravity of the situation, and blushes deeply at her mention.

"You never even asked how we were doing. You know, Teacher had the ability to stop the fantasy at any time if she felt you wanted to quit. This is a fucking health spa, you idiot, not a prison! The fucking front door was always unlocked!" Teacher breaks in respectfully, "Molly, we locked the door on the first day to help with food jitters, and Kali was startled by that, but it has been unlocked since." Molly, taken aback, explodes "It was locked on the first day and you never fucking tried it after that!?"

I cry openly and shake my head looking down, knowing I never went close to the door after the first day. Even when people were coming and going, even strangers and delivery men. Sissy Molly leans over to comfort me, whispering something. I man up and make myself push her away, but pull the blanket up higher trying to hide more of my chest.

Molly sees that little interaction and shakes her head with disgust. "Teacher, tell me in your own words- did he ever ask to leave? To try and get Cleanse Company back? If our daughters were okay? If (emphasis) I was okay?" My beautiful daughters Shannon, Kelly, Cindy.

Teacher blinks her clouded eyes, as if weighing her response and trying to be honest and truthful without burning and bridges. Her stare is ominous as she looks me in the eyes steadily for long seconds.

Turning directly toward Molly she consoles "Madam, Molly. I have to honestly report that he never talked about his old life, or asked about how the people in it were doing. And he never asked to stop, or finish sooner. He knew we were tacking on days and weeks, but he never complained, and never asked for a pardon or anything like that. He never wanted to check his email or voicemail or send a text or talk to anyone outside this room. In fact, he seems more content here than I've ever seen him at Cleanse Company before, and I've been here for eight years."

Molly is at a loss, and asks Sally merely "Does he enjoy this life?" "Very much so, Madam, but she prefers Kali now, the name she picked for herself." Now my former wife is openly crying "Will it ever look like a real girl?" "Once she works out the remained of her stay here, another two weeks, she'll look much more feminine. The hormones and rapid weight loss worked wonders, as you can see, but she needs much more training, and possibly some minor plastic surgery for the adam's apple and the cheek structure." Shrugging, Sally continues "She has an excellent chance of living a rewarding life as a childless, adventurous girl."

Molly stares in disbelief. "Why did it play with that-that thing-instead of doing her duty and earning the XP? And why does she have two (emphasis) more weeks of time?" "Madam, I think Kali lost herself in the wine. She made multiple mistakes over time, and our demerit system involves constant extensions to her stay." Molly looks at me one more time, as if asking "And? Your rebuttal?"

I am silent as Molly calmly states "I want her to be the stay-at-home wife of a man he is scared of, one that might beat him but one that can make her have mindblowing orgasms, since that is obviously what she lives for now." She continues, I can't hear, as Teacher and Sally nod in supportive, calming gestures. "Please let her finish out her training, I'll of course pay for any overage in the expenses" (Teacher shakes her head, the Joan made it clean company is paying) "and send her to a man that lives in the country. Keep her there, make her stay with that wife-beating, cheating, big strong man. It's what is best for her, I know."

She looks to me as if she'll say something, some last thing, as Sissy Molly tries to comfort me in an awkward sideways hug. My wife Molly looks for a long second, and leaves. No good-byes, no complaints. Sally and Teacher both follow Molly, ignoring me, and this time the door bangs shut and the deadbolt drives home.


Locked In

In my new house Cleanse Company (the company I used to own) installed large monitors to show live stages as people live their fantasies and become healthy. On at least a dozen occasions, people left their water fasting routines early, just deciding they didn't have the willpower or time to continue. But I kept up with it, even after my wife Molly told me the grim news. I finished out the last two weeks of training with Sissy Molly and followed the surgery recommendations, and went through two more weeks of recovery. The water fasting stopped the day Molly say her goodbyes to me, but that brought in a whole new set of feminization skills- eating properly, setting a table correctly, portion control and etiquette.

Joan was here when I was introduced to the house and my new husband and life. Joan's mean laugh made me shake as she suggested "Kali, this way you will be able to see your legacy and pretend you are still in charge. Pay special attention to how many clients change their fantasies mid-stream or quit early, this is an important point for you. And remember, Kali, we are a service industry, a health spa."

As her expensive limousine drove off into the dusty distance, my new husband Johnny laughed randomly, "Be sure to watch the monitors Kali- maybe you'll get some ideas from your old job how to please me." He dumbly laughs again and smacks my ass hard before leaving for his job. CC wanted me out of the way so they put feelers out with some of the people from my vacation and Johnny (he and Ronda pierced and tattooed me early on) seemed willing to take care of me. So CC relocated us, set up out house, got Johnny a quiet tattoo parlor outside of town; he made friends at the local bars. I'm normally stuck here, Johnny has an override but surgically implanted deep in my chest is a large pain device that has GPS to keep me near. Our neighbors are nice and respectful, and it is the peaceful, if dull, life that I built for myself.

I don't really have a lot of friends, but sometimes the neighbor ladies come over to do a picnic or gossip. Johnny isn't really abusive, just a drunk; he sometimes smacks me around but normally treats me okay. One time I asked him, "I want to stop the fantasy. Can I go back to my old life?" and he laughed so hard beer came out of his nose, and then he slapped me on the cheek "It's too late for that, Kali! We're married" before laughing more and returning his attention to the football game.

I look to the monitor near my kitchen window, and it reads "Case 30021- Mark" "Water Fasting for Health, 1 week goal, sensory deprivation and public speaking encouragement hypnotics" before showing his signup. On the screen, Mark nods and repeats his agreement to the terms "Yes, I want to be held in sensory deprivation for up to two weeks."

Sighing I continue washing dishes, in the full French maid uniform, with stupidly high heels. At least it gives me something to do: cleaning and cooking for Johnny makes me happy, or at least keeps me from being mad and bored. I just wish he'd bring more male friends, my subconscious utters outside my control. Johnny is very jealous and doesn't let me play with anyone but him, even though I know he spends nights with some of his old girlfriends, and I know he has lots of male friends I could meet. At least I have my toys here at the house, and a healthy allowance to buy things on the internet.

Marks' fantasy is going to be fulfilled today, with Joan running the ship as the new head at CC. My life is in shambles: CC is gone, I don't have a penny to my name, and my family left me. My wife Molly thinks I am nothing. I couldn't even be a good enough sissy, let alone a good enough man.

Smiling, Mark sighs the last of the paperwork as a Notary carefully aligns and applies her stamp. "All set, sir. Whenever you are ready." Mark gets up, and two men in white orderly scrubs, like a mental hospital might have, come collect him.

Mark is guided to his stage, a small room with a vacuum bed. Blinking and shaking his head a little, Mark gets fitted with the Hypnosis Mask and earphones. Then, blinded, they lead him to his bed. The black leather is freshly oiled and squeaks as his naked body drops into the custom-molded space. Built to dimensions from a laser scan weeks before, the bed will make him feel weightless- more than any water floating pool or salt water sensory deprivery chamber- and his arms will slowly grow numb, as if they don't exist.

There are no tubes, no wires. Every six hours, Mark will be pulled out of the bed, cleaned and allowed to use the bathroom, and put back into another, identical clean bed. Then the bed he was sweating in will be cleaned. The change-over is done silently, Mark cannot see, and no-one talks or touches him. Instead, they use floggers to drive him from position to position.

Mark paid $5,000 for the opportunity to be locked away from his life, his friends, his job and his goals for a week of unending silence, his fantasy. And he did it: Mark left with an inner peace that most people can't imagine.

That's all I ever wanted, a short fantasy, a week at a health spa, lose some weight, live another few years. Molly and her stupid 5,000 Experience Points- Joan and Sarah, Jen and Sally. Fuck those bitches. I only have eyes for men now. Sometimes I wonder back to my 'gross ugly boy days', and how I could have been so different from what I am now. Wearing an ugly boyish suite and tie, being so pedantic and boring, not seeing men for the pleasure they can provide. And taking responsibility for so much!

No-this is so much better-thinking to myself silently I move my lips tasting my lipstick, and my thumb feels the slippery nail polish on the half-inch nails on the pointer finger of the same hand. My bra feels so natural and my posture so healthy, perched up on reasonable heels with my back straight like a proud girl at finishing school, I would never change anything.

Doubt comes occasionally, like a wave of nausea, shaking through me to the core in my sissy maid outfit, making me second guess the choices and consider what might have been. I grab the last dish and start washing it in the sink. I have a hard time believing I did as good as Mark, he will be able to go back to his family, but Brandon is forever lost. As I dry the plate and align it perfectly on the shelf where it belongs, I smile. Everything is good for Kali. I know Johnny will fuck me tonight and I feel my inner anus shift a little as my body remembers his large member. Brandon is dead, but Kali is excited as Johnny sneaks up behind me to slap my ass before he grabs another beer from the refrigerator.