Author's Note: this is sort of a dark fantasy of mine, while I'm 33, single, only did it with one lady, and am quite straight, the idea of sliding into a simple lifestyle without challenge always held some allure to me


Chapter 1

I'm Brandon and I figured I'd write a few sentences about life with Jessy, my best friend and my girl. She is cute and we met in a local mall, and she gets me more sex than I can handle. Her hair changes colors seemingly weekly, although normally a purple streak or two is involved. Today she is a blonde, some black at the roots, and yes purple above the eyes. Jessy is green eyed, just a hair shorter than me, and about my age (28) though considerably more 'perky'. But on paper all relationships look like sun and rainbows. Even across the way they tend to seem sweeter than what either participant might consider.

Right now we are at a little get-together, about 12 people, most are our age and know Jessy from work (she sells cars, mainly to middle-aged men that can't afford them). Amy asks the dreaded question: "So Brandon, tell me how you guys met!" I am not out of shape, but I calculated my belly would last me a month of starvation and my clothes style is basic. Let's put it like this: my boy wardrobe cost $250 to replace. Anyhow I start into the answer to how Jessy and I met, answering Amy's simple and good natured question, with what married couples always generate: a well-rehearsed play that puts a good light on a happy event. Amy, incidentally, is a black woman about 25 who I kind of know, she likes to flirt and tempt me more than most men, although she has her reasons.

I smile and begin: "We met in a mall, complete strangers. Love at first sight!" I am proud of that. Jessy would normally leave it there too, smiling sheepishly, unless there were a mainly girls in the room, her friends were around, or maybe if she had a couple drinks already. Then, and for my benefit only then, she smiles and says something like 'Oh silly, tell the story right'. Then she looks me deep and straight in the eyes, expectantly like a girl who knows the next time she even lifts her tongue or breathes funny her man is going to orgasm deeply into her throat. She used to have to prod me a hair more, like a kick in the knees, and before this was much harder for me to relate, but practice and time make everything OK for someone my age.

So I relate- "I was walking in the mall near PJ's, a hip women's clothing store. There was a group of nice attractive men (she won't let me say jocks or machos or gangsters) and Jessy and Amber and there was me. The guys were talking boisterously (Jessy scripted my tale but the boys were trying to out-do each other) when Amber got one's attention. It was Tony, right dear?"

At this point Jessy always comes in and sits closer to me. If she at all can, Jessy will try to pinch one of my nipples, poke my rib, even harsh my little man- it depends how much she had to drink, how well I have been behaving, what her cycle is, who is around, I really don't know. But I pretty much need to follow the script to this point. Then she has two simple answers she uses to prompt me forward. One is good, and the other really bad. Unfortunately for me the bad one is closer to real history.

"Come on Brandon, tell it right! You were staring at Tony and...", Jessy repeats with more emphasis and giving a few more details.

This telling happens more often then I'd like to think. "Right dear, I was staring at Tony's crotch a little too much, and he got annoyed. So he said -Hey dude, why don't you stare at her?- and with a hand motion I couldn't help but follow, Tony pointed out Jessy's then smiling face. All girls like getting put into the spotlight by a hunk. Anyhow (Jessy doesn't like me using anyhow and I figure eventually I'll be saying 'and then' gleefully) Tony shoved me towards Jessy while Amber, a couple shop girls from PJ's (high school aged, cute, one had a tattoo on her ankle) and the other four men (Darnel, Shawn, Sue and Frankie) watched excitedly. Not knowing what to do I stood there silently, staring away from Jessy- basically trying to avoid her gaze. Amber giggled and said -Hi, I'm Brandon- loud enough the shop girls and some other customers (older couples mainly, but one 40-year old woman made up well stuck out to me) noticed."

At this point Jessy normally takes the ropes from me. She finishes graciously, even though it is clear I didn't really beast my way into a relationship with anyone. And that is what really happened: I was bullied into meeting Jessy, and she became my second girlfriend and then my wife. That was about five years ago now, and I haven't really met any other girls that way since. She is important to me and I would never leave her, Jessy is my life and I've given my life for her. Jessy does have other men she likes, but I am OK with w2it. We might have kids, she says, but she normally is very careful about her cycle and my penis's various latex sheathes. Jessy: "So I said -Hi Brandon, I'm Jessy. This is Amber and she says you are nice.-. And we smiled at all the boys, and giggled with the shop girls, Amber and myself. Later that afternoon the nice men took us ladies for a big dinner, nicer Italian place, and you were the gentleman and paid for everyone- even those mean boys. And we set our next date up alone at the mall movie theatre and did some shopping after. That's how I met my husband Brandon."

Jessy is almost always very girly at this point in the story, and if you can imagine a western cowboy or rap gangster walking up to a woman, grabbing her by the hands, and pulling her in- Jessy loves to embellish and imply that is what happened, that I won her over like a cave man or a beast, especially when she said "You were staring..." and I know I need to tell the longer, more embarrassing version. But Jessy is nice that way, she always tells me 'a little sugar helps the medicine go down' and I think she is right. Jessy happens to be wearing a modest sun dress today, nothing provocative by large, although I enjoy thinking about her and how she basically does not wear underwear or panty hose. Tennis shoes, to be sure, when we are out except church and maybe the off funeral or wedding.

Amber and Jessy really aren't that much friends any more, and I tend to not like Amber so much because I felt like she kind of forced or tricked me into marriage. She is cute, to be sure, and has had different boyfriends over the years though she is single. In fact, Amber and Jessy's 'boy fights' basically pulled them apart, notwithstanding I have been married to Jessy the last five years.

Now Jessy is not a slut. She is my girl, my love and my life. I could never leave her. But let me explain what can happen when the man is not in charge, because as you saw from our well-practiced response to the small-talk question every newly-wed couple gets, she gets a lot of say. Jessy is my life, true, and beyond that she runs my life and determines my life. She chooses and I get what she decides.

At mixers like this one, Jessy almost seems to want me to stay in the dark. She doesn't normally introduce me to anyone, almost never the men, and I tend to stay quiet and shy. That has just been our way, and Amy is a rare exception. Jessy herself is much more talkative and always seems to know everyone by name, giving hugs and not-so-on-the-cheek kisses freely. So as the party goes on, we got here around 7 PM and I think we'll stay until 1 AM or so, I tend to find a couch or a TV and kind of zombie out. I know Jessy doesn't like it, but she could include me in more conversations if she wanted. Today, here at Al's house, I only know Shawn, Amy and of course Jessy. I grab some sauce and a generous handful of tortilla chips on a paper plate, along with a plastic cup of champagne (I avoid beer and liquor) and found a quiet nook with a good view of everyone. Amy seems to be really happy right now, she is talking to a well-dressed man I don't know and peeking at two other dudes that obviously have the hots for her.


Amy

I'm Brandon and I met Amy through my wife Jessy. Or I could say Jessy made me buy services from Amy. Now Amy is a bit taller than me, muscular and pretty, brunette. She dresses normally with a skirt above the knees, pretty solid color shirts that let her bra lines through, and she tends to have a pony tail- straight back or to the side- except at evening parties when her shoulder length hair is loose behind her.

The day after our honeymoon, which was a normal honey moon by most standards (I paid for a week vacation to the Bahamas and we enjoyed each other while drinking and eating) Jessy had a surprise for me. It was 8 AM on a Saturday, and she smiled and said- her exact words- 'Come meet Amy.' I smiled back and that is all I remember, I think she had put something in my morning coffee.

Later I woke up, obviously in a trunk. Whoever put me there was being cute, there was light, a large green arrow pointing towards the safety release to open the trunk from the inside, and in large marker handwriting the words 'Come meet Amy'. I was tied up and spent the next few hours trying to reach the handle, and then the next hour trying not to piss myself. My morning coffee was part of my routine, and I always hydrate with several large glasses of water first, to help keep regular. Luckily I could hold in my shit. So I started urinating, no steam but I could smell myself, and about half-ways through the car stopped. I couldn't stop mid-stream, and the trunk was open before I was done- a puddle growing around me. My clothes- morning robe, boxers- didn't leave much to the imagination for Amy. As the trunk popped, the sun outside didn't seem bad because the light inside was bright enough. And there, smiling down on me, Amy. "Hi Brandon, I'm Amy and Jessy wanted me to meet you! I know we're just going to have so much fun getting you all ready for married life now that the honeymoon is over. I helped my friends Rebeca and Kelsi with their men, and they're still happily married, so you are in good hands!"

I was a bit taken aback: how did she open the trunk not just after I wet myself, but while I wet myself? And there she was, smiling like she had no sense of smell. She knew me, she knew my wife, and she was obviously free to move wherever- she knew where we were and what time of day it was, she was well dressed and had her cell phone, she was smiling down on me. I uttered in creaks and moans like some cornered puppy- "Hi Amy."

The trunk went back down and the light turned off immediately. I think I passed out from some gas, but maybe I just fell asleep. When I woke up things were different. Very different. I was in a single lady's apartment, and by the look of things a cosmetologist earned her degree on me. Looking in a full body mirror set near the bed I woke on, pink comforter with flowers, I saw a 'girl next door'- my facial hair was gone, my eyes were plucked into perfect arcs and well made up. The effect was very close to an actual woman, nothing like a cross dresser or 'queen'. I had a bra and felt panties, and short shorts (yellow) with an aqua blue top that showed my belly button off. It had a white collar and three buttons, shaped for a flat-chest woman.

I knew the hair was a wig, although it didn't look bad to me at all. An experimental tug and a harder pull proved some kind of good glue was at work. How could Amy do all of this in- well, how long was I passed out? It was bring when I first saw her in the trunk, and the room's two large windows let me see out into what looked like midday sun.

Not tied up and not locked in the room, I started looking around the house. I took for granted my clothes, or boy clothes, weren't going to be in the obviously feminine room. Maybe there was a room with some boy clothes here.

As I walked in the hallway, Amy came over and smiled. "Hi Brandon, Jessy sent me to help you be a good husband! Isn't that so sweet, she wants you to stay with her in love forever?" I responded meekly, "Yes, I love Jessy. We had a great honeymoon." Amy smiled again and gave me a big hug. She really did look nice and my penis was obviously erect ever with the short shorts holding it back. Amy felt it while we hugged, smiled even more, and bent down and blew on it before she put her mouth over it and warmed me up. I stood there speechless for a good ten seconds, and she kept doing it, until I backed up. Smiling, she stood up and said the same again: "Brandon, I want to get you started on a long and happy marriage with Jessy, and she sent you her so I can help you two stay together. I've been able to keep my other friends' marriages, Rebeca and Kelsi's, going strong! Rebeca has been married for 10 years and she is only 30!"

I admittedly had well developed fetishes about being a sissy, and I enjoyed the idea it would help the new relationship between Jessy and myself. A part of me swore coldly that being a sissy- even without Jessy knowing, even though Amy was mentioning her name, would be destructive. But here I was, no work on my part, looking feminine enough to work out any feminine fantasy, and with a more-than-willing helper who really thought we were making the marriage stronger. So, after a year or so of engagement, and a 'normal' honeymoon, my life was immutably changed. The voice in my mind thought of it differently: when I met Jessy, back at the mall, I was already playing the girl's role- I was merely not doing it well enough yet. Those thoughts would go to the background and be forged into my future personality, well outside the sphere of my consciousness, as time went on.

Amy's Place

"So Brandon, I want you to know what is going to happen. You and I will be friends, and I am going to stay up with you for a long time so we get to know each other." I didn't think of it at the time, but sleep deprivation, sensory overload, and massive outward change were all being used to put me in a weak, accepting and fearful mood: I had no phone, no idea where I was, and in lady's clothes chances of convincing a neighbor or cop of my plight seemed weak at best. Amy continued: "I'm Amy. Brandon, introduce yourself to me. I want to hear how you say your name." To which I replied: "Brandon Relelito." I think I said it fairly confidently, but her reaction and all those factors I listed above made me second guess myself before I was done. It might have been Mickey bashfully saying 'I am a Wizard'.

"Brandon, couples need to understand the other side of the picture. So today let's pretend we are girlfriends, the two of us, and have a fun day. That way, a couple years from now when you and Jessy are about to have a fight or if some disaster like a fire happens, you can keep her because you are able to understand her and work with her. It's my marital trick." Amy made some sense, although the trunk abduction seemed over the top to me. I could have walked right then, I'm sure she left the house unlocked and I know now that Amy didn't have any guns or thugs or anything like that. Amy really is a sweat girl, and she was single back then (as she is now).

I've been to her house, the same house, lots of times since that fateful day. Sometimes with Jessy, sometimes with other people and once in a very seldom while just Amy and me like back then. It is actually a couple blocks from home, which is how I think Jessy met Amy, jogging around the neighborhood. Jessy told me years later that Amy knew Sue, one of the men from back at the mall when I 'hit on' Jessy, and that Sue helped Amy get her car into a dyno at his auto shop and let it run on 'road test' mode for hours while they watched and recorded me with a camera in the modified trunk.

The truth is, and I know now what I could have easily guessed or bravely assumed then: Jessy was outside Amy's front door hoping in her heart of hearts I'd come running out. She really and honestly wanted me to 'man up' and 'save' myself from this 'kidnapper', a girl half my size with a great smile trying to be helpful. As the years went by, this scene was relived in many incarnations: everything from me wanting to cheat on my Jessy with Amy to hoping I'd just get to orgasm before leaving, to me being scared to run or interested in becoming a real lady. And I just know if I had 'broke' out of that house, even wearing feminine clothes, and said something Alpha Male to Jessy- "Come on, let's go home" or "I love you, but I am a boy" or even "Baby, let's go play lesbians"... anything. Such is the past, affable to new views and thoughts or options, yet hard set in enduring fact.

I never got to see Jessy that day, but Amy told me something special later on in the afternoon, several hours ahead of what I'll explain next. After hours of assistance Amy had me a bit tired, but I remember exactly what she said and did. It made little sense in my state back then: "Brandon, Brandon. Listen, for the last time. You can go to Jessy now, or you will have to wait. Do you want to?" To which I replied happily, loudly and immediately: "LATER!" Amy then showed me her phone (with the date and time) and forced me to read her the lead story's headline off the local newspaper, along with the date on the top. They matched, I thought, not shit. Then Amy left me alone for a while. Maybe an hour. A few years later I would get to see what happened- she turned on her phone and hit record, put herself in focus and said "Hi Jessy and Brandy! I'm Amy, today is xx and I am letting Jessy know she can go for the day, because Brandy wants her to come back later. The newspaper comes into focus, then Amy's front door opens and Jessy comes in. The recording goes for a half hour as they discuss what happened.


Amy's Place- Why I Told Jessy to Go Home without Me

I left my manhood in that place. Instead of running out an abductor's house into my wife's waiting arms (let alone rescuing her from her crazy friend Amy), I made her wait standing outside hearing me zealously shouting things she should have never known her man could consider possibly true. Maybe I thought Amy's house was isolated, but the large windows give a good view of middle class American suburbia. Maybe I was just too taken by the situation in general. One embarrassing phrase went something like "I wish Jessy would put me in her dresses! Then we could understand each other for sure!"

"Brandon Relelito, I am Amy. Today you are going to get to experience what most men only dream of. You get to be a girl, you get to play with me your girlfriend and you get to play with yourself. Relax, settle down, and enjoy. We can pillow fight, we can eat ice cream- anything you like." Another great smile, and seeing me waiver she leaned in and gave me another big hug and a huge kiss on the cheek. "Come on, what do you say? Want some ice cream? I like chocolate!" Amy purred, sweet as sugar, grabbing my hand to lead me to the kitchen. "Here, sit, and I'll make us some. Do you like chocolate ice cream?" she smiled. I said "It's OK but I love rocky road...", hoping I could bring her to Earth and maybe get out of these girl clothes, or at least get my robe back, without pissing her off. I was thinking a lot about how to avoid pissing Amy off, since I was in her house basically as a hostage, even though she hadn't done anything (excepting kidnap me) to suggest it. She just smiled and turned to the cabinets, then the refrigerator and back. And gently set down two bowels, then grabbed spoons from a drawer and set one to the right of mine and sat herself down with her spoon in hand.

"So tell me about yourself Brandon! This is so exciting!", she said in a girlish tone starting to pick at her ice cream. "It's not too cold because I kept it in the refrigerator since I was expecting you, dig in! So where were you born?" Amy cooed. I couldn't help but respond, even though I was wearing a bra and mascara, like I was the quarter back being hit on by the hottest girl in the cheerleaders. She was interested in me, and giggly and happy around me, we had food and I was comfortable and safe.

We finished the desert and I had given her some potentially dangerous information about myself, like my boss and parent's name, in less than a half hour. Of course Jessy could have told Amy all that, but as Amy later told me, she likes to 'go the extra mile to prove she can do it'. At that point I was just so happy, like being indoctrinated in some kind of social cult, that Amy was always there smiling even if I was annoyed or scowled. After Amy cleaned up she said "OK Brandon, so do you want to watch a cool movie or compare breasts? Or maybe we can do both-". I cut her off, feeling macho after her flirting and general niceness, and said "I want to compare breasts like girls do!" Now Amy didn't respond like some women might, kind of smugly or even to make me feel sorry I said that. She took it the other extreme.

"Me too! I can't say it as the first option because some girls just aren't into it, but men know it is one of the perks of being a girl!" Amy blurted giddily, running over for another big hug and smiling the whole time. I couldn't believe my luck, boys' fantasies like 'threesome with twin girls' or 'be the panties for a hot actress' only come true once in a lifetime. "But how..." I said, feeling like the low energy bummer again. I couldn't seem to pull Amy down and she just smiled and said: "Brandon, we'll go up to the bedroom of course! No-one can see me up there, you'll be safe. But there is an issue..."

She pulled my arm again, leading me back to the feminine bedroom I had woken up in earlier. Smiling and giddy, she said: "Brandon, I can't compare breasts with a man, so can I call you Brandy so it is OK? So that way it is really like we are two girls? It would make me feel a lot safer." I suppose I could have said no and walked out her house right then, a stomach full of ice cream worse for the wear, and Jessy's open arms would have been there. But I said, louder than I needed to thinking back since Jessy was right there out the bedroom window, standing outside hopefully waiting: "Amy, I'm Brandy and let's compare breasts!"

Her smile was to die for, thinking back she probably was imagining Jessy's reaction. We got to her bedroom and she threw on a chick flick anyhow. "I wanted to do both!" Amy said indignantly. This was the first statement I heard from her all day at a normal level of cheery, everything so far had been so super-energetic, girly and fun. And that fun, happy, high energy Amy would be there far into the evening.

So we did. I didn't have breasts, obviously, but all my hair was gone and basically I played with Amy while she humored me. For hours. The whole chick flick, a couple glasses of wine, and another bowel of ice cream (I tried her chocolate this time). While she didn't actually make me orgasm or take out my penis, there was a lot of 'brushing' and she was an expert with my nipples. I'd get bored and watch the movie, and she would be there working my nipples with her teeth and tongue- a little pinch at a climax in the movie, and a soft caress during the sadder parts. It was like a light show to music, but over the whole movie.

"We can really enjoy the movie too, Brandy. Since you are trying out the girls' side you can cry or scream, you can get into the movie if you want to. I really like this one."

The movie was like most chick flicks, patently dumb. Boy meets girl, girl meets other evil boy, original boy gets girl back, shotgun wedding with questionable father in law, yacht for the honey moon (boy is actually rich). Somewhere between when the girl met the evil boy and the original body got back, admittedly a pretty heady spot for a guy wearing girl's clothes, made up, being encouraged by Amy and trying to get into his feminine side, out of the blue Amy leans back off my chest (she was still 'comparing') and smiles, asking straight-forwardly: "Brandy, I am having fun, but maybe you should go before the movie quits." I said no, of course.

She asked a couple more times, and finally she said: "Brandon, Brandon. Listen, for the last time. You can go to Jessy now, or you will have to wait. Do you want to?" And so I yelled "LATER!" She looked at me for a second like she was shocked or sad, almost like I wrecked the night by yelling (now I know this as her main victory of the night). "OK, Brandy, but I have to go freshen up for a second- enjoy the movie, there is another half hour left I think." Amy said, a little more serious but it seemed like I didn't wreck anything after all.

So I watched the movie, cried and laughed, and Amy and Jessy hashed out the details. I was staying, and Jessy would get me out of work for one more week of 'celebration'. Amy was going to have me for a while longer.


Evening

Amy came back after a little longer than I expected, but before the movie was done. She paused it and asked gingerly, "Sorry about before Brandy, but can you tell me what happened in the movie? Did [such-and-such] really [whatever]? I was so excited!" So I filled her in and we giggled about a joke I remembered. Amy looked at my still exposed chest, and grabbed my hand and made me play with her feminine breasts for a while, maybe ten minutes, after we finished talking. By the time we hit play and finished the move it was pretty dark outside. "Sleepover!" Amy yelled in that feminine, fake loud way. Jessy of course was long gone and I was about to enter the less voluntary portion of the visit, which would end up going into late into next Sunday night- today was a Saturday- so that I would get about 9 days with Amy all to myself. While she promised to stay up with me, and I certainly didn't sleep much that week, from Amy's happy attitude I can only assume she got here solid 8 every night I was her guest.

I opted to sleep over, concerned about my makeup and sleeping arrangements and not really considering if I should stay or not. The wine, the movie, the fun with Amy- it was too much, I really had no chance of leaving on my own free will. Or so I tell myself today, every time Jessy gives me a command, instills a punishment/lesson or takes away something I love.

"OK so go take a shower Brandy, and then I'll take one. You can borrow my robe, and don't worry about makeup- it's just us girls!" Amy said happily. "Here, use my shampoo, it is really nice!"

We got cleaned up and Amy put on a sexy nighty. She had me wear clothes than were much less erotic yet more comfortable- soft pajamas with cute teddy bears on them. Amy had to help me with my new hair to get it nice again. "OK, I only have the one bed so we will share. It is just us girls!" Amy said cheerfully. We watched a bit of TV before going up, and Amy made some hot chocolate we both loved. In her bed, Amy put on some calming music and sort of spooned me, explaining girls like touching.

I fell asleep happy as a clam. I think it was only a half hour later I was rudely awoken, but I have no way to really know. The 'choice' part of my week was done.

Amy was standing over me, smiling. She said sweetly, "Brandy, for the rest of the week you should call me Mistress, and your name will be Sissy Brandie." (she spoke the ending with an exaggerated flourish). Brandie seemed a bit more submissive and girly than Brandy, and later it would slide to Brendie- which seemed even a bit more girly. I sometimes remember my old name Brandon but mainly because Brendie sounds similar to it, none of the girls call me Brandon any more.

The situation back then was a lot: I was no longer in a comfortable robe next to Amy, a hot girl my wife asked me to work with for the improvement of our marriage, who had just played 'compare breasts' with me and was spooning me as I drifted off to sleep. Amy explained my situation rather simply: "Sissy, tonight you get to suck and your ass will be plugged. You do not get to talk, move, see or hear, although I have some programs you will get to enjoy later on if you fall asleep." Amy's attire was not an outright leather dominatrix, but it also was not comfortable sleeping clothes or robes. She had pulled her hair back and wore comfortable working clothes, closer to someone getting ready to paint a room or mow the lawn.

As it happened she was letting me know the key to the evening: falling asleep was optional and did reap dark rewards. Every time I quit sucking on her dildo, that is just let it sit strapped in my mouth, a super-quiet warning sound would sing. Then, a second, slightly louder sound. We are talking just above whisper. There was one more warning, and then if I still hadn't given the cock in my mouth some action, the programs. Oh, the programs. They were varied and obnoxious, obviously mind-altering hypnosis material, starting at a normal TV volume but slowly stepping up as I accidentally fell asleep letting my cock (the one in my mouth that I was taking care of) idle for too long. I think 'too long' was being randomized, but at least the warning tones were consistent, so I could rest my mouth if I stayed awake.

The first program really set the mood for the rest. It was a quiet, even hard-to-hear, twenty-minute show where cute girls told the camera man "Yes, for $300 I'll be happy, nice and respond to whoever talks to me. And if they ask, I'll fuck them. I'll do it for the next hour on this mall bench, or quit if I get offered to fuck, either way." It was the literal mind-fuck of a boy 'scared to talk to girls'. The show went on to display highlights over the hour (no-one fucked the girl, she was 23 at the oldest, dressed fairly provocatively and super smiley and happy to everyone male near her age). Maybe 5 boys looked at her, one said some compliment ("I like your shoes) and smiled before leaving, but no-one got her name. At the end the camera man asked "What happened?" and the last words of the program were her unsurprised but sad response: "Men are fags." I was interested and awake enough to hear this whole program through, and as the night went each successive program's volume increased, keeping me up.

Later in the night, my mouth sore and drying out, I saw Amy. She smiled and asked "Sissy, is your mouth dry? Would something wet help?" I nodded vigorously, and she smiled again even sweeter. There was no malice in her face, even though I could see a lesser Mistress relishing a boy's first taste of semen.

"OK Sissy, from now on, if you want to get some liquid to help keep your mouth comfortable, you can use your hand like this to push button 1. Don't worry, it didn't work before, I just turned it on." Amy said confidently and helpfully while almost completing a gesture using her two hands to move my one. Clearly there was a console next to me, and it had a row of numbered tactile buttons with raised dots. Button 1 was what she was indicating. I nodded a bit, confused why she didn't just take out the cock so I could get some water right now.

"But be careful Sissy, that stuff is addictive and while healthy you will grow to need it if you taste too much." Amy said, again without any ill intent, before leaving. I hadn't tried her 'liquid' while she was in the room, and I didn't for another two or three 'programs'. I lost count even though I was rested from yesterday that very first night.

Most of the programs for the first night hammered in what I knew with Hollywood-quality video and effects: shy men are fags, most men are shy and ergo most men are fags. Programs included similar themes but different people, and were very repeatable (probably cherry picked, but the tired mind does little to filter for ethics). Men shown seeing a girl, maybe starting her lunch alone in a food court, then brought to the 'private room' and asked: "Did you see [such-and-such girl]? She's hot, right!?" "Did you know she is an obscure model?" And after the macho fun with the camera man, the challenge- the men always punked out- "Well, I know she is here in town this week in [local hotel]. And she is modeling alone here. I'll give you $200 if you get her name, and $400 if you get her hotel room number. No strings." Invariably the men accept, some even say "Forget the money! She is mine!" The men are hot too- muscular, jocks, young and well dressed. Real catches. And of course they act like I would: uncomfortable stare, maybe an awkward squeaky 'Hi' and they run. The end of this style of program was always the girl: "Yes, hunk number one caught my eye before you guys grabbed him. I noticed him as he noticed me. Too bad he didn't come meet me, I don't know anyone in [this town]."

Another disturbing part of the programs came just before dawn. They ended in sort of porn, up till now it had been entirely clothed and no sexual nothing. The last couple had the girl do sexy strip teases before the scene, like her ordering a coffee at Starbucks, and at the end of the program after the girl complained about 'shy guys' the camera man cut in. "We all know these guys wanted to win some money, so I took their cell numbers for a 'second prize' later. Well, Bob here accepted our runner-up prize. So, Bob, come do a strip dance and we'll show you [girl's name] doing her strip tease. $100 if you get nude, $105 if you cum." The directors knew almost no-one could resist cumming to their well-done strip teases, especially in their nice private room with a huge screen and a view of a girl they thought they could never have because of their own actions, and for money. For 4 programs they spent $415 in prize money.

I think it was 9 AM when a cheery, well-rested and dressed-for-the-day Amy walked in: "Hey Sissy! Do you like semen baby?"


Morning Routine

Amy undid my, Brandon's, ropes and the didlo gag, collecting various liquids on a white towel like a professional. Smiling down, she said "Sissy Brendie, I like Brendie better than Brenda when we are here at home. You'll be my little slave sissy Brendie, won't you?" And I nodded slightly. Her cheeriness would make any kind of inaction seem like shitting on the star atop a Christmas tree in town square, through the various assistances of a cherry picker man lift and pajamas having a flap to expose one's backside.

"Sissy Brendie, let's get you made up!" she said indicating the shower. I took a nice shower and Amy put lotion everywhere. She did my hair nice with conditioner, and then put me in another robe, more 'morning' oriented. Breakfast was ready miraculously once I got downstairs (I think Jessy was around and had made it), and we both enjoyed, even though I was in a robe and Amy was in everyday town clothes.

After she pampered me in the bathroom vanity, doing my makeup and such, and got me dressed like her. She forced me into a bra with padding, similar to B cups, and the clothes were modest but feminine and comfortable.

"I want" came out of my mouth at some point between the pampering and the final dress touch-ups, an obvious mistake. Amy looked at me seriously for the first time in two days, and her eyes scared me. "Sissy Brendie, yesterday you said you didn't want to go see Jessy. Is there something you want more than Jessy baby?" she asked seriously and with a sort of evil poison I think most men only see in their divorced wives just before the alimony payment amount is established, or perhaps right before their salaries are garnished for the amount due.

With Amy and Jessy working together, as she made it painfully clear to my sleep-deprived mind, my life could become difficult. No prenuptial agreement, obviously. She had put a good share of 'our' funds into a decidedly 'her' bank. My family is traditional, and Jessy assured me she had some less than flattering videos of me watching a chick flick in girly clothes, crying and running mascara. There is always a way out, but after 10 years I've never had the strength to find, risk, dare, whatever- never. She has no job and as the breadwinner I would be paying, no questions. We don't have kids yet, but, our state tends to award 100% custody with visitation to the mothers in almost every case. That will be another leverage point in the future, I am sure, and Jessy is always talking about kids- although not my sperm. In any event, back ten years ago at that first week at Amy's, and right now, Jessy (and by extension Amy) have enough dirt on me to make my compliance a forgone conclusion. I don't even consider defiance any more. Back then in that first week, I considered it, but never acted.

So it went for the rest of my 'second honeymoon.' Amy and I 'woke' up around 8 AM, she was ready to go and I was knocking off the pains of the last of my 'programs'. I kept getting more and more tired, more and more willing and fearful, I had willingly pushed myself into Stockholm Syndrome and started thinking for Amy, justifying her actions, feeling bad for her, even explaining to others. I remember one day we were at the clothes shop (PJ's again, Amy liked bringing me in front of the shop girls there, a couple of whom had seen me meet Jessy) and playing. She did something a little out there, spanking me in the view of one of the shop girls. "It's OK, I misbehaved and let Mistress down in public" I explained helpfully to the shop girl as she watched somewhat amazed, somewhat surprised. Smiling, Amy said "Wait here Sissy Brendie for a moment" and went to the back with the shop girl to "find a different size" even though we hadn't picked anything.

Amy really was the socially key player in my life that week. Sleep deprived like a crazy person, it was all I could do to remain femininely silent and not put my feet in my mouth with dumbness from my little head- when I did try to speak, it was dyslexic and stupid. I said things like "Is yours shoes from here?" or "Hi Brendie Sissy I am" to people whose names I didn't know, and Amy stepped in and made it all right. And it worked the other way too: Amy had a knack for introducing me to people. "Brenda, this is my good friend Elizabeth, and Elizabeth, this is my new friend Brenda." "Brenda, nice to meet you, but any friend of Amy's can call me Liz- I like the shorter name better." "Hi Liz, nice to you meet."

Really the core of it was I was lost without Amy to help. I would stay in bed, scared, unsure what to do (a more logical outlook would be I was locked in bed watching my programs, but that is not how it felt) until Amy let me go tinkle and poos. Then Amy helped me clean, got my lotion for my skin, helped me do makeup. I was learning, for sure, but her motherly hand was all the difference for me. Without, I would be unable to get by even making myself up for normal circumstances, let alone if we had something special to go to.

Hump Day

Up till Wednesday, Amy had just been making me (Brandon or Brenda or Sissy Brandie) comfortable and safe as a woman. I had to suck a dildo at night, and I hadn't slept since last Friday, but she encouraged me to become an emotional nutcase, and she helped me live through the experience. If I wanted to be mad, she would let me, get the rise out of me, and bring me back to girly giddy. If I was sad, she let me indulge, even added to it and picked normal things to make sad ("Look at that poor kid in the park, I just know he doesn't know that Fido there only has a couple months left. Let's go ask his mom how she told him." "Let's watch Titanic. I think you are in the mood." "I wonder what happens when homeless people die."). Amy was always full of ideas to keep me at extremes of emotions, but she seemed to know when and how to bring me back to normal- giddishly happy, ready to accept and generally silly- and she kept me there most of the time.

Until Wednesday, there were no other men or women other than Amy, and I could cum at will. She didn't really encourage it, but she would give me blow jobs when I was really horny, and she would always let me play with her no matter what- "Come on, you're a girl now, we both belong in the lady's bathroom!" Wednesday after the normal morning routine, Amy had a new surprise for me. "Sissy Brendie, come quick, we have a guest!" Amy said cheerfully. I was just out of the shower and gleefully threw on my robe, running downstairs. It was Sue!

Sue, from back when I met Jessy, was there smiling at Amy. He was a larger black man, baseball cap, orange T-Shirt and boxers showing over his low pants. Amy was talking happily with Sue once I got there, and she smiled and said "Hi Brendie, this is Sue. You might remember him from when you met Jessy. Sue, this is Brendie." After a slight pause, Amy continued, "Amy, what do you say?" "Hi Sue, nice to meet you."

I was already looking at his crotch before I sat down, and even though Amy hadn't helped me with makeup, Sue apparently was interested in me. Amy must have let him know about me before. She always had so much control over situations, and I was just the pawn in whatever we did. But there I was, so I tried again: "So... Sue, good morning, what are you up to today?" I asked casually with a feminine voice. I don't know if Sue was a faggot, but I certainly acted very homosexually that morning. And I am not sure how much Amy and Sue pulled me into it, or how much I participated willingly. I think it was my choice to sit next to Sue and sort of ignore the breakfast Amy always had ready without fail, which she kind of made a face at me for. I know I reached over and touched his cock, because of the myth: "Once you go black, you'll never go back." Everyone knows what a magnum condom is for.

Maybe Amy suggested I try kneeling, or maybe Sue stood up. Anyhow, there I was, in front of my first cock. Sue said helpfully "You don't need to do anything you don't want, and no-one will ever know what you did or didn't do" in a decidedly safe, white tone. Amy actually got on her knees next to me and caressed me, petting my hair, patiently touching my nipples and face, smiling and giddy. "Oh, I'm so excited, Brendie! No one ever gets to see Sue up close, he is a very selective- and very rare- man!"

Of course I realize now that they had cameras for the next hour of me sucking Sue's large dick. He was really well hung, really gentle and supportive, and he had no problems being nice and calm even as I got him close. He came when he wanted, Amy said "Men get to choose who and when," and I think he came in my mouth three times. With all the nighttime training, I was somewhat used to the idea and it wasn't bad, rather, it was interesting and helped bridge gaps that had formed in my mind with all the programs (including masturbating men who took the runners' up challenge) and just the mouth and tongue stimulation that became second nature to me (due to the punishment for not constantly pleasing the cock gag at night). Watching the video a few years later, it seemed like I was a whore that needed cock, a far cry from a boy who was unsure of his sexuality. Without makeup, it was obvious who I was, and that I was no natural-born girl.

"Thank you Sue, this was fun! You should come back again for me!" I said happily at the end. That phrase took about ten tries before Amy was happy with it, we practiced in the bathroom in front of the mirror alternating. She said it, then I said it, and we critiqued each other. When I finally said it to Sue, I was so worked up, I said "Thank Sue, come again." like a creaky mouse. Amy just laughed giddily, and Sue pretended he didn't hear. My third try was the charm, Sue and Amy encouraging me, I said it just right. "I sure will, a cute girl you Brendie can get my cock whenever you want. Just call me, I am happy to come over here or to Jessy's house." he said helpfully. "Jessy..." I muttered, but Amy cut me off. "Brendie, of course Jessy understands girls need cock once in a while! So don't worry, we'll just let her know that for your marriage to last, you need to be feminine a bit, and to do that you need to know some men that come help you once in a while. Everyone does it, so she'll understand for sure."

Around 3PM Jessy had another surprise for me, a double-blind date. She told me "Blind dates are the most fun when they are surprises, no-one wants to sit and think of what might happen meeting a stranger but once he actually meets you interesting things can happen." It was a dinner date, followed by an optional movie. John and Adam met us at a diner, and we chatted happily. I was so groggy that I wasn't making much sense, and Adam seemed to like that, while Amy seemed pretty on top of things. So after we ate (I had a vegetarian salad and skipped most of the dressing) Adam grabbed my hand. "Want to see [movie that releases in a week] on the internet?" "Of course!" So we decided Amy's would be the best place, she had the big TV and internet. John liked Amy, and she hugged him and whispered things in his ear. Adam and I had fun touching his cock and my 'breasts', and we kissed some. Kissing a man seemed strange, but I was so tired that he made it seem like the normal thing to do.

Wednesday was hump day for me. Adam fucked my virgin ass for the first time, as John and Amy made love loudly next door. I was tired, but sober.


Pain

The out days of my (Brandon's) week with Amy were different. Instead of the soft hypnotics, she met to introduce me to pain and how it can add flavor and spice to my existing emotions. Whenever she would set me on a rollercoaster of emotion, there was pain involved. It leveraged reality (my body) and imagination (my mind) into constructs that I have tried to reach since, like a drug addict desperately upping the dosage and never getting close to those first highs. If I had any selfish reason to be a sissy, Sissy Brendie, it would be to regain the experiences of those last four days of my second honeymoon.

I think Jessy can give me what Amy gave me. Jessy seems even better at it, and she knows me of course much better since we have been married for ten years.

Unfortunately, Amy had her shot at me when I was a virgin, so to speak, and I can't unlearn what I know now. Before a light slap of a whip was my limit, now my limit would be blood and damage. Before, twenty seconds with no ability to breath was invigorating to me, now I almost pass out before I am impressed. Jessy and Amy can still give me a sub-space experience, but nothing like those days.

Before I move on, I should explain about the 'programs' and the dildo Amy had me suck, keeping me awake at night. The dildo had three warning tones if I fell asleep and it would then start a program, each with increasing volume, if I failed to start working it with my tongue. The amount of sucking required kept getting increased, and the tones got quieter. Also I hadn't slept well for about a week, and Amy added some more fun to my situation. I could still use Button 1 for a liquid (obviously cum, it tasted just like Sue's had).

Button 2 (with two raised dots so I could feel it) gave me an interesting compromise. The dildo in my ass, which too had been up-sized over the days, would send some 'cum' into me. This had the benefit of giving me a 'reprieve': for a half hour, I got a nice, relaxing program, like a springtime prairie or a rushing brook, at a very quiet, relaxing volume. I could also stop worrying about sucking the cock in my mouth, and rest if I wanted to. Button 2 had a couple less fortunate side effects. It would add a bit of size to my anal dildo, maybe an air pump, and each press released about twice as much 'cum' into me. "Be careful, Sissy Brendie, if you are too ass-greedy you might explode!" Amy had warned me. "Since it doubles each time, after only about 10 presses it will squish your whole body weight up there! So be careful, for my sake, please darling."

The programs were changing considerably as well. Some included me in my worst light, like when I met Jessy (they video-taped the black man pushing me towards Jessy) and certain moments in our (Jessy's and mine) honeymoon when it was starkly obvious Jessy was leading me on, and I was acting like a lumbering idiot or just fat and old ("Come on Brandon, I need you! Come fuck me!").

There were also many more gay porn scenes, and the occasional 'sissy hypno' where I was bombarded with random images and a binaural tone, and a girl telling me to suck cock or some such. While there were exciting girls in the pictures, almost all turned out to be transvestites- and the program often explained "Your goal" or "You want to be her."

Throughout I was allowed to cum as I wanted, and I did. I came a lot to these programs, half-asleep, letting them down into my subconscious and consenting fully with my mind and body by experiencing them in the throes of orgasm. Amy had started putting my cock into a fleshlight or similar, locking it down so I couldn't get 'mad' and throw it away for the evening. I would cum, then swear stroking off- only to cum again in less than an hour. This total lack of self-control would become a cornerstone of my inner guilt, my ability to blindly follow someone- anyone- else, my doubt in my own resolve or bravery.

The nights were shifting from pain to pleasure, and the dick in my mouth from a pain (Monday) to annoyance (Wednesday) to pleasure (Friday). The cock was like a toddler's thumb or his favorite blanket- it helped me through, like a shot for a drunkard or a smoke for someone addicted. I found myself looking forward to the cock, and the sleep that came from Button 2.

Also the days were getting more difficult. We still did our morning routine, but then Amy had me work around the house until about 3 PM, doing menial and routine housekeeping tasks that were pointless. Of course, to teach me obedience and patience, but they were so silly. Amy would measure a bag of beans, half a pound or 7.78 ounces, out on the floor. Then I'd have to pick them up, get them in the bag, and report back to her the exact weight. At first Amy did this the straight forward way: "Here Brendie, use this dust scoop to help out!"

Of course, things got progressively harder. She got less careful about dumping the bag out, and quicker to punish inaction on my part. Before, I could wear my normal 'girl next door clothes'. Now, it had to be a maid's outfit, and shoes to match. The shoes were a definite challenge, luckily I was on hands and knees for most of the beans.

There was cleaning, folding, cooking. We made full meals and threw them out, then made more. We made a Thanksgiving-style meal, and didn't eat it. She was helping me do the most basic of things. We took the trash out together. So much focus and attention from Amy onto me. It is really amazing.

Of course, Amy was doing more than coach me. She was helping me to accept, to submit, to become what I needed to be. She was helping me to get used to pain, and in that way I would be able to understand the feminine experience, and from that I could really love Jessy, and we could stay together forever. Because I have no other women like Jessy I would ever like, and no other women like me like Jessy, and anyhow if we got divorced I'd be destitute- broke, on welfare, probably drinking during the day- I need Jessy more than she can and could ever want me, I will do anything for Jessy. She is my love.

So that is how I made it through the days. Jessy was in my mind, but I was growing stronger due to Amy's ministrations. Her carefully calculated balances, her gentle prods made me the man I am today. Amy spent those days watching me continuously, even in the bathroom, and making comments. She would generally start any particular failing of mine with a suggestion, something that only made sense: "Dear, good girls fold their skirts up when they sit, it is the proper thing to do." Then she would move into a commanding tone, and finally start punishing failures. Punishments were normally dished out on the spot as a slap from a riding crop, and generally her sadness at my failings and happiness at my success.

Now I know it is hard to understand what when I say putting beans into a bag was my turning point. Amy would give me specifics- "OK Brendie, this time, one bean at a time, and give each one a kiss before you put it into the bag, which will sit up on the counter."- and then make sure I followed them exactly. I had to be happy ("Sissy girls are always happy, like me!") and keep good posture ("Stick up your butt, baby, it's your only real asset!"). Amy seemed to have a vast repository of rules and laws that somehow rhymed or sounded sing-song, as if she had poured through books from the 1950's for homemakers.

At the slightest hesitation, I got a slap and a reminder. She tended to do this in a 'long form' with me. I remember picking up a bean, and putting it in my mouth ("This time, hold 6 beans in your mouth, then bring them to the bag Sissy Brendie!" she had said smiling with glee, "It will go so fast!"). It was bean number 6, but Amy yelled: "Hey!" and slapped me with the whip. I looked at her unsure, with my mouth somewhat imposed by the six beans. "Sissy Brendie, you know sissies should look at what they are doing! Did you look at the bean as you brought it to your mouth?" Amy cooed. "No", I said shifting the beans to my cheeks. "What do you say?" "Sissies should focus on what they are doing. If I am sucking a man's cock, I should look him in the eyes. If I am dusting a shelf, I should stare at it. If I am serving coffee, I should focus on the cups. Sissies do not need to know what is around them, I just need to focus on doing what I am working on right." "Good!" Amy replied. The last two times I had forgotten the reasoning, and that went much worse.

"What do you say?" "Sissies should look at what they are doing." Slap. Slap. Slap.

"Sorry Brendie, I have to give you another black star on your board. I couldn't believe it. Amy continued: "You know the right answer: Sissies should FOCUS on what they are doing."

Amy's system of stars would come into play in the evening, after supper. Basically Amy counted up all my stars at the end of the day, and gave me a menu. Sort of like a desert menu, she said: "OK Brendie, this is so fun, you get to pick how to spend all of your black stars! This is so much fun, I get to make a menu for you each day, and you get to pick!"

Amy's menus, for those last days, Thursday-Sunday evening, were varied and imaginative, and their content depended on how many stars I had, although I normally got about 50 black stars to spend in the three or four evening hours before I went to 'bed'. I was more sleep deprived than ever, and normally I didn't even read the whole menu, let alone consider it, but just told Amy what she suggested I say: "This Sissy would like the Chef's pleasure, please, Mistress Amy."

I am not sure if Amy was trying to give me a certain number or stars or make the punishments a certain way, but, I know I am doing this for Jessy. Amy is helping me to understand what being feminine is, and that will let me keep trying to stay with Jessy. Jessy could even stay with me until I retire, or until we have kids. I am so happy she helped me out that week. She gave me the key to a happy marriage with Jessy, even though I wasn't quite sure back then.


À la Carte

Those few evenings were hard for me (Sissy Brendie) and Amy. She would normally spend some time spooning me after, before she had me get into the familiar 'program' bed. I wasn't sleeping, but I was taking as much 'relaxation' (Button 2) as I could, and that was helping. And the lack of sleep was really helping me to accept what Amy had to teach me, the knowledge she imparted to me.

The menus (lists of punishments I could pick to work off the stars from total failures I earned through the day, doing menial tasks like picking up beans, cleaning toilets, nutting and un-nutting bolts- "We girls call it nutting, to spin the nut all the way up to the top of the bolt" -and sorting colored sand grains like Buddhists) ranged from simple to vague, complex to devious. Most of the names were ominous enough to turn Sissies like me on, to spark the imagination and let me masturbate on the thought. They were like the Saw movie franchise, questions of what will hurt most and they always involved pain and correction.

The most basic were to 'Take X whips from Mistress's riding crop, thanking her and counting' which Amy liked because she would dock whips for miscounts and she played little tricks, like distracting conversation, to break my focus. Maybe she lied on some of the counts, but as the Sissy I generally accepted she was right no matter what. I know I was wrong more than a couple of times.

Amy enjoyed 'Pain Fellatio", where I had wires attached to sensitive areas and she had a control knob. She would tell me where to focus on her body, and adjust the knob depending on how I did. She also liked whipping me if I did wrong during those sessions.

Amy was also fond of self-inflicted torments, where I would have to do something to myself or maintain calm and pain: a thirty pound weight arranged just so that I could set it down and stand tippy-toe, and still feel a good stretch in my balls from a noose and rope, or hold it up (away from my chest- I had no leverage) and feel the tension in my arms. Or a sort of 'the splits' exercise that challenged me to keep my feet together, yet on the rollers it was easy for them to slide away from my center line, lowering my torso and stretching my inner thighs to the burning point. She liked encouraging me the 'right' way to do these, yet passively suggested the 'pain' way, giving in to the weights, may be the best in the end.

I personally more liked the 'gym exercise machine' challenges. Maybe because while I've always had a belly, I've always aspired. And I think it is sexy to see girls exercising, so maybe I can be sexy too. Amy would be my 'personal trainer' and help me out. Some of these we actually took to the local gym, where I got some stares to be sure as my sweat made my clothes obvious. She liked to run the controls, and have me just try to keep up. Once I grabbed the handles of a treadmill to try to keep up, and she slapped me on the spot. Over time, I would get lots of exercise on cardio machines and in step aerobics classes, normally with my 'programs' running in the background or at least in my earphones.

We had a setup with the typical bench press stack weight machine, where I would do bench presses for my chest, but added an extension that reached from the handles (which move up and down with the weight) straight out horizontally towards my toes. This has a bit of spring to it, and we would make it work different ways- too low with the weight crushes my balls, or too high (like locking out my shoulders) pulls my nipples, or with a pulley too low lets a safe but ominous weight compress my neck. Amy always knew what was safe, and I trusted her, but it is a strange and scary feeling, at the bottom of a bench press, to not be able to get a full breath- I had to push up first to breathe normally.

Maybe my favorite was a personal favorite exercise from the beginning, and while Amy had her doubts, I think it is fine for a lady to do to improve calves and leg muscles. Front squats. She had some minor interventions to help me out, but they make an excellent punishment routine and almost always have me shaking in agony before she lets me go. The power rack is rigged oddly, so that if I let go of the bar bell, or if I let the bar bell touch the safety stops (which keep you from dropping the bar on the floor or hurting yourself), I get a shock. She also sets a 'weight goal' so I have to stay there squatting until I 'lift' say 500 pounds, or do 10 good 50-pound squats. Amy counts, and sometimes she subtracts for a half-done squat that is not deep enough to the ground.

Amy offered me some more 'efficient' punishments too, which would eat up two or three stars quickly. Things silently accepting so many whip lashes, with doubling counts or forfeits on noise, holding heavy weights for long times and getting whipped for failing, and taking memorization tests that made no sense while being forced to lay in an ice water bath until I passed. Amy seemed to have everything planned, for example the tests would have insane details ("Jessy's favorite nail polish color for fall is Army Brat, but for summer it is Maya Blue") interweaved with simple logic ("Are you smarter than Amy?", "Is it better for you to be happy or Jessy to be happy?").

We also had an "isolation chamber" punishment I liked, it was about the size of a dog kennel box and I would bend down and get into it. She had six inches of water in the bottom, no way to rest, and she would slightly cool the water to room temperature or so while keeping the sides hot enough to sting and almost burn. Since the chamber was so small, I was constantly hitting the sides and (slightly) burning myself, then trying to get the slightly cool water onto my burns. She also added a steam spurt once in a while and had the chamber set up on a sort of roller system, so it would turn or move easily if I shifted my body weight or she pushed. The last piece was 'relaxing' music that ironically was really relaxing ("Brendie, baby, you'll love this- it came from an orchestra, it always puts me to sleep!" Amy had smiled) causing me to doze off while trying to avoid touching the walls and getting brunt. One time she spun the chamber like a merry-go-round and I did actually get a minor first degree burn.


Jessy and Sleep

After Sunday evening was about done, Amy took me (I'm sissy Brendie, she took me in my 'normal' girls clothes, modest but decidedly feminine) to my new wife Jessy. I had been told what to do and say: "Jessy, I am so happy you are my wife, and I will do anything to keep you. Please let Sissy Brendie stand with you, I love you more than anything." Amy and Jessy just smiled, and Amy gave me a big hug. Jessy raised an eyebrow when she saw me, and seemed unsurprised I was dressed feminine: I thought she kind of enjoyed it. She seemed to be supportive and nurturing, she didn't say this out loud but her body language conveyed it: "Baby, it's OK if you want to be a girl around me. I can take care of us."

"Well, I'm sure you are tired, and tomorrow you need to get to work bright and early Sissy- you've been on vacation for two whole weeks now!" Amy said helpfully, leaving me at Jessy's front door. The two girls made a gesture while parting, but I was too absorbed in myself to really understand what happened. Happy to see my wife, and scared what she thought of me as a Sissy, I was awash.

"Come on in, I know you are tired so I just have one small favor for you before you go to your bed Brendie." Jessy said, leading me in and closing the door to my own house. Our house is laid out with an entryway leading into an open living room, and Jessy timed it so that we entered the living room, which I basically backed into while concentrating solely and only on her, she said the word "Sue." I was taken aback that she would mention Sue's name. She paused ever so briefly, while I stared at her, and then continued: "here (I noticed Sue sitting in my living room from the corner of my eye at this exact moment, silencing me with fear) says you like him, and that you want him to come over and help us out once in a while. He said you wanted to suck his penis until it is hard enough to fuck me, and then you wanted to go to bed and let Sue do whatever he wants with me. Is that right Brendie?" Jessy asked, very impartially as if I could say no at any time. I indicated yes with a tentative nod and slight smile.

At that moment, I could have turned around, I could have balked or complained, could have just walked out. I could have turned and yelled at Sue, called him out as a homosexual, or even made him leave my house. I could have made Jessy suck him off, I could have gotten proactive and openly grabbed Sue or Jessy... I could have done anything. But somehow I knew what felt right.

Amy had to have hinted to me what to do in this situation too, she seemed to know the future long before I could comprehend the present. From deep in my sleep-deprived mind, the obvious right thing to do just came out of me: "Jessy, I love to dress and act like a girl, and Sue has the best cock ever! Sue let me touch it and it is so big! I want you to get to experience his cock, but first I want just a little lick before I go to bed." As is Jessy and I were going to a young teen's high school sleepover for movies and pillow fights, I was excited and happy for both of us. Then, smiling giddily, I walked toward Sue. It was surreal to know I was doing this. Doing it was making it seem all the more natural, and my doubts were fading with every step I took as I smiled and looked towards Sue's crotch and then his eyes.

"Sue, is it OK if I take you up on your offer to come back any time?" I asked earnestly. I could blame being tired, which I was because I hardly felt the weight of what I just said. Jessy kept a poker face, but in hindsight I know she had to be struggling to keep from laughing or crying. I vacillate between those two options, the sober and logical face she showed me that evening wasn't a possibility in any kind of reality. I had basically admitted I'd had gay sex and wanted more and then for my gay partner to fuck my wife, while I go to sleep.

Sue smiled calmly, very business-like in demeanor. He did nothing like hoot or jump or 'lay claim', and his almost attorney-like presence made me feel like the crazy one asking for favors, even though he was going to get the 'rewards'- a blow job and a fuck, at least. And he did. I sucked on him until he was close, then told Jessy "Please let him cum in you tonight" and started for bed. Only Jessy sort of broke the mood as I was leaving with the problem of sleeping arrangements.

"Baby, Sissy Brendie, if you are going to help me have lovers here you know you can't just sleep in my bed with them. So I have three good options you can take, Sissy. You've love each one, and you should alternate or at least try all of them." Sue was genuinely interested in this, apparently he hadn't known there would be 'rules' and 'plans' laid out right in front of him. Jessy continued, addressing me but clearly letting Sue hear, "Option 1, which is off the table tonight, is your sleeping bed from Amy's. She'll bring it over later this week if you want, and she talked about adding a 'third button' if that means anything to you." Jessy said matter-the-factly. Sue finally chuckled a bit, and let down his solid lawyer-like demeanor, saying under his breath "Bet it has something for Sissy to fill up with." He was right of course, Amy's bed for me had the cock gag I had to suck, keeping me awake, and the butt plug that offered to give me rest- half hour chunks- if I took large enemas and held them until morning.

Jessy looked at Sue somewhat annoyed at being partially undermined. "What are the other options, Baby?" Sue asked Jessy. Then they smiled at each other, his penis still pretty erect, and Jessy rubbed it a bit and got some of Sue's precum on her hand and then in my hair. "Sissy, be a good girl, cup Sue's balls and give him a lick or two so he doesn't get bored." Jessy said calmly before continuing. I got back over by him and resumed, not that his penis was much softer than when I last left it.

"Option two, Baby Sissy Brendie, Baby Sissy Brendie... I like that..." Jessy started. "You sleep under my bed, tied stretched out with your feet and hands pulled towards the four corners, stomach up. There is a 'fleshlight' on your cock that responds to noise and vibration. As Sue and I fuck, you will be masturbated faster and faster. If later he snores, you'll get mild stimulation. Also there is a camera and TV setup we can turn on and off that will let you see us from different angles if we like, in case you need help imagining how powerful a man Sue can be."

I had to admit, this sounded interesting. Surely they wouldn't fuck all night, I could sleep after. Anything for sleep. Any the cuckold fetish did turn me on at least a little, otherwise why would I be caressing Sue's balls? I was absently licking up and down the length of his shaft as Jessy went on with her speech.

"And, because I care, I have one more option for you. This is a good option if you don't really want to see me with a lover, but you need to get some sleep and Amy's bed just won't work." I sort of looked at Jessy, but I remembered something ("Sissies focus on what they are doing, stare at the cock") and quickly went back to just listening to my wife as I kept Sue erect and standing ready.

"I don't like this one, Brendie, I have to tell you I would never do it." Sue commented. I looked up in his eyes, and saw truth, while licking his cock. It was actually very pleasant, the feel of him was growing on me. Thinking to myself, if a big man like Sue who was silent at the other options didn't like this one even before Jessy told me about it then it must be terrible... Amy and Jessy always seemed to have in inside track on people, information, secrets, everything, and they seemed to let all the real hunks know before letting me in on any of the good stuff. Sue was of course in their club, and here I am on the edge, just able to enjoy Sue's hard penis before they get to go sleep in Jessy's bed together.

"Option 3 is my favorite, because it involves skill and daring, and because you could get to sleep soundly in the guest room most of the night. But, there is more to it than that, of course. But you will get to sleep in a nice bed, nothing in your mouth or Sissy pussy, and no ropes or handcuffs any bondage gear." Jessy said happily. So far, so good. "The problem is, you have to do 'extra lessons' before you go to bed. So while Sue and I will be sleeping, you might still have homework to finish. And if you can't finish your homework by morning when you need to go for work, you'll have to try the whole task again tomorrow- no choices, no taking another option. It is a sort of bet, because most of the tasks are repetitive and take a half hour if you make absolutely no mistakes, but the penalties are steep and it could easily take you three or four hours if you get flustered or tired and start screwing up. Does that make sense Sissy Brendie?" Jessy asked. I backed off the penis slightly: "Yes, Mistress, please continue." Came out as my gut reaction.

Part of me knew this situation was a bit strange, sucking Sue and having Jessy explain rules to me, but a growing part of my mind was really enjoying it: I was the center of attention, Jessy and Sue were focused on me. Albeit for different reasons: Sue looked at my high heels and occasionally my fake breasts, and Jessy really cared about my wellbeing and wanted what was best for me to happy.

Amy really had put some key phrases right at the tip of my tongue, which at the moment was happily spelling out 'Mistress is my love' onto the head of Sue's erect member. I think I may have wrote 'is' twice, because Jessy had me a bit flustered when she asked me if her instructions were making sense.

"Right, so, Brendie, I'll tell you tasks and let you pick, based on behavior and other factors, kind of like the menus Amy had if you go with option 3. But be careful, because if you start a challenge that is too hard, you'll just have to get better at it until you pass- even if that means 5 sleepless nights. After 5 nights, each night I'll relent and let you take Option 1 if you want. But 5 nights is a lot with no sleep, as you already know." Don't I, my mind said to me as I continued licking into Sue's cock: "ss is my love. Misstress..." I was so tired that any option seemed OK.

"Tonight, to start easy, Option 3-a is play Simon Says up to 10 colors, and 3-b is fold 50 shirts using Retail Store Trainer. But remember, if you make mistakes, there are penalties."

"Mistress, I need a good night's sleep for work on Monday, and I think Simon Says should be easy enough. May I choose option 3-a please Mistress?" I asked sheepishly. Sue looked at me somewhat surprised. "Didn't think you had the balls to play Simon Says, Sissy Brendie." he said as I returned to sucking his cock from my long, improper speech. It felt almost cold, even though I had my hands cupping his balls and trying to keep heat, my saliva's evaporating seemed to require a constant replenishment of heat. But Sue didn't complain. Jessy didn't seem to mind either, as if the decision had more weight that I was putting on it. I was a bit worried about that.

"Baby, that sounds great!" Jessy said, taking on parts of Amy's happy characteristic, but obviously unable to maintain the level of energy that Amy found so natural and innate.

"So Simon Says is just like the Simon Says video game and has just a few changes. You still need to remember colors, and you still get sounds to help. You can make songs out of it if you like to help, because 10 is a lot of things to remember, and most people can really only remember 7 (which is why phone numbers have 7 digits). The first difference is Simon doesn't really say. You have to guess what the next color is, and there are four options. So if you guess right, you'll see the color and hear the sound. And if you guess wrong, then, it gets interesting. You'll get a short punishment program and you'll get a spanking." Sue pulled up his pants and they sat down for a bit, with me on the floor.

About a half hour later, after Sue and Jessy had a small snack and I ate some of Sue's left overs ("I don't like the butter cookies too much, Sissy Brendie") and Jessy was letting Sue play with her breasts. I ate gratefully ate the cookies, and Jessy asked: "Baby, would you like some wine? I don't know if it will help you with Simon says, but you might enjoy it." I had a couple good glasses, probably more than I should have, as Jessy and Sue enjoyed themselves, and Sue let me focus on the food and drink and ignore his beautiful, warm cock. He had quietly tucked it away without a word, as he continued teasing my wife's nipples. Of course I was staring- at him, her, the cock, her breasts. And I was drinking enough wine.

Eventually Jessy said "Bed time!" and we got up. I went toward our guest room, and Sue and Jessy followed to explain what to do for my first time. "The bed will be all yours once your task is done, the door has a lock (no bathroom, sorry) and the alarm clock will get you up for work. It is a special alarm, and you won't be sleeping through it, at least not in this room. The door lock is timed and once it closes at night it will stay closed except from the outside."

I walked in and Jessy closed up a mobile folding table, just like what I had seen shop girls at PJ's use to fold clothes as they walked around the store. Smiling, she said, "Maybe next time. The table uses some of the cameras in this room to help decide how well you folded each article of clothing, and there are speakers and display monitors to simulate men hitting on you; you have to stop working, set the clothes down, and turn to the monitor and happily agree to whatever they say before continuing. Now, Simon Says." She put the table away in a closet.

That left the bed, which looked amazing- it was a king bed, with a great comforter and big plush pillows, extra blankets and white sheets. The colors were somewhat feminine, and there was a body pillow and a larger teddy bear in the bed on one side. Jessy smiled and said, "No matter where you sleep, you'll do your makeup and clothes in this room. But for tomorrow you can dress like a man, of course your wig will be staying, but you can keep man clothes. Except of course you need some sort of bra and panties, we'll get you straight tomorrow." Jessy seemed to control and know about my future all the time, and with Sue there supporting her I had little choice but to agree ("Yes Mistress, I am excited to go to work again.")

The business part of the room was the Simon Says setup, most of Jessy's night 'Option 3' items were one-person automated affairs so she could get her beauty rest. This one had a bench to kneel next to, she had me put my stomach and chest down on the bench, exposing both breasts downward and keeping my legs flat and pointed backwards. Jessy got me down and clicked in a couple simple straps, one at chest and one at waist level, letting my legs free to move and my arms and head free as well.

"This game has a touch screen monitor right under your head, so you don't really have to lift your chin too high. But some of the games will have the monitor up on the wall, so remember, you might have to strain to see it. The touch screen is how you will play Simon Says. Go ahead, try it out."

I saw the screen turn on, and 4 colors displayed- red, orange, purple, blue. I tapped purple, and I heard "I'm" spoken out loud in a sexy girl's voice. Curiously, I tapped purple again. "I'm". Then I tapped red. Thwak, something like a fly swatter hit my butt, not too hard but if this was automated I could tell it would start to turn red and get painful pretty quickly. The whole screen faded, and went into a sort of twisted music video. The screen showed something like a transvestite strip club, very interesting and erotic graphics, and I realized Jessy had slid my penis into some sort of a comfortable silicon orifice, when vibrated as the video started. Jessy said (I think she was smiling but I couldn't see her) "You might be tempted to waste some time by making intentional mistakes before you really get down to business, Sissy Brendie, but trust me you'll get enough fun by the time you figure out all 10 colors in the right order."

The first video seemed to have expected Jessy to talk before audio came on, since the rest started right in with music and lyrics. Maybe Jessy had a mute button. The lyrics went: "I'm a sissy slut whore, I love cock in my warm moist holes." Very upbeat, happy, and matched to the glamourous video, which did show bulges and cocks, but no-one that looked masculine at all.

After, the colors came back. "OK, enjoy Brendie. If you don't press anything for too long, the machine will deliver a shock to your cock, and play a punishment program. The programs are there to help you be a good Sissy, and they sort of match the colors so be careful if you try using them for memorization not to get confused. Good night, Sissy." "Mistress Jessy, I love you more than anything, please enjoy your evening with Sue. Sue, please take care of my Jessy like you took care of me, I know my wife is in good hands." I said on auto-pilot, barely believing the words as they came out, but Jessy took them for granted and Sue was getting really excited. They left and I heard a distinct electronic click on the room door as I felt my cock get shocked fairly hard. It wasn't enough to take my breath away by any means, and I still could masturbate for sure, but no way I was going to sleep through that even if it was only once an hour.

So I tapped purple (from before). "I'm". Then I hit blue, since I had already tried red. "Slutty" a pretty girl's voice elicited. "I'm Slutty", OK. I guessed purple again, and got an immediate cock-shock, much less than the one for inaction. Then the screen faded, and I saw images of girls giving men blowjobs. They were very motivated, and kept wanting more, like animals. The upbeat music and words "Slutty girls love cocks because they don't care! I'm a girl that loves cocks!" were catchy, to say the least, and I think five minutes was on the short end of this video's real length. The silicone piece was masturbating me as well, although this scene wasn't really doing it for me, I was a little excited. Back to the four colors.

As I watched, something interesting happened. The colors briefly showed images overlain, each image fitting the color, kind of like a dress code or season. For purple, it was a picture of me, close up to my head, in full makeup with a dark purple comforter under me, and each color had its word shown as well (Nothing, Girls, I'm, Slutty for red, orange, purple, blue). I hit Orange this time, which worked (the voice said "Girls"). Purple, Blue, Orange - I'm slutty girls. Three down, seven more to go, maybe 15 minutes in, awesome. Next I tried purple. Ouch, no go, the punishment video was one girl putting on makeup intricately to the beat of "Slutty girls want to get fucked, slutty girls want to love cock".

The night wore on and I certainly got 6 colors right, but it was too much. I tried sleeping through a few shocks, and then started again with Simon- I forgot colors 5 and 6. By morning, I might have gotten to color 8 once.

I heard the electric lock on the door click, and my alarm went off. The straps on my chest and waist stayed attached, and the alarm got louder and louder until I thought it would hurt my ears. Then, the straps released. I got up and walked towards the blaring alarm. It wasn't a normal clock with 'snooze', it was a touchscreen that had a picture of Jessy and multiple choice questions, and a scoreboard of sorts. It was so loud I couldn't think, but to turn it off took a test.

That first test went something like this: Sissy, what is 2+3? a. 5, b. 23, c. 32, d. 40. Answer b was correct. A new, different picture of Jessy came up and the question was Sissy, what is better? a. cock, b. bread, c. masturbation, d. chocolate. The answer a was obvious, and so the test went; get five right, subtract points for wrong answers. It took me about 7 questions to get the 5 points, and I got the impression most of the questions would be rote memory, and they would be changed as time went on. They were of course, Jessy put in questions I had no idea about (Sissy, your wife hates which number the worst- a. 5, b. 23, c. 82, d. 33; answer is d; Sissy, if you go out of line, Jessy and Amy will show you begging for dick to this person first- a. your mother, b. your younger sister, c. your boss, d. your older sister ; answer is c).

Once I finally passed the test to shut off the alarm, I started thinking about work. Jessy had remarked about panties and a bra, and since I was so used to it by now, they slid on under my work clothes. I opened the door, and walked to the kitchen where Jessy was waiting for me. "Sue left last night, but you were right about him- I would have played with his penis all night too if he would have let me Brendie! He didn't... get up in you did he Baby?" Jessy asked right away. "No Mistress, Sue only let me orally pleasure his cock, he didn't use my pussy." I said like nothing. "OK dear, so I know you need to go to work, and I am happy you put on your bra and panties." Was it that obvious? I tried to look at myself, knowing I had the long hair, and see if the panty or bra was noticeable. But you can never tell on your own body, even in a mirror. Anyhow Jessy seemed happy and had breakfast ready for me. As we ate she happily showed me her iPad after she had been playing on it a little.

"Option 3" seemed like a custom-written App for her, and it had a picture of me in the logo. She showed me still close-ups of my face at certain moments in the evening right after I made mistakes, and a funny one where the idle shock caught me totally off guard. I was also impressed to see she had an array of statistics and charts available, and she showed me how I got up to color number 7 around 1:35 AM, but then never got past color 5 for the rest of the night. "It's a shame dear, but tomorrow you'll get better. And don't worry, if you ever finish an Option 3 challenge before 3 AM, we'll keep it around so you can pick it again- but we'll make it a little more fun for you. Like for Special Simon Says, we could go for 11 colors, or maybe change out the words and colors, turn up the electricity, lengthen the programs for your ongoing entertainment (she meant the punishment videos that made me forget the sequence), or add another color to the wheel so there are five to choose from. But don't worry, we'll track that on the charts to so it doesn't look like you are falling behind."

I was impressed. This looked very interesting, and while a part of me thought it was at my expense, I was really happy and excited Jessy would put so much work into making a fun play environment for me, even when she wasn't around to be near me at the night time. She let me play around a bit in the app, and it was fun like reviewing the tracking results from a gym workout- I could see how the night unfolded, which videos got me the most excited (one that featured up close black ass holes seemed to be near the top) and how quickly I remembered the first colors (it looked like one time I hit the first 4 colors correctly in under five seconds before messing up on color number five).

If I ever wanted to be childish and not sleep near Jessy, under her bed, she gave me Option 3 to be able to masturbate and cum at will, while continuing to move forward serving her and generally filling whatever fetishes I felt like at the time. I love my wife and I'll never leave her ever.


The Work Day

I'm Brandon and I never told you what I do for a living. How silly! I'm actually pretty happy with my career, a bit too much for a 'Sissy Fetish' guy. Maybe someday Jessy or Amy will get me something more fitting, or maybe someday I'll get too 'Bimbo Dumb' or too 'Shemale' to do it. For now, my job is a good source of fear for my ladies to use on me: I make nearly $100k salary, and as a housemaker Jessy would get a good alimony if we ever got divorced. I'd never leave her, but sometimes she has to remind me what could happen if she decided she would try to make a marriage with another man and how that would go for me, the type of impact it would have on my own life. It is hard for me sometimes to think outside the box beyond myself into what Jessy might end up dealing with if certain things happened in the future. For Amy and Jessy, it seems like they always have a good idea of what the future of my own life might entail, like they had it all planned and thought out.

Now I think it might be cool to be a strip dancer or a prostitute or something, but there is a real benefit in having a '9 to 5' job. It adds structure and keeps disease from my life, and it lets Jessy have nice things. It also lets her come into work and meet me, and talk to my coworkers and boss on occasion. Over the years, I think having the outside job has really added to our relationship, especially when I consider what life would have been like if I stayed at home as a maid or if I picked a more menial job like coffee barista or (the travel wouldn't work for Jessy of course) stewardess. The only thing I would say I miss is the opportunity to get flirted on by strangers, and the occasional person who knows what I am and who insists I take my break right now, knows I can't say no. But that is my imagination running wild.

At work, especially in the first couple weeks and months after my first homey moon (with Jessy) and my second honey moon (with Amy) I was scared people would think of me as being different. The hair, obviously, but I had changed so much internally- I was a totally different person, as far as I could tell, on the inside. Amy's training to help me understand femininity and how to live with Jessy for the long term was really effecting other areas of my life, for instance, if my boss said something totally stupid I would come back with "Sir, that sounds like an interesting idea and I wonder if you could tell me more about it." instead of a more familiar "But what about the [obvious flaw]?" that would get the rest of my coworkers to snicker, and the couple cute ladies at the office to stare in a sort of awed admiration, stretching the limits of a corporate conference room's expectations of logical bureaucracy.

No more, now the ladies were not impressed with me. But I took to being their friends naturally, and in time we got to reading certain kinds of magazines and books together, and talking about them. We spent much more time together, and they began to think of me like another one of the girls. Lily, a 30-year old, gestured towards me one of those first days and grabbed my shoulder, emphasizing a point about an ongoing work project. She obviously felt my bra strap and stopped, smiling down at me. She was behind me in my cubicle. "Brandon?" she said ominously. I was silent, and she continued: "I'd like to go... have a drink later this week, would you Jessy your wife to come with us? We have some catching up to do after your honeymoon." she said, with some ado. Thinking on my toes, I knew Jessy would be around Thursday, and like a man I offered a time and place: "How about [local bar] at 7 PM after work Thursday? I think Mistress Jessy could explain my actions much better than I can." Out it came, automatically like clockwork, since I was thinking bra I thought Jessy, Amy, Mistress, and out it was. Lily smiled and bit back a laugh, but agreed quickly and gave me a mini-behind-the-back hug, whispering "You will really be one of us girls after all! I thought you were just trying to get someone in our group by reading [model fashion magazine] and starting on our book club with [Oprah Winfrey best seller]."

Nothing else really changed at work that first week, other than my boss was a little surprised how accepting I was of his ideas. Normally he thought his ideas were just 'rough sketches' or 'layman's terms,' but now he was gaining the confidence of knowing even I, one of his senior staff, basically agreed with him all the time. It made him seem more in charge and in control, and I was starting to feel better about not needing to start arguments or confrontations needlessly. I could focus on my work and ignore the mistakes I saw around me, letting their consequences fall on someone else's shoulders.


Work Catchup Night

Thursday evening rolled around sooner than I expected. I had just barely got Special Simon Says complete around 3:15 AM Wednesday evening, and so had some solid rest. The comfy bed was really great, and the alarm clock behaved differently on a night that I won the game. This morning, it was much quieter at first, and the questions were actually kind of fun: "Sissy Brendie, Good Work! Did you enjoy Special Simon Says (no wrong answer)? a. Yes, b. No, c. A lot, d. Hated it." I picked 'a'; "Brendie, I love you. Do you want new Simon Says to be harder? a. No, b. Different Words/Colors, c. Longer Videos, d. Longer Shocks" and I picked c for longer videos if I got a color wrong.

I had forgotten the cutoff for mandatory 'harder Option 3' was 3 AM, so I didn't need to make the game harder, but on the other hand I really enjoyed the videos Jessy was picking out for me. They turned me on super well, were tailored toward my tastes, and I didn't have to go hunting and pecking the internet to find them or pay for them. They were Jessy's secret gifts to me over the years.

Work went normal, and Lily did nothing odd all day. As we left, she did say loud enough for at least a few other people at work to hear, "See you at seven Brandon!"

Jessy and I made it to [local bar] without issue, and she immediately got me taking some libations. At her prodding, I had worn the kind of clothes I was used to from Amy's during the day- feminine, but normal everyday and comfortable, with the padded bra and some basic, basic makeup. The long hair made me appear wholly feminine from the back, and my face was passable as a girl, although it could clearly use some work. The shirt was high-cut enough to conceal the breast pads, obviously, and for our climate was appropriate.

Jessy had only seen Lily once or twice, so this was one of few opportunities I would ever have to introduce my wife to someone new. Normally, Jessy (let alone Amy) knew everyone in the room, and they were introducing me to all the new people and people I had forgotten the names of. I was savoring the idea of being the one who knew all the names at this table, for once. Lily arrived soon after us, not late by any means, and ordered a drink immediately. By this time Jessy and I had ordered a couple rounds, although I had had more than her, and I ordered my third with Lily. Wine, champagne and the like were my go-tos, although Lily liked craft micro-brew beers and Jessy seemed to know the names of the crazy mixed drinks girls love to slowly savor that come with flag poles and umbrellas and the like.

Of course I know now Lily had talked to Jessy before, they knew each other well enough before she gave me the 'hug of death' after learning about my bra, and they had talked at length Wednesday during the daytime about me, my marriage, and what Amy and Jessy liked to do to men who don't always stick up for themselves.

Lily had another surprise, which she let come after the awkward introductions I made to the ladies, they already knew each other but sort pretended not to and my intro wasn't that great. Lily got a text and said "Oh, I asked my boyfriend too. Is that OK, Jessy?" directly to Jessy and only Jessy. I wasn't consulted at all, and I was taken a little aback, but Jessy confidently said "Yes, that sounds great!" and I was inclined to agree, and I sort of nodded to indicate my general compliance with the situation at large.

At least Dave wasn't one of the men from back when I met Jessy at PJ's, but he was a good looking man a bit older than Lily who seemed to have the confidence and control you'd expect form a success his age. He introduced himself to Jessy and me, and like Lily seemed blind to the fact I was calling myself Brandon but dressed as a girl. He ordered his first drink, and got me one, so I was on number four and tired from last night (I had got to sleep around 3 AM) and compliant. I was counting my blessings there was no big deal being made about the way I was acting or looking, everything was going well.

As the evening ran to a close, we all did the standard goodbyes, and just as we were leaving Dave leaned in to Lily and whispered something. Lily and Jessy looked at each other, and did some kind of girl Morris Code with their eye lids, smiling once they had agreement.

Jessy and Lily looked at me, obviously hoping for a 'Yes', and Dave said calmly "I hear you like to see new things, new men. Would you like to see what I have?"

I was shocked, but not really. I said- less automatically, in public here, but I said- "Yes Sir, I do enjoy exploring new terrain and trying new things. If Mistress agrees, can Dave and I have a few minutes?"

I didn't give him a blow job, he just expected me to pull his dick out and get it hard, look at it. Then he said, "There you go Brendie", and zipped up walking away. I was dressed like a girl in the men's bathroom, and I as I walked quickly back to the main group I didn't really consider how we never used the word Brendie up until that point in the evening. I did have a lot of alcohol, true, but maybe this was more a sign of my sub conscious being glad I got to touch another man, to explore someone like Sue but totally different. Dave shared my race and his penis was similar to mine in some ways, but different in other interesting ways. While he didn't let me get my lips around it, I was already starting to imagine what may be going on under the hood.

That night I found myself comparing the penises in my 'programs' to Dave's, Sue's and mine, and starting to unfold my wings to understand how exactly a worker boy like me, Brandon, could obtain a sort of ram-shackle understanding of women felt about cocks. Sure, there are lots to choose from, and if I played my cards right one might provide a long-term, loving relationship. Of course for me Jessy is life: she helps me to avoid any marital strife that would certainly leave me homeless in debt, and with no family and alone.


Option 3- the Rock Challenge

One of the Option 3 challenges I, Brendie, like to think to when I'm bored and I want something to masturbate to is the Rock Challenge. It is the old game, to pick up a pile of rocks, move them to the other side of the room, and then move back to where they came from. Typically a show of male power and masculinity, a way to really "move weight", the version my wife Mistress Jessy created for me is different. Instead of "heavy lifting" Rocks takes the delicate hands of a skilled nurse, who under the strict supervision of a superior man, can help her make a go of it in the world. The good doctor looks out his nurse telling her what to do, how to get ahead, and on occasion when to give a favor or two to the senior staff (this game involves a dildo and a monitor above to look into while sucking).

Like all Option 3 challenges, the Rock Game is played in the soundproof extra bed room (Jessy related "Is your alarm clock loud enough, Sissy Brendie? I can't tell because no-one could hear it from outside your room, and I've never been in there right when you need to wake up. Because I think it would be loud." and giggled as I muttered "Yes Mistress Jessy, the alarm clock you generously provided to make sure your slave wakes up early enough to get to work is very effective at helping me to provide for you."). So she never heard me scream, sure, but I know Jessy always had me in her heart. She was always thinking of and about me, and I loved her all the more for it. Jessy is my soul mate.

Instead of huge rocks to lug around, the nurse moves small polished marbles carefully from one basket to another- around the bed, to make the path a little longer and cumbersome- one at a time based on the Doctor's orders (he requests up to five at a time to be delivered in sequential order) balancing the rock in a special health spoon. Dropped marbles are left on the floor for morning (if more than five are dropped the challenge is forfeit and the rest of the night). The baskets are on the floor on each side of the bed's headboard, and there is a vacuum hose to automatically return marbles from the goal basket back to the starting basket. Both baskets can detect which marbles are inside, and all 100 marbles are numbered visibly.

My nurse outfit, white with a short skirt and a cute hat, has super high heels and no panties. I need to keep my legs straight to bend at the waist to reach the baskets on the ground, showing some ass. Both of my hands are tied together in front of me, with my fingers all bound, and the spoon is locked in between my hands so it is all I have to work with. "You'll love it, Sissy Nurse Brendie! Just listen to the good doctor, he'll keep you on the straight and narrow!" Jessy had said as she left me for the evening.

An authoritative, calm doctor-sounding voice spoke from near the monitor and dildo, and the monitor showed a face that looked like an experienced surgeon. "Hello Sissy Nurse Brendie, I'm the doctor here and I'll be helping you tonight. Now just do what I ask, little lady, and we'll get along just fine."

The monitor shifted to a view of his crotch, and held for twenty or thirty seconds as I stared mindlessly. Then the strong voice: "Sissy Nurse Brendie, I need 10, 50, 33, 43 and 27 Stat!" So starts the game, I have to remember these numbers and find those marbles in the pile, move them one at a time to the second basket and carefully set them in without dropping them on the floor.

The voice starts going into the fine detail rules for the first five or ten minutes, explaining little details and gotchas: "Brendie, if you take too long, we'll send a marble back for you. This will help you to quit day dreaming in the office, and make you a better worker. Just keep moving, princess." "Sissy Brendie, you know you can't drop a marble, and if you try to pick one off the floor that's a black star for tomorrow. If you drop one, leave it. If you drop five, then we'll just spend the rest of the night practicing- I'll keep moving marbles back for you so there are plenty more left for you all the way until the end of your shift." and, "Baby, you know if you bring the wrong marble, that just won't do. If you put the wrong marble in the basket, baby, we'll have to send five marbles back so you can get better at your numbers and counting." "If you harshly drop a marble into the basket, you should bend at your waist to carefully place it, we just might need to send two back because of your carelessness. Be careful Sissy.:"

The voice had one more introductory phrase. I had already moved 3 of the marbles without incident. "Sissy Nurse Brendie, if you forget what marble goes next because of your little fluffy mind, or if I somehow break your concentration, or if I ever directly ask, you should come over to this monitor and take a break with me. I'll let you suck my dick whenever you want, once you get some liquid I'll give you a new list of marbles to pick out for me."

I had finished all 5 requested marbles in order, and so the doctor said: "Great, Sissy Nurse Brendie, you are really doing a good job! I wish I had more smart cuties like you. Now, get me 21, 19, 22 and 9 please!" I looked momentarily at the screen and saw the doctor's crotch, followed by an artistic '69' that was stylized with fetish nurse crosses and diagonal. Even the images were going to try to make me forget what numbers I had to grab.

As I grabbed 21, the voice starting saying other less helpful things- "Brendie, I'd love to 69 you!" "Nurse, those curves are hot, but let's get a move-on!" "Sissy, I wonder what you have going on down there?" "Brendie, quick question, what is 21+18?" "1, 2, 3, 4, - o-clock rock! We are going to party all night...: sorry." Just random stuff with numbers or workplace harassment themes, but as I grabbed rock number 8 (the last one he asked for) I was a bit worried I might be taking the wrong one. "89.. 86.. Brendie, what do they call it when they drop a menu item? I think it's 86, 10-4, let's 86 it... 8 or 9.,." the confident male voice went on and on, trying to lure me into just listening to his macho nonsense. "Look, is there a stain on my jacket?" the voice said innocently as I glanced at the monitor- he had a slight mustard stain to the right of his crotch. I had rock 8 up in my health spoon and was walking to the other basket.

Of course, 8 was wrong, and after I carefully set it down the good doctor informed me curtly before I heard the vacuum go and saw the tube shake as two random marbles were pulled back. "Nurse Sissy Brendie, I asked for a 9, silly girl! Let's practice so you remember my commands better. This time, give me a 7 and a 59."

So it went. After about twenty, I made another mistake, and around 35 the male voice said "Come here, you deserve a reward my little hot nurse." Of course, that meant warm up the dildo and get it to 'cum' into my mouth, while watching a TV that showed lots of strong, alpha doctors and hearing audio that ranged from "Sissy Nurse, I like your style" to "It takes a real man to be a doctor."

I was able to finish the whole challenge, feet sore and back stiff, around 3 AM. "Sissy Nurse Brendie, good work! I just knew you could do it!" the voice congratulated. "Enjoy your bed. If you want, you can slip out of your clothes, except you have to keep your hands bound and hold the spoon so you get used to the posture. Nighty night Sissy!" After a brief pause, Jessy's voice came on, recorded: "Sissy Brendie, I knew this challenge might be too easy, so think about how to make it more fun tonight- one thought is that we give you a nice dildo above each basket and you have to put it in your mouth before you can get into the basket. Or, maybe we can have you put the marbles into a patient... good night Sissy."

Jessy told me the next day "Brendie, I'm glad you did good at Rocks last night. I wonder if you could be a real life nurse? Your costume looks so cute. Well, to help you train better for it, we'll change the game a little teensy bit. I think from now on you will always suck the cock to get any orders, and once you suck it, he'll give you 10 balls to find. But you can always go back and suck him again for a new order. Let's see... we'll make the monitor have the doctor hinting he wants you to suck him, whenever you aren't doing it. And... one more tweak... I know. We'll put a box from your aerobic exercise stepping video behind the bed, so you can step on it to move the marbles, or walk around it, up to you. I just can't wait to see how these changes will effect the game! Aren't you excited?" I kind of was. "Yes, Mistress Jessy, I wonder how well this Sissy can do with those changes. Can I suggest an idea?" Jessy slightly nodded, apprehensive. "Well, when I drop off a marble, maybe I should have to kneel down and put a cock into my mouth before I can set down the marble." Jessy smiled happily at my idea as the conversation changed topics without any further consideration.

Jessy was always good at taking care of the details, because she knew how things would turn out. Over time I really enjoyed the Rock Challenge more and more, Jessy seemed to know how to make it so I could almost always win but still stay interested. I don't know how she is so perceptive: even though I live through every challenge, she seems to be able to pick exactly how to make it work out for me.


Devotion

Jessy, my wife and Mistress, has a lot of fun during the days and I (Brandon) have been kind of bored at work. So Jessy suggested I start putting time into something just for her- like how girls sometimes knit their men a hat or a scarf, something slow and menial that makes me think of her and how special she is to me. "You know, sometimes people draw pictures or make crafts for the ones they love." Jessy said one day. "Or write lines, play video games, build models, that kind of thing." she said.

Ideally something I could do while I am at work, but not actually working, or, something I could do before my evening bed arrangements (I had been using Option 3 regularly, and that of course took a lot of my time). I wanted something mindless, but something Jessy really wanted me to do- the simpler, the more brain-numbing, the better because she would have an easier time making fun of me for it.

Sudoku puzzles and crosswords were out of the question, maybe normal jigsaw puzzles or something like solitaire, the card game you play alone. We spent some time brainstorming and Jessy, like Amy, had the final best idea- those ladies really do have it all figured out, I am glad to be around them so much.

"I have it! Sissy, get over here! This is the perfect thing for you!" Jessy said happily one morning, right as the door to my room opened. Half-asleep, I came over to see what she had picked for me to do. She was sitting at the kitchen table all smiles. "Come quick!" would have been the comedic thing for her to say, she was so excited, but Jessy just said "Sit down Sissy."

"OK, so this needs to be something difficult, but doable, easy, but hard, silent, but loud, quick, but slow, and it should have some kind of punishment for doing to wrong or slow." Jessy said to me excitedly, as I enthusiastically nodded. My mind was entirely in the "What fun did she give me" camp and I had no worries or fears. Jessy, my wife and only girlfriend, loves me more than I love her: she would never make me do something that I cannot do.

Jessy continued ranting, "Something involving as much of your body as it can, and something that is simple but complex, that you can start now but will learn over time how to perfect and get better and better at over time." She really was excited for me, and for me to try this out. I was becoming just as excited as she continued on for some time.

The idea she had in mind was great. Jessy is one of the '5%' or the 'super class', she knows me better than I know myself. I sometimes get scared, kind of like if you thought someone was trying to get into your house one night when you are home alone, and think to myself about her leaving. I would never leave Jessy, my perfect wife, and the she always looks out for my special interests like no-one else could.

And Jessy is so smart, I was wondering what she would have me do for her. Definitely not making something for her to wear, probably not doing silly things like color-by-numbers or tracings (although Jessy always wanted me to learn how to draw). I had no real idea what could be coming, and so I was at the edge of my seat as she let it out.

The task was to write a special diary. Jessy smiled coyly as I sat listening to her specific instructions and trying to understand what she wanted me to do exactly. First, before touching my actual diary, which she held in her hands (it was leather, had a lock, and a cute girlish phrase on the front) she explained I needed to use an App on my phone to practice penmanship. Since my phone is key for work, it should be easy to spend two or three hours on it every day, she explained, working on my "Perfect girly letters, all print, each more beautiful than the last." Handwriting had never been my strong suit.

I was even more excited to see Jessy had put more effort than buying a nice diary into this. She said "From now on" I'll be wearing a padded bra with electrodes that interface to my phone, allowing little shocks to each nipple or to both at the same time, all ran from the same app.

"Baby, this will be great. You start Lettering on your phone, get your stylus out, and follow the dotted guidelines exactly. As you get better, we'll tighten the margin for error, and of course there are nipple-shock (she giggled at her fake word) punishments if you don't trace correctly or if the overall letter takes too long. The App lets you stop at any time, although it does give you a 5s shock if you spent less than twenty minutes practicing. This should help you keep focused on your phone at work."

"As you get better, we'll put you on a treadmill and have you practice walking while you write. It'll make writing standing still so much easier!" As it happened, the practice texts were long hypnotic scripts, with simple messages like 'I enjoy sucking cock', 'Big Boys ARE Big Fun' and 'I want to be pretty'. She put at least four different fonts for me to learn different styles, mostly themed based on the texts (so 'I love pink' was in a cute font, and 'Cocks own me' in a more business-like, boxy lettering).

The diary itself was another affair. Given the writing practice, which alone was a lot of work, Jessy explained about the diary. Many masters encourage their slaves to write their feelings, their thoughts, fears, loves so later the slave can review and relive their past. Jessy liked that idea, but she also had other, more interesting purposes in mind for my time. She wanted me to write mainly about her lovers.

"First you should explain every dick you see, especially if you touched or sucked one. Then I want you to talk about his balls- if it is big, or if it is small, or shaved. But you should explain it as if the penis is a person- is it a Ronald Regan or a Hillary Clinton, does it smile and dance or is it quiet and strong? I want you to think about the veins and arteries, consider the foreskin, of course the taste. Does that make sense Brendie?" Jessy asked, quickly obtaining my approval of the overall plan. I would be practicing my penmanship so that my writings would be efficacious in their end goals: to let my loving wife think back, from a removed and unbiased third perspective, to some of the amazing cocks she had experienced.


Old Age and Fear

As an older man (don't worry, there is more story back in my thirties to come) I started getting a little scared about life and Jessy. I had never known any other girl like her, and only fucked one or two girls. Because I know Jessy, I've had my 'pick of dick'- judging by the diary we implemented in my late thirties, I've had about 400 cocks in my mouth. I suppose that skips over the ones before then, and any I forgot about. Jessy was always nice to let me experience her lovers, and she was careful to let me know which ones would be OK seeing my bulge and which ones I would have to be more careful around.

But I should introduce myself, I'm Sissy Brendie and Jessy found me back when I was in my early thirties. We married quickly, had a beautiful honey moon, and then Amy took me on a second honey moon where I learned how to stay with Jessy forever: to be feminine, to really understand my loving wife.

Jessy mandated early on that each dick should have two pages of pristine diary writing describing it, and later she added another special rule to my task. After each 'day' (cock description) in my diary, I should write a short comparison to my own dick. My writing went like this: "His cock stays hard so long, and even blowing on it gets it erect. He has hair at the base of his beautiful penis and his cum tastes much richer, I can feel it is much thicker." Jessy tended to read these parts out loud and agree, and occasionally she would go farther fantasizing and threatening to leave. I of course always got worked up at any threats, and she relished the feeling.

More than that, Jessy liked to proofread my work, and have me redo it. She would cross out paragraphs and ask for more detail, mark up grammar, and occasionally circle poor penmanship (although I was pretty good at writing style, sometimes she specifically asked for 'softer' or 'harder' lettering, meaning use one of the fonts I learned from my iPhone app). Re-writing was time consuming because she mandated a two-step process: first, write the new version in a scratch notebook, then re-copy it into my diary. This way, I could keep my diary intact with all of my descriptions.

Jessy was specifically harsh on vague descriptions and wanted vivid detail. "Make it so a prostitute could read it and know more than what you say, make it so she could picture the penis in her mind. Use metaphor and bright imagery. And pick out specific, odd details- always in a positive light." She explained one day after rebuking "His cock was warm and long" as useless claptrap.

"Brendie, you are right, Buster's cock does have a birth mark on the one side. I like when you write specifics like that, it makes me so happy to know you are really getting in touch with your feminine side and I like thinking back to the past too. Too bad you don't have any special marks down there, maybe we should get you a tattoo..." Jessy said happily one time. I was falling over myself to pick patterns and shapes, words and mottos. While the idea of tattooing my little man seemed painful and I started wondering if it was medically possible, I picked a design I thought Jessy would like. It was a swirl effect that would go all around the shaft, except the urethra at the bottom, and end with an arrow going down towards the slit at the tip. We never did it, but I think Jessy liked my offering to try making up some ground and getting closer to real man penis.

Maybe I'll put some of my favorite passages in this story later, I am so happy with some of my work since Jessy helped me to improve it that maybe it will help encourage some other men to really love the cock, or at least to consider it. I wonder if I can get the images of the diary scanned up on the internet, because to me hand written words have so much more meaning. Jessy also thinks hand written work is worth so much more, since there is no automatic spell checker and you can't just 'delete a line' without re-copying everything that came after it.

Like all near-retirement men, I was getting cabin fever. Worse, like all middle-aged women, I was no longer a 'hot chick'. While Jessy and I could do OK in the dimly lit smoke filled bars, we had little hope of bumping into 30-something men in the grocery stores. OK, I had little hope of doing that, Jessy still gets hit on more than I'd like to admit. After years of marriage, I'm sure she'd never leave me, but she does get a lot of offers from well-to-do men that are bored and a bit older than her, men that want some adventure or a little kink, and I know Jessy can make that happen.

Sometimes I'm scared and lonely. As an older man, I quit doing 'Option 3' and Jessy just laughed. I normally take the 'sleeping bag' route, sleeping with a dick in my mouth and watching programs. On our anniversary day, Jessy normally lets me sleep in her bed. It is not that we don't make love, we do that, but then I go sleep on my own while she enjoys her bed. As we got older, she had men over less often, but she still has 'new cock' once or twice a week. Sometimes I joke "You'll break your hip", but she normally just smiles and says "You might too Sissy, be careful."

I devoted my life to Jessy, and when we die we really can't take much with us, so she'll get my stuff along with my kids. Jessy had four kids total, and I was a super-active parent, taking off time from work and doing most of the brain-bashingly boring stuff for them- explaining why, how, for what reason a zillion times, cleaning, putting away, on and on. "But why do you wear a bra?" my daughter asked on day, she was 12. "Mommy likes daddy to feel like a girl." "Why?" "It makes me closer to mommy." "Why?" "Mommy is a girl." "Why?" "The extra chromosome." "Why?" "Luck." "Why?" "Darling, 'luck' does not have a reason, it just is." "Why?" "Some things just are. Air is light, water is heavy, iron is heavier still. Chance, luck, or just the existing state of affairs." "Why?" "When the Lord created the Earth, he spent seven days..."

Now the kids are grown up. We decided, well, Jessy and the fathers decided and I heartily agreed, that the way we talk to our kids about my special status was to explain me as a failure, and Jessy as a mother making things work, and the other fathers as Jessy's helpers. So if I made a bad decision, or if something bad happened I didn't prevent, that was my fault. Sort of like the man missing a leg, the girls felt sorry for me but just accepted that I was like this. There were some episodes as they grew older and talked to friends, in many ways (friends using me through my daughters, other people trying to 'free' or 'help' me). We made it through OK and my kids are well-balanced, also none of them are overtly sexual or dominating like Jessy is toward me. I'd like to think they grew up better than me.

While I'm an old retired man with a loving wife, and I am able to give my kids some inheritance and nice gifts, old age always makes people second guess their lives. I wonder at times if Jessy really was my one, if I could have been a different type of man or lived a different form of relationship. If I could have done for a woman what Jessy does for me: if I could have set the plans and made the choices, so she could relax and enjoy the emotions and the comfortable glow of submission.

Sometimes the cheating (Jessy's dates) got to me, and sometimes the constant submission made me feel wrong. I figure with a different approach I could have been a more 'Alpha' man, I could have fucked more women and I could have provided a different experience for my wife. Now Jessy did get to be submissive with many of the men she dated as we were married, and, truth be told, those men were the ones that seemed to get the 'green light' when they tried to fuck her. She was loath to tell those strong men that they needed a condom, or they could leave.

I did fuck Jessy, maybe four or six times a month, and she was careful to consider her cycle and make me use condoms when there was any question. "We wouldn't want any accidents, Brendie, now would we?" she used to smile, and I'd feel proud of myself if she would do a little trick to get the bag over my man- like hold the condom in her mouth or maybe give me a sort of hand-job while putting it on for me. The sad times were when she just threw the condom on the floor and normally then the sex was mechanical, but when she wanted to get off she normally did. Sex wasn't something she kept from me, I just didn't need much sex with girls. I was more into a strong man most of the time. But we did fuck. I'm pretty sure none of my kids are my own, but I do enjoy thinking they could be, and I raised them right.

I'm not afraid right now, I know I picked the right life for me. I know Jessy loves me, and she can put so much good into the world because of me. I'm happy with my kids and I like my body. It is just that in old age, certain lingering thoughts always seem to filter threw- 'what if I had spoken up when I first gave Sue a blowjob in front of my wife?', 'what if I left Amy's and stormed out, swept Jessy off her feet and we found another sub to both be on top?', 'what if I fucked someone besides Jessy and it was better?'


Sleeping with Jessy

I'm Brendie, Jessy's sissy husband. Sometimes she has me say that literally to her boyfriends- some of the men really do get turned on by being the superior man, even if the other man is weak, and some have various levels of gay or sissy fantasies on their own. I think a couple had experienced male love in prison, and liked the idea of seeing it brought to perfection with resources that aren't available inside.

For whatever reasons, Jessy sometimes decided it would be best if I watched her and her men, who always had long and hard sex with her. There were a few ways to do that, but normally I'd suck their cock, make their super (or a snack), and wait in her bedroom. Sometimes I was told to wait under her bed, where they would be making love above me. Other times, the man wanted me to be watching. And once in a great while the men wanted more interaction on my part. While blow jobs were old hat for me, at least six times men had specifically asked to fuck me, and Jessy never disagreed. My opinion was not relevant for matters like these, the question was more if Jessy wanted to go first or second.

Jessy was always loud in bed, but I like to hope she was exaggerating when she fucked other men. One man, Jose, took one look at me in the front door in my apron and laughed, "Brendie, you're everything Jessy said. You know what, I'm going to fuck you after I fuck your wife. Will it be your first time sissy?", to which I meekly (and femininely) replied "You would be cock number 4 this sissy has taken in her sissy pussy, Mister." This was basically the right response and Jessy giggled. "She maybe lost count a few times, baby." Jessy said sexily to Jose.

That night, they fucked three or four times while I listened under the bed. "Let him masturbate if he wants, baby. If he cums before I fuck him too bad, during would be better since I want him excited." Jose had said to Jessy. I wasn't quite sure how to handle that- of course I could cum laying there hearing my wife fuck, and of course she had put my penis in the fleshlight with the vibrator ties to how much noise they made above me to keep me excited, but Jose somehow made the other option seem interesting and fun. "I want him excited" played in my mind as I heard her third orgasmic scream, and Jose mouthed quietly "Baby, I think I am ready for your sissy pussy". Jessy, apparently relieved for the short break, said "Can I watch? Make her face me and stand behind her so I can see both of your eyes." While Jessy normally didn't pick men she could control or manipulate to fuck, Jose seemed to think this was a good idea and rolled with it as if it were his own.

He pulled me out from under the bed. Jose was a good four inches shorter than me, and I had some shorter two inch heels with my maid's outfit, but he was running the show. I was bent at the hips, holding my calves, and he worked into me without much effort on his part. The cock he was blessed with wasn't very special, compared to some of the specimens I had seen, but he had obviously practiced various techniques and as I moaned Jessy watched somewhat impressed.

"Jose, why didn't you do that when you were in me?" "Because I normally start with women easy, and later in the night when they are tired I show them some of these techniques. It's my trick to get you excited again." "I am pretty tired, baby." Jessy replied, although she was clearly considering and calculating. After about twenty minutes, Jose was fucking her again, and I was back in my sleeping spot- tied spread eagle under her bed and listening to her moan. They turned on the camera at some point in the evening, giving me mainly views of Jose's manhood to watch and shame to. I came while he fucked me. He fucked me for the fifteen minutes but said "You will need to work for it if you want to cum, baby, sorry but I don't rub little clitties." So as he fucked me, I had masturbated myself. Now, I was still a bit excited, although the fleshlight was starting to wear thin on me.

Jessy seldom let me actually be on her bed with her, and she never slept on my bed- the Option 3 room- or otherwise with me. Well, aside from the honeymoon, when she was the main active participant and did all the work, and we made amazing love time after time. As my wife, she explained, she had to stay sexually potent and since I was a sissy it would be hard for us to really have normal relations of any type. While I always understood this is what life would be for me, and to tell the truth I knew it since the moment I met Jessy all those years back at that mall next to PJ's, while the shop girls watched amused as I fumbled around the ladies, once in a great while I still get little twinges of guilt.

It's not like I would want to or could fuck a girl other than Jessy. And for sure any girl other than Jessy would not interest me anyhow- she's the only one I can love. But once in a while I feel a little sad we don't fuck much, and that she gets to fuck other people but I don't, and that she has so much more sex than me with better men. It's not like I want to fuck other people, I just don't get to. I do get fucked by men fairly regularly, but I know the feeling is different and sometimes I just want straight sex with my wife where I am in charge. I wonder if it has something to do with my body's natural libido ebbing and flowing over time, as the seasons change.

On one occasion I was particularly horny, and as Jessy asked that daily question for my sleeping plans, I thought I'd stand up and maybe get her to fuck me. After all I am her Loving husband. "Baby, how would you like to go bed tonight?" she asked sweetly, handing me the option three menu- "Cock Concentration," "Pumping Iron," or "Major Enema." I stammered out- "I want to have you tonight, Jessy my love." The words were well rehearsed, I had spent most of the day in front of the mirror considering them carefully, but the delivery was squeaky and begged her to say no.

I'll explain the Option 3 menu items before I go on. They are boiler-plate and not particularly scary or fun, although I had 'leveled up' Pumping Iron several times and Jessy had made it more challenging for me. Cock Concentration is a memory skill game where I suck literally dozens of automated dicks, which are on a sort of storage belt and get shown to me one at a time. The first time I suck a cock, I get a yummy reward, not like cum but closer to honey. The game is to suck each dick once, and if I accidently suck one twice then I get a gross, sour liquid and I have to put the dildo up my asshole. Just once, nothing fancy, but sometimes I end up making a lot of mistakes. Jessy offered, "Well... we could say you have to just suck each dick the same number of times, so if you suck one twice you have to re-suck the rest..." Pumping Iron is more of an endurance sport, I have to pick up five pound pink weights higher than a certain level in the room a certain number of times and if I wait too long in between efforts the counter goes up (Jessy 'leveled' me up to 400 pumps and a 5 second maximum rest). The TV shows an ultra-feminine workout tape for this, interspersed with rare "this is why you do it" lyrics and cock videos. And, last but not least, Major Enema is a military-themed game where I take enemas delivered by a dildo and drop them off (as soon as I want) in the appropriate toilet. The monitor has 'training sergeant' who says where to go before the enema starts, and then degrades me and tries to throw my memory as it is delivered, before saying "Off you go, little lady!" to let me go to the right toilet.

"Jessy, my love." Had been the last few words out of my mouth, and these sounded the strongest. My hopeful request to sleep near her, seemed doomed to failure but Jessy figured it would come sooner or later and she had a little plan ready for when it did. Smiling, she said, "But Brendie baby... you are a girl and you know I like men." Now I obviously had my cock and could still get hard, but I was also a practiced and good sissy, and currently wearing some sort of 'everyday' lingerie that was mildly sexy but relatively comfortable.

She continued after a long pause where I could have said something- anything- but remained silent and started looking guiltily downward. Now Jessy could have taken it to me, punished me and said 'Never again' without being at all out of place. She took a slightly different route, like parents sometimes do with young children who are misbehaving. "Brendie, baby, you like being a girl, right?" "Yes." This answer, probably due to hypnotic suggestion and mere repetition, came out fast and firm, as a given known to my mind. "And baby, girls fuck guys, right?" "Yes.", equally firm. "So baby, what are you saying? Do you think I am a boy or are you saying you are a boy or that guys should fuck other men or that girls should fuck girls using strapon dicks? What do you mean?"

I stammered a bit, kind of losing my train of thought. "Let's fuck" was a bit beyond my ability to fit into Jessy's logical web of contradictions and facts, known truths and possible minor sins. So I was already doubting my original idea. But, then I fell into another idea- and this is what Jessy and I would do the few times we did have the same bed. "Jessy, can I make you orgasm and then cuddle with you?" I asked, confiding in her my true desire to make her happy and my true apathy towards my own cock or any orgasm I may have. While I'm not entirely sure I was really thinking that way back then, my actions that evening and almost every time I've been allowed near Jessy have proven it true.

Once in a great while, sometimes after I really impress one of Jessy's men and sometimes after I do something really hard and different for me, Jessy will say "Yes" if I ask to sleep next to her. We sleep sort of like sorority sisters, I'll make her cum and she'll play with me kind of like if I had no cock, without directly stimulating it. Jessy was always happy to let me cum if I wanted, but if I was in her bed she wasn't going to cause it. "It's OK, Brendie, just be sure to wash my sheets tomorrow." she would say helpfully if I came in her bed. My wife was always very understanding about issues like this.

If I was bad I wasn't getting in Jessy's bed, but if I was really good sometimes we would watch a romantic movie and she would play with my nipples, or we would get two vibrators that synced with each other and she would control their speed. Also she liked to put largish penis gags in my mouth and then cuddle with me, or tickle me, as we laid together.

While we do occasionally have sex, normally I don't get to stay in bed with her after fucking her. Our sex is more of a 'rapid fire' thing, when she wants it, and we do it different ways- sometimes normal sex, more often she uses a strap-on with my, and even more often she puts me in a strap-on so "I can please her" and "Be a girl just like me, having fun imagining about real penises."

Certainly sleeping with Jessy is a reward for me, and it lets me out of the normal nighttime punishments (Option 3, the cock-bed, or sleeping under her bed tied spread-eagle). And that's the way I want it, Jessy is my special lady and every moment I get to spend near her is precious. I almost never actually fall asleep next to her, instead, I spoon her softly and listen to her breath, feel her light weight partially on my arm, and imagine about the future and the past we've had together. Jessy is my favorite and I appreciate every moment we get to spend together, when she is able to justify it and let me be near her. As a sexy, hot babe Jessy has lots of other things on her plate so I know these moments, when I can spend the evening right next to her, are numbered and rare. It makes me appreciate her and our relationship all the more, and I love my wife Jessy.


Pain Day

Jessy loves to have fun and enjoy life. At some point in my relationship with her, I am Brandon, she said something special and hard: "Brendie, would you like some pain?" I agreed immediately and smiled. She too was happy. "OK baby, let's take care of you. This will be hard."

I was a bit surprised that Jessy started to be explicit. She was always careful to soften or anneal the work she offered to me. "It will hurt, but I will think you are more of a man." she said calmly. I was a bit scared as I listened. Our relationship put me through a lot, and as her sissy partner she had me perform humiliating tasks. At night, we had arrangements so I seldom got more than a few hours of sleep, and life had become something of a normal fog to me. "It makes you just like a blonde bimbo!" she used to tease, but that has become just normal now. I routinely would forget I brushed my teeth and do it again, or get started applying makeup only to see I already had it done. Also I tended to make lots of little mistakes. "Brendie, just concentrate a little more on what you are saying and doing, and a little less about your favorite cock or what tonight's Option 3's will be like." Jessy said helpfully when things like this happened.

Jessy has done very well in training me to default to certain responses- for instance, yes/no questions are almost always properly answered with a sure, confident smile and a bold 'Yes', and questions like 'Am I ...' and 'Are you ...' from her are also normally answered in the affirmative: 'Yes I know that [repeat the statement].'

In this case, Jessy was getting me to buy in to what would be a Saturday of pain. She sometimes spent more time with me on the weekends, since I didn't have to go to work, and sometimes she would go date one of her boyfriends or shopping. I was a bit happy to know I would be the focus of her ministrations for the time being.

"OK, here we go baby. I'm going to make you hurt a lot today, so much that it'll up your pain threshold. Are you excited?" she cooed. "Yes Mistress Jessy." I replied, again confidently and immediately. "Come on, let's go." she said, and as we drove she reached over (I never did the driving when we went somewhere together) and played with my cock. "This is going to be fun, Brendie. Aren't you excited?" "Yes, I am." "Her name is Sarah and she will be helping us out. And I think Amy will be there too. I can't wait." The trip was about an hour, and took us into remote country and finally a farm site with a large machine shed. Getting out of the car, a women wearing ranch-like clothes came out and met us. Smiling happily, she said "You must be Jessy and Brendie! Hi!"

We met and she ushered us into the house, where we had a light brunch. Sarah, Jessy and I talked normally and got to know each other, while they kept eluding to details I had no idea about: "So we want Plan C to be on the table?" "Yes, of course!" They would weave questions in strange spots during the everyday conversation that was going on at the same time: "Yes, I like Johnson hot dogs." "Well, they are the better cut on beef." "Hmm... and we still agree about the Cut Rule, right?" "Of course! So where do you use hot dogs?" "With potatoes... sometimes scalloped potatoes and franks cut the long way work well together."

As the food wound down I cleared the table, did Sarah's dishes (she had a couple sinks full of dirty dishes), and got the ladies tea to drink. Amy arrived and everyone was ready to start.

"So, girls, let's get started with Brendie here." Almost as if on schedule, I felt a strong gurgle in my stomach, and a slight cramp. "Brendie had some extra ingredients in her food that will help make her day more fun. A sort of gut de-stabilizer, the key ingredient makes the digestive system behave similarly to if you ate something way too hot and wanted to vomit- but nothing comes up. In a half hour, she'll be bending over in pain. The effect normally lasts quite a while, at least three hours."

Amy and Jessy thought that was great, and started asking what exactly the ingredient was and how it worked. "OK, OK, let's go to the shop before Brendie gets too bad." Sarah suggested helpfully. So we all went out, the large machine shed was of course Sarah's dungeon. Not really sound proofed, and with just one person-sized entry door, the shed had plywood interior walls and was sectioned into two main sides- the back half had a plain dirt floor, and the front half was concrete. Near the entry was a large bank of shelves and cabinets, at the opposite side were about a dozen 'jail cells' and two 'tiny' 3 foot square cells. The place was brightly lit and had audio and video set up throughout, with a nearly theatre-quality projector on one full wall.

The cramps were starting to set in, although nothing like Sarah had described. My stomach seemed to be making a decision: was that food OK or was it bad. It had tasted totally normal. Looking down, I could literally see my stomach and end trails vibrating, trying. I was a little afraid.

"So let's start! Sissy, come here, eat this!" Sarah yelled helpfully. I was a bit concerned but ran over. Amy was already laughing out of control. "Brendie, go for it! You will love it!" she said loudly. I ate what looked like an apple and then some grapes off the vine. Smiling, both girls looked directly at me. "Well, maybe the effects come on a bit quicker if you eat something acidic." Sarah said helpfully. I did feel a strong change, maybe they 'enhanced' some of the food they fed me.

"Let's get you ready!" Sarah said happily, smiling and blinking rapidly at me. I was getting scared. She ended up tying me deep in a form of pain I never experienced before.

We walked towards what looked like a high tech inversion table, with a padded board that would like the person laying on it be spun in different directions. It also had what looked like several shower heads, a tiled surface below with a drain, and some large HVAC air vents pointing toward the center.

First she shoved a couple high tech ear buds in my ears, which muted the outside world and gave me a specific program. The next thing was contact lenses, scary for me, which had a two-mode functionality. Mode one was simple: blind me. They would turn opaque, giving me what the girls explained as the "look of a Martian" or even a real blind person. On my side, the lenses still could produce vision for me, a special vision that I could not avoid with my eyelids. I got a first taste which was obviously for humor: it closed off and said "Hey Brendie, I hope you are readie!" in a sort of stenciled aerosol paint can effect, bright red. Then, as if to show the capabilities of the system, I was watching a high definition scene of fish in a coral reef.

The other function was perhaps superfluous: it would force my eyes to be open. While some similar devices measured light to imagine if the eye lid was open, this one had integrated sensors to test for pressure. The subject could be forced to open his eyes in total darkness, or 'see' whatever it projected. Its internal mechanism had an RFID tag which reported to the overall discipline system. So why would I need to look if it could feed me video?

At this point Sarah's 'real-life' voice probably went away, although the earbuds were high enough quality I was unsure. She said to me "Baby, what do you like the most in the world?" and immediately was looking at smart, successful men with obvious erections: business suits and bulges.

To further confuse my senses, they kept my clothes on but inserted a butt plug and strapped me to an inversion table. Then, with my stomach starting to turn for the worse, they demonstrated the table's abilities: I could be turned upside down, rolled like a log, and spun in any direction. "Pitch, yaw, and roll." Ann said simply.

"The way this is going to work is every time you see a cock, you read the caption out loud. And every time you see a cunt, you yell 'Yuck'. Jessy and I will rate you based on if we believe you, and if you say the right things. Jessy will have cold water to spray you with, and I'll have hot water. Don't worry, it won't leave permanent damage. We also have a strong fan system and heat controls at our disposal. And we'll help your little tummy by keeping you moving. This is going to be fun, aren't you excited?" Ann said happily. "I can't wait to get started!" I said anxiously. This seemed like it was going to be very interesting indeed. The cramps were starting to be painful, and my stomach and gut were making a lot of noise, as my ear buds started playing a white noise sound drowning out anything the two ladies may have been saying.

Giving me a starting spin, the first images came up- a handsome man, wearing a suit, walked over and exposes his penis. The camera zoomed in and the picture added an overlain caption reading "I want to suck your dick please Mister." I read it out loud, hoping to be convincing. Obviously I wasn't convincing enough, because I felt scalding-hot water hit my feet and legs. Seconds later, a blast of cold water hit my head. They repeated this on and off for about fifteen seconds, sometimes getting water in my mouth and making me gasp for air besides the normal effects of cold water on your back and neck. Their blasts were timed to make me spin head over feet, horizontally so that my head and feet made a circle like a merry-go-round would. The table had a low friction device and it probably would take thirty seconds to stop after a fairly quick spin, slowly losing momentum.

Next the image changed to a female porn star. I waited, expecting to see her undress. That was not the right move, and immediately the ladies started spraying me. They switched sides, and for a moment the hot was warming my cold head and the cool was helping my feet. That little pleasure lasted just a second or two before I was again being pushed to thermal limits of pain. I wasn't being permanently hurt, but it was close. Realizing what I needed to do, about ten seconds later, I yelled "Yuck!" and the blasts stopped. The next image was also a porn star and I yelled "Yuck!" immediately, and for the first time earned no punishments.

Someone started me spinning again by hand, making my body literally go head over heads (vertically now, like a Ferris wheel) and with a slight log roll motion. Along with the stomach cramps, I was starting to think my best option would be to throw up. The next image was a football star, and as he was walking on the field it looked like I was sitting in the bleachers. My first phrase was "I wish he would come say hi to me, he is so handsome." which I apparently said well enough because I got a small reward- dry, warm air started blowing down on me.

The video continued, after a fade-out, with me next to him and he was wearing street clothes. My line was "Come up to my bedroom baby." and I only earned a bit of hot water as I said it. The final video in this series was one of him masturbating, and my line was "I wish my tiny penis was big and strong like his. Maybe I can at least put his penis in my mouth." I didn't do well on that line, and said 'it' instead of penis in the second sentence. This earned me the longest punishment yet, and when they were done the air breeze was an uncomfortable cold temperature. The water evaporating off me made it worse, and the cramps were getting unbearable. It was like the cramping increased as my body was forced through different unpleasant temperatures. Again I got another push, this time I was almost in a log roll with a slight twist in another direction. With my eyes forced open, and seeing what looked like a normal horizon, my body was having serious issues dealing with my inner ear and other senses of gravity, like the pressure the straps placed on me as I spun.

Next was a hot schoolgirl and I yelled 'Yuck!' immediately and enthusiastically. The air became markedly warmer as a reward. The next image was a group of black men with the first line "You guys seem fun! Let's watch a movie at your house!" The scene changed, and all three were in boxers. One by one each showed their penis, and I had to say "I love how long and big your cock is Sir!" to each one at a time. Before the fourth penis, a female porn star was shown, and I yelled "Yuck!" again. I seemed to be doing well at the game, but the nausea was getting to me and I had to vomit.

Chunks fell all over my body, still in the clothes from this morning. I continued to dry hurl, not responding to the screen, as my insides felt like they would tear themselves up. The ladies blasted me for about five or ten minutes as this went on and I couldn't say anything, still struggling to get my chest toward my knees to get a better position to throw up in. I think I cleaned my stomach out, and the butt plug they had inserted was getting very close to going too.

They decided it was time to offer me some choices, and a pre-recorded video appeared to me as someone stopped the table and put me in a normal standing position. It was a bit surreal, kind of like imaginary heaven, and both Jessy and Amy stood in front of me with normal clothes smiling. Jessy started first, and a light cloud of fog started spreading from behind them toward the camera: "Sissy Brendie, we know you are getting a bit anxious and uncomfortable." Amy chimed in smiling, "It's like your first real period! Painful, right? Well... we can help you out."

I was still struggling hard and making noise, but their voices were pretty loud. "If you want us to let you poop, make your left hand into a fist. We'll pull out your butt plug (giggles) and see how long you can wait. You will be getting an enema after, but the longer you manage to go before pooping, the smaller and more comfortable it will be." Jessy said helpfully, while Amy chimed in matter-the-factly: "For instance, if you poop before ten simple minutes are up, you will have chili pepper in your enema."

The Jessy started speaking again. The fog was at least waist height, and I got the impression it would fill the video once their interlude was done. Of course I was still dry hurling, so it wasn't really much of an interlude for me, but at least I wasn't expected to yell lude comments to male porn stars.

"Option 2 Sissy Brendie, if you make a fist on your right hand, is interesting. Or, you can continue the caption game like before as long as you don't make either fist, but we'll start requiring a bit more enthusiasm because we are probably getting bored." "Yep!" Amy added. "So.. option 2 is an oral challenge. You will be trying to get as much cum as you can into your mouth from dildos, and then you will dump it in a bucket we put under you, attached to your plug. Once you fill the bucket, the plug will get pulled out. Then, if you make it to a toilet, you can poop and come back to swallow all the yummy cum. But if you poop in the bucket or miss the toilet, we'll make you mix you poop with the cum before you eat it. So... three good choices, Sissy!" Jessy finished. Amy said smiling slightly as the fog filled up the room in the video: "If it were me, I'd go a bit further in the caption game first, maybe it would settle your stomach princess and I just know you enjoy looking at those beautiful cocks!"

The video left, and my eye pieces showed a simple diagram showing my choices and which hand to use for each, reminiscent of a Chinese manual. In black and white line drawing. Cutely, it illustrated poop like a carton with lines emanating for emphasis. It also had a caricature of Amy happily holding both hands open and a label '..or keep going!' with another happy face. My stomach gave a particularly bad groan as my contact lenses turned see-through for the first time since we started the caption game.

Amy and Jessy were there, smiling from a desk. Jessy said "Having fun?" and Amy chimed in, "I want you to keep at it baby, I know it's so good for your subconscious to see and hear you make good choices. We'll start it back up, and you can pick either option using your fists at any time." I watched them smiling and got to see them both unleash a blast of water towards my crotch and then quickly down my legs. Of course that pushed my legs back and spun my head forward, like falling, and I saw the ground coming up. My stomach and bowels didn't like that one bit as my contact lenses faded in with some sort of visual effect, and I was back planning captions.

While Amy seemed to want me to continue this brainwashing task, Jessy seemed supportive of me no matter what. A little part of me wondered if Jessy wanted to eventually have me be like a man, and if that little piece of her worried about me getting too good at captions. Amy would have had no such worries, but she did also mention I maybe could get my stomach a little more settled before I started worrying about enemas and pooping at the right time. As for the options, either I could poop at any time with no clear punishment but maybe a worse enema, or poop once I got enough cum out of automated dildos. Each had its own 'punishment'- enema or drinking a lot of cum- and I wasn't looking forward to either. It wasn't really a factor but I knew holding my bowels would not be training me to be a sissy, since anyone can do that, where the caption game and all the cum in option 2 were obviously girl.

I stuck it out with captions for probably another hour. The images came in sort of groupings, there were ten in a row with close-ups of assholes and I got good at noticing hairs, balls, or the shadow from the balls or penis. Another interested series had me yelling things like 'I'm lost, can you help me out?' or 'Can you help me find a place around here?' or 'I lost my coat, did you see it?' to men who were attractive and fully dressed; another, more twisted, had me try to cat-call men who were apparently working in my house ('For a plumber, you have a hot ass sir' 'How do I turn on the light bulb, can you help me?')

So it went, and I was calming down somewhat in the general torso region. I am unsure if Amy gave me a secret, but I think she was trying to help me pass whatever other challenges came up. Growing bored of captions, and I was doing quite well at yelling 'Yuck' for girls even when there was a normal caption under the image, I decided it was time for change. I balled up my right first, really feeling a bit horny and wanting something in my mouth. One or two captions went by before the ladies noticed and started extricating me from my table. The last one was 'I love the caption game so much maybe I should do it at home!' to a group of six hung black men smiling and laying down, as if they had just finished an orgy.

My contact lenses turned see-through again, after a video showing various videos of cocks being examined up close faded away. The Mistresses had me on my feet and walking towards the next game before that happened, so I was blind as they unstrapped me. Also I felt my clothes being taken off, and Ann (I assume Ann) had to keep me from falling several times because the penis program kept throwing me off balance. My gut was almost feeling normal, although I definitely wanted to shit and I was wondering if any of the penises in the video would be modeled in what was coming up for me.

Ann had me walk to the other side of the shed, with the dirt floor, and opened a door: it had a lot of gang tags and was beat up, with the ubiquios 'ladies' room' sign on it. Of course there was a glory hole, but the toilet would be right there for after. She pulled my legs apart and set ropes, holding my feet far apart as she lowered me to my knees and leaned me forward towards the hole. Obviously I wouldn't be looking any men in the eye, at least not in real life although my lenses were always a thought.

"Suck as much cum as you can into your bucket." Ann related calmly as she put a gallon bucket on the floor in front of me. "When you think it is enough to help you let your butt plug out, yell 'Fuck me now' and we'll come pick you up and attach the pail to your plug. If all goes according to plan, you'll be able to let it out and take a nicer breather on the toilet here. But if you get stuck, well, that would be a bad thing." Ann continued with a smirk.

Leaning slightly forward, a penis emerged from the glory hole. It was large, black, two prominent veins. As I leaned forward to start on it, and the look was definitely real, I heard a 'whoosh' noise and felt a whip hit me on my back. Hard enough to scare me, soft enough I knew I might be in store for a lot of whipping. "Pain day." was Jessy's simple explanation. Ann went into more detail: "Baby, if there is a cock that isn't satisfied, this whip will be going. It's really based on the scale under your bucket, you'll need to maintain a certain average speed and of course since you are just starting that average is zero..." as she shut the door and they all walked away. Jessy later related they had a nice meal, toyed with some of the men who had come to the farm for a free blowjob, operated some of the fake dildos (since some dicks were real, the fakes seemed much more believable), and finally how they backed up the toilet.

The toilet bit was especially clever, sucking dicks as I was I almost didn't notice the shitty water overflowing from the toilet onto the dirt floor below, or how it seemed I was in a minor depression, until my legs and feet where covered in piss and shit. I glanced at the toilet and saw it was full; disgusted, I started wondering if I would be able to use it to shit after this mess. I had maybe a half inch of cum in my bucket, and while I had no way to tell how much weight I was going to need, my butt plug was feeling very snug and my calming bowels weren't going to give me as much help as they might have.

I love my wife Jessy, and we are great together. She knows my future before I can imagine it, she takes care of my needs and wants before I realize I have them. Ann would go on to help Jessy in ways Amy just couldn't, and I am so happy we had Pain Day that I can't imagine summarizing the events that occurred in the late hours in this one chapter.