THE DOCTOR

The receptionist was a tall, large breasted African-American woman with long braided hair streaked with red and gold. She looked at me like she had never seen me before although this was my third visit to Dr. Weinstein.

"I have a 2 o'clock appointment," I said.

"Your name?"

"Allen, Jon Allen."

She looked at the computer screen on her desk, flicked a couple of keys before saying "Oh the sissy boy, she will see you at 3."

Sissy boy! Did she call me a sissy boy? There were three other people in the waiting room, two middle aged men and a younger woman, who I am sure heard what she said. I was somewhat flustered and didn't know how to respond so I said nothing about the sissy boy thing and instead pulled out my card showing her I had a 2 o'clock appointment.

Looking at her screen she said "Yes you were to be here at 2 and she will see you at 3."

"Oh is she running late?"

"No she never runs late."

Confused I said "OK," and turned to take a seat to wait but she stopped me.

"She wants you to,'' reading from the screen "stand against the wall over there with your nose on the red dot."

"W w what?"

"I think you heard and understood every word I said," standing up to her 6'4" height she continued "and if you don't want me to come over there and make your afternoon a very different experience than you better do it right now," and then for emphasis she added "sissy boy."

I could feel all the eyes on me. I knew I could just walk out and face those consequences but I was so intimidated by this woman that I just meekly went to the bare wall she indicated. There was a red dot at roughly the height of my nose. I pressed my nose against it and waited for my next instruction.

OK time for a little backstory. My name as I said before is Jon Allen. I am a recent college grad. I went to New York University and got a BA in BS. In other words, a liberal arts degree. I grew up in New York City in a large duplex overlooking Central Park. Money was never an issue in my life. My mom is a wealthy business woman running several different businesses. Her latest venture has been in real estate. I have a sizable trust fund which I will come into in a few years and a generous allowance I hardly spend. Dad is never spoken of so I have no idea who he is. Mom owns several garment manufacturing companies mostly based in Asia and is on the road a lot and so I was raised by nannies and housekeepers. I have never been close to anyone but her. I am not good at social interactions to say the least. What I am is a social Chernobyl. I have no friends, never dated. I went to NYU so I could run home after classes to the sanctity of my room The psychologist started when I was about 12. There had been six. They tried every therapy you can imagine from wilderness programs (second day out I curled up into the fetus position and refused to come out of my tent); art camp (painted a canvas totally black and returned to the fetus position); performance therapy (they did Shakespeare; I did fetus). Right after my 18th birthday a woman doctor set me up with a sexual surrogate, who was supposed to teach me how to be intimate with a woman, including real intercourse. I won't tell you how bad that went except to say I believe that woman is now selling perfume at a Macy's in Jersey. Dr. Weinstein was going to be my last chance. If this didn't work, if I didn't try real hard then it was going to be tough love and I was going to be cut off from my allowance and trust fund and forced to move out and live on my own.

Dr. Rita Weinstein's office was in lower Manhattan in an area called Tribeca. It wasn't an elegant testimonial to modern medicine like the other doctors I had seen. This was up a flight of stairs in a old office building of some kind. The doctors name was not on the door; a sign next to the door said "Suite B2" and below that a hand written card said "Ring for Admittance." I pressed a button next to the card, heard a bell ring in the office and a second later a buzzer alerted me to come in. I did. The receptionist I described earlier took my name and told me to sit. I was the only one there but decided to sit in the back. In five minutes I was told to go in.

Dr. Weinstein is a 50ish year old woman, a tad bit plump, and a couple inches below my 5'9". She has short brown hair with streaks of gray, she wore frameless glasses and little make up. During my first two visits she wore the same gray pinstripe suit and white blouse buttoned to the neck with a broch spanning the collars. The very model of a prim professional woman. During that visit we spoke about my life, my other therapies, why I felt they didn't work and what I wanted to get out of this and how hard I was willing to work to achieve it. I thought it was a nice and all but totally useless.

The second week was totally different. Once again I waited for about five minutes with the scary receptionist before going in. She, as I said, was dressed pretty much as she had the previous week but what was different was the week before we had two comfy chairs in front of her desk where we sat and faced each other but now there was only one chair facing her desk which had a large computer screen. On the desk was a headband with a bunch of electronic things attached. A small arm protruded from the front about 8 inches a another gizmo of some kind hung there. I looked at the doctor.

"This is my own protocol. It is simple really. I am going to show you a series of pictures and using these," she said indicating the headband and a laptop "I can measure your responses".

I asked about the thing sticking out and was told that would track where my eyes went on the picture. "The first pictures are pretty generic but once the computer sees a pattern it will try to get more granular. For example, if it sees you react to red haired women it will try to determine if you like tall or short red hair woman, long or short hair etc. Understand?"

I said I did, she hooked me up and we started.

The first picture was that of a pretty girl about my age. The picture stayed on the screen for about 5 seconds and then was replaced by that of a male, the picture was nearly the same. Same background, same color of clothing, same dark hair. They even looked alike. As I thought about it the picture changed. This was another young woman. Her hair was a different color, blond this time. This was followed by her male counterpart. Another half dozen pictures followed, all pretty much the same except I started seeing more girls than boys and the pictures started getting sexier. I mean the first dozen or so pictures were like yearbook pictures, just head shots from the collar up then I started seeing more skin. Not much at first, just bare shoulders but then I got pics showing more body, both male and female. One button undone, then two, then three. Cleavage and glimpses of lacy bras or hairy chest. Next were bikinis and Speedos. Twenty minutes in and I saw my first nipple (female) and naked ass (male). Soon there was full frontal nudity. A little later there were the first couple's pictures. Namely two women kissing. Then naked men fondling each other. Then a couple fucking missionary style, then m/f anal and oral. Two woman sixtynine-ing. Three woman doing something too complex for, me to understand. The pictures were getting raunchier and also changing quicker. Then came the first kink picture. A women was tied spread eagle on a bed. The next picture was another woman tied to a cross her back covered in welts one had to believe from the dominatrix standing on the side with a single tale in her hand. Well that was interesting. The picture was on the screen for what seemed longer than others, then I remembered the little camera looking at what I was looking at. I was looking at her. The next picture was similar but the dominant was a man, a few more other fetishes; a guy dressed as a raccoon, yeah I don't get it either, weird Japanese porn (lots of tentacles with dicks on the end), chicks with dicks, a male maid and other crossdressers. Soon three out of four pictures were BDSM related subjects. A picture of a man bent over a padded bench, his ass red from the paddle a woman held standing next to him. Next were two women tightly tied together, hanging from an overhead hook, their toes barely touching the ground. A man laid on the floor, his cock in a metal cage a black Domme sitting on his face. You get the picture. Soon it was all F/m stuff. I was shown a wide variety of woman. Some were TV beautiful, some were pretty ordinary. Black, Hispanic, Asian and white. BBW and thin as a supermodel. Eventually the woman and activity in the pictures became more and more similar. And then it stopped. The final picture remained on the screen. A young man wearing only a pink leather collar and matching gag stood holding a tray. A wine class sat on it. Sitting in a chair next to him was a woman in full dominatrix drag. She was older than the slave, with long dark hair and a toned body. Several whips, slappers, cats etc. lay at their feet. After a minute the picture shut off.

"Thank you Mr. Allen. I will see you next week."

I was dismissed. I had a huge erection.

I was thinking about all that when the receptionist said "Alright sissy boy, you can go in." As I walked past the people in the waiting room I realized there was no reason for them to be there. The waiting room was only for her patients so why would there be people sitting in it for an hour other than to see my humiliation. I did not make eye contact with anyone and went in to the office closing the door behind me.

The office had been rearranged again. This time there was what I think of as a traditional psychiatrist couch of brown leather. Next to the couch was one of her chairs. There was the computer monitor sitting on her desk where someone laying on the couch could see it. Something else had changed. It was subtle but the doctor seemed to give off a sexier vibe than before. She wore a little more make-up. Her lips seemed darker as did her eyes. Her blouse wasn't buttoned all the way up as before and I am sure she hadn't been wearing high heels in the past. Maybe she had a date later, or maybe it was for me?

"Please lie down on the couch Mr. Allen," I did. "Is there anything you would like to say before we discuss my findings?" I said no. She was sitting in the chair looking down at me, a bit intimidating. She had a notebook in her lap and an iPad in her hand. "The protocol I use is simple and complex at the same time. As far as sexual attraction goes most people think they are straight,gay or bi. but that's too simplistic. Many people are attracted to both sexes even if they have no intentions of physically acting on that attraction. I give a value to the attraction 10. You can be a 10/0 or an 7/3 or a 5/5. You are a 8/2. With the 8 representing your hethrosexuality."

"You are saying," I asked "that I am bisexual?" I was surprised at that.

"No I am saying that under certain circumstances you find some men interesting."

"Oh."

"We will get back to that. How often do you masturbate."

Well that caught me off guard. How did she know I masturbate? "I, uh...I don't..."

"Mr. Allen, you are not going to tell me you don't self-pleasure. Please." She looked at me like I was crazy. "Would it be safe to assume most days."

"Not every day," I said still being defensive.

"Did you masturbate today?"

"Yes," I said in a small voice.

"Yesterday?"

"Yes."

"Every day since you were here last week?"

"Yes."

"Do you recall the last day that you did not masturbate?"

"A couple of weeks maybe..." I had no idea. My name is Jon; I am a masturbator.

"When you masturbate," she certainly liked using that word, "do you look at pornographic pictures?"

"Yes."

"Naked woman?"

"Yes."

"Naked men?"

"No." Finally a no.

"People having sex?"

"Yes."

"That would include naked men, no?"

"I guess, yes." Damn.

What percentage would you guess was female domination material?" She asked. I knew the answer and I believe she knew it to but I hemmed and hawed a bit, "Is it 25%, 50% more?"

"Maybe." In a very small voice.

"100%?"

"No!" Yes.

She wrote something with a stylus on her iPad. Then a picture popped up on the monitor.

"Do you remember this picture?"

I did. It showed three people in a room. Two males and a female. One of the males was naked and in some complex rope bondage. The second male just wearing street clothes, had a crop in his hand and seemed to about to strike the naked male. The female in the picture was sitting in a chair off to the side and seemed to be enjoying the show. All the people looked my age and looked normal.

"You had a strong positive reaction. On a scale of 1 to 5 you gave it a 4."

"Oh."

"On the other hand you gave this one a 1."

The next picture to pop up was a scene in a dungeon. A man, bound and naked with another man holding a crop. This time however there was no woman in the picture and the Dom was dressed in leather to the point of being a cliché."

"What does that mean?" I asked.

"What do you think it means?" And then when I started to struggle with words she said "Never mind let's get to the crux of the matter."

"From what I see in your test results I believe you are a sexual submissive. You are attracted to "the dominatrix" meme. You have a rather strong fetish for the accoutrements traditionally associated with the BDSM world. The leather garments, the various bondage and torture tools. You have a desire to be humiliated. You are drawn to the "clothed female, naked male" scenarios. I think being made to wear certain woman's garments would be pleasurable for you. Undergarments, sexy nightwear or "the French maid" look. Anything that displays a rejection of what is considered traditionally male. You are not homophobic and I think you would be comfortable being submissive to a male dominant if a female dominant was present. I do not know if you would have sex with the male. You would also be comfortable with other male submissives serving women. "

Well there it was. My total inner turmoil wrapped up with a pretty bow and laid out in front of me. She had stopped speaking and was looking at me. I tried to say something but didn't know what to say except "Yes," in my smallest of small voices.

"Do you enjoy pain?"

I like the concept of pain and I like the idea of being whipped or spank but didn't know how fantasy pain would be compared to the real thing. "I don't know," I squeaked out.

And then she absolutely shocked me. She put the iPad aside and bent down and reached under my shirt. She grasped my right nipple between her thumb and finger then squeezed and twisted it hard; and it wasn't a quick tittie twist. She held it like that for a good 5 seconds before releasing it. She then did the same to the other one holding it for even longer this time. Nothing needed to be said she could tell from my face. She made a note on the tablet.

"Is any of this new to you?"

"I guess not. More detail than I ever thought about." Then I got a little brave. "Why did the receptionist do what she did?"

"I told her I wanted her to push you around to see what you would do. The waiting room is her domain. She does what she wants out there. She is pretty good at knowing what should be done"

"And the people there were just there to watch."

"Yes. They are acquaintances of hers."

"And what if I didn't do what she said?"

"Well knowing Renee I suspect she would have pulled down your pants, taken you over her knee and given you a serious spanking. She has done it before. She keeps a well-worn leather paddle in her drawer."

"Oh."

"Well your hour is almost up. You won't be seeing me next week. I want you to see this woman at the same time." She handed me a business card.

"Is she going to cure me?"

"Cure you? On no Mr. Allen..."

I looked at the card

"...she is not going to cure you of anything..."

Printed on it was a name.

"...she is just going to make you good at what you already are."

Mistress Evelyn Winters, Dominatrix.


THE DOMINATRIX

Although I lived in NYC my whole life I can't remember ever being in Brooklyn before but that was where I found myself a week later, standing in front of an old but well-kept brownstone. I looked at my phone to check the time. I had been looking forward and at the same time dreading this moment. I climbed the half dozen steps and as the time on my phone turned over the next hour I shut it off and rang the bell.

A minute went by before the door opened enough for a head to peek out.

"Can I help you?" said the head. It was a young head with a slight goth-punk thing going. Lots of ear piercing and one in the nose. Hair was short, black and spikey and her eyes and lips were dark.

"I h..h..ave an appointment."

She looked me up and down, her eyes penetrating to my inner soul. I half expected to be told to get the fuck out of there. But instead she said "OK, c'mon in." She stepped aside and opened the door wide enough to let me through and then closed it with a loud click. I hadn't expected someone so young.

She was wearing a pair of torn jeans, not the kind of chic pre-torn but a something more organic and a black and red Mettalica t-shirt. She had a small tattoo of a pixie or something on her wrist. She picked up a pad that was sitting on a small table.

"Jon?"

"Yes, Jon."

"OK, wait here." She walked down the hall and opened a door a said "Mom, your two o'clock is here."

When she came back I said "Mom?"

Laughing she said "Yes Mistress Eve is my mom."

Wow that was a shock but it shouldn't have been. I know that there a lot of people out there into kink but I never thought of them as people with the same kind of lives as everybody else.

I tried to be nonchalant about it and made a little joke "Discipline was probably pretty stiff growing up?"

"Well yes and no. Mom's pretty much a softie. Grandma, now that's another story. She caught me stealing when I was 15. She gave me a bare bottom spanking I still wince about to today."

"Grandma. Is she a a a..."

"She likes the term Domme. Yes. Mom is second generation at least. There is some evidence about great grandma too but we are not sure."

"Are you going to carry on the family tradition?" I was fascinated.

"I don't know. I like sex and I like kinky sex so we'll see. Haven't figured myself out yet. Did you do Rita's machine?"

"Dr. Weinstein? Yeah. Kind of freaked me out a bit. You do it?"

"No. Maybe after I graduate. I am in my final semester at NYU. I have been on the six-year plan."

"That's where I went. Graduated last spring."

"Oh yeah. Don't think I ever saw you."

"I hid a lot."

She laughed. We had been standing in the hall just inside the door. "Ok Mom, Mistress Eve to you, said to wait five and bring you in. So you ready?"

"Sure," I lied and we headed down the hall. On the way I reflected on what just happened. I had a normal conversation with a girl my age. Well sort of normal, we did discuss the fact that her mom, grandma and possibly great grandma were dominatrixes but that wasn't the point. The conversation wasn't as smooth as I presented it here but it was a big deal to me anyway. When we reached he door she had spoken into before she stopped and said to me "You know that thing I said about Mom being a softie? Well that doesn't apply to you." She knocked on the door once, waited a second and opened it and stepped aside all the while never breaking eye contact with me. And the fly stepped into the spider's parlor. I had been thinking about it all week. By the time that day arrived I had this vision of a Valkyrie biker chick. Not quite.

The room was a small study. One wall was book cases, opposite was a small table and two chairs. Directly in front of me sitting behind an antique looking desk with her back to a window Mistress Evelyn Winters, Dominatrix.

"Hello Jon," she said with the barest hint of a smile. "I'm Mistress Eve."

From what I could see at that point was she was a 40 something woman with long dark hair hanging free down her back. Her makeup was not too out there except for the blood red lipstick and matching fingernails. She wore a white blouse opened enough to show the slightest amount of cleavage. Her breast were notable. I could smell a delicate yet spicy perfume drifting through the room. If she were to walk down the street she would draw admiring eyes but nothing said Dominatrix.

"Hello," I said. Then remembered what I had planned and got down on my knees and then added "Mistress Eve." She got up and walked around the desk. The bottom half was all Domme. The white blouse was tucked into something I don't know what to call. It was made of black leather with some buckles and studs. More than a belt, less than a corset. Her pants were also leather. Black and skin tight; they in turn were dressed into a pair of high heeled boots that came up to just below her knees.

She leant back against her desk and aid "Crawl over here Jon and kiss the tip of my boot."

I got down on all fours and crawled the few feet to where she was and lowered my had to the proffered foot. After a single kissed she pulled it back and offered the second boot., I kiss that one too and instantly rewarded with a smack on the shoulder from a crop that had been sitting on her desk. It wasn't too too hard but I did flinch a bit.

"Did I tell you to kiss it?"

"No Mistress Eve." I said properly chastised.

"And what valuable lesson did you learn just now?"

"To only do what I am told?"

Whack! Another smack.

"That is correct. Now you may kiss the other one."

When I did she said "Stay on your knees but remove all your clothes."

OK. Here it was. I was almost 23 years old. I was about to get naked for the first time in front of anyone let alone this mature sexy woman. I did what I was told.

Taking my pants off on my knees was a bit tricky but I got through it, pilling my clothes under one of the two chairs. She had me scoot back so she had a better view of her new...what? toy? Client? Slave? With crop in hand she walked around me, giving me a poke here, a pinch there, a couple of not hard but noticeable taps with the crop on my ass. She paid no attention to my semi engorged dick. Eventually she had seen enough and told me to stand. When I did she went back to her desk, opened a drawer and removed a leather collar and a leash. She had to get very close to put the collar on and this was the most erotic thing that ever happened to me, OK it was the only erotic thing that ever happened to me but you get my point. I told you I could smell her perfume throughout the room but now I could smell her. I could feel her touch as she fastened the 4" leather collar around my neck. I could feel her warmth up and down my body and then one magical moment her side brushed against my dick. How I didn't orgasm all over her leather pants is something I will always be grateful for, probably my nerves. There was a place on the collar for a lock. She did mess around, she used a big, heavy Yale lock to secure it. With the leash attached she said; "Time to go downstairs," and led me out of her office and down the hall to a staircase to the basement. Just before I went through the door I looked up and saw the young woman peeking out of the front room and seeing me in all my now fully erect glory.

If upstairs was the fly going into the spider's parlor, this was the fly going into her torture chamber. At the bottom of the stairs was a small sitting room with dark paneling. It seemed to be used for storage as it had a dozen or so big Tupperware containers. There was a door in the back of the room and that is where we were headed. Mistress Eve opened the door and reached in flicked a light switch. This did not light up the room but simply turned on a few lamps with red bulbs in them. We went in. I will describe what I initially saw in the dim light to give you a sense of it.

The wall on my right was brick, the others were sheetrock. Couldn't tell the true colors because the lights made them look red. The ceiling was open to the joist above providing a place to hang hooks and such from. On my left was a bondage table, padded and about six feet long. The base of the table was a cage made up of some serious steel rods. Of course there were plenty of places to tie someone to. On the opposite wall was another cage. This one was upright, about 7' high, 2' across and 18" deep. Someone locked inside didn't have a whole lot of room to move. In the middle of the room was a padded sawhorse, a spanking bench. And on the back wall they had what they called the "rack". Attached to the wall were 3 4"x4" pieces of lumbar running from floor to ceiling. They had attached 1"x1" and 2"x1" boards running horizontally for about 8', offering innumerable possible ways to attach subs to. The floor had several oriental carpets spread around the concrete floor.

"Over there," she said pointing to the upright cage. I walked over to the cage and did nothing. "Open the cage and step inside." I did. She came over and pulling my wrist behind me she slipped on a pair of very heavy handcuffs. Then closed the cage door and locked me in facing the wall. The cage was about 18" from the wall. She stepped in between the wall and the cage. She had a pair of nipple clamps with her, two metal clips on either end of a heavy chain. They bit down hard into my nipples like nothing I had imagined. And there I stood for maybe 15 minutes. Like I said there is no moving around.

I heard her heels slowly coming across the outer room. The rugs in the dungeon muffles the click, click, click but I could still hear her as she approached me.

"Miss me?" she said.

"Yes Mistress Eve." She opened the cage and spun me around. She had changed her cloths. She now was wearing a black corset which barely covered her breast. Below the corset she just wore a pair of black satin panties. The corset had garters holding up dark stockings. On her feet were a pair of red very high heeled open toed shoes. She rad replenished her perfume. I never ever even dreamt of anything as hot as what was now leading me out of the cage over to the spanking bench. In a minute I was bent over it my legs were spread apart as wide as they could and chained to the benches legs. My wrist were attached to the legs on the other side. The chain on my nipple clamps pulled down heavily. My ass was very vulnerable. She didn't say anything she just began with the beating.

The first tool she used was a flogger. It was heavy pieces of leather. To me it felt more like getting punched than it did a whipping. A dozen or so hits on my ass and thighs. Next she switched over to a tawse, a three inch wide piece of leather, 9" long and split down the middle. This hurt more than the flogger. After another dozen blows and she let me rest a few minutes. She asked if I was OK. I said yes. And she began again.

This time she used a wooden paddle. I think it was then that I started to cry. Just a little but definitely tears and snot. I bit my lip not to cry out, I didn't want to quit.

"Almost done," she said. She gave me a couple more minutes. Then came around the bench and squatted down next to me so I could see her. In her hand she had a long thin piece of wood in her hand.

"This is a cane, she said. "This will hurt more than the others. Much more. I am going to give you only three hits. I will deliver them in quick succession. I am going to gag you with a ball gag so you can scream as best you can, but not disturb anyone." She actually looked sad. She put the gag in my mouth fastened it tightly then stepped around the other side. I heard the horrifying sound as she swished the cane through the air a couple of times. Then she brought it down in the middle of my ass. It was all she had promised. A second later the second harder blow came down at the top of thighs. I was full on bawling behind the gag now. A second later the third, by far the hardest came down on me in between the other two hits. I saw stars. I almost couldn't breathe. Then she reached around and yanked the chain pulling the clamps off. I almost passed out. She just stepped away and let me settle down for about five minutes before she removed the gag and released me from the bench.

"We're not done yet. I want you to go over there and lie down on that carpet. Lie down on your back."

I looked over to where she pointed. There was a rug and a small pillow for my head. I didn't know how much more I could take but I pulled up something from somewhere and said "Yes Mistress Eve." And went and laid down on the carpet. My ass hurt like hell. I waited for what was to come next. And then she did something amazing. She straddled my face and lowered herself. Her women part hovered inches above my face. I believe I could feel the heat and moisture I imagined was there. And if that wasn't enough she reached down and took my cock and balls in her hand. There wasn't a whole lot of action going on down there. I am afraid the beating shut down any desire in me both emotionally and physically. But that wasn't her intentions. I wasn't sure what she was up to at first but when I felt her pull my balls and cock through a metal loop I knew she was putting a metal chastity thing on me. When she was done she lowered herself onto me. Just a thin strip of cloth between me and her pussy. But it was only there for a few seconds before she got off and told me I could get dressed.

She had brought my clothes down and left them just outside the door. I was moving slow but managed to get everything on. She had put on a long black robe and sat back drinking a bottle of water. When I was done she gave me a bottle of water and led me to the top of the stairs where her daughter met us.

"I'll show him out," she said and took me by the arm and led me to the door as she opened it she said "My names Janet. My friends call me Jet."

I took the subway home, standing all the way. It took me an hour to get there. By time I got there most of the fire in my ass had gone out but there was still a tingle. Back in my room I explored the damage. Ouch. A lot of angry red marks that turned black and blue over the next few days but I was mostly interested in the chastity device on my cock. It was small leaving absolutely no room for an erection. The side was solid so there was no way I could get in there for some forbidden contact. That wouldn't have been a good idea anyway since any erection was painfully suppressed. It was going to be a long week until my next visit and that was the soonest I would get out.

That night as I laid in bed and reviewed the day and kept getting back to one thing, "My FRIENDS call me Jet."

The week went by awfully slow. I don't do much. I usually hang out in my room, watch TV or surf the internet and jerk off to porn. With 33% of my activity off the table I decided to spend as much time in non-sexual temptation activities as possible. Museums, parks and PG movies. But everywhere I went something would pop up (no pun intended). A woman in high heels there, a goth girl looking like Jet there. I watch a comedy on Nickelodeon. A big sister catches her younger brother spying on her sleepover. Program ends with him tied to a chair while the girls give him a makeover. Give me a break huh. Long long week. But finally it was Thursday and I set off to the wilds of Brooklyn.

"Hey," Jet said as she opened the door. She looked a lot less goth this week. Red gym shorts and black t-shirt. I don't think she had on a bra.

"Hi," I wasn't sure if I should say Janet or Jet. Jet was for her friends. I decided "Jet. How are you?"

"OK." Jet was acceptable.

"You look different." Once again this was smoother than the way it came out.

"Yeah well I work in a used bookstore and they like that look. She needs about ten minutes. Come into the parlor."

The previous week I had just walked past this room and barely glanced in, now I saw what a nice room it was. A fireplace was in the middle of the opposite wall from the entry. A sofa was on the left and a pair of comfortable looking chairs were on the right. There was an industrial looking cart used as a coffee table in-between. It was covered in books and papers. Jet went over, pointed to one of the chairs for me to sit and then picked up a book. "Did you read this?" I looked at it and replied I had and even wrote a paper on it. "Can you give me some insights because I am fucking lost." We discussed the book for a while and I think I helped her. Ten minutes into the conversation her phone ding and she picked it up, read the text message and said. "She wants you in her playroom."

"Playroom," I thought. I was nervous all the way there but my time with Jet calmed me but now as I headed down the steps I got that feeling in my gut again. The door to the room was closed but there was a note for me. It said simply "Crawl into the room naked." I got quickly undressed and opened the doors and on all fours I entered her playroom.

She was standing in the middle leaning against the spanking bench. She was wearing a pair of very short black leather shorts and an untucked black shirt. The shirt was see-thru and she wore no bra, but two opaque pockets covered her nipples. She put her left foot forward, it was bare. I approached and lowered my head but did not kiss it.

"Good. You may kiss my foot and keep doing it until I tell you to stop."

I proceeded to do so. Kissing each one in turn, covering her foot with adoration. While I was doing this she spoke.

"A couple of things. First. The way you came in to the room is how you will always enter this room. Naked and on your hands and knees. If we are upstairs and you are dressed and I send you down to get something you are to get naked and crawl in and out. Is this understood?" I said I did and continued kissing. "Good. Use your tongue."

I stuck my tongue out and ran it over the toes. "Next. Last week you weren't given any safe words. That was because last week I was going to do what I was going to do. From now on we will red, yellow and green. If I ask how you are you can respond "green" or "yellow". You understand?" I understood. "Put all my toes into your mouth." I could feel small pieces of detritus on the underside of her toes but didn't care one bit. "OK. There are a few more things today but we will talk about them in a few minutes. Your fun time is over. Stand up."

I got up and she took my arm and led me over to where there was a wooden crate under a hook hanging from the ceiling.

"Put out your hands." When I did she put a pair of leather cuffs on me. She clipped them together and then had me step up on the box and said to loop my hands over the hook. She went over to the wall where there was a crank and started to turn it. I was afraid she was going to lift me in the air but that wasn't her intent. She just raised me enough so that I was standing straight up. One more click and I would have had to lift my heels off the box. Standing on the box brought my metal encased cock to the level of her breast. She took it in her fingers and examined it. It started to get hard, began hurting and started to deflate.

"Has it been difficult going a week all locked up." She said in a fake sympathetic voice.

"Yes Mistress Eve." Truest thing I ever said.

"Well you are going to have to make a decision." Around her neck was a necklace with three little keys on it. The kind of key that would fit the lock on my cage. "You can choose one of the keys or you could pass. If you pass I will unlock you next week and leave you unlocked for at least a week. If you choose to pick a key it could go one of two ways. If you pick right, you go free today for at least two weeks. If you guess wrong" she made a pouty face "then you have to wait two weeks before you get out. And..." she gave me a wicked smile ..." I will take it off next week for cleaning and I guarantee it will not be a pleasant experience. You have 5 seconds to make a decision or you get the two weeks. 1...2...3"

"I'll pass Mistress Eve." I blurted out condemning myself to another week of chastity. Ugg.

"Good boy," she said and reached out and gave one of my nipples are hard tweak. She walked around to look at my ass. "Need a little more light," she said turning on a nearby floor lamp. "Oh not bad. Have you been watching it all week?"

"Yes Mistress. It seems to have clear up quite a bit in the last couple of days." It had been pretty ugly.

"The crop left some beautiful color. Is it still sore?"

"Just a tiny bit Mistress. It tingles at time when I sit."

"Oh. Does this hurt?" And she hit me 10 times, back and forth with a 8" slapper."

"Red, yellow or green," she said.

I foolishly said "Green."

Ten more swats then "Red, yellow or green?"

"Yellow."

10 more "Red, yellow or red?"

"Red."

10 more. "Good."

She left me alone for 5 minutes but when she came back she scared the shit out of me. She had an object of some kind in her hand, then with a dramatic flair she flicked her wrist and a long scary straight razor blade swung out. So I'm naked, stretched out and she has a blade in her hand. And oh yeah she is a sadist.

"My boys are not allowed to have this," she said tugging on my pubes. She had a small squeeze bottle in her hand and proceeded to squirt it into the hair surrounding my encased dick. She rubbed the soap in and worked up a lather and then scraped off all the hair she could.

"You will keep it that way. And you will also start shaving your, legs and underarms.

"Yes Mistress Eve."

"Good. I'll let you down now."

She let me down but she wasn't finished with me yet. She undid the clip on my wrist cuffs only to reattach them behind my back. She walked me over to the bondage table and bent me over it. With one hand she spread my butt cheeks. "Oh yeah, your gonna need to need to shave back here too. I'll get you started." And with that she picked up a pair of needle nose pliers and pulled out several hairs all at once. I'll say no more of the incident. The real reason I was bent over the table was to introduce a butt plug into my butt. She used a lot of lube before the insertion, thank you for small favors. Once in she did this complicated rope thing around my waist and between my legs which prevented the rubber dick from slipping out. She tested her work by having me walk around the room several times to be sure it would stay in for my subway ride home. "And of course you'll have that in when you came back next week. You can go home now."

Dismissed I crawled out of the room as I was required, got dressed and headed up the stairs and out the front door. On the way I met Jet who watched how I was walking.

"Butt plug?"

"Yeah."

"Big?"

"I think I can manage."

"Good. So thanks with the help on the paper, you made everything make more sense."

The next day I received a copy of her paper. It was good. I got a B- on mine, she would eventually get a B+.

And so it went for the next month or so. Most Thursday's I was in Brooklyn getting beaten, humiliated and such. I spent about half my time in chastity and wore my plug at times even when not required. I was happy and feeling better about myself knowing I wasn't alone in the world. There was one more memorable visit I would like to relate.

It was my 7th visit the Brooklyn brownstone. I had been in chastity for the previous weeks and was very hopeful of being set free. I had been criticized in the past for not shaving close enough or missing something so I spent extra time and care getting it just right. I got there early and sat in the park to get myself calm. I had started running and doing some light workouts in the apartment buildings gym. I lost 2 pounds and I didn't see the difference but it was a start. Maybe physically there wasn't any change yet but mentally or maybe spiritually I felt something happening. I went up the steps and rang the bell.

As almost every time it was Jet who answered the door. She had her goth shit on and was carrying a coat.

"Hey," me.

"Hey," her.

"Going to work."

"Yeah picked up a few extra hours."

"OK. Have fun."

She started to say "You too," but instead she gave me one of those tight lip sad smiles, and then she said "Sorry," and then she was off. That did not sound too good. What could she be sorry about? I entered the hall looking for Mistress Eve. If she wasn't down here I would go to the basement and wait. I didn't get that far. The moment I closed the door and turn a strange voice from the front parlor said;

"Boy, come in here."

As I came to the living room entryway and looked in. On the sofa sat what a fleeting glance would have suggested to be a nice little old lady but once you took in her riding boots, jodhpurs and red corset it was apparent that this was Mrs. Winters, Grandma.

I approached her cautiously not knowing if she was going to spring from the sofa and swallow me whole or not. She didn't. Instead she invited me to sit down on the floor in front of her. OK so she did it by pointing to the ground with a particularly evil looking crop but she had a friendly look on her face.

"Jon, my name is Mrs. Winters. I am Evelyn's mother. She was called away and asked me to attend to your appointment today. I am not going to ask if that is OK because we both know that you have no say in it." She smiled for a second and then the smile disappeared and the new look was impressively stern. "You may lick my boots."

I didn't dare hesitate. I rolled forward and started licking. I was required to cover every inch of the boots, that ended just below her knees, with my tongue. She did nothing to help me. I had to contort myself into several uncomfortable positions but after about 10 minutes she begrudgingly said I had done an adequate job and had me kneel up.

"Your sessions are usually an hour or so."

"Yes Mistress," I said.

This brought the crop down on me. The crop was about 30" long with a 1" wide 3" long tab on the end. The tab smacked me hard on my left shoulder. The shirt I was wearing blunted the pain a bit but I could imagine (and later experience) it's true potential.

"I am not your Mistress, Evelyn is. I am Mrs. Winters or Ma'am. Do you understand:" She held the crop against my cheek.

"Yes Ma'am," I said.

"Your sessions are usually 1 or 2 hours. You will be here a considerably longer today. Once I start I like to keep going. I have no concern for what you are into. I do what I like. You are in chastity now?"

"Yes Mrs. Winters."

"How long."

"One week Ma'am."

"What was the longest period you have been?"

"Two weeks Ma'am."

"You should hope I never get the key. I think in terms of months."

"Yes Ma'am." Yikes.

"Alright let's get started. I want you to take of your shirt, shoes and socks." When I did, and as just dressed in my jeans and jockey shorts she sent me to retrieve a woven laundry basket from the other side of the room. It was covered with a cloth so I couldn't see what was inside. I laid it at her feet and waited. She bent and removed the cloth and I saw it was piled high with many coils of different types of rope,

She took one coil, unrolled it and the folded in half. She wrapped it around my upper arms pulling the loose ends through the loop on the other end. Once she had done that she encircled my body with the two lengths of rope wrapping them in opposite directions eventually tying them off. I now have t-rex arm but not for long. She pulls my arms, uncomfortably, up behind me and tied my wrist to just below my elbows. Next she put a bit in my mouth. It was made from a piece of a branch, with bark still on it. A elastic ban of some kind that went around my head. It might have been a bungee of some kind. That was unpleasant. Finally she took a bag out of the basket and reached in and removed a handful of clothespins out. She put two of them on each of my nipples.

"I like to undress little boys myself. Boys like to jump out of their clothes whenever they think there is a pussy around. I like to take control. Tie em up and take them down." With this she unlatched my belt, undid the button, slowly lowered the zipper and reached in and gave it a squeeze

"Even in your metal cage you aren't very big, are you?"

"No Ma'am."

"Ever cum in it?" She was kneading my balls fairly hard."

"No Ma'am."

"Never took a vibrator to it?"

"No Ma'am. If I get hard it is very painful."

"Hmm." She pulled my pants down and had me step out of them. I stood before her in just my white jockeyss. If she had any thoughts about my hairless legs she said nothing. She pulled my belt out of my pants and looked at it. "I sometime like to use my subjects own bet, but I have so many better options."

She then pulled my undies down, she took the cage in her hand a examined it, turning this way and that with no concern for my comfort.

"The problem with these things is it make it harder to torture your cock. But I have my ways. We have plenty of time for that later. But for now." She let the sentence hang in the air while she dug through the coils in the basket and withdrew an anal hook. You know what they are. Think of a 12" steel fishing hook with a 1.5" ball on what would be the pointy part of a fish hook. The other end has a loop to tie a rope to. About 5" goes up your ass. She didn't say anything she just started spreading a thin coat of lube on the ball. I was on my knees at this point and she told me to stand and bend over. When I did she slowly worked the hook into me. There was some initial resistance but she just kept working it until it went in. She next took a rope and ran it through the loop and then tied the other end to the rope going around my chest holding it securely in place.

"Walk over to the wall then walk back." I did and as I did I could feel the hook moving around. It was a pretty weird feeling. We weren't done yet. She took a thin leather cord and passed it through the metal ring circling my balls and tied it off. On the other end she tied a 5lbs. dumbbell and then set me out walking across the room again. The weight pulled heavily on my balls. Which, if you recall haven't been emptied in quite some time. She made me walk back and forth a few more times dragging the dumbbell behind me. Whenever I was within reach of the crop she would strike. My ass, thighs and chest were her targets. She did not hold back and there was a scary look in eye. Eventually, "Time to go down stairs." She took the dumbbell and threw it over my shoulder so as not to damage the stairs as I went down them and then we headed downstairs. At the bottom of the stairs she put the dumbbell back on the ground.

You remember the rule that I had to crawl into the dungeon and considering my bonds this was going to hard. Mrs. Winters did nothing or say anything she just stood back to see what I did. What I did was slowly lower myself to the ground, I figured if I fell it would be a "I've fallen and can't get up" moment. So straining I got down on one knee and then the next and started heading through the door. The floor in the outer room had some kind of vynle flooring. It was hard and cold but easy to slide my knees over, well that was until the cord went taught and I added the extra 5 lbs. to my balls. I strained for a step or two but then found myself unable to pull it any farther.

"What's the matter boy?" she said in an innocent voice.

"I can't move," I said through my bit.

"Try harder."

At this point I realized that she had her foot on dumbbell but I strained to move forward anyway. The crop help with the encouragement. Eventually she tired of this little game and lifted her foot and I almost fell over but I managed. to get into the room. She had me kneel in the center of the room and removed my bit. I was directly under the hook which she lowered and stuck under my chest rope and then going to the winch she slowly pulled me up. I did not dare do anything but just let it happen. As the rope got tighter it pulled the hook deeper inside of me. When my legs were almost straight she stopped, fetch another piece of rope and tying one end around my ankle she bent it back and tied it so my whole weight was on one leg and the rope. Yeah it was painful.

"Have you ever been caned?"

"Yes Ma'am," I said thinking back to my first time with her daughter. That was the only time I had been caned but the memory was seared in my brain."

"A dozen strokes are traditional but you already know I am not a traditional lady."

A dozen? More than a dozen. How would I manage that when three nearly drove me nuts? Well I did. It was every bit as painful as I had imagined. The rope and hook might have blunted it a bit but not much and my bent leg may have meant she had to modify the angle a bit but this also gave her the opportunity to give me some strokes on the bottom of my foot. I believe in all she hit me 16 times but to be honest I lost count. Then she released me from all my bounds. But we weren't done. Far from it.

"Go lay down on your back over there, she said indicating the area in front of the rack. There were two bungees coming off the opposite walls. The bungees had leather cuffs on the ends which she buckled around my wrist and ankles spreading me eagle on the hard concrete floor. She straddled me then squatted on my chest. She had several short metal rods with her.

"Do you know what these are?"

I said no but I had a suspicion of what they were for.

'They're called sounds. I am going to put them in your dick. The small one first then the bigger ones. And after that I have a special treat. And that's what she did My cage had a pee hole in the front which gave her access to my pee hole. "I just picked out three. Three smallest in a set of 8. Let's see what we can do.'

She took the littlest one and put some lube on it. She took the cage in hand a carefully and slowly slipped it into me. It was cold and at first that was all I noticed but after the probe got about an inch in I started feeling an unusual pressure pushing out. I won't say it was pleasurable but it wasn't too bad. I didn't feel I was being tortured. She quickly abandoned the little one and moved on to the next size. This one was a whole different feeling. I thought I was going to cum. She liked my reactions so she left it in and twisted it around a bit. The big one made me crazy. It is hard to explain but you know how a guy's cock can become super sensitive after he cums, well it was like that only amplified and non-stop. My breathing and squirming told Mrs. Winters she was getting what she wanted from me. After I wondered what the larger sounds felt like. Maybe I don't want to know.

I was kind of miserable but also amped up. Kind of proud of myself for the amount of abuse I could take without complaining. I felt her pull the rod out of my rod. And then I remembered she said something about something special. After she took the last sound out of me she was there for about minute before getting up and leaving my view. And then something started happening with my dick. At first it felt like someone was pinching it. Like a clothespin was squeezing it. But no one was there to put it on me and besides that part of my dick was locked away. And then it started to feel cold, cool at first then more intense and after a minute the cold started to change to heat. What I found out later was that she had dripped a liquid Indian spice of some sort into my urethra. The burning built to its maximum level in about ten minutes. I so wanted to grab my dick and squeeze, but I of course couldn't After it had reached its maximum and after another ten minutes it was just a unscratchable itch. Surely my night was over. That fantasy ended when Mrs. Winters came back into view. She was naked and had a double sided cock gag in her hand. The side that went into my mouth was a stubby penis about 3" long. The other side was an 8" inch well detailed monster. She strapped in on my face tightly and quickly mounted it. I heard her gasp as she slid down the huge dick. She started slow, taking long slow rides up and down. As she got closer to her climax she had the whole thing inside her and just did short pumps up and down until a long moan and quick intake of air signaled her orgasm. She kind of collapsed and I had a feeling that the dick was the only thing holding her up. I hoped she wasn't dead. I did have this unwanted vision of a future Darwin Award article about the young man being smothered under the body of a naked grandma. But then she moved and slowly lifted herself off of my face. It was probably traumatic for me but hopefully I won't have to be lying on Dr. Weinstein's couch recounting the experience twenty years from now. But it was my first pussy so there was that. So then she stood up straddling me and for good measure she let a long stream of piss flow out of her on onto my chest and groin. And then she left me there while she went and took a shower and got dressed in regular street clothes. She took the gag out of my mouth and threw it aside and left alone with just the red bulbs for light. And there I laid for nearly an hour.

I heard the front door open and footsteps coming down the hall. I was about to call out when I heard someone coming down the stairs and in a few seconds Jet was in the doorway.

"Oh Grandma," she said sounding a bit dejected. "She told me she wouldn't be so hard on you."

"Do you think you can unhook me."

She did but then said we needed to clean-up the room. If we left it the way it was her mother would certainly take it out on me. Something I wasn't up for. She sent out to get a mop and bucket from a closet in the other room. She made no comment on my crawling through the door. She understood. Besides her just being a girl who will talk to me I think the most important thing about her is she understood or at least accepted me for who I was. I mopped and she organized and put everything away.

"You stink," she said. The reason for that was left unsaid. "Come." She took my hand and we went up the stairs to the main floor and then another flight to the second floor. There were three bedrooms up there and a couple of bathrooms. We went into one of the baths. She pulled back the curtain on the tub shower combo and turned on the water. She didn't' say anything we just stood there until the water was warm enough and then I stepped in.

As the water ran down my body I realized how exhausted I was. I wasn't even sure I had the strength to wash myself. Maybe I could just stand there and let the water get me clean enough to get me home but then it happened. The curtain slid back and a naked Jet stepped in the shower with me. She stood in front of me for a few seconds. She has a nice body; I'll leave it at that. She let me look at her for a second and then she spun him around.

"Just relax. I'll do the work." She had brought with her a bottle of sweet smelling soap and one of those stiff scruffy things women use to wash. She started on my shoulders. She poured some of the soap into her hands and started rubbing it into my skin. It burned where the crop had come down. But that was OK. Her fingers on my skin pushed everything aside. She massaged my shoulders and neck. She washed behind my ears and shampooed my hair. She lowered her hands and washed my arms, pits, and chest. She carefully rubbed my sore nipples and then my belly. She thoroughly washed my ass, running her hand deep between my cheeks and then squatting down she washed my legs and feet. She had skipped one notable area. She took one of my arms and turned me around to face her. That was when I noticed she was wearing a thin silver necklace with a small key on it. She slipped the necklace off over her head and bent and unlocked my cage and took it off. First she cleaned between my balls and leg. And then she washed my balls. I thought my head would explode, however my dick hadn't woken up yet. Maybe it was pouting? Standing she spun me around again and then reached around with a very soapy hand and began to "clean" my cock. It woke up. The feeling was something unlike anything I had ever experienced. Of course I whack off as soon as I can after getting unlocked but that that's nothing compared to this long slow stroking by her sweet gentle hands. Her nipples were pressing against my back, her head rested on my shoulder. I wanted the feeling to go on for a while. Fuck I wanted it to go on forever. An eternity of this feeling wasn't going to be enough. I lasted maybe thirty seconds, maybe less. It was a huge load. She aimed it so it went down the drain. She turned off the water and we stepped out.

There were two large fluffy towels sat on the toilet. I wrapped myself in it an made some effort to dry off, but now I was even more exhausted than before.

"Sit on the toilet Jon," she said when we were mostly dry. I did. And then I sadly watched her pick up the chastity cage and turned to me. "This has to go back on. I should not have let you out at all and I certainly should not have jerked you off but I thought you deserved it. Mom shouldn't have left you alone with Grandma. But now I have to put you back in. Don't tell her, OK?" I agreed.

When she finished putting it on she took my hand and led me down the short hall to her holy of holies, her bedroom. I don't know what I expected of her room but it all seemed right. It wasn't big, but she squeezed in a dresser, a book covered desk a nightstand, a nightstand and a truly inviting bed with a dark comforter and many pillows. I sat on the bed while she rummaged through one of her drawers and then pulled out two overlarge t-shirts. She threw a white one to me and slipped a yellow one over her head. She also brought a small bong and a baggie back to where I was sitting,

"Ever smoke weed?"

"No," I said.

"Didn't think so. This is pretty smooth to smoke and will give you a nice buzz."

"Ok. You go first." She did by taken a big swallow of smoke and holding it in. When she finally exhaled she said "Your turn." She reloaded the bowl and handed it to me. She put her finger over the hole as I inhaled. The smoke rose slowly into my mouth and lungs and then she moved her finger and let the bong worth of smoke shotgun into my mouth. A short coughing fit followed.

"Happens to everybody. Try again."

I did and this time it stayed in for a couple of seconds, "That's all you'll need. C'mon." She pulled the comforter down and we crawled in. The pot kicked in after about 2 minutes. She laid on her side and I spooned against her. I was asleep in about 5 minutes. I slept until 8 the next morning. She woke me with a cup of coffee and then she sent me on my way. A night that had seen me beaten and pissed on by an old woman ended up being the best evening of my life.

After that things got back to normal, my normal that is. I didn't see Grandma again for several months but I didn't get to spend anymore one on one time with Jet either. She had senior papers due as she got ready for graduation. Mistress Eve introduced me to electric play and humblers. Yeah normal.


MRS. PO

One morning Mom called and asked if my calendar was clear that afternoon, that's the way she spoke.

"Let me look." As I wasn't in chastity and I planned on jerking off but I didn't tell her that and said I was free.

"I have a car picking us up at 1."

"Where are we going."

"You'll see.

Living in Manhattan you don't own cars. Lots of public transportation with bus, taxis, subway and now Uber. Mom liked to travel in style so she used a car service that featured Mercedes Benz limos. The one I got into that afternoon was black with a light gray interior. The driver headed towards the FDR and then headed downtown. I didn't say anything just let her have her little surprise. And I was surprised as we got on the entrance ramp to the Brooklyn Bridge and then drove into Park Slope heading towards Mistress Eve's house. I was getting a bit anxious but then we turned north and eventually stopped in front on a block of row houses.

"What's this?" I asked.

"I bought that building," she said indicating the one in front of us. "It was built in1908 but its been renovated with all the modern stuff people want. There are twelve apartments. I have sold eleven and made a bundle. I want to show you the other."

Wondering where this one was going I said "Cool. Let's go."

I followed her up a half dozen stairs to the entrance. She used a key to open the door and then climbed a flight of stairs to the second floor where she unlocked another door and we stepped into the apartment. It was so cool it was almost a cliché. It was situated in the front of the building overlooking a quiet tree lined street. The first thing you notice when you walk in is the exposed brick wall. Looking down you see a dark stained hardwood floor. The kitchen was granite counters and stainless steel appliances. The apartment was fully furnished with an old library table for dinning, and a L shaped black leather (!) sofa to watch the stupid-big TV.

"Sit," Mom said. I sat.

"You've changed a lot since you started seeing Dr. Weinstein. Changed for the better. You're out of your room a lot more, doing things. It's great, expensive as all hell but who cares. Right? So I was speaking with her last week and she suggested maybe it's time for you to move out and get a place of your own."

And it became clear. "This place?

"Pretty cool bachelor pad. No?"

Long story short I moved in a few days later.

The first thing I did was to figure out where I was in relationship to Mistress Eve and Jet. I was close, about a 20-minute walk. I was on a quiet street but about 2 blocks away was a main street with a dozen restaurants and other shops I would need now that I no longer had the housekeepers I had at Mom's.

I was there for about a week when I received an odd text message.

"I will be there 9am Monday Mrs. Po"

Who? I texted back asking who are you. But got no response. Got the message on Saturday so I would have to wait. I would be home Monday at 9 anyway since I seldom rose before 10. I'd set my alarm.

I didn't set my alarm and I was somewhat startled Monday morning when someone in my bedroom said my name. I jumped up and so a very attractive Asian woman standing in the door way.

"Who are you?"

"I am Mrs. Po. I know you knew I was coming since you responded to my text. I thought you would be up."

"How did you get in?" Wow, I actually asserted myself.

"I obtained a key. Why don't you get dressed and come into the living room and we can talk," she said this with a friendly smile and only the slightest bit of accent. She left the room and I threw on a pair of gym shorts and joined her in the living.

I found her sitting on the couch. "So why are you here?" I said.

"Because you were raised with a domestic and never developed the skills or ambition to maintain a house, cook a meal or do any of the things required to make a house a home. So I'm here to help."

"A housekeeper?" Cool!

"Not quite. You've been seeing Evelyn for four months now..."

Uh-oh.

"... and she has made you comfortable as a sub, she taught you to obey without hesitation, that actions have consequences and helped you overcome your need for instant gratification." She looked down at my crotch. Gym shorts do not do a very good job of hiding one's chastity device. "But what do you have to offer?"

"What do you mean?"

"As a submissive what do you have to offer to your Master or Mistress?"

Master? "I guess very little."

"Yes very little. You may think it is 24 7 bondage and discipline, that the women want to wear 6: high heels and corsets all day long or your master wants you sucking his cock all day but that is not the case. You have to provide worth to these people otherwise who needs you? And that is why I am here."

"To teach me..." I let the sentence hang.

"To cook, to clean, laundry among other things."

"Oh," I cleverly said. I see women in three way. The kind I can talk to. Like Mom, Jet, Dr. Weinstein. Women I can't talk to, mostly everyone else but I am getting better. I had a great discussion about whether or not it was going to rain with the lady in the pizza shop. And then there are the Dommes. Sometime in the previous 2 minutes I understood where Mrs. Po fitted in.

"We will begin now. Come to the kitchen." I followed her into it. I saw a small Igloo ice chest sitting on the counter. "I did not know what you had so I brought a few things. I will give you a list of instructions and things to buy before I leave." She opened the chest and withdrew two eggs and three pieces of bacon and placed them on the counter. "Make me breakfast." I never cooked anything in my life.

I knew how to turn the stove on. I knew you fried eggs in a pan. I guessed you did the same with bacon. I knew eggs came in several styles but had no idea how you made sunny side up vs. scrambled. And how the hell do you get cheese inside of an omelet? What I served her did not look like the bacon and eggs I had eaten before. While I cooked she toured my apartment. I meant to clean up but hadn't gotten around to it. It wasn't bad just a little messy. She sat at the counter and I presented to her her breakfast. She looked down at it, then at me.

"Is this something you would serve your Master?"

I was wondering if I should explain to her the Master/Mistress thing as it pertained to me but I decided to wait for a better time.

"No Ma'am."

"Yet you served it to me. And it is Mrs. Po."

"I am sorry Mrs. Po. Would you like me to try again?"

"Is there any reason to think they would be better."

"No Mrs. Po."

"Let me try it." She cut a small piece of the egg and put it in her mouth, chewed a couple of times then spat it out onto the plate. "somehow you managed to make it burnt and undercooked at the same time."

I said nothing. Next she tried the bacon.

"Same thing," she said after also spitting it out. "Burnt and chewy. I would not serve this to a dog. However, you are not a dog." And with that she picked up the plate and dumped it on the floor. "Get down there and eat every bite of that mess.

As she said I was trained to obey and as I accepted her as a Domme, my better, I did what she said.

"Don't use your hands. Eat it like an animal."

It was kind of nasty. Besides the poor quality of the preparation she had chewed up some of it and of course the floor was not as clean as it should have been. Not my usual breakfast. When I was done she told me to stand next to her at the stove and she showed me how to cook a bacon and egg breakfast. Did you know you were supposed to butter the pan? When it was done she sat down at the counter and ate it while I watched. I already had had mine.

"Why are there dirty dishes in the sink? You have a dishwasher," she said when she finished her eggs.

"Dishwasher is full."

"Why didn't you run it?"

"I did. The dishes in it are clean. I just didn't empty it yet."

"When did you run it?"

Never lie to a dominatrix. "Two days ago."

She just stared at me, then said "Your apartment is a mess you have been in here just a week and it is already a disgrace. If you can't keep a home for yourself how are you going to keep one for someone else? Today we are going to clean this place. We are going to go over every surface and you will learn to have high standards. You will also learn that I am not an easy person to please. Understand?

"Yes Mrs. Po." I understood. At least I thought I did.

Then we will start in here.," she said indicating the kitchen. But first you are not properly dressed for your duties. I left something on your bed for you to wear. Go put it on. And nothing else."

I went into my bedroom and found the garment she wanted me to wear. It was a maid's dress. Now before you get the wrong idea, this was not a French oo-la-la sexy maids dress. No don't think Fifi think Rosy at the Quality Inn. It was gray with pink piping and pink collar and cuffs. Over the left breast was embroidered my name. It also had a white apron and cap. If anything was sexy about it, it was the skirt was pretty short. I put it all on, looked in the mirror, felt stupid and went back out to the kitchen where she waited.

"Stand there," she said indicating a spot on the floor. I did and she examined my new look. She straightened my skirt and retied the apron, making it a big bow in back and once satisfied she said "Lift up your skirt. I want to look at your cock cage."

"What's the longest you have been in there?"

I thought about it for a second and said "three weeks."

"How long this time?"

"!0 days."

"I have the key. I will control your chastity. At this point I do not think you should be unlocked without supervision. Generally, I won't even bring the key with me except cleaning day. I will see to the hygiene and maybe change the cage. Do you get hard at night?"

"Yes, it hurts and then goes down."

"Being permitted to have an orgasm is something you will have to work for. It will not be soon."

Oh shit. With Mistress Eve I knew there would be some freedom sooner or later. Nothing about Mrs. Po made me feel any mercy at all. I simply said "Yes Mrs. Po."

And then we cleaned. I scrubbed the kitchen floor tiles on my hands and knees. She had brought with her a duffle bag with her. She had produced some cleaning equipment, some special cleaning material and some discipline equipment for naughty maids. From there she produced a long piece of stiff leather on a wooden handle which she had no problem using it whenever she thought there was a lack of enthusiasm on my part. We did the floor, the counters, the cabinets. I emptied the dishwasher and did the dishes in the sink and dusted the light fixture. In the living room I vacuumed, dusted, Windex-ed the windows etc. She saved the bathroom for last. She had a special tool for the bathroom. It was a gag with various attachments. She also pissed all over the place. I had to crawl into the room and kneel in a puddle. She put the gag on and attached a long toilet brush to it. I had to use it to clean the bowl, which she had managed to get some of her pee in. Another attachment was a sponge I had to use to soak up the piss on the floor and wipe down the seat and finally a short scrub brush to do a general wipe down.

It was about noon when we finished. I was beat sore but had to admit I was happy my apartment was clean.

"I plan on being back the day after tomorrow. I will be here sometime between 7 and noon. I expect you to be wearing this dress when I get here. I also want you to purchase three pairs of different color panties and matching bras. Nothing too sexy. You are just a maid. Also I want both of your ears pierced. I left you a list of things I want you to have in the house next time." And with that she left.

I grabbed my phone and quickly texted "Help!"

An hour later I was letting Jet into the apartment.

"Panties and bra huh?"

"Yeah. I need three pair for tomorrow. Different colors. Can you come with me so I don't look like some kind of little perv?"

"Jon, you are a little perv."

"Yeah but I don't want some lady salesperson knowing it."

Laughing she said "OK. I brought some stuff so we can figure out what size you are," With this she reached into the big bag she was carrying and dumped a pile of lingerie on the coffee table.

"Get naked so we can try some of this on."

"What is this I said picking up a pair of red bikinis.'

"Some of Mom's clients like to be "forced" to wear woman's clothes. She has quite a collection.

"But Mrs. Po said nothing to sexy." I looked down at the pile. "This looks sexy."

"Yeah, her boys want to look like sluts. But we are just looking for size. Take off your clothes and put those on.

I had taken off my dress and put on a pair of shorts now I stripped down to nothing. I asked "Do you know Mrs. Po?"

"Never met her but I know who she is. She has a reputation."

"What kind?" I slipped into the panties and tried to get the cage to not poke out.

"Well maybe it's best if you don't know."

"She pissed on the floor and made me clean it up with a sponge gag."

"Yeah. That's sounds right. I always wondered about Mr. Po. Oh those are cute. Turn around and let me see the back."

I did a spin and she fussed over the fit. She picked up another pair and had me put them on. These were very sheer black with red lace. They were tight and we discarded them and moved on, The fourth pair, a lacy pink one seemed to fit the best. She then picked up a bra. Black strapless. It seemed to fit OK but she had me try some more on. Finally I had on a shiny black one and she said that was perfect.

"Did you really need me to try on all this stuff or were you just fucking with me."

"Oh yeah. I was fucking with you. You wear the same size as me. Time for you to get dressed."

I reached around to unhook the bra but she said, "No no no. You're gonna keep the sissy stuff on." I gave her a puppy dog look but to no avail. I put on a pair of jeans, a t-shirt and a pair of sneakers.

"It's cold out, Got a hoodie?"

I did but I didn't think it was that cold but I went and got it anyway. She asked me to give it to her. She pulled a knife put of her bag and proceeded to cut a slit in the inside of the pouch. I said nothing after all she had a knife. Next she told me to take my belt off and give it to her. I wasn't sure where this was going but I of course complied. She put the belt back on me but this time the buckle was in the back.

"Put on the hoodie," she said. When I did she took a pair of police handcuffs out of her bag and put one cuff on my right wrist. Next she had me put my hands in the pouch and then cuffed the other wrist. But she wasn't done yet. The final piece of the puzzle was a padlock that she looped around my belt, through the hole she had cut in the hoodie, around the cuffs and back through the hole and locking it there. It was basically a poor man's straitjacket. She took my wallet and put it in her purse.

"OK," she said. "let's go."

We took the subway to 34th street and went into Macy's. She took her time as we strolled around the store's various departments. She looked at shoes, and casual wear. She tried on a couple pairs of jeans and sat at a cosmetic counter while a lady put something on her face; and all the while her patient "boyfriend" sat quietly with his hands stuffed into his hoodie. Eventually we made our way over to the panties department and I had hoped to stand aside while she picked up the stuff but no. Jet brought me over and made me pick out the colors. I made some protesting noise about the pink ones but in the end we left the store with one pair of pink panties with lace, one white pair with an embroidered roses and another pair in baby blue. And of course the matching bras.

Outside on the street she hailed a cab and gave him n West Village address. If the driver thought it was unusual that she opened the door for me he didn't say anything. It was a ten-minute ride to the tattoo parlor.

"Hey Jet," said the heavily tattooed man behind the counter. "You gonna get that big back piece today?"

The shop was empty. I had never been in a tattoo parlor but it was pretty much the way I would have imagined it. Scary equipment, comfortable chairs and a zillion illustrations on the walls.

"Not today, Phil. Just need a couple of ears pierced for my friend Jon here."

Phil the tattoo artist looked at me, smiled and stuck out his hand. I looked at Jet who said "Well don't be rude. You can do it." And I did. It took some effort but I managed to twist things around enough to get my cuffed hand free. Phil looked at it laughed and took it into his and gave it a squeeze.

"Nice to meet you Jon. Any friend of Jet. So Jet can't help but noticed your friend is in handcuffs."

"Yup. He's wearing panties and a bra too" No further explanation was given.

"One of your Mom's?"

"Sort of. Long story."

"Want me to do his nipples?"

"Just the ears today."

"OK. Jon why don't you sit there. This will only take a minute and won't hurt a bit."

An hour later we were back at my place, two small gold hoops hanging from my ears. After I was uncuffed I had to get undressed again to give her back the undies I was wearing.

"I really appreciate your help today. If you hadn't..."

"No problem. Getting ready to graduate has made me a bit crazy. Today was a break."

I was still naked when she gave me a hug and left.

That night I gave my apartment a careful cleanup and vacuumed it for a long time. I practiced making bacon and eggs. I went through a half dozen eggs and a half a package of bacon and I thought I was in pretty good shape. I got up the next morning at 6, showered, dressed (chose the white undies) and waited. It was a quarter after 11 when she let herself into the apartment. I was sitting at my laptop when I heard the key in the door and immediately got up and went in front of the door and got down on my knees.

She walked in past me and looked around. She looked in the bathroom and my bedroom. Finally she got around to me.

"Lift up your skirt."

I did. She looked at my panties and said "Does your bra match it?" I said that it did and she sent me off to make her bacon and eggs. She tried to throw me a curve by asking for scrambled eggs but I had watched a video last night and knew what to do. She didn't eat much but since she didn't make me eat it off the floor I guess it was acceptable. She next handed me a box of Bisquick and told me to follow the recipe on the box for a pancake. They came out burnt on the outside and undone in the middle. This time she stepped on it and made me eat off the bottom of her shoe.

"Next time you serve me something like that I will make you eat it out of the toilet.," she said. This wasn't an angry threat. Just stating a fact. "Now gather up your dirty clothes."

Although the apartment had a brand new washer and dryer my plan for laundry was simple. I still had a lot of clothes in Mom's place so whenever I started running low I would pack a suitcase of dirty clothes take it uptown, leave it with the housekeeper and take fresh stuff from my closet. She asked if I ever did laundry and of course I said no. She took this well and then vary patiently told me what to do.

Once I had the first load going (dark clothes) she took me into my bathroom. In there she produced a large plastic bag filled with 15 pairs of women's underwear.

"These you will hand wash," she said handing the bag to me and then some special soap. Following her instructions, I filled one of the bathroom sinks with warm water, the other with cold and took the first pair out of the bag. If you think these were all Mrs. Po's, you are wrong. That first pair had to belong to someone twice her girth. I rubbed them together not really sure what was the proper procedure and only got a couple of smacks on the head so I guess I was doing something right. After washing them in warm water I rinsed them in the other sink and then hung it to dry over the shower curtain. The next was the tiniest of thongs. Followed by a purple bikini that was still moist in the crotch. By the time I had finished we had stopped twice to attend to the clothes in the laundry. The last load was in (towels) and whites were in the dryer.

'You will do your own laundry from now on. You will stay in here until the clothes in the dryer are done and then you will bring all your boy underpants and the ones in your bedroom and bring them out to the living room." And ten minutes later a pile of tidy whities sat on the coffee table in front of her.

"You will donate these to a charity. You are no longer allowed to wear male underwear. The three pairs you bought yesterday are just the beginning of an extensive wardrobe you will acquire. Most of the underwear you washed today belong to men. You will start buying items such as those for yourself. When you wear this maid dress you will only wear proper underwear. Understand?"

I said "Yes Mrs. PO".

"Good. I also want you to purchase several pairs of pantyhose to wear with this outfit. I believe you are seeing Evelyn tomorrow. You will of course wear your panties but I also want you to wear a bra there. I'll be back Monday. Have the panties folded and ready for me to take when I leave." And she walked out the door.

The next day Mistress Eve thought my new underwear was the funniest thing she had ever seen, took pictures and sent them to various people and then made me keep them on while putting me in a very uncomfortable bondage position.

On Mrs. Po next visit, I was wearing the pink undies, a pair of white pantyhose and my dress. The day started with a cooking lesson, a lightly breaded chicken and rice, after which she informed me that she would no longer be teaching me but I would be given assignments to learn to cook different dishes on my own. Although my apartment was very clean, that day was spent cleaning every corner of the it. She stopped me on two occasions; once for an over the knee spanking with a wooden spoon and once for cleaning my cock. She did this by removing the cage and using ice cold soapy water. She did it quickly and got it locked up again before it got any ideas about getting erect.

I was finishing up in the bathroom, using the toilet brush gag when I was called into the living room. She had me sit in a kitchen chair and then produced a small cosmetic bag from which she took out a small silver tube and other items. She first put foundation on me, followed by light blue eye shadow and finally a pink lip gloss.

"I will be gone for a few days. Every morning I want you to practice with the make-up. You will send me a picture 8 every morning wearing your dress and make-up."

And so it went for several months. I would see Mistress Eve every Thursday and Mrs. Po would come over two or three times a week for domestic training. I thought I was getting good at cooking, although praise from Mr. Po was rare, but as long as I wasn't licking chewed pieces of meat off my now very clean floor I was OK. She also introduced eyeliner, and mascara and eventually fake eyelashes to my make-up routine. My orgasms were few and far between.

During this time, I had collected a fairly large collection of lingerie. At first I was buying stuff on-line from regular store's websites. Then I found a cross dressers website and was able to get panties with pouches for a guy's junk. At first it was just the required panties but I expanded my wardrobe to include bras camisoles and eventually garters and fishnet stockings. And then one day...


WHEN WORLDS COLLIDE

It was a Saturday late afternoon when I got a phone call from Mrs. Po. Someone would be arriving in one hour and I was to put on my sexiest ladies' garments and my sluttiest makeup and wait for them.

I did my makeup first. I had gotten pretty good at it and during my morning practice sessions I had tried different looks. I could do slutty. The foundation was pale so the other colors would stand out. Heavy eyeliner and mascara. Two tone eye shadow and blood red shiny lips. I also selected a short blond wig. Next I dressed in white fishnet stockings with a white and pink lace garter the panties and padded bra were in the most delicate shade of pink. I added a pair of pearl earrings (real pearls) and a matching necklace (not real). It had taken me fifty-five to get ready and five minutes later the intercom buzzed.

"Yes," I said nervously., not knowing what to expect.

"Mrs. Po sent me," said a male voice, "I have a package for you."

I really didn't expect a male and didn't know why he was here. What did he mean by a "package"? Was I supposed to have sex with him? Mrs. Po often referred to me serving a master but I wasn't sure I wanted to go down that road. I buzzed him in and waited the minute till reached the door and knocked. I open the door with the chain on and peeked out.

I saw a man walking away down the hall. There was a large package sitting in front of the door. I brought it in and put it on the table. It was bound with a cord which I had to cut. I opened it and found two garments.

The first was the oo-la-la French maids dress. Pink satin with white lace, petticoat and a white apron. The other item surprised and confused me at first and then it terrified me. It was an ankle length black leather trench coat. There was only one reason for a coat like that. I was going out. There was a note in the bottom of the box in Mrs. Po's handwriting.

"Be at Mistress Eve's in 30 minutes." Oh fuck.

I didn't have any time to worry about it. It took me five minutes to get into the new dress, I hadn't put on any shoes had to wear something. I had been practicing walking in heels but a 20 minute walk was out of the question with anything but the lowest heels I had. I pulled a pair with 1" heels slipped thm on, put the trench coat on and headed out the door.

I had been thinking about walking down through Brooklyn on a Saturday in drag. But I hadn't considered seeing one of my neighbors in the lobby. He was over to the side where there was a series of mailbox. I saw him look up as I went out the door and I wondered if he thought "Now there is an attractive woman I would like to fuck". Or "There's a sick little pervert I would like to fuck."

The sun was just about set but there would be plenty of light along my way. There was two possible courses to Mistress Eve's. One was through a more residential where I would run into fewer people but more likely to stand out. The other would take me past a bunch of restaurants and shops but hopefully I could get lost in the crowd. I chose the latter.

My street was empty but as soon as I turned the corner I was in a crowd. It was pretty much as bright as daytime and I was convinced everyone I passed knew I was a sissy little submissive with a tiny caged cock. The coat had a collar that I tried to turn up as much as I could and I kept my head down. Whenever I reached a corner and had to wait for a light, a small crowd would surround me. I kept expecting someone would out me but they were New Yorkers and stayed in their own bubbles I guess. I walked 12 blocks down 7th Ave. eventually turning on her dark residential street. The only one I passed was a man walking his dog. The dog barked at me. The dog knew.

I climbed the steps to Mistress Eve's townhouse and rang the bell. I had no idea if I was on time or not, it seemed like hours since I got the package. I waited a minute and then Jet answered.

She hustled me in and said "You're late."

I started to apologize but she stopped me.

"Only kidding. Let me look at you." She stepped back and looked me up and down. "You look fucking great. Mrs. Po said you were good at it. If I ever need a good makeup job I'm giving you a call. Take off the coat. Now she laughed. "You look yummy. Best get in there," indicating the living room. "They're all waiting."

"Whose waiting," I said feeling my ass tighten a bit.

"Everybody. Go."

Well it wasn't everybody. Mom wasn't here, that would have been creepy, but everyone else was there. They were sitting in a semi-circle. On the far right sat Mrs. Po, she stared at me looking for flaws in my makeup. But said nothing. I guess I passed. Next was Renee She laughed when I entered the room. Next to her was Dr. Weinstein, looking professional as always. Next was Mistress Eve, then Mrs. Winters and finally Jet had taken her seat on the end. None of the ladies wore kink, Jet and Renee wore jeans, the other ladies had on skirts and nice blouses.

"Jon," Mrs. Po said. "There is a bottle of champagne and glasses in the kitchen please fill six glasses and bring them in here."

I followed her instructions. There were six champagne flutes sitting on a silver tray. The wine was in an ice bucket. I popped the cork and filled the glasses careful to give each woman the same amount and returned to the living room.

"Place the tray on the table and bring me a glass."

I knew what she wanted, we did this before. I brought the glass over to her curtsied, handed her the glass got down on my knees, lowered my head and kissed each toe.

"Now Miss Renee." I did. Renee was wearing a pair of Doc Martins.

I didn't expect Dr. Weinstein to participate. But she did.

Then Mistress Eve, Mrs. Winters (she took off her shoes and told me to lick her bare feet) and finally Jet.

Dr. Weinstein spoke. "Well Jon, we are done with you. I think the Evelyn and Mrs. Po have taken a basket case and made you into someone. You are a submissive, that's who you are. Like I said that time we just wanted to make you good at something. But besides the kink stuff you are a much better person. I think you will do quite well in the world.

"Now go clean my bathroom," said Mistress Eve. I paused to see if she was kidding. She wasn't.

When I was done and returned to the living room the only one left was Jet.

"C'mon I'll walk you home."

She held my hand as we walked thru the street. Nobody seemed to care.

Back at my apartment she told me to shower and clean up. When I got out of the shower I found Jet naked in my bed. A dream I had almost every night. As I approached her she held up the silver chain with the tiny key on it.

"I have some more stuff to teach you."

When she left in the morning she left the key on my nightstand.


WHERE ARE WE NOW?

That was all about a year and a half ago. So what's what these days?

I still see Dr. Weinstein from time to time. I still have issues and I have found an hour or two with her seems to get my head back on straight and yes she still has some unorthodox practices. Like the time I was whining about my latest existential crisis. Halfway through the session she got up and went out of her office, returning a minute later followed by Renee. She came over to where I was sitting, grabbed me, pulled down my pants and panties (yes I still always wear panties. These were red.) and gave me a most memorable spanking with the infamous leather paddle. That was not my last spanking from her. Oh here's something. Renee has an 8" dick! Yeah I know. Who knew?

I am basically on call with Mistress Eve. I get called to do errands, clean the house or from time to time assist in one of her session. I'll just leave it at that. I haven't seen Grandma or Mrs. Po since that night.

And Jet? Well life isn't a movie and the good guy doesn't always get the girl. We had several long talks and basically she sees me as a little brother. A slightly incestuous brother for sure. She is up in Rhode Island getting her master's degree in psych and like the Reel Big Fish song "She's Got a Girlfriend Now". Her name is Sue, she is also going for a masters in psychology, knows my complete story and finds me fascinating. Currently writing paper on your truly I've been up to visit them a couple of times and we all slept together in their big bed. I was of course caged.

As for me, I'm OK. I'm doing great. I went back to school, taking some business courses with the idea of eventually getting an MBA. After all I will have a company to run someday. I don't run home after class or hide in a dark corner of the library. I even joined a couple of clubs. Look at me, Mr. Social. And that's the story. I went from a total train wreck of a human being to ... well whatever I am today. I am comfortable in my own skin for the first time. Now if you'll excuse me, Mistress Eve called and said she needed the full Fifi this evening and I have to prepare.