The Society

"Why don't we get to work on making you a woman? Corinna you can return to your chores." Catherine offered as we watched the well built blonde walk out of the dungeon.

And with that I spent the rest of the day doing things that I had been doing my whole life only now I was going to do them as a woman would. I was learning how to walk like a woman did, both in bare feet and in heels, how to move my arms more effeminately and just about anything else that a woman would do differently than a man. The women were deprogramming me changing everything I did and they were able to get it done by teasing me and touching me coaxing me like a dog with a bone as a reward for my hard work. They knew that with every step I became more and more like a woman. I discovered very quickly that both Catherine and Valerie were very adept at getting young men to do what they asked of them and I was no exception. By the time the morning session was done I was smitten with the both of them. I would do anything they asked.

I was amazed at all the detail in a woman's wardrobe. As a young man I put on underwear, a pair of pants, shoes and a shirt and I was good to go. In the afternoon the women had me try on just about everything a woman could wear and showed me how to walk and act in them. Cocktail dresses, business dresses, latex bondage gear and formal gowns all covered various types of lingerie that I learned how to put on and wear like a lady. And, oh yes, sucking cock and just about anything else phallic. The two dominant women made sure that I had something in my mouth all the time. They took turns between each lesson making me suck cock, their cocks, the rubber ones belted around their waists and sticking straight out. They had me do it on my knees, bending over them as they lay on their backs, in a 69 position as they sucked on my trussed penis driving me closer to madness with no relief in sight.

"Just ignore the taste of the rubber Carey. The goal here is to get accustomed to sliding something thick and hard down your throat. That's it just relax and let it ease down. There isn't a man that will be able to resist you once you master the art of fellatio." Valerie had a satisfied smile on her face as she looked down at me on my knees sucking hard on the strap on dildo attached to her shapely body.

At one point I was alone with Valerie. She was continuing nonstop with my lessons in feminization. As she taught me how to walk and move my body I couldn't take my eyes off of her. Her body was flawless and just looking at her was making my cock ache. Although it had only been just over a day since ejaculating I was used to jerking off at least three times a day add to that the fact that two of the most beautiful women I had ever laid my eyes on had been touching me and I was in real pain and needed it to end.

"Madam Valerie I need to cum. Is there any way that you would let me masturbate?" I pleased with the gorgeous blonde.

"Oh my goodness Carey of course you may relieve yourself. All that you have to do is submit completely to your Madam." Valerie's slight English accent was only making me hotter.

"How do I do that?" I asked. I was now willing to do just about anything to blow a load.

"Well you and I can go upstairs and you promise to obey Catherine and her fellow members of The Society and you promise to commit to becoming a Sissy." Madam Valerie informed me.

I couldn't do it. I shook my head and followed my instructor's orders into the next lesson. As for Valerie she simply smiled and continued her instructions. She was the picture of patience as was Catherine who returned later in the day to assist her fellow Madam. They must have known that I was close. They poured on the teasing touches and caresses all over my body. At one point Valerie even briefly sucked my cock. I thought that I was going to hyperventilate myself into a heart attack she was just so good at the art of cock sucking.

As with last night I was secured to the comfortable lounge chair and made to view an even stranger instructional video than the previous night. As I lay back exhausted from the day's work, my feet in particular throbbing from hours in high heels a beautiful blonde appeared wearing only sheer black stockings and high heel pumps. She had the body of a fit woman with legs that looked spectacular in the hosiery. I noticed just a hint of masculinity in her face which actually went quite well with the penis hanging between her legs. It was getting hard to believe anything that I was seeing at this point. How could someone so sexy have a cock?

"Hello my name is Suzanne and I'm a Sissy in The Society and in this video we're going to teach you how to accomplish the ultimate act as a Sissy, having anal sex with your man." The blonde shemale had a fairly thick accent that I couldn't quite place.

"I'd like to introduce my partner, Roy. Roy, how are you?" Suzanne smiled at a very athletic looking black man who walked onto the stage sporting a sizeable semi erect penis. The blonde Sissy grabbed the large black prong and gently stroked it.

"First things first you have to excite your male. You can do some cock sucking or get a little original like this." Suzanne lifted a leg and began rubbing the black man's penis along her knee and thigh. The result was as expected. The black man began moaning and his cock hardened to the stiffness of a metal pipe.

"Now you need to lube your man so that he can slide in and out of you. Some bottoms are happy taking some spit and spreading it on their man but I'm a little too tight for that so I use a little lube like this vasoline." The blonde took a small jar of petroleum jelly and with a finger took some out and smoothed it along the shaft and over the large head of the erect penis. I noticed that the blonde shemale's own cock had become hard.

"Now you've got your man just where you want him so it's time to present yourself to him." The sinewy blonde bent over in front of the well endowed black man and grabbed her ankles allowing him to line his erection with her sphincter.

"Now is the time to relax, especially for you beginners. This is going to hurt a little but don't worry your rectum can take it and once he's in... mmm heaven." The gorgeous shemale described what was happening letting out a gentle sigh as the black man slid inside her.

I was then treated to an incredible display of sex between two men. Sure the blonde had been completely feminized but there was no mistaking the 6 inch erection bouncing wildly in front of her as the black man thrust himself in and out of her. Suzanne's face showed a painful expression for a few moments and then a smile came across her face and it was obvious that she was really enjoying what the black man was doing to her.

I watched the two of them undulating against each other and although there were two cocks and no pussies in the picture I once again became excited just as I had the night before. The sight was incredible. Suzanne had a body that would have made just about every woman jealous and she knew how to use it to pleasure her man. Roy took the shemale like any capable man would a woman. He fucked her so hard that he drove her down to her hands and knees and then rolled her over and fucked the blonde missionary style kissing her and making her moan and sigh. In the end he lifted Suzanne up off the floor and took her from behind while they both stood. The shapely blonde moved her body and thrust her own cock into the air while the black man used her ass. Suddenly she let out a loud groan and without touching herself milky white cum spurt out of her penis like a fountain. Ultimately the muscular black man quickened his already violent thrusts and came deep inside the blonde shemale's rectum. I watched the two sweaty heaving bodies amazed that the gorgeous shemale could be so excited having a black cock sliding in and out of her that she would orgasm simply fucking air.

The video turned off and I found myself even more excited than the night before. I found it almost impossible to fall asleep and I tossed around in the chair as much as someone handcuffed to the arms of the chair could. I so badly wanted to jerk off which was quickly taking the place of escaping as my most desperate desire. In fact getting away wasn't so important. I had a mad crush on Valerie and I certainly no longer minded the feel of Corinna's body. I was thinking about my situation as I finally drifted off.

I was in a slumber when the same black man who had explored my tonsils with his penis the night before appeared in front of me again. I couldn't believe that I was having another dream with this same stud and it excited me. He was stroking his large cock into a raging hard on and smiling at me. The penis was shiny with some sort of lubricant. The naked stud spent no time leaping into action. He grabbed my silk encased calves and lifted them into the air and then got into position to mount me. I didn't resist. I just lay back and let it happen. I felt the pressure on my sphincter and I relaxed letting the thick member ease into me. The black man was gentle and the pain wasn't that bad. I spread my legs wide and he was very quickly balls deep inside me.

He climbed up on top of me and leaned down and kissed me. I returned his passion and thrust up into him with my pelvis. My black lover took the hint and grabbed my legs and began to fuck me. The sensation of being fucked like a woman was so real, so incredible I had given up thinking I was in a dream. I was moaning and grabbing at the black stud's churning buttocks. My dream lover was pounding into me with each thrust. I had never felt like this before. I so badly wanted to cum into the air as the blonde shemale had done on the video I had just watched but the electronic nylon tube was secure around my erection. Still I was mimicking Suzanne trying to pleasure the stud even if I was going to be denied I wanted his hot cum up my ass.

The stud's pace quickened and our bodies began slapping against each other. I was dressed in all the right garments silk stockings, a garter belt and a brassiere to look like a white woman craving and now enjoying a huge black dick and I felt like it as my legs kicked in the air. My African lover grunted loudly into my ear and began taking erratic lunges deep into my body. He was cumming, spewing his seed into my rectum. I took it with a smile on my face. Just as quickly as he had appeared the muscular black stud kissed me deeply and disappeared. I fell into a deeper slumber dreaming of the gorgeous black man and my future as a sissy in The Society.

"My goodness is that as painful as it looks?" Corinna put a finger on my throbbing member as we showered.

"You have no idea!" I answered nearly doubled over.

"Oh I've got a very good idea. I've been living here for a while remember?" Corinna tried to soothe me by soaping up my back.

"Which brings me to how you got here and became her husband? Catherine is probably 15 years older than you." I asked with my eyes closed.

"Twenty actually but you've seen her naked and sank your cock into her so what difference does that make?" Corinna smiled and kissed my neck.

"You have a very good point. So are you going to tell me how she got you?" I persisted.

"Sure. Are you going to show your gratitude by showing me your new found oral skills at a time of my choosing?" I could feel Corinna smile behind me.

"Sort of a sex IOU? Okay." I assumed I'd have the blonde amazon's dick in my mouth anyway so why not.

"Of course. Now let me see. Oh yes we met at a wedding. I was from the Midwest and had been invited by my girlfriend at the time. So here I was this fresh baked boy from Wisconsin and this gorgeous mature woman came up to me, introduced herself and then asked me to dance right in front of my girlfriend. After a couple of dances she had me. I would do anything she asked. I was just like you, good looking, horny and I thought heterosexual. I was in Catherine's bed as her plaything." Corinna began.

"So you had a pretty girlfriend and you still went with Catherine?" I asked.

"Well before you try and get me on a guilt trip my former girlfriend, Ginger is happily ensconced as Madam Helga's lesbian concubine. She was turned easier than I was." Corinna massaged my shoulders.

"No guilt trip intended. I know how this works." I turned and faced Corinna as she turned off the water.

"Well she got me good. Over the next couple of months I fell head over heels for Catherine. Why wouldn't I? A gorgeous sexy woman with a fabulous estate and all the money in the world, I have to say that you didn't have to ask me twice. Yet it was Catherine that was making the decisions. She told me we were in love and should get married. I couldn't fight her so we got married and I thought I was as happy as I could ever be. Sure Catherine was older but you tell me if that made any difference in bed. The three months I was fucking Catherine as her only lover were bliss and then I found her with Lateef." Corinna handed me a towel as we walked out of the huge shower area.

"Lateef?" I wasn't sure who he was.

"Catherine's scenarios are planned with particular attention to detail. She had seduced me, entrapped me and now she was going to make me her cuckold. Lateef was a very well built older black gentleman. He was handsome and very smooth. I found them on the couch in the living room talking with each other. Catherine could have plunged the knife in quickly. I could have found them in bed with her legs around his waist and his dick deep inside her. Instead she took her time. She introduced me to her college friend who had come to visit. Lateef was a very dark skinned African and as I had said a perfect gentleman. He shook my hand and then returned it to my new wife's arm. They were way too friendly to be just friends. That night in bed Catherine told me she was hot for some oral sex, ordering me down between her legs. She was so wet. I knew then that she was slimy with his come. I ate her pussy just the same.

Like I said she went slowly telling me that she liked her men smooth so I waxed my body and then had all my hair lasered off permanently. Then there was the experimentation with women's lingerie. Why not have some fun in bed Catherine suggested in a tone that was very much an order. So I would dress for her and during one of our sessions she put make up on me. I thought that it was all sexual excitement between two consenting adults. I had no idea that I was simply a pawn being moved about the board by a very skilled player. And while Catherine was positioning me Lateef would visit and when I was with Catherine later I was on my knees between her legs licking his seed right out of her well used hole. I was in complete denial and too young to even understand what was happening. One day I came home and found Catherine and Lateef kissing on the couch. I was mad and excited at the same time but Catherine told me I was acting silly that she and Lateef were just doing some harmless petting.

It all came to a head one night when Catherine and I were lying in bed. She asked if I thought Lateef was handsome and if I was attracted to him. She told me that she had watched me checking him out from time to time. I told her I thought she was crazy and that I thought that she had been fucking him. I have to say that it was the one time I actually stood up to her but it didn't last for long. Catherine told me that indeed she had been screwing the handsome black man. When I asked her why she looked into my eyes and said simply because he was a much better lover than I was. Then she told me that sex between men was natural and that it was clear that I was the submissive to Lateef's dominant top. She informed me that the sight of me on my knees sucking on that big black cock would be an extraordinary turn on. She started making comments in front of Lateef about how I thought he was a very attractive black man. Before I knew it I was warming up his penis with my mouth for my wife's pussy. At first I did it to please Catherine because that was so important to me and by the time Lateef had seduced me, making me his woman I was doing it because I loved the feel of a man inside me.

While Lateef and Catherine became lovers right in front of me my wife had a suggestion. Since I looked so good in drag why didn't I dress full time and take my own male lover? I had a big dick but Catherine said that it wasn't much use to her now that she had a real man to fuck her. And I actually did just that. I dated several men and entertained them right down here on this bed. Ultimately Catherine told me about The Society and how it worked. She told me that white men were subjugated by women who lived a lifestyle dedicated to all forms of dominance. She instructed me that two of the most significant of these dominant forms was the art of cuckolding and feminization which I had just experienced by her hand. She had me. I was hopelessly in love with Catherine but when I saw her kissing Lateef, when I tasted the thick liquid in her pussy and knew that it was Lateef's sperm and then finally when she suggested that I suck her lover's cock as a form of surrender to his superior sexual prowess there was an indescribable excitement that coursed through me and I still feel it today. There was something else and Catherine had known it from the beginning. I found that I very much enjoyed sucking cock and the feel of a man inside me. I am bisexual and she's some sort of a savant when it comes to picking out a man with this sort of desire, no matter how deep it's buried inside him. That's why she so deftly picked you out of seemingly nowhere at that cocktail party. Although I will say that it wasn't just Catherine. Every Madam at that party wanted the joy of training your ass. Your landlord Patty is a madam and an old hand at wrangling sissies like us. Jodi Mapleton as well. So like me you were chosen. I have no doubt that the excitement I felt when I saw Catherine lying underneath that black man and when I felt my first black stud penetrate me you'll experience as well." Corinna ended her story and I had a million questions. The last comment about my landlady, a rather mature woman who none the less had great legs really threw me for a loop.

"I'm not certain I could choose between women like Catherine or Valerie. It's going to hurt when I see either of them with another man." I admitted.

"Maybe but let me give you a heads up, your friend Jill? Our Society is chock full of sexually charged young sluts just like her and they love playing with feminized Sissies that have learned their place. You're a submissive boi plain and simple and for a sissy like you there's no better place to be than right here. Now do me a favor and get on your knees and give it up today. That cock of yours is taking on a permanent purple color from lack of relief and I'm about ready to explode at the thought of being able to fuck you anytime I want." The blonde shemale kissed me on my lips and sent me on my way in my uniform, a pair of high heels and a sheer blue nylon cock sock.

As I moved through the workout room I noticed that again no one was holding my ball leash. I could run for my life if I wanted. Sure the sight of a 20 year old boy in makeup, high heel pumps and a cock sock might draw a few chuckles downtown but I'd be free. Then I thought about what Corinna had told me. In the last couple of days I had discovered a few things about me that I would have never thought would have existed. Just like Corinna I liked sucking cock and taking it in the ass. At the very least I was bisexual and may have been more attracted to someone like Corinna than Catherine and most importantly I looked better dressed as a woman than a man. I checked out my body in high heels and make up in the full wall mirror before leaving the workout room. I looked longer and leaner in the shoes. Most of the masculinity had been hidden behind eye shadow and lipstick. My buttocks were upturned and stuck out like a couple of round apples and my legs looked like they belonged to a member of a women's college swim team. I couldn't believe it. How had they done it? It had to have been more than just some makeup and a pair of shoes or was I just what Catherine, Valerie and Corinna had been telling me for the past few days, a sissy.