The Society Ch. 04

I have a little explaining and an apology to make. The last installment of The Society, called The Society part 4 was uploaded by mistake. If you are following this story you will find that the first part of this installment is very similar to part 4. Please take this story for what it is, parts 1 through 3 and then followed by this installment, part 5. Sorry about the mistake but part 4 was a draft that mistakenly got uploaded instead of this installment which is the finished product. Please enjoy this installment and as always please feel free to write with any comments.

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Preparations for the madam hosting The Society's annual gathering were intense, especially for her concubines and sissies, even a full two months out. The Supreme Madam changed every few years and during a year when the supremacy changed lands the sitting madam always hosted this event. Serena, Corinna and I had been working like dogs to get things ready. The mansion was enormous but wouldn't hold all the participants which consisted of the entirety of The Society, so beds had to be brought in and rooms rearranged to make the crowd's stay a comfortable and most importantly elegant experience. Our estate was set up pretty well for the event. The large mansion could hold about half the members while Jodi's and Kathleen's smaller yet very opulent mansions on either side of Catherine's would handle the rest of the guests. We were working with Jill and Michelle, the two madams' concubines to turn the three estates into what amounted to a campus.

Today, Serena and Corinna were taking a sort of break from our chores heading out to an antiques auction with Madam Tyffany and her sissy, Heidi to find if they could discover anything interesting pieces for the event. Tyffany had a well earned reputation as an expert with a strap on, using it with effective skill on both females and sissies alike. I noticed the silver Mercedes pull up our driveway. I could see Heidi and her sandy red hair behind the wheel. I opened the front door and watched her open the car door for her Madam. Both of them were so incredibly well built. It was hard not to get excited at the thought of being trapped in Tyffany's bedroom or dungeon with the two of them.

"Why Carey! So efficient you've opened the door for us without the need for a bell." As usual Tyffany had a smile on her face and was effusive in her aristocratic dialect.

"We put in an effort for our best friends." I called to them as they walked up to the large portico.

"Poor little sissy. You have to wear your maid outfit. At least you're in one that'll get you laid. Who is on tap for you to tap today?" Heidi commented in her rich husky voice.

"Oh this little thing? I'm just working today." I was wearing a nylon and black leather basque that attached to a pleated leather skirt. Underneath, garters attached to Eleganti full fashioned silk stockings. I smiled as Heidi ran a finger along the sheer nylon portion of the basque. During the dinner party Catherine had called to discuss the situation with The Black Rose, she had commanded over a glass of wine that Heidi and I put on a show, since our wrestling match many had figured that we were an item. We ended up 69ing on the dining room table while the Madams in attendance cheered us on. I was so impressed with the redhead's body. It was taut and sinewy with muscle yet so smooth and feminine it was like touching warm glass. I thought that the only reason that she didn't beat Corinna or Lena on the mats was that at about 5'-7" she was a bit smaller than the two amazons. Today everyone was dressed casually and Heidi was wearing jeans and a backless body shirt that showed off her toned back and arms. Like about a dozen others in The Society I was quickly developing a serious crush on Heidi.

"No one dresses like that to feather dust the furniture. If Madam Catherine put you in that you'll be on your back while we're picking out cushions and chairs. Still, wish you were coming along." Heidi leaned in and gave me a long kiss on the lips and waved as she walked out.

"Good luck with Madam Sinn." Serena gave me a hug and a kiss as she walked by to join the others in our parking area.

Serena's attitude towards me had changed from night to day and as a result my life had become so much less stressful. It showed in my work for my Madam and the house and in my efforts to become better adjusted sexually as a transvestite. During the many dinners and social events held between the madams and their families I was running into black studs that had become more and more attracted to me. Now I was regularly having sex with the male members of The Society and they were leaving very satisfied. I had competed in a couple of wrestling events and had won with my only loss being that first to Heidi. I was beginning to flourish under Catherine's tutelage.

I watched the car pull away with a tinge of jealousy. I knew a day with Madam Tyffany meant a nice lunch with at least a couple of glasses of wine, a tour of a few antique stores and art galleries and maybe a stop for another glass on the way home, a very enjoyable day. Instead I was going to be the maid on duty when Catherine met with Madam Sinn to discuss strategies for the upcoming Supreme Madam election. I was also going to entertain two of Madam Sinn's people as the women talked. Sarah was Sinn's concubine and for all intensive purposes the black woman's partner and a young man who had recently joined Madam Sinn as a stud. If reports from women who had sampled this young African were true he was raw but extremely handsome, virile and a sexual athlete beyond his years.

For several years, Sarah, the prim and proper brunette was a seasoned concubine on the verge of being bestowed with the ultimate society prize, being named a madam. Yet there was another concubine up for a madamship. She was a hard charging slut who had broken the color barrier becoming the first black woman to join The Society. Sinn had climbed the ladder quickly showing a particular skill at enticing black men into The Society. Further she was very good at finding studs who were comfortable handling confident white women, women who were used to getting their way. Most importantly she found men who would allow and actually enjoy having a pretty white boi suck their cock and have no qualms about mounting and fucking the fairer and more feminine male. In short, Sinn was a wizard at convincing a bisexual black man who may have been fucking feminized white bois on the down low and train the black man to give the white bois what they so richly deserved totally uninhibited and in front of The Society.

Sinn met Sarah a party, an event actually put together to show them off as potential Madams. For the black woman it was love at first sight. While Sarah was bisexual she had plans to have a stud and a sissy under her once she was a madam. Sinn took it slow but in the end she seduced Sarah and at first gave her a couple of nights of utter sexual bliss. The relationship blossomed from there and they became lovers with Sinn assuming the role of the dominant partner. Sarah was so taken that she actually gave up her place to become a madam to become Sinn's concubine. More than anything, the madams appreciated a woman who knew how to get what she wanted. This personality trait was the hallmark of any dominant madam and Catherine, in particular, admired the black woman's moxie and the two became close. Now Catherine was pushing Sinn ahead of another friend, Gerri, to lead The Society. It was easy to see how many had come to the conclusion that Catherine was as Sarah had become Sinn's bitch.

The doorbell rang and I opened it to find Madam Sinn, Sarah and their newest stud, Quetto standing on our large portico. Both women were dressed in tight fitting summer business suits. Meanwhile the young stud was wearing a black blazer, leather pants and a white low neck tee shirt underneath. He was incredibly handsome and I could tell by the way he was standing he knew it.

"Good afternoon. It's nice to see you again Madam Sinn. Let me show you to Madam Catherine." I smiled brightly in order of rank at Madam Sinn, Sarah and a sideways glance at the irresistibly gorgeous young black man in leather pants. He caught my look and smiled knowingly. I led the small contingent through the foyer and into the living room.

"I have to say Carey that since the last time I saw you and now, today...well you look spectacular. Now Quetto, you see that is what a sissy in The Society is supposed to look like. Interested?" Madam Sinn complimented me and then turned to her newest stud.

"You certainly have a point Madam. This is a very pretty white boi. The best I've seen since I've joined but still, without a pussy..." Under normal circumstances the black man would have been considered to have overstepped his bounds speaking to a madam like that but he was young and fresh having only been with Sinn for a month and on top of that so damn sexy my tucked prick was filling with blood just looking at him.

"Why don't you show me to the library Carey. Catherine has set aside a couple of books for me." Sarah interrupted the young black man.

"Yes, of course, I know exactly where they are." I responded.

"And how is everyone today?" A smiling Madam Catherine emerged from the back of the mansion wearing a summer weight khaki business suit, the skirt short enough to show off her long sleek legs.

"Good morning Catherine. It's wonderful to see you." Sinn responded with the genuine smile of a close friend. The two madams kissed on the lips.

"Sarah it's so nice to see you." Catherine stepped over and gave the brunette an equally passionate kiss. "And I see that the hits keep coming Sinn. Is he as good as he looks?"

"Oh very much so, just ask Sarah, she broke him in. And as you've no doubt already heard Madam Valerie still can't get her toes uncurled after an afternoon in the saddle." Sinn replied with a wry smile.

"That particular session was described to me in exquisite detail by the aforementioned madam. I very much trust my Valerie so this is at the top of my to do list in the not too distant future." Catherine nodded towards the African.

Meanwhile Quetto seemingly used to the lecherous discussions in his presence was spending the conversation checking out both Catherine's and my legs. I gave him a knowing glance and then walked with Sarah to our library. The room was large and filled with books read and written by Catherine as well as other society members. My madam had written a plethora of manuscripts and how to manuals on female dominance, feminizing a male, turning your cuckolded male into a cocksucker and a host of other related subjects. Everyone in The Society with an expertise including Madams Catherine, Valerie, Elizabeth, Paula and even Diane from The Black Rose wrote about their specialties and they were all on display in this library along with books full of erotic artwork, pictures of transvestites in various stages of feminine dress and of course hardcore bondage pictures all available for exploration by the residence and any guests of the mansion. Even sissies read up on how to apply makeup and dress and act like a woman. Sarah took a seat in one of the comfortable leather chairs and picked up one of the three books that were on the table.

"Thanks for bringing me here. I can't wait to dig into these." Sarah nodded towards the books on the table.

"No problem Sarah." I smiled at the brunette who, with her wire rimmed glasses looked quite at home in the library.

"You know that you really are beautiful. There hasn't been a sissy like you transformed in quite some time." Sarah smiled.

"You're very nice. That means a lot now that I've accepted who I am in The Society." I thanked her for her compliment and was about to leave when Sarah continued.

"You must know by now that you can't get by on just killer legs and a pretty face." Sarah told me with a smile.

"Well from what I've seen just about everyone has great legs in The Society. I've also been asked to become a superior cocksucker and a nice lay and trust me, I'm working on perfecting those skills as often as possible." I returned with a wry smile knowing that Sarah could handle the satire.

"And as I've said, having a nice ass will only get you so far in The Society. We have more than our share of feminized white bois who feel that spreading their legs for any and all studs and groveling at the feet of their madams are their only chores. Carey there's a lot more to fulfilling yourself in The Society, just look at your sister, Corinna and Valerie's Samantha. I believe that they have each written books that can be found in this library." Sarah stated.

"At the risk of being tied up and whipped, I find it interesting that you of all people would be counseling me to be ambitious since it was you who passed up being a Madam." I felt comfortable enough with Sarah to speak frankly with her.

"You make a good point but falling in love with Sinn became an ambition in itself. Do you think that apart either one of us would be on the precipice of becoming the Supreme Madam? Sure I had to submit but I did so gladly. You have to admit that we make a pretty good team." Sarah responded.

"Well you certainly make a good point yourself. I get the feeling that now you're going to give me a suggestion. For someone as smart as you I'm certainly going to listen." I smiled.

"You know that just about every stud in The Society has at least a few pictures of you and when they don't have a concubine or madam to fuck they use those pictures to masturbate. Carey you're one of their favorite flavors." Sarah shocked me.

"How did every black man in The Society get pictures of me? And these pictures are nasty enough to get them hard?" I asked with a sanguine smile. I couldn't be upset. The madams got to use me anyway they wanted, in effect my body belonged to them.

"Oh never mind. Your picture gets taken at the strangest moments, you know when you're jerking off wearing the most intimate of lingerie, when you've got your legs wrapped around a black lover. You no doubt remember the moment just not the camera. Nevertheless someone with your, how shall I put it, sexual charisma should use it to make a name in The Society." Sarah advised.

"What sort of name?" I asked totally unaware of where she was going.

"Your madam and her friend Madam Valerie are known as the best at bending a young white boi's mind to their way of thinking. You should know. They did it to you. Corinna is the most dominant sissy in The Society. My lover, Sinn, can spot a young black man who will happily stick it to a pretty sissy just as easily as a woman like me." Sarah explained.

"You mean a bisexual stud?" I inquired.

"She never misses. In the end they all excitedly fuck gorgeous sissies like you. Yet sometimes they need some convincing, like Quetto. Perhaps that could become your specialty." Sarah smiled now that she had made her point.

"That would be one way to make a name." I replied smiling down at the seated concubine.

"He's down by the pool. Time to make your bones, sissyboi." Sarah gave me her order and a gentle slap on the ass.

I walked down to the pool with a tray. After all, I had been instructed to make sure that our guests were comfortable. It was my duty to make sure the young black man was comfortable. I found Quetto laying back on one of the heavy duty two person lounge chairs. I couldn't take my eyes off his well developed body and the immense bulge pushing upward in the blue thong bathing suit.

"Can I get you anything?" I stood over the black stud unable to hide my admiration.

"Just water if it's not a problem." The young black man answered politely.

"Of course. You should know that I'm here to serve you." I replied suggestively.

I walked over to the outside bar feeling his eyes on my backside as I moved. I poured water from a quart sized bottle into a pitcher, cut a lemon into slices dropping them into the pitcher and then shoveled in some ice with a scoop. I returned with the iced water and a glass. His eyes remained glued to me while I poured a glass for him.

"I have to ask. How does it feel?" The black man smiled and took the glass from me.

"How does what feel?" I asked.

"You have a penis but you live as a woman." Quetto inquired his jet black skin glistening in the sun.

"Quite frankly, it feels pretty damn hot. I get to fuck as either sex depending on the scenario. It's very exciting." I smiled back at the black stud.

"So you've always been a sissy?" He continued.

"No. Actually I had no idea I would love living like this until I was brought into The Society and acquiesced to my madam's vision of how I should be. I guess you could say after a little convincing I saw the light. It has happened to every other sissy here." I told the aspiring stud.

"Acquiesce. Submission is what you do. I have to say that there's no way I could live not being able to use my cock." The handsome man stated.

"Oh I use my cock. Make no mistake, I get plenty of pussy, madams, concubines and sissy pussy. I've fucked them all. And of course submitting isn't just something I do. It's something I love to do. Being submissive is really what made me a sissy in The Society. It's the perfect fit and why I'm here. Of course you're right, your role will be different. Look at you, muscular, as handsome as any man I've ever seen, the madams are already talking. " I was getting hard just talking to the young black man.

" But as often as you have been on top, you've pleasured and taken plenty of dick as well." He added.

"Of course, I absolutely adore playing with another man's penis. Do you mind if I take a seat next to you. I have to say man, woman or sissy these high heels are killers." The black man moved a bit to the side and with a smile and a wave of his hand invited me to join him. I made my move taking a seat at the foot of the lounge chair.

"They say that if I am to stay as a member of this society I have to learn fuck white sissies. I'm not wired that way." He was talking one way but I had seduced enough men during my time in The Society to know the telltale signs that he was very interested in me.

"Why don't we get you acclimated by getting some practice in right here and now." I asked confidently.

"I told you that I wasn't interested. What would make you think that I want to fuck you?" He lay back on the lounge chair exuding the same arrogance he had displayed when he had walked through the mansion's front door.

"You've been screaming to everyone who would listen that you refuse to screw any of The Society's sissies because "you're not wired that way" which is that you're not gay, it's abhorrent or whatever. That tells me that you're hiding you're true feelings and of course you've been staring at my ass and legs ever since we met. You should know that this isn't about two men because I haven't been one for some time now. Why don't you take a bite?" I calmly ran my hand up his muscular thigh until I found the silky material of the man's bathing suit. The material was so taut I thought that if I kept massaging him the suit might explode from the pressure of the black man's hardening penis. I ran my hand over the genitals until the head of the penis popped through the top of thong. I knew that I had him now.

"Don't you have tasks that your madam requires that be done?" The black man was in the final throes of protesting.

"Oh I think that you know by now the task that I was assigned for today." I announced my intentions while I leaned over and pulled down the bathing suit exposing an enormous semi erect penis.

I quickly reached out and grabbed it before any second thoughts could take hold. I smiled at the growing penis my hand gently stroking it. I had handled a lot of dick since joining The Society but as I watched Quetto's inflate in my hand I could tell that this dick was very special. The shaft was still thickening and my hand was barely able to get around it and most erotically it was the darkest penis I had ever seen. I massaged it with my hand taking special care to touch the pressure points at the base and just under the head. Once I got him rock hard I could see that his size would rival Corinna's while he was as thick as mine. I opened my mouth and went down on the African. I engulfed the head and part of the shaft comfortably but that was it, anything more was going to be a chore. I had become a very good cocksucker, in fact, an exceptional fellatrix. I very quickly had the black man moaning and running a hand through my hair. I was licking and kissing him in all the right places in between moments of applying suction by sliding him in and out of my mouth and throat. Then I added one more sensation that I was sure would drive Quetto insane. I ran my fingernails along the silky skin of the scrotum and juggled the egg shaped testicles in my fingers. Quetto's body shuddered and he drew his legs upwards. It allowed me to trail a finger down to his hole. I pushed against the puckered muscle and the black man groaned.