The Society Ch. 03

Heidi's erect penis was sliding in and out more easily now. When she first mounted me being gentle wasn't her first priority. It was my first match and I had almost beaten her according to the wrestling judge. In fact many in the crowd of 60 or so spectators had disagreed and showed it by booing the decision, it had been that close a contest. This didn't sit well with Heidi who besides the more muscular and aggressive shemales, Corinna and Lena was the most successful wrestler among the sissies. We were wrestling in the last match before the election weekend which was about 8 weeks away. Catherine had called for this event hoping to lift the spirits of the members of The Society. As expected and as a sort of protest The Black Rose had kept their sissies at home so I didn't get a chance to watch Corinna take on Lena, the pride of The Black Rose sissies. Instead my housemate had made quick work of Alana, Madam Elizabeth's sissy and a very pretty example of a feminized boi. The shemale was of Mexican and Irish heritage and after her surrender everyone was boiling over watching her with her legs wrapped around Corinna taking the huge cock on the wrestling mat while her own 9" cock flopped around semi flaccid, a useless appendage as she took the role of a defeated woman.

We were in Madam Kelly's mansion and her expansive basement had been set up with a wrestling mat and opulent furniture spread all around the edges on which madams and concubines lounged watching the fight. Sissies served drinks and food and studs added the perfect amount of sexual excitement to the event. It was a scene right out of Roman times only in this empire the women were the superiors.

Now it was my turn, I was on my hands and knees enjoying the full force of the redhead's thrusts. I couldn't help letting out a groan each time Heidi's body slapped against mine. She wasn't in a league with Corinna's hammer but she was still strong and she knew how to make a bottom squirm. She went from fucking me from behind with her hands on my hips to draping herself on my back and forcing me down to the mat. As humiliating as it was to have lost and then having to submit to another sissy there was a flavor of excitement mixed in with the defeat. Even the most aggressive sissy was still feminized and by nature there was at least some degree of submissiveness in them so being used in front of so many people was a thrill. I was hard as a rock while the redhead rode me.

"That's it you're taking it like a champ now! Spread your legs more! Fuck you feel so good!" She growled into my ear loud enough for the crowd to hear.

She fucked me down to the floor so that I was prone beneath her. I could feel her hands on my back and her penis pumping in and out of my ass as the crowd egged her on. I could hear them all around me through the cheers. "Fuck her lights out Heidi!" "Make her your bitch!"

"Roll over." Heidi whispered into my ear. I had no choice but to obey. The loser was the winner's slut in front of the entirety of The Society until the winner achieved an orgasm.

I rolled over and put my arms around the gorgeous redhead. We kissed on the mat for a moment, Heidi's tongue sticking out and into my mouth. She reached down and grabbed my legs forcing them up into the air. She began licking and kissing one of my calves and then pushed them further down into my torso so that my gaping asshole was easily accessible. I groaned loudly bringing a response from the crowd as her erection slid up inside me and we were off to the races again. She couldn't resist smiling as she moved on top of me. I ran my legs up around her shoulders. I let myself go singing out high pitched sighs with each thrust.

I grabbed my calves and held them to give the redhead better position on me. I would look to the side and see the crowd cheering on Heidi, urging her to fuck me harder to make me scream her name. The cheers got louder and it fueled Heidi. She grabbed my buttocks and rolled me up onto my shoulders so that now she was standing over me with her hard cock buried deep inside me. She reached down and began milking my cock while she was fucking down on me. She was going to make me cum in front of everyone, a humiliation I was hoping to avoid but the gorgeous shemale was insisting. The feeling of her hardness stretching my sphincter and now her warm soft hand milking my cock was too much. I moaned and my legs began to shake.

"Cumming! Oh cumming!" I looked up at the triumphant Heidi as I announced my orgasm loud and clear for the watching crowd to hear. They roared their approval as the first spurt of sperm flowed from my erection and landed on my belly. I could hear clapping as more cum dripped down my torso onto my chest.

"Ugh! Take it on your pretty face!" Heidi managed to get her prick out of my hole and pointing it at me began to shower my face with gob after gob of her seed. One of the thick white ropes of liquid landed in my open mouth and the rest splattered all over my face. She got in the prone position so that her spent cock was over my face and pushed it into my mouth so that I could clean her. I tasted more warm semen as the softening penis slid in and out. After a head to balls rinse Heidi stood and gave me a hand up and slapped my ass firmly. She was smiling knowing that she had escaped the embarrassment of a rookie taking down a practiced veteran.

There were three matches that night, two shemale contests and one with two studs. In the case of the black men the winner claimed the loser's madam for the night. This particular debauchery took place in private as there were definite advantages to being a madam in The Society. Tonight Madam Paula was led to a bedroom by Royce, Madam Alliene's Stud. By the lecherous look on her face the blonde Madam didn't seem all that upset that her man had lost. I had heard that she was very enamored of the muscular bodybuilder and fucked him anytime Alliene allowed it.

Meanwhile I was being congratulated rather than consoled with regards to my match. Even Heidi gave me a kiss and asked that I not get any better lest she be forced to retire. As was custom after the wrestling there was a cocktail party which slowly but surely developed into an impromptu orgy. This was the first event I had been a part of so for a moment I stood there and watched it evolve. The madams, of course, were the aggressors. Elizabeth, Valerie and Catherine each paired off with studs while Alliene began to get amorous with Abigail, a blonde haired concubine who belonged to Valerie. The groups began to form and I would have continued to just stand there in shock watching 60 people pair up with a remarkable ease of coordination if a couple of hands hadn't come from behind and covered my eyes. I knew they were women's but couldn't figure out who was messing around until I was able to turn and see that my old classmate Jill was laughing behind me.

"Hey good job tonight! You're going to be fucking your share of sissies in the not too distant future." The dirty blonde haired concubine leaned in and kissed me.

"I got my ass stretched tonight but what makes you think that I don't get to fuck them now?" I replied beaming a smile back at her.

"Because of the sissy you live with. Corinna's not letting anyone up her tailpipe with any kind of regularity. And by the way, she's the only sissy who has ever won her first time out but you came close. I admit it. I was fingering myself while the two of you got it on out there. You've become so sweet in the short time you've been here. You're as passable as any of the veteran white boi cocksuckers here." She kept her arms around my shoulders giving me a long kiss.

I couldn't believe it. I had been one of dozens of guys that had followed Jill around admiring her from afar and dreaming that there may just be a chance that she would notice my existence. Jill had everyone taking notice of her, including teachers and most of the football team, but she knew how to handle any situation with a smooth ease. When she graduated everyone was left to guess whether she would end up married to a wealthy and famous celebrity or become a celebrity herself. Instead the gorgeous dirty blonde haired beauty had simply disappeared. I had become the one to find her being the submissive half of a lesbian couple in The Society.

"You know this is a beautiful cock." Jill whispered into my ear.

"I know that you've seen much bigger and I just came, real hard." I admitted with a smile kissing her on the lips.

"Oh I bet I can get you hard again. You're healthy and young. I'm sure that there's plenty of cream in these nuts." Jill laughed as she continued.

I stood there watching bodies writhing all around us. There were piles of beautiful white women and sissies being penetrated all around the large room. Catherine, as usual, was surrounded by a couple of black men, one on top taking her from behind while the other lay underneath her allowing the blonde madam to grind down on his ebony cock. Corinna's dominant performance on the wrestling mat was short lived. She was face down on a couch with Madam Elizabeth on top of her pumping her strap on into the blonde shemale's asshole. Meanwhile Jodi was bent over at the waist with her face buried in a reclining Vera's pussy while Serena stood behind her fucking her hard with a strap on. It was strange to see a madam giving it up to two concubines in such a public setting. It made me think of Catherine's admission that her friend and ally was indeed weak.

I was kissing Jill with my tongue in her mouth. She was kissing me back and running her fingers up and down my chest. There was no way to describe how excited I was. My heart was practically leaping out of my chest. I had such a crush on Jill it was impossible to put to words and then the ultimate happened, Jill slid down my body and began sucking on my hardening penis. She smiled up at me while my cock slid in and out of her mouth. Right then and there I knew that this whole adventure as Catherine's maid had been worthwhile. Jill was very talented. My formerly unattainable high school friend was doing an incredible job on my dick. I could tell that she was thoroughly enjoying the thickness of my dick. She was quickly discovering what she was missing laying down with all those small cocked heavily muscled football players.

Jill may have been the property of a woman and her lover but she was intimately familiar with a man's genitals. She was all over my erection and scrotum licking, kissing and sucking me. I wasn't going to be able to hold off much longer. I wanted to fuck her so badly but Jill was showing me no mercy. She was going to get a load of my seed down her throat and all over her face when suddenly I felt hands on my shoulders.

"Congratulations. It looks like you won the cupie doll. She's absolutely fantastic on her knees or on her back. Why don't you fuck her while I top you? Your girlfriend didn't let me cum so be a good sport let me splash some seed up that gorgeous ass of yours." Alana was behind me and when she finished with her request she gave my ass a strong slap.

I turned my head and gave the statuesque latina an air kiss while Jill stood and put her arms around me. I spread my legs a bit more and let Alana slide up my ass . Without high heels I was the shortest of the trio so I went up on the balls of my feet to accommodate the gorgeous shemale while Jill in a pair of pumps grabbed my cock and pushed it into her pussy. The three of us wiggled around getting comfortable with each other and then we started to fuck. Jill and I were really into each other, kissing and touching while she moved up and down on my hard cock. Alana didn't mind the lack of attention. She had my ass and that was all she needed. With her hands on my hips she was taking long powerful thrusts. The three of us joined in an undulating dance our bodies writhing against one another. Jill was tight and her pussy was gripping down on my throbbing dick. Meanwhile Alana's penis was huge, bigger than mine, and was pressing up against my prostate. As was often the case with this combination the participant in the middle quickly became the object of the two on either side. Jill was literally jumping up and down on my hard cock her excitement was so high while Alana was fucking me as hard as she physically could her thrusts now short bursts of energy plowing into my buttocks. I was moaning loudly while the two worked me over from in front and behind. I couldn't hold off any longer. I let out a howl and let go inside of Jill's vagina.

"Oh my God! Ugh! Oh my..." I yelled while my balls drained and I experienced one of the most intense orgasms I thought possible my voice trailing off into tears of bliss.

With her pussy full of the cream that Jill had so desired. The gorgeous blonde untangled herself from my spent cock and sank down and took it into her mouth cleaning it while the statuesque shemale continued to take me from behind. Meanwhile one of the studs approached Jill from behind and began caressing her hoping to entice her into taking some more dick between her legs. Yet instead of arching her back and spreading her legs so that he could mount her from behind, the lithe concubine pushed herself between my legs tucking her ass and genitals underneath licking at Alana's hanging testicles and in effect rebuffing the black man. At the moment I didn't care. I was getting a huge portion of Mexican cock up my ass and it felt real good. And as soon as Jill's tongue hit Alana's cum filled balls the tall shemale's breath was heavy on my neck. She was grunting into my ear and I knew it wouldn't be long until she shot her load. I clenched my buttocks tightening my sphincter around her erection and it was quickly over.

"Ugh! Oh fuck yes! Take it you slut! Take my fucking cum!" Alana let out slurring her speech drunk with the excitement of the oncoming freight train of an orgasm.

Alana's sperm shot hot and hard up my ass. There was a tremendous amount of thick fluid and it was everywhere flowing out of my ass and down into Jill's open mouth. Alana hugged me tight and kissed me on the neck while her nectar spilled inside me. I felt her cock pulled from my ass by Jill who was still between our legs. She sucked and licked the long cock cleaning it of cum and then slid up to her knees while Alana came around and faced me. I could feel the tongue up my gaping asshole. I let out a guttural moan while Jill cleaned between my ass cheeks. The feeling of her tongue and mouth up there was exquisite. I was actually getting hard again.

"Let me just say that I've been looking to top that sweet ass of yours since the moment I laid my eyes on you! You are a great fuck!" Alana gasped as she rained kisses down on my face.

Jill was up and joining in on the kissing for a moment and then she disappeared up the staircase to the main floor. There were bodies all over the place now moaning and moving in sexual rhythm and it wasn't just down in the basement. There were Society members attacking each other in beds and on couches and making use of Madam Kelly's dungeon so I thought that maybe Jill was simply looking for a new partner. When a rather well built stud slithered over to Alana and me I took the opportunity to excuse myself. The tall Latin sissy seemed quite happy to br his bottom and I snuck away upstairs to look for Jill. There just seemed to be something odd about my friend taking off so suddenly.

I pranced up the stairs and got a good look at Madam Valerie on the living room couch sandwiched between two studs humping wildly into her body and on the floor continuing what they had started downstairs Madam Elizabeth and Corinna were locked into a sixty nine furiously licking at each other. I wandered into the kitchen and found Jill leaning up against a counter chugging down a cold beer.

"Taking a break from the action?" I inquired with a smile.

"Yeah I guess you could say that. I had to pee and clean up a bit. We worked up a pretty good sweat down there and of course you put me up a quart in the sperm department." By the way Jill smiled at me I was convinced now that something was bugging her.

"So having a beer to fill up the bladder again?" I smiled at the tall blonde.

"You looking to finish up the night chained to a post taking my whip?" Jill said only half joking.

"Come on. What's wrong? You may not have known me from a cafeteria chair back in high school but I am your friend now, maybe the closest besides Madam Jodi." I tried to reason with Jill to get her to talk.

Jill grabbed my hand and dragged me to the wall behind the large kitchen table and pulled me down onto the floor so that we were somewhat hidden. She was about to talk and then instead leaned in and kissed me. I looked out of the corner of my eye and saw that there was a pair of black legs on the other side of the kitchen table. It was no doubt a stud looking for some fresh pussy or ass to violate. Seeing that Jill and I were already coupled the legs did the right thing and turned and walked out of the room. Soon after Jill pulled her lips from mine and set her big brown eyes on mine.

"So... you were saying?" I wasn't going to let Jill drop what was bugging her.

"Black men." Jill looked around to ensure that no one else had come into the room. "I can't say that I don't like them that would be mean and racist but I've never been with a black man and I'm not so certain that I ever want too. At this point it's like jumping out of an airplane with a parachute, some, like you, don't have any problem with it others, like me, won't leave their seat no matter what. Maybe that's still racist. I'm sorry I just don't want too."

"Wait a minute in an organization that reveres black dick as much as The Society does you have not yet even sucked a black cock? How? I mean you're weaned on black cock as soon as they get you in a dungeon around here." I was amazed at her statement. Within my first couple of days as a fresh captive in The Society the Madams were already indoctrinating me into interracial sex. Serena had been whored out to groups of Africans at a time in order to insure the success of Madam Catherine's new business venture. I couldn't imagine that Jill hadn't gone through the same sort of rigors at one point or another.

"I came into The Society in a different way. Denny I'm a lesbian." I was taken aback to hear my old name again listening to Jill. "I like dick from time to time too so I guess you could say that I'm bisexual. Yet where you could kiss a girl, suck a cock, lick a pussy, take it up the ass all in one glorious orgy I like mostly women and I knew it from high school on. So it was in college I was dating a professor who was showing me the ropes as it were. We were out one night at a lesbian dance club when we ran into Jodi. She was friends with my girlfriend and we sat and talked in between dances. The professor made the mistake of letting me dance with Jodi. I fell for her that night and within the next couple of weeks I had moved into her mansion and taken the job of executive assistant/lover. Now I'm in love with her and this switching of Madams that happens from time to time scares the hell out of me even more than the thought of one of those giant black cocks sliding in and out of me. In short I never had to be broken down to join The Society. I joined The Society because I had fallen for Jodi."

"So no interracial indoctrination for you?" I asked.

"No. The first time I was at one of these orgies I was horrified to find that the white men were actually feminine submissives and that black men were the dominant lovers. I was lucky. Paula and Kelly wanted me for the evening. They took me up to a bedroom and tied me up. I felt for sure that a black man was going to be ordered in to fuck me but it never came. The women wanted me all to themselves and believe me that was just fine. Since then I have played these orgies and any other encounters very carefully but the pressure is getting to me. Sometimes I wish that we weren't in this Society anymore." Jill explained.