My New Life in a Frat

"Okay girls for the next 15mins your task is to tease these poor boys until they surrender and then the next boy and then the next. She who conquers the most wins. But the stakes are higher now." He leaned in close to us. " Jennifer, if you win this round Avery is out. Avery, you need to win the next two rounds to beat out Jennifer." He stepped back and in a cool tone bid us to begin.

We both just stood there not knowing what to do but always quick to an idea. Avery quickly rushed her couch and straddled the guy and shoved her fake breasts in his face while giving him a lapdance. I was stunned at first and looked over to my couch and the guy just winked at me. I followed my opponent's lead and straddled my guy too but I was at a disadvantage since I didn't have breast forms.

The guy I was grinding against didn't seem to mind. His hands were running up my legs and squeezing my butt. I gasped at his brazen actions but saw that Avery was practically humping her guy. I got off my guy much to everyone's groaning but I had to rethink my strategy. I wanted to win. How weird is that? Then it came to me Avery might have fake boobies to her advantage but my butt was all natural and way more bubbly than her anything. So I turned around and grabbed my ankles and shook my panty covered booty in the guy's face.

The crowd started to chant my name "sissy sissy sissy." I was back in the game. I lowered my butt up and down on his lap before finally resting on his lap and drawing my chest back up and began to grind my butt onto his crotch. His hands rested on my hips and I continued to grind when I felt it. I felt his boner pulsing beneath me. I'm not going to lie, it was rather exhilarating that I was in such control.

"Oh my I think someone brought more than a pencil to class... " I spoke rather loudly so that the crowd could hear me.

It was a good move because everyone laughed and whooped. That's when the guy I was giving a lapdance to spanked my butt causing me to squeak in surprise. Looking at the crowd I thought quickly.

I looked back at the guy and in my innocent voice, "have I been a bad girl? "

As I ground even quicker on his pulsing boner. The man nearly jumped out of his seat. I barely caught myself as he ran away into the crowd. Everyone was laughing and cheering.

I turned around basking in the crowd's attention when I heard the couch squeak as another toga guy jumped into the seat. I looked at him like a wolf looks at a sheep and I pounced. Quickly I sat down in his lap and this time I leaned all the way back and wrapped his arms around my waist.

I looked over to Avery who was still on the first guy and I saw her whisper into the guy's ear and you could see his eyes bulge before he tapped out. What did she say to him? And just as quickly as the first man left another man sat down and she again straddled him and began dry humping him aggressively.

I rolled my head back to rest on my guy's shoulder and I rubbed his hands all over my body.

In a conversational tone I said, "I may not have large fake breasts like some slutty cheerleader... " the crowd ooooh at my obvious diss to Avery. " But... " I brought the guy's hands to my chest, "at least I can feel it" and I let out a sultry "mmmm '' and bit my bottom lip dramatically. My guy tapped my shoulder and I got off him and he took off into the cheering crowd.

I looked over to Avery who was looking at me with such hot venom. I'm not going to lie, I actually liked the competition and that I was getting to her. I looked to my couch and another guy was sitting down and I took my position in his lap. This guy was already hard. I sat down and his hard dick poked me in the butt. I stood back up in surprise.

I rubbed my butt for effect and in a loud voice said, "oh my this one is already fully cocked." Making the crowd laugh. "Have to be careful not to hurt myself on this one" I chuckled.

I sat back down but this time much slower. His hard dick rested in the small of my back. I slowly ground my hips into his crotch. I could feel every inch and he was definitely big. He came to play too. He was synchronizing his own hips in time with mine. Which provided a stroking effect on his dick. The idea that another man was humping his dick on my butt oddly turned me on and I was reminded that I, currently, had my penis locked in a chastity cage.

A benefit that Avery did not have because as she finished up with her second guy his erection was quite obvious and it seemed like a much longer time for another guy to step up. This time Avery took a play out of my book and turned around to face me and sitting on her guy's lap. Probably so that she wasn't rubbing her dick on the guy in a competition to see who was the most girly.

I leaned back and whispered in my guy's ear. "Pull my hair back."

"What??" He whispered back.

"Pull my hair... give the people a show."

He was a little hesitant but he reached a hand up and gathered up my blonde hair and pulled it back, not hard but enough that I could work with it.

I moaned a little too loudly and in a breathy voice, "easy cowboy it's my first time."

The crowd lost it at that and started chanting "sissy" with all kinds of whoops and cat calls.

I looked over to Avery and saw she was whispering in her guy's ear before he immediately got up and not too long she was on to her fourth guy. I needed to pick up the pace.

"Oh cowboy keep this up and you won't have anything for the next challenge."

That seemed to do the trick because he let go of my hair and tapped my shoulder. Before I could even get up all the way another man sat down and he pulled me down to sit in his lap.

"Oh my, aren't you an eager beaver?" Everyone laughed

He wasted no time grinding his already hard dick onto my panties. He grabbed my hair roughly and pulled my head back as his other hand squeezed my hip

"Seems I set a bad precedent mmmm easy baby."

I tried to just go with it but this guy was being rather aggressive. I needed to regain control and fast. I reached a hand back behind me and found his hard dick that was poking my back and I wrapped my hand around it.

"Something is poking me....oh there it is... "

I made a show of pulling my elbow up like my hand was stuck, "I can't seem to get it out."

My hand tightened around his dick and I continued to move my hips and I felt it slide in and out of my hand. In a couple of seconds the guy tapped out and I was on to my fifth guy. The fifth guy was a guy that was previously one of Avery's guys. I looked around to see if this was legal but no one said anything and I sat down.

I leaned back and he whispered in my ear, "Avery said if she wins she will give me a blowjob."

In shock I looked over to Avery who was whispering in her guy's ear and again he tapped out and she was on to the next guy. She was catching up and now I know how.

"What do you want?"

"I want a shot at the next challenge."

"What's the next challenge?"

"Loophole... you know poophole loophole..." he explained to me in a patronizing tone.

I froze on the guy's lap. He tugged at my hips and I began to grind slowly.

"You didn't know?"

"No I didn't know the next challenge was going to involve anal sex," I bit back at him.

"So what are you willing to do to end this right here?"

He ground his dick on my panties.

"What do you want?"

"Well it is well within the rules if you jerked me off right here."

I shot my head back to look at him. He was serious. Tentatively I reached a hand back behind me and searched around for his dick. Finding it I wrapped my hand around it and I started moving my hips and he mimiced the movements so he was basically fucking my hand. I felt his hand trail up my body to grab my hair and he gave it a tight pull as well. It forced my head back and neck to his head where he whispered in my ear some more.

"Do you remember me from the first challenge? Because I remember how good your mouth felt wrapped around my hard cock. How about you tell the crowd you remember?"

I gathered my words and cleared my throat, "something is familiar about this one. Are you from the first challenge? " The crowd whooped, "seems like someone couldn't get enough." I continued

He whispered in my ear again, "I also contributed to the drinking game. Did you like the taste of my cum in your mouth?"

I gasped as he dug his dick hard into my hand. I squeezed him in response and I heard him breathing deeply. I looked over to Avery who was onto another guy already. How many was this now? Was she even with me? Was she ahead? If I win this then there will be no need to proceed to the next challenge.

I whispered back, "Avery put you up to this, didn't she?" He stopped surprised by my quick deduction "you are going to drag this out so that Avery can win with challenge and you can get your shot to fuck me in the next challenge." I squeezed his dick as I ground my hips up and down it. "But if I make you cum right here that would be the ultimate surrender. And I could be the next guy... " I taunted him.

I felt his breath on my neck quicken. I decided to double down and loud enough for everyone to hear I started to moan and groan.

"Mmm baby I think someone is about to explode. Wouldn't want to waste your wad before the next challenge."

The crowd started chanting "finish him finish him."

I picked up my pace and he pulled my hair back so he could whisper in my ear, "you win this round you sissy slut but I'll be back for."

He tapped out and I slid off his lap so he could sulk into the crowd.

Another guy sat down and I gave him the royal treatment before the announcer's voice broke my train of thought.

"60 seconds left. And we are currently 6-5 Jennifer! Can Avery finish her man, make this a tie and put us in the next challenge? Or will Jennifer get another victim and end this right here and now?"

"Sissy sissy sissy." The crowd cheered and whooped for me.

I leaned back on my guy and whispered in his ear. "I need to win this challenge."

He whispered back, "is that so...?" he ran a hand up my chest and grabbed my throat lightly. "What's in it for me?"

It was time to pull a play out of Avery's book. "If you tap out I'll suck your cock after this."

"Mmm that does sound good but I hear Avery is promising the same thing to those that help her. What else have you got?"

I looked around and saw Avery whispering in her guy's ear. I didn't have much time and she was about to close on her deal.

"What do you want? Name it." I begged in his ear.

"I want to fuck you. "

I bit my lip and looked over to Avery and heard the announcer start the countdown. Avery's guy tapped out putting her even with me.

" Fine fine yes I agree " the man tapped out immediately and the crowd went wild.

"Time! We have a winner! 7-6 Jennifer!" The crowd gathered around me and there were hands all over me in congratulations and some just wanting to get a feel. "We ask that the other contestant please leave the house. Better luck next time."

The crowd cheered and chanted for me. "Sissy sissy sissy." I was grinning like a fool. I won this. I can't believe I won this. Everyone loved me. I could get used to this. Pushing his way through the crowd, rich made his way to me. He leaned in close so I could hear him.

"You did good! Congratulations!"

"Where were you? I would've thought you wanted in on this last challenge?"

"That's not the last challenge."

"But I won, there's no need for the final challenge...."

Before he could respond the crowd got louder and he disappeared.

"Alright alright alright settle down you filthy animals. Jennifer you have just won an all exclusive spot in all our parties for the next semester. Which includes a spot in our very own house. How do you feel? "

The crowd waited for my answer.

"It feels good to win something."

The crowd cheered before the announcer's settled then back down.

"Well you won today girl. You are the best girl of Sissy Bowl."

"Sissy sissy sissy" the crowd cheered.

The party started back up and I milled about the basement still closed in my pink panties and my schoolgirl top. I chatted with some people and shook my booty for some others and I looked for Rich. I tried to avoid the guy I promised to fuck whenever I saw him.

The night went on and people slowly left. Eventually it was just me and everyone wearing togas who were part of the frat. Before we end the night we have one more bit of business to take care of.

"We are a close knit group here. We all look out for one another. We had to know whoever we let in our house wouldn't affect that. So in the tradition of Sissy Bowl we end this night like we end every night.

I looked around the room and hadn't noticed that all 15 guys were surrounding me in a tight circle. Nervously I chuckled and began to panic.

"What do I gotta do?" I asked, heart in my throat.

On that all the guys dropped their togas and they all stood naked and they grabbed their already hard cocks and began to stroke themselves. My heart was racing so fast. This was a circle jerk and I was the center of attention. This whole night was foreplay for all of them. I felt hands on my shoulders pushing me down. Obediently I sank to my knees where I was now eye level with over a dozen hard cocks.

"It's time for your baptism, you sissy cock tease" sounded a disconnected voice.

One man stepped up. I recognized him from the lapdance and he was stroking his cock inches from my face and before I could think of what I should do he erupted. Strings of cum hit my face and I gasped in shock. Just as he finished another guy stepped up and he shot his load on my face. The first six loads on my face were all the guys that I gave a lap dance to. I guess they were the most pent up.

"Did you guys hear that slut Avery was offering blowjobs if we helped her win?" one guy asked, talking to one of the other guys.

"She said I could fuck her," the second guy pointed out.

" Me too! " chimed in a third.

Without acknowledging me the next six guys stepped up and came in my face too. 12 loads. I just knelt here and let 12 guys cover my face in their cum. The last 3 guys were holding out. They were the last 3 standing around me.

One of them stood up to me and I looked up at him. He was the guy I've been avoiding all night.

"This little slut promised me her ass too. I guess they are both whores."

And without warning he stuffed his cock into my mouth and he pumped his hips fucking my face. He put a hand on my head carefully to avoid the stray strings of cum in my hair.

"But there is plenty of time for that over the next semester." He pumped fast until he erupted in my mouth. I swallowed what I could and as he pulled out some cum dropped out of my gaping mouth.

The last two guys took their turns fucking my face.

"It is a shame we didn't get to the last challenge. Would have been nice to fuck both those bitches in front of everyone."

"Oh there is plenty of time for that." A familiar voice rang out from the other side of the room.

I looked around one of the guys and saw Rich leaning on the wall.

"We got all semester to turn this little bitch into our very own fucktoy. " He dangled a set of very small keys in the air.

It was the key to the chastity cage still around my penis. He planned this. Did he rig the games?

The last two guys finished up in my mouth and I swallowed both of their loads. Nothing else to do. I just knelt there in the center of the room dripping with cum and my costume soaked with man juice.

Rich brought me a towel and cleaned up. I wiped my face and the towel came away soaked.

"Thanks Dick" I couldn't hide the resentment in my voice.

"Oh don't be mad this is what you wanted. You got a spot at the coolest parties on campus. You have a crowd of adoring fans. And you are getting out of that rut from high school."

"Yeah but I didn't expect to this gay stuff." I raised my hands in the air to gesture to everything.

"It's not gay if you're a girl" he pointed out.

That made me freeze. That was a good point. I wasn't being gay. I was a girl right now. I looked the part and everyone treated me like a girl. I guess he had a point. Which just made me more mad at him.

"Come on, I'll show you to your room." He offered his hand and I took it.

He led me upstairs and up to the second floor. We passed his room and at the end of the hall was a door. He turned to me and motioned for me to open it. I have to admit I was a little anxious to see the room I was going to have for the next semester.

When I opened the door I froze at the sight. It was wall to wall pink and girly. There wasn't a closet, just a clothing rack of sexy clothes and lingerie. There was a clear drawers unit that was full of panties in one drawer sex toys in another. In one corner was a sex swing and on the bed were cuffs on all four corners. I looked too rich in horror.

"Don't look so scared it's going to be great."

"Am I... a sex slave? "

" Slave is a bit harsh. You can leave anytime you want. But if you do then you can never attend an alpha beta chi party ever again. Do you want that? The next 4 years will be much like high school all over again. "

I looked back to the room and took a step inside. I looked around and tried to come to terms with all this. I turned back to see rich was still standing at the door. He smiled at me and closed the door. I heard a lock being set.

What have I got myself into?