My New Life in a Frat

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Theme party leads to a new lifestyle.
7.2k words
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Part 1 of the 5 part series

Updated 06/11/2023
Created 10/01/2022
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I was so nervous. This was my first college party and it's at the best frat house, known for their crazy parties. The theme for the party was gender swap but as I walked across the sunset lit campus in my Japanese schoolgirl outfit I got a lot of strange looks. What really made me blush were actually the catcalls and whistles I received. I am fairly slender and have naturally long blonde hair so a little bit of makeup I picked up from my theater department really made me passable. Which was the whole point. See there was a prize for the most passable "girl" tonight. The winner gets to live in the frat house for the semester. That might not sound like much but it means you get an automatic in at the coolest parties on campus. So I am all in but I am still super nervous.

I get up at the house and it's quiet. You ever go to school on PJ day and the first people you see aren't in PJs so you panic wondering if you had the day wrong and you are going to be the only one wearing PJs? I'm feeling a lot like that right now.

I rang the doorbell and a half naked toga wearing muscular guy opened the door.

"Oh great, our first contestant! Points for punctuality brah. Or should I say... babe?" he said out of the side of his mouth, shooting me a wink.

I averted my eyes to try and hide my blush. Why was I blushing so hard? He motioned me to enter and informed me that I was early. Apparently if it says the party starts at 8 it actually doesn't start until 9. What a nerd. Is it obvious I didn't go to a lot of parties in high school?

"Anyways you can chill out over there. I'm sure some other people will show up soon." He said as he shrugged noncommittally

I didn't really believe him.

I looked around the house and all of the guys were ripped and wearing togas.

I turned to the guy and asked, "Why is everyone in togas? I thought the party was a gender swap?"

"It is babe. Gender swap for y'all. We already live in the house. We are the judges. It's a Turing test. If you can make us forget we are talking to a guy and not a girl then you pass."

I was a little shocked to hear a frat guy at the party house talk about the Turing test. That was AI robotics stuff. I expected more "football good. Beer is better. But football good. '' From a jacked up frat guy at the party house. How was I supposed to make them forget I was a guy?

I slumped on the couch and watched the toga clad Adonis's milling about getting ready for the party. Then I realized if I wanted to pass as a girl I needed to act like one, not just look like one. I was wearing a skirt. I should cross my legs or something. I sat up and crossed my legs and fussed over my posture and outfit.

"Nervous?" a voice startled me from behind.

"Geez you scared me!" I looked back at a guy sitting in the recliner in the corner.

"Sorry I was sitting here wondering when I should let you know of my presence. Should I clear my throat? But then you started picking at yourself. It got more awkward the longer I just sat here. Do you want some help?" the stranger offered.

"Um yes please! I'm super nervous. I really want to win this. I don't want to pass college like I did in high school." I told him hoping I didn't sound too desperate.

"I get that. Stand up, let me look at you." he gestured to me.

I stood up and looked down at myself and kind of shrugged half heartedly.

"You look great but you have one issue... " he trailed off looking at my crotch.

I looked down and the skirt was so tight that in the wrong posture it showed my front bump.

"Oh I didn't think about that. I should go change or something shouldn't I?"

"You don't have the time. You have a good chance by getting here early. The guys will see you and get used to seeing you and seeing you looking like this they will get used to seeing a girl. But as soon as you stand up they will see that," he motioned to my crotch, "and all the extra work goes to waste."

"What can I do?"

He looked around and waved his hand.

"Come with me."

He led me upstairs and into his room, I assumed. Once in the room he closed the door behind me.

"I'm Rich by the way. Some people call me Dick."

"Can't get them to stop?" I quipped, causing him to chuckle. "Cute. Okay so first, take off your underwear."

I hesitated looking around the room.

"Don't be shy here, I'll turn around and you can just toss them in the hamper."

Rich turned around and I reached up under my skirt and pulled my boxers down and tossed them in a mostly full hamper. Rich tentatively turned around making sure the coast was clear.

"Okay great, so first you are going to want to conceal so put this on...." he handed me a funny looking device with a ring and a hard shell. I looked at it questioningly.

"It's a chastity cage. Best I got. It'll keep everything contained. It'll add a little bump by itself but that's what this is for." he said as he held up a pair of bright pink lace trim panties.

"Uh....I don't know..." I stammered, getting uncomfortable with the idea of wearing women's underwear.

"If I had granny panties I'd give you granny panties but the girls that leave panties here aren't exactly granny panty types. Besides this has an added advantage. At some point you are going to forget you have a skirt on and some guy is going to peek and it'll be better for the illusion if he sees these." he rings the panties in the air. "And not whitey tighties."

I nodded to myself. That really did make sense but it was still weird. I took the panties and the cage and looked back at him in awkward silence.

"Oh right, right, I'll turn around," he said.

I fumbled for a bit getting the cage on but finally got it locked in place and slipped the panties on. They were tight and kept riding up my butt. Rich was right though they tucked my front bump in so I didn't have a noticeable bulge in my skirt.

Rich turned around and whistled before saying, "That's better. Now you look the part. Oh you should introduce yourself with something girly too. All the psychology you can get right?"

"Right right. Um, you can call me...j-j-jen--ifer....Jennifer."

"Nice to meet you Jennifer. Welcome to Alpha Beta Chi (A B X)."

After some time hanging about trying to build credibility with the guys more people started to show up. Some girls as guys and some more guys as girls. Some guys are kind of passable and some clearly not even trying. I have to admit I think I got a pretty good shot given by the occasional slaps on my butt and the "hey babe can I get you a drink?"

There was a ringing of a bell and an announcement for all contestants to gather at the foot of the stairs. I milled my way to the front and lined up with 6 other "girls".

"Time to thin the herd. You five." The MC pointed to four of us in line. "Out."

There was a groan of disappointment and the four, clearly guys, stormed off leaving just the two of us left. The other "girl" was dressed as a cheerleader but much more slutty but she came with some breast forms. Plus 10 points for boobies I guess.

"Now with just two contestants left we need some challenges to help our decisions. What shall it be?"

The man waved his arms to a board with a list of challenges:

Suck-and-find

Talk dirty to me

Rain dance

Nectar of the gods

Loophole

The crowd was all chanting "SUCK SUCK SUCK!"

"It is decided! The first challenge shall be SUCK-AND-FIND! Bring out the WALL!"

Through the crowd a wall on wheels was rolled into the hall. On the wall were various holes and dildos. The sight of it made me anxious and I looked at the other girl and she looked back at me just as nervous.

"Your task is to find the real dick! Keep the dick hard for 60 seconds but be warned you wouldn't want to be too good." He motioned a jerking motion and an explosion. "The blindfolds please."

Blindfold were put over our eyes and we were led to the wall and guided down to our knees. I felt my hands being tied behind my back. We heard shuffling around the room and behind the wall. I felt something move next to my face. I don't know if it was the booze talking or the encouragement from the crowd but I didn't really second guess that I was about to get a dick in my mouth.

"Contestants, are you ready?"

"Yes." we announced in unison.

"Then on 3.....2.....1.....suck!"

I moved quickly to the spot I felt something move earlier and was greeted by a fleshy hard dick and I fumbled to get it into my mouth. For the first time I wrapped my lips around another man's dick. I sucked it a few times and then a bell rang and the dick disappeared. I vigorously bobbed my head left and right and felt hard cold objects hit my face. I shuffled further down and nearly missed the warm dick before taking it back into my mouth. This kept up for some time. I started to wonder how long it was. 60 seconds can feel like a long time. More than a couple of times I bobbed my head forward too eagerly and hit my head on the wall. A couple of times I choked myself getting the dick to the back of my throat but that just made the crowd cheer louder. Then to my relief I heard the countdown.

"5....4...3...2...1." and then a buzzer sounded.

"Congratulations you filthy cocksuckers. It's a TIE! On to the next challenge! What shall it be!?"

"Dance Dance Dance." chanted the crowd.

"The Rain Dance! Let us convene to the dungeon!"

The "dungeon" was just the basement and unlike its flashy name suggested it was finished and there was carpet and couches and games and right in the center of the room a pair of stripper poles. I looked at my fellow contestant, the cheerleader, and we shared nervous looks. What did we get ourselves into? We were ushered to our respective poles on a raised stage while the crowd clapped and chanted "Dance! Dance! Dance!" My heart was pounding and I was blushing so hard I thought my face was about to melt. I have never been the center of so much attention.

"Alrighty girlies. I think the object of this challenge is quite obvious. You have 10 mins to dazzle us with your spectacular show of sexiness! She with the most chants will win this challenge!"

The crowd cheered and roared and my hands were shaking so bad.

"On the first pole our HEAD cheerleader..." he exaggerated the title head to everyone's amusement. "Whose name is...." the room got silent and turned to look at the cheerleader contestant.

"Uh um I'm Avery...." he/she stammered nervously. It probably was his real name, Avery is fairly unisex.

"AVERY!" The crowd cheered.

"And on the second pole our innocent schoolgirl." Not as much laughter at my description but enough. "Whose name is...."

Before the room fell silent, with unprecedented confidence, I announced "Jennifer!" and followed by a little booty shake as I stuck out my hips and grabbed the pole with both hands.

The crowd's cheer was deafening "JENNIFER! Whoop!"

"Alrighty Jennifer and Avery on your marks....get set....dance!" rave style music pumped through speakers and the crowd cheered and clapped.

Spurred on by the energy of the crowd I grabbed the pole again and slid up and down it. Trying to remember what I've seen on tv shows. Trying to be as sexy as I could. I caught glances of Avery and he/she was so clumsy and mechanical. It wasn't a surprise that I was getting the majority of the cheers. I was getting so sweaty from the heat and constant up and down I was doing on the pole. It caught me off guard when paper started flying up to the stage. It was monopoly money. I was making it rain.

I looked back over to Avery who was looking at me desperately and then she did something unexpected. She started to undo her top. She was actually stripping! That slut! I froze on the stage to watch her myself. As the top began to slowly come off money started raining down on her and the crowd started cheering "Avery" more than "Jennifer". Avery got down to her bra and I was expecting some obvious breast forms but it turned out to be a whole upper body piece. I was going to lose this round if I didn't come up with something sensational.

"Looks like our head cheerleader has some tricks up her sleeve! 1 minute left!" the announcer called out.

I looked around the room hopelessly trying to dance but I lost the crowd. I found Rich in the crowd and he was looking right at me. I shrugged that I didn't know what to do and he motioned to his hips. Confused, I squinted my eyes back at him.

He mouthed the words, "take your skirt off."

Getting the message I swung around the pole wildly to get the crowd's attention and began to shake my butt in the air while I slowly slipped my skirt down my hips.

"Uh oh Jennifer is upping the game to the next level!" the announcer pointed out.

The crowd started to cheer my name again and I was spurred on by the encouragement. I got my booty hanging out to reveal my pink lace panties, courtesy of Rich, and the crowd loved it. Bent over completely and pulled my skirt to my ankles and money started raining down with even more cheers. I swung around the pole spreading my legs wide showing the pink chastity cage. I heard someone point out the cage and among the cheers and chatting my name was another title.

"Sissy Jennifer!"

I didn't know what a sissy was but it seemed to be a good thing. The buzzing rang and the crowd groaned in disappointment.

"And that's time. You filthy animals! Who is our winner? Avery?" The crowd cheered and roared as Avery bowed and put her top back on her bright red face. "Or was it Jennifer?"

The cheering was deafening and they continued to chat, "Sissy! Sissy!"

In response I grabbed the pole one last time and shook my booty to the crowd.

"I think we have a winner! By popular decision, the point goes to Jennifer!"

The crowd cheered and I saw Rich at the foot of my stage. His arms reached out to help me down. I put my hands on his shoulders and hopped down. I turned to remember my skirt and he pulled me back and I looked at him questioningly.

"Leave it, trust me."

I smiled and turned back to him. I felt hands patting my back and even squeezing my butt which caused me to jump and laugh. The crowd was getting worked up and I was loving this. I was the crowd favorite and all attention was on me. It was intoxicating.

"Our next challenge is decided...." the room fell silent to hear the announcer. "The next challenge is.....Nectar of the gods!" and the crowd went wild.

I turned to the Rich and asked, "What's Nectar of the gods?"

"I hope you have a strong stomach."

I got nervous because I did not have a strong stomach at all. I thought we would head back upstairs but instead I was ushered to another part of the basement and sat down at a table across from the cheerleader. The announcer stood up to the center of the table and motioned for the crowd to silence.

"Nectar of the gods is a holy ritual. To gain strength heroes would beseech the gods for their nectar and we just happen to have some of our own nectar." he motioned to two toga clad guys carrying trays with shots of milky white substance.

I assumed some sort of alcohol.

"Freshly squeezed!''

The crowd laughed and I looked around confused by the joke. Avery didn't get it either.

"Produced fresh from those that helped out with our first challenge!"

The crowd began to laugh and chat "Suck Suck Suck."

I still didn't get it but when I looked at Avery she seemed to get it and she looked horrified. I looked at the shots and went back to Avery and then to Rich. Rich made the jerking motion with an explosion and then winked at me. I looked back to the shots and it hit me. It's cum! Its shots of cum!

"After such a great job from the last challenge we all decided you two needed a refreshment." and everyone laughed except me and avery as we stared at each other wondering how we got here.

I looked around panicking. This couldn't be the challenge, there must be a trick. They didn't really expect us to compete taking shots of cum.

"This challenge you will compete taking shots of cum." the announcer explained, making my heart sink. "If you puke you will be disqualified. Good luck girls."

Panicking still, I looked around the room of adoring fans and looked for Rich but didn't see him. I looked across from me and Avery already had a shot glass in her hand and with a shaky hand was bringing it to her lips. I just stared in amazement. How could he do this?? He was about to swallow a shot of another man's cum. I mean the dance stuff was just messing around. It was fun and the first game....oh my god I sucked a dick. I had a dick in my mouth earlier and i didnt even think about it. Now it was hitting me what I've been doing. Am I gay now? No I can't be gay it was all just fun and games right? Wanted to see how far I would go for the sake of a party. Yeah that was it! They were testing us. Making sure they weren't going to let in someone would be a constant party pooper.

I stopped and saw Avery bringing the shot glass down. She just swallowed that jizz. She looked queasy and a little scared but she did it and now it was my turn. I felt all eyes on me now so I reached a shaky hand out and grabbed a glass. The liquid smelled salty and it jiggled like something was floating in it. I think I was going to puke the moment it hit my tongue. I took a deep breath and steeled myself. I opened my mouth and slung the glass up and swallowed the thick salty liquid as fast as I could.

The crowd cheered and there was a mixture of chants for "Avery!" and "Sissy" which apparently was my new name. Avery was getting some courage as she grabbed another glass and without hesitation this time slung it back just like I had. I took after her pace and downed my second glass straight away. I looked back at her and gave her a look that said, "Bring it bitch I can do whatever you can do."

It didn't take us long to down 5 glasses of cum and we were down to the final 6th cup. I felt really funny inside. Kind of like my stomach was turning. I just had to not think about the fact that there was cum swimming around in my stomach. Avery grabbed the last glass and I could see she was in the same boat as me but she slammed the last shot back causing the crowd to cheer like the challenge was already over. Then I heard a voice settle the mob.

"Hold up hold up Jennifer here still has one glass to go.'' It was Rich.

I saw him as he stepped up next to me and rubbed my back. It was comforting but a little weird at the same time. He began the chant low and authoritative, "sissy Sissy Sissy Sissy."

It didn't take long for the crowd to join in and I grabbed the last glass and quickly spilled it into my mouth but I didn't swallow it right away. I knew that I should've but for some reason I didn't and I was left with a mouthful of cum coating my tongue. I gagged and covered my mouth trying not to puke. I closed my eyes tight.

I felt someone lean in and whisper in my ear, "You can do it baby, I believe in you." It was Rich again.

I don't know why but at the sound of his encouragement I steeled myself and looked at Avery and smiled and in a big dramatic gulp I swallowed it and stuck out my tongue. The crowd went wild.

"AMAZING!" the announcer stepped forward "We have another tie! Leaving two challenges left and the score stands 1-0 SISSY JENN-IFER!"

I stood up and raised my arms into the air and I felt pats on my back and a mixture of pats and squeezing to my panty clothed booty. I jumped up and down in celebration as the crowd ushered me to the couches where on each couch sat a toga frat guy. I was laughing and felt good at the appreciation I was getting and ready for the next challenge.

"Alright alright alright settle down settle down. As some of you know the next challenge is indeed....talk dirty to me! "

I looked around the room for some sort of clue but it wasn't apparent. I looked at Avery who was just as puzzled as I. Then the music started, it was slow and rhythmic. The announcer's voice got slow and sensual as well.

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