My New Life in a Frat Ch. 02

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Jennifer gets some training.
8.6k words
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Part 2 of the 5 part series

Updated 06/11/2023
Created 10/01/2022
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I had fallen asleep on the bed really well. I didn't realize how tired I was until I laid down. I took off my soaked top and the panties Rich gave me. Once I was in the bed it was so soft that I fell asleep almost immediately.

When I woke up I was a little disoriented at where I was but I got my bearings and remembered what I had done last night. It was a crazy party. I can't believe I did all of those things. I touched my face and it felt really smooth. I could still feel the warmth of over a dozen men cumming on my face. I touched my hair and it was a little crusty in some spots. I needed a shower immediately.

I got up and went to my door but it was still locked. I knocked on the door and, not immediately, Rich opened the door.

"How'd you sleep Jennifer?"

"Um good I guess um hey can I maybe take a shower?"

"Absolutely. Right this way."

He led me down the hall to the bathroom. It was huge. There were 3 sinks and 1 toilet but in the main section behind some short walls was a shower tower. 3 guys were already naked and showering.

They saw me and they all smiled. I realized I was naked except for the pink chastity cage.

"Uh" I stammered.

"Don't be shy. You remember these guys. You danced for one of them."

He gave me a little push and I walked into the bathroom.

The guys reached out their arms and I walked into them and under the warm water. I basically moaned at the soothing water hitting my skin. The guys huddled around me. Their ripped chiseled chests inches from me. They looked huge next to my slender and petite frame. I felt hands on me as they lathered me in body wash. It was a foreign experience.

I shied away from them. I wasn't comfortable with being touched at the moment but they didn't leave me much choice. One man was behind me, his arms rubbing soap up and down my back and a hand roamed to my butt and I squeaked. The guy in front of me was washing my front and he kept me from running.

The man washing my butt probed around my asshole. I reached a hand back to push his hand away. Inadvertently I touched something hard. I looked down and saw his dick was standing at attention. I gasped in surprise and saw the guy in front of me was also hard. His dick pointed up at me. The third guy was to my side and he was stroking himself.

The man behind me resumed fingering my butt. He ran his other hand up and grabbed my long wet hair and whispered in my ear like a lover.

"Do you want some breakfast sissy?"

My knees got weak under me and I heard Rich's voice resonating off the walls

"Easy boys remember she's still a virgin. We gotta train her up a bit first."

The man behind me let loose of my hair but his other hand kept up its probing but this time with more intent. I felt him find my hole and with a soapy finger he pressed it into my tight asshole. I gasped at the sudden invasion and brought my hands to the man in front of me who closed the gap for me to lean on him. His hard dick poked me in the stomach.

The talk of breakfast made my stomach rumble but I don't think he was talking about food. The man fingered my ass with his long finger a couple of times before pulling it out. My knees were really weak now and I felt a pressure guide me to the ground. I knelt down and looked up at the guys crowding me with their big hard dicks inches from my face.

One of them slapped me with their dick gently. I inhaled sharply and my mouth opened and a dick pressed its way into my gaping mouth. Surprised, I opened my eyes and saw a muscular body standing in front of me. To the side was another hard dick pointing at my face. My hand was raised and grasped the other dick in waiting. Once my fingers wrapped around the hard meaty shaft I instinctually began to stroke it gently. I heard the guys moaning.

I was now kneeling on the hard wet floor jerking off two guys while I sucked on another guy's hard cock.

I looked and saw Rich just leaning and watching the show. I looked up at the guys in front of me and they were biting their lips and looking down at me with hunger in their eyes.

I steeled myself and I remembered how I got here. I brought my other hand up to grasp the cock in my mouth and I started to stroke it while I passed between sucking that one and the other one and the other one. I quickly stroked both cocks. I was really making the guys moan now. It felt validating that I was doing something that brought pleasure to someone else.

I looked up at the guys and in my feminine innocent voice I played the part.

"I'm so hungry, boys. Do you know where I could get something to fill me up."

I stuffed my mouth with their hard cocks and I felt them tense.

One guy grabbed my head and started really pumping into my mouth really fucking my face. I thought he was going to cum right there but the other guy stopped him and took his turn fucking my mouth hole. This guy did cum though. This hard cock tensed and warm liquid started shooting the back of my throat. He pumped a few more times before he pulled out and the third guy took his turn. It wasn't long before he came too. Straight down my throat. I'm not going to lie after swallowing both loads. My stomach was a touch less grumbly. Finally the third guy came but he sprayed my already wet face with his sticky cum.

The guys stepped away and left me on my knees on the shower floor with the water running. They grabbed towels and high fived as they left. Rich lifted up a towel for me to get. I stood up and turned the water off. I took the towel and dried it off. I looked at Rich kind of ashamed.

"Don't be ashamed Jennifer. You did good. This is why we have you here. Well that and more. Come on, I'll help you get dressed."

He led me back into the hall where many more guys were in the hall. They all stopped and looked at me like a pack of hungry wolves. I held my head down embarrassed.

We reached my room and Rich closed the door behind us. He walked over to the drawers and pulled out some pink panties and in the other drawer pulled out a silver object and bottle and threw them on the bed. He then walked to the clothes rack and sifted through the outfits. He hummed to himself. I just stood there wrapped in the big warm towel. He turned around with a floral romper and a pair of tall pink heels.

"You want me to wear that?" I pointed to the very girly dress.

"Not just this" he motioned to the bed.

I looked at the object on the bed and it was a small butt plug. I gasped. This was the training he was talking about.

"What's that for?"

"Well I can tell you are a virgin and I also know that if it came to the final challenge last night you would've lost. Avery could take a dick in the ass. You could not. So we need to train you up before your first time tomorrow."

"Tomorrow? What happens tomorrow?"

"It's your coming out party! You think last night was crazy, wait until tomorrow. "

I gulped audibly and stared at the small butt plug next to a bottle of lube.

"Don't worry I'll make sure you are ready. Now get dressed and come downstairs for some proper food. "

He walked to the door and shot me a wink before closing it. I didn't hear it lock. I looked back to my bed and dropped my towel. The panties I could get used to. The romper was basically a jumpsuit but the butt plug made me nervous.

As I descended the stairs onto the main floor I saw all the guys milling about with plates of food and joking and laughing but upon seeing me they all stopped and stared.

I tried to be as graceful as I could. It was awkward to walk with something lodged in my butt for the first time. The stairs were a challenge by themselves. Once I reached the bottom I was self conscious about how short this romper was and I kept trying to pull it down. Slowly I walked to the table and a couple of times nearly fell over. The guys all laughed but when I reached the first empty seat it was pushed out for me and I nodded to some of the guys as I sat down.

The butt plug drove deeper into me as my butt hit the hard wooden chair and I let out a subtle squeak and tried to reposition myself. Sitting down made the romper ride up and was nearly as tight as the panties on my crotch. Luckily I had that rigid cage to prevent squashing my bits.

I saw the other guys were eating big breakfasts loaded with protein and I was so hungry but before I could grab anything a bowl was put down in front of me. It looked like porridge with some fruit and a piece of bacon. I looked up at the guy who delivered it in confusion. I looked back to what everyone else was eating and then looked for Rich.

"We can't have you putting on that freshman 20 in the first semester now can we?" Rich said, chuckling.

Everyone laughed and I looked down at my bowl in disappointment but I grabbed my spoon and dug in anyways. It was really good and really hit the spot without being too filling. Then I remember the two loads of jizz I just swallowed earlier and I got a little queasy. It was just a lot to imagine that I let two guys cum in my mouth and I willingly swallowed their loads. In front of me a glass of whitish liquid was put down next to my bowl and it took me a second but I recognized it as a glass of cum.

I looked around and was horrified to see all the guys smirking at me as I stared at the glass. I tentatively reached a shaking hand out and picked up the glass and as I brought it up to my mouth I smelled its salty musk. I nearly lost my breakfast right there. I looked around hoping that someone would come to my rescue but no one did. I brought it up to my lips slowly and it seemed like the whole room was holding their breath.

When the liquid hit my tongue it was slimy and salty and copious. I should have just gulped it down quickly but I wanted to empty the glass so I didn't have to take a second drink. Once I got the whole thing in my mouth my cheeks were puffy trying to hold it in. I felt my throat tightening in rejection but I took a deep breath through my nose and gulped down some of the thick cum which was also a mistake because I choked on it and I brought my hand up to my mouth and coughed and spit the rest of the liquid into my hand and it dripped down into my lap. I've never seen guys move so fast away from me when they thought they might get cum on themselves.

I held my head down and tried not to puke on the floor. The room was clapping and laughing. I finally caught my breath and sat back up and whipped my mouth with the back of my hand. My eyes were watering so bad.

"Don't worry you'll get used to it" Rich said as he raised his glass to me.

At that moment a glass of water was put down in front of me and quickly grabbed it and gulped it down. I finished eating but everyone else was still talking and eating. I didn't know if I should just go or not so I just sat there. A bell went off and everyone stood up and grabbed everything on the table to take it to the kitchen and started to clean up. I tried to stay out of the way but it was difficult to move quickly in these heels. Some guys seemed to intentionally bump into me so that they could have an excuse to squeeze my butt.

As most of the guys left, I assumed for classes, I remembered that I should probably get to class as well but I couldn't go looking like this. I looked for Rich and found him in his room at his desk.

I knocked on the door frame, "Rich, am I supposed to go to class like this?"

"Oh right sorry I nearly forgot. You won't be going to classes."

"I can't just not go. I'll get kicked out in less than a semester."

"Don't worry we are talking to your professors and some of the guys are going to your dorm to get your stuff. Anything not needed for school will be put in storage and everything else will be brought to me. The professors will have notes and coursework delivered here and we will help you with your classes. On the occasions that you need to go to class you can either go in what we pick out for you or something more neutral, up to you."

"Wow, I did not expect that. How did you get the professors to sign off on me not showing up to classes for a whole semester?"

"Most of the professors are alumni and know about the Sissy Bowl. We give the other professors an incentive."

"What kind of incentive? Wait, I don't want to know" I raised my hands to stop him from answering.

"Best not yeah" he laughed, "in the meantime I have something for you just give me one second. Have a seat" he motioned to his bed and I sat down again remembering that I had a butt plug in my ass.

He swung back around and handed me a USB drive. I took it and looked at him questioningly.

"These are some videos I want you to watch in your down time. There is a TV in your room, just plug this in and it should start playing automatically. Have it run in the background even. In an hour take out the plug and rest for 30 mins and then put it back in. At noon I want you to get the next size up. Let me know how that goes."

"Um yeah sure right. Um about this whole thing about getting fucked. I don't know if i'm comfortable with the idea of it...''

I hung my head to avert my eyes but the silence made me look up at him sheepishly.

"I get that. You've spent your whole life indoctrinated to thinking there are firm lines between straight and gay but that is just not true. I'll tell you what. Tonight I will have a surprise for you that should help you but until then just stick to the schedule."

"Oka. Yeah great," I stood up, squeezing the flash drive in my hand, "um thanks. I guess I'll just go.''

I tried not to be so awkward but that's just who I am.

I walked back to my room and immediately took off the heels and rubbed my feet. How do women wear these all day? I walked over to the TV and plugged in the USB. Immediately the screen started flashing images of porn, specifically of women sucking dicks and taking cumshots.

"Subtle Dick, obviously his major is psychology." I said to myself as I turned away from the screen and looked around my room.

I looked through the sex toy drawer and found various butt plugs and anal beads and dildos and gags. I've never really seen such variety of sex toys in person before. I looked through the panties and they were all sexy. Lace or satin. Some thongs. I looked through the clothing options and found several schoolgirl outfits. I wonder if Avery won how many cheerleader variations there would be?

Not much else to do I laid on my bed and flopped the cuffs around like a cat. The lighting changed from the TV screen and I sat up to look at it. It was a psychedelic swirl of colors and waves. I have to admit I was a little mesmerized. By the time the screen went back to pornographic images the first clip was of a trans woman getting fucked up the ass.

"Well played Dick." I said to myself. "You got me with that one."

I rolled over and it had been an hour already. How long was I staring at that screen? I slipped out of my romper and pulled my panties down so I could reach around and pull out the small butt plug. I set it down on the drawer unit and I looked for the next size up. Finding it I carried it to the seat of the bed and put it next to the bottle of lube. In 30 minutes I'm supposed to try and put that in. Until then what should I do? I am really thirsty. I should see what I can get to drink.

I put my romper back on and the high heels and stuck my head out the door and didn't see anyone. I walked down the hall only hearing the clicking of my heels in the hardwood floors. I reached the stairs and less gracefully, since no one seemed to be home I didn't have to put on a show. I reached the kitchen and opened the fridge. Options range from beer, beer, water, milk and oh yeah beer. It was too early for beer so I grabbed the milk. I looked for a glass and found one and poured myself some.

When I drank it I thought it would quench my thirst but it didn't. My mouth felt dry. I tried the water but that didn't work. Finally I gave it up and washed my glass and set it out to dry. Walking back to the stairs I heard voices coming from the basement. I reached the stairs and slowly made my way back down stairs.

The basement looked huge without the crowds of people in it like last night. The stripper poles were still up and on the couch were two guys playing video games. Not wanting to be alone I continued down the stairs and walked to the other couch. The guys noticed me and greeted me.

"Hey Jennifer. What's up?"

"Oh not much." I said sitting down as gracefully as I could. "I just came down for something to drink but all there is in the fridge is water, beer and milk."

"That didn't do it for you?" The other one asked.

"Not really. I don't know what it is."

I didn't see it but the two guys gave each other side long glances.

"So has Dick given you any videos?"

"Oh you mean the psych 101 subliminal messages? Yeah" I chuckled, "kind of obvious really. "

"Oh really you didn't find it... CuMpelling?"

For some reason I got instantly warm and my mouth got even more dry. I cleared my throat and tried to lick my lips.

"Um no hrm not particularly. I don't really believe in that um hypnosis stuff. Is it hot in here?" I stammered as I started to fan myself.

The guys pause their game and got up and sat next to me. They ran their hands on my body and I felt shivers running up my spine. I didn't mean to but I let out a slight moan at their touches. They brought each of my hands down to their crotches where I felt their hard dicks through their shorts.

They pulled down their shorts and their hard cocks sprang out pointing straight up.

"We heard about what happened in the shower."

"I um what? Shower?"

I was mesmerized. My internal body temperature seemed to be through the roof. The only relief I was getting was from them touching me. My fingers seemed to move on their own as they wrapped around each other their hard cocks and slowly began to stroke them at the same time.

"We heard you give great head. Rather CUMpelling."

Upon that word again something coursed through me and my head rolled back and I moaned louder. It felt like I was running on automatic. I was burning up and my mouth felt so dry. I couldn't stop panting. I felt hands pulling me to the ground where I knelt and it felt like the walls were closing in. Then something amazing happened. My mouth was full of something that was sending shivers down my body.

I focused and saw the bare skin of a man and his cock sticking in my mouth. Still running on automatic I bobbed my head sliding the foreign member over my tongue and it poked the back of my throat. I gagged a little but I pulled back and took it back in. The whole time my other hand was stroking the other cock mere inches from me.

"Oh yeah, she does give good head. She's a natural. We made a good decision with this one."

I heard the clap of a high five above my head. I pulled off the one cock and took the other cock into my hungry mouth. I couldn't stop. The more I sucked the better I felt. I had this incredible urge that if I just kept sucking that everything would be better. So I continued to bob my head between the two big hard cocks while I knelt on the thick carpet.

Together they pulled their cocks away and started slapping my face with them.

"Beg for it sissy. Tell how much you want it."

"Please give me your cocks. I'm so thirsty I need to suck your cocks. Please let me suck your cocks."

Pleased with themselves they let me continue to bob between the both of them. I just needed to suck cock and suck it fast.

I felt the man I was sucking tense and he pushed my head back and he grabbed his cock to start stroking it fast. My mouth was left open and suddenly sticky liquid was being poured onto my face and into my mouth. My thirst began to be quenched and I felt much cooler but I still needed more. I turned to the other cock and began sucking it fast and hard.