My Sissy College Experience Pt. 02

It couldn't be true, could it? I lay awake in bed for the next four hours, unable to get the image I saw, or thought I saw, out of my mind. Jackson was in a deep sleep, but I still couldn't discover the truth because he had covered himself with his comforter. Instead, I spent the time trying to come up with reasons as to why someone like him would wear a buttplug in the first place. I could only come up with two reasons in the hours that I was thinking; he either had a really kinky girlfriend who thought it was hot, or it was part of those hazing rituals that they do at frats. My little cock twitched at the image of him proving to all the other hot frat boys that he did what he was told. Bent over with his ass exposed for them all to see. Mmm, maybe I should join a frat...

As my mind started to drift towards pleasuring myself, a loud siren snapped me back to reality and I heard Jackson slamming his fist on his desk, looking for his phone. I quickly pulled my hand out of my pants, disappointed, as he finally found the snooze button.

"Sorry dude, I've been used to being alone. I'm a pretty heavy sleeper." He rubbed his eyes and looked at the time on his phone. "Shit, I need to get ready." Jackson quickly got out of bed and stood in the middle of the room with his eyes aimed upwards, like he was trying to remember something. I let out a yawn, my tiredness finally overcoming my curiosity, but it was cut short when I sat up and looked at him. The bulge in his underwear was larger than anything I had ever seen. It was nice and round, and perfectly centered. The fabric of his underwear was completely taut. No wonder I could see through them, they were probably hanging on by a thread. I had to force myself to avert my eyes and looked up at Jackson.

"It's no problem man, I should probably get up anyways. Do some exploring around campus." Jackson seemed to remember what he was trying to and rushed off into the bathroom without a word. I wasn't able to get a good look at his backside. I stood up and looked down at myself. My fully erect penis barely made an indentation through my pajama pants, but I saw them twitch as I again pictured Jackson's bulge in my mind. He came out of the bathroom rather quickly, now dressed in a plain white tee and black jeans. His hair was messy, but he still looked put together. Another benefit of being so hot, I guess.

"Hey, sorry, I'm just in a bit of a rush. Actually, do you want to come with? I'm grabbing brunch with a couple of friends, the ones I told you about yesterday. It's a place right off of campus, maybe a five-minute walk?"

"Umm, sure, yeah, sounds great," I said.

"Awesome! It's called, "Late Risers." And it's the one on Main Street so you can just look it up on your phone. I'm going to head down there now and when you come just let them know you're with Jackson."

"Perfect, sounds good! Thanks!"

"See you there!" Jackson grabbed his keys and wallet and left after giving me a smile.

I quickly got changed and did my hair, which is to say I brushed it quickly and put it in a "man bun." I took a look at myself in the mirror before I left, hoping I looked presentable enough. I found the place on my phone and made my way there quite easily. It was an open-air restaurant and there were almost no seats available. Everyone must have known the weather was going to be nice today because there was a large group of people waiting to be seated. I weaved my way through the crowd and reached the hostess. She was gorgeous. She was 5'3", had shoulder length blonde hair, emerald green eyes, and what had to be at least a C-cup chest, which looked even bigger on her petite frame and underneath her white crop top with the restaurant name written on it. I lost control of my hand from just looking at her and phone fell out of it and next to her feet.

"Whoops! Let me grab that for you." She bent over to pick my phone up, and while her black shorts were long enough to not expose too much, her ass was so big and well sculpted that I could clearly see each cheek underneath them. She was exactly what I dreamed of looking like. She handed me my phone.

"Th-thank you..." I could barely get any words out. "J-Jackson told me to tell you that I'm with him."

"Oh! You're Jackson's roommate! Aren't you lucky? Right this way!" I followed her as we passed multiple tables. How is Jackson already so popular that one of the most beautiful girls I've ever seen knows him? I thought about this until we reached a quiet corner that looked more private than the rest of the restaurant. A few tall plants surrounded the square table, where Jackson and his two friends were already seated. I sat down in the open seat. As the hostess placed a menu and my silverware on the table she spoke to Jackson.

"You didn't tell me your roommate was so cute! Maybe I should play with him instead!" Jackson's friends made "ooo" sounds before the four of them laughed.

"Thanks for that, Jess," Jackson said, as she turned to walk back to the front of the restaurant. So maybe it's her plug that he was wearing? If he even was wearing it. She did give off a kinky vibe... While I was lost in thought, a hand jutted towards me.

"Name's Beaux, nice to meet you."

"And hey, I'm Sam." I shook both of their hands and got good looks at both of them. Somehow, they were even bigger than Jackson. Although Beaux and Jackson looked to be the same height, Beaux was beefier. He had light skin and had a bit of stubble on his chiseled jaw. He wore the same college baseball shirt that Jackson was wearing yesterday. Sam had dark skin, and while he was similar in build to Jackson, he was definitely taller. He was handsome as well, and was wearing a cap with the school's mascot on it. All in all, it was clear the three of them were either athletes or frat boys, or more likely, both.

"Do you guys play baseball?" I asked.

"Yup," Beaux answered. "We're all on full rides." Sam seemed to be eying me.

"Maybe you should try out, Jackson could definitely use the help," Sam said. He and Beaux laughed and Jackson and I followed suit, even though I didn't really understand what he meant.

"Yeah, maybe... haha." It became a little quiet as we looked through our menus. The guys all ordered huge dishes with multiple protein pancakes. I simply ordered a waffle and scrambled eggs. We engaged in some small talk, learning more about each other, while we waited for our food. They all came from the same town and went to the same high school. For as "bro-like" as they seemed, they were actually very nice and we got along well. We seemed to have a lot of common interests in movies and tv shows. I also got a chance to ask them some questions about the school. It seemed like most of the baseball players came a week early to get some extra time on the practice fields. When the food finally arrived, the boys devoured it as though they hadn't eaten in weeks. Just looking at them made me remember how feminine I was in comparison. I studied their bodies any time they weren't looking in my direction. They looked as though they were sculpted by gods and I lost myself multiple times imagining them filling my holes. After an hour we finally finished and the guys got up.

"Sorry, we have to go to practice. Meet the other guys and do some drills, stuff like that. Maybe we'll hang more tomorrow?" Jackson asked.

"No worries! That sounds great. Nice to meet you guys!"

Beaux and Sam waved as they walked off. Jackson paused for a moment.

"Sorry again about the alarm, I feel bad."

"Don't worry about it, I'm a super heavy sleeper, I could barely even hear it," I lied. A relieved expression formed on Jackson's face.

"Great, later then." He jogged to catch up with his friends while I went to explore the campus and actually pick up the textbooks I was going to need for my classes. The rest of the day went by quickly and after eating dinner at one of the dining halls, I came back to my room, exhausted. I was finally alone with my thoughts. And of course, they were thoughts filled with Jackson, Sam, and Beaux. I desperately wanted to take my dildo out of the box underneath my bed but I was too tired. I simply rubbed my little cock, wishing it were one of them, or all of them, doing it instead. I quickly got hard and began to leak precum. I rubbed a bit of it onto my lips like one would apply lip gloss. I had gotten pretty used to my slightly salty cum by now, as I ate most of my loads when I came, but it still never failed to make me tingle and feel feminine. I took a little more precum off my tip and ran my finger around my asshole, very lightly prodding it, teasing myself. Before I could fully push it inside of me, however, I fell asleep.

"Shhh, he's in here," Jackson whispered.

"Are you sure we should do this?"

"Yeah, it's fine, he said he could barely hear my loud ass alarm this morning. Just don't be loud like you usually are."

"Shit... I'll try, but you know how I get when I'm with you."

I was awoken by the sound of Jackson's bed creaking. He must be back, I thought, as I lay underneath my covers. I was still tired, and too socially exhausted to try to make conversation, so I simply tried to go to back to sleep. I almost succeeded until the moaning started. It was quiet at first. Just heavy breathing, but as the sound of the creaking started to increase in frequency and volume, the moans came with it. They were high pitched, and very cute, for lack of a better term. At first, they were pretty consistent, but as the fucking became faster, the moans were intertwined with gasps for breath. The only thing I could think of was how much I wanted to be Jess at that moment. My cock was rock hard at this point, and despite knowing it was a bad idea, I was too horny to stop myself from slowly pulling my comforter off my face enough so I could watch the show. I waited until the moans were very loud, and finally got the covers off. My eyes took a moment to adjust to the dim, moonlit room, but when they did, the sight was even better than I could have imagined. Jess' face was pressed deep into the bed, and her ass was pushed high into the air, with her back arched like a gymnast's. I could see a large hand gripping her waist as she was plowed. The moonlight illuminated a cock as thick as my forearm sliding in and out of her almost balls deep. I started rubbing myself, feeling my fingers get covered with precum. The slaps of their bodies against each other became louder as they fucked, and I saw the hand move to smack and squeeze Jess' ass. I heard Jess say something, but her voice was muffled by the bed.

"Me too," A deep voice replied. "Fuccckkk..." After moving his hips faster and faster, he finally slowed and pulled his cock out, slowly stroking the half hard member against her ass.

"Now, lets make sure none of that escapes." I watched as he took some sort of object in his hand. As he moved it towards the ass on the bed, the moonlight shined onto it and a little pink light flashed against the dark wall. He quickly plugged the ass and bent over to kiss it, chuckling to himself as he got up. The figure was a lot taller than Jackson. He put his clothes on and whispered again.

"See you tomorrow, sissy."

A muffled voice replied from the bed. As he got up, he unlocked his phone, and as the light flashed on his face, I could finally confirm that it was Sam doing the fucking. He tiptoed across the room and quietly opened and closed the door. Even though I was ninety-nine percent sure I knew who was in the bed I still couldn't believe it was true. That was until the person unlocked their phone and held it out behind them, taking a photo of their ass. The flash illuminated the room, and there Jackson was, not Jess, posing doggystyle with the plug in his ass. He quickly put his phone away and wiggled under his covers, going to sleep.

I was stunned. I never thought that Jackson of all people could be a sissy. It never even crossed my mind. How long has this been going on? Does Beaux know? How is Jess involved with all of this? I was unsure about everything except one thing. As I licked all of the cum off of my hand, I was sure that it was the hottest thing I had ever seen.