My Sissy College Experience Pt. 01

It had finally arrived, move-in-day. I was going to get to be my true self after pretending to be a normal guy for all of high school. I got accepted to a college out of state where I didn't know anybody. I was finally going to be the sissy I always wanted to be. It was going to be perfect.

My parents were sweet enough to offer to pay for an apartment for me to live in, but I could not wait to get my hands on my first cock. From the way it had been portrayed in all the porn I watched, the easiest way to get fucked was to "slip up" in front of a roommate. So I declined their offer and live in a dorm on campus instead. My parents were a little confused, but happy to be able to save the money. This school did not let us choose our roommates; there was a survey where we needed to fill out our interests and they'd use that to match us with like-minded people. I knew exactly how to answer the questions to get what I wanted. I smiled to myself thinking about my answers as I followed my parents towards the dorm, carrying a large box of my things.

"Yes, my favorite things to do are play sports, watch football, and work on my car." Those were the manliest hobbies I could think of.

"Of course I like to go to sleep really late and sleep in." That captured the people who liked to party.

"And yes, having multiple guests over at any given time is just SO great." I mean, the popular jocks are definitely going to be hanging out with people more, right? It was a foolproof plan. I peeked around the large box in my hands and saw my dad open the door to my dorm down the hall. It looked like he was speaking to someone inside. This was it! I got myself ready to see the guy whose cock I'd be riding every night, hopefully. I arrived at the door and entered the room.

As I tried to move the big box through the door, I tripped over my feet and nearly dropped it. A strong pair of hands caught it before it fell, and when I looked up to see who it was my jaw dropped. There he was. Jet black hair styled well, tan skin, clearly defined muscles visible through his shirt that had the school's baseball team on it, and clean shaven which accentuated his jawline. He was my opposite in nearly every way; my pale skin and blonde longer hair, along with my slim 5'5", 120 lbs. body was probably half his size. Maybe my butt, which I had been working on for the past three years, was a little bit rounder and bigger than his, but that's it. My dream was actually coming true.

"Hey, my name is Jackson. Nice to meet you!" Jackson took the box from me and easily placed it on the ground.

"Oh, hi. Sorry, haha, thanks for the... box and all..." I did not think I would be so nervous. I felt butterflies in my stomach as I continued to stare up at him. "My name's Casey." There was an awkward silence.

My dad sensed this and quickly said, "so Jackson, are your parents here as well?"

"No Sir, they're home. I don't live too far from here so I was able to move in a few days ago, actually. I've just been taking the time to get ready for school."

"Oh that's just wonderful. So how has it been so far, do you like it," my mother asked.

"Yeah, it's not too bad so far. I've met a few people already." Jackson turned his head towards me. "I've tried most of the dining halls on campus too, so I can show you what's good and what's not." He let out a chuckle and the three of us followed suit.

"Well, I'll give you the space to move in. I'm going to head out and meet a couple of my friends from high school who are also here. I'll introduce them to you sometime."

"Cool, thanks. See you."

Jackson stepped out and my parents and I set to work on unpacking and setting up the room, if one could call it that. There was barely enough space for the two twin sized beds and two desks to fit in it. My bed was next to the wall with the bathroom while Jackson's was lined up with a window. The bathroom wasn't anything special either.

"At least you don't have to worry about sharing the bathroom with an entire floor of guys, I do NOT miss those days," my dad said.

"Yeah, that would be the worst..." I replied, wishing I were as lucky as he was.

After a couple of hours, I was finally moved in. There was a bit of a scare when my mom nearly opened my small taped up box of girly clothing and sex toys, but I was able to take it from her and slide it underneath my bed before she opened it. I told her it was a box of textbooks I had ordered. We left the room and went out for dinner before spending the night in a hotel. My parents were going to leave the next day, so we wanted to have one more night together. It was nice. I was definitely going to miss them, but I was so much more excited about what was to come.

They dropped me off the next morning pretty early because they had to catch their flight. After our tearful goodbyes and watching them drive away in the rental car, I slowly walked to my room. It was about five in the morning when I turned the key and entered. Jackson was sleeping in his bed. I was tired and thought that after I went to the bathroom I'd go to sleep as well. I peed, and after flushing the toilet, I realized there was no toilet paper on the holder. I opened the cabinet underneath the sink to get a roll, and to my surprise, there was a metal buttplug with a pink heart shaped jewel laying next to a bunch of Jackson's toiletries. It was similar in size to one of the buttplugs I had in my secret box. I immediately felt a tingle in my crotch as I imagined what the hot girl who Jackson was going to use that on must look like, and wished I was her.

"He must be kinky, then," I thought to myself happily. If he's open to using buttplugs on people, hopefully he'll be open using mine on me one day. I left it in place and went to my bed. I didn't even change the toilet paper because I didn't want him to know I opened the cabinet. I pulled the covers up to my chin and lay on my side so I could look at Jackson again before I nodded off. The sunlight began to shine through the blinds and covered parts of his face, making him look even more attractive. The light landed on his eyes and he stirred and slowly rose. When the blanket fell from his chest I realized he was only wearing a white pair of boxer briefs. He spun his legs off the side of the bed and rubbed his eyes. I watched as his muscles rippled with every movement. When he stood up I quickly closed my eyes, not wanting to be caught looking at him.

"Yo, bro, you up?" I stayed silent, and after a few seconds I heard him walk into the bathroom. He was in there for about ten minutes, which was odd because from what I could hear he flushed the toilet after two minutes of entering the bathroom. I heard him open the door and slowly walk back towards his bed. Even though I knew I shouldn't risk it I just had to get a look at his body once more. I half opened my eyes just as he was bending over to get back into bed.

"Mmm, those briefs are leaving almost nothing to the imagination," I thought to myself. "Wait a second... no way..." As I watched him flop into bed from behind, I could have sworn I saw the bright pink of the buttplug's jewel through the stretched white fabric.