When I started college I had already been dressing up for my two friends in high school for four years (that’s another story for another day). At this point it’s all I wanted to do when I finally moved out on my own. I wanted to dress up in my own space and just spend countless hours touching my smooth body and using an extra large sharpie on my tight hole.

For the first semester I ended up living in a dorm by myself. My roommate moved out shortly after classes started so I had a room in a men’s dormitory all to myself. Everyday after class I would come back and dress up. I had stockings, panties, dresses, makeup, and everything to feel absolutely fem. Sometimes I would go to the gym with my panties under my shorts but I wasn’t ready yet to venture out in public as a cd girl. I discovered also that I could order things on Amazon with my own money. So right away I started to order toys and better makeup. The works!

Second semester I got paired up with a roommate from the high school I went to. It was somebody I knew but we weren’t friends or anything of the sort. He changed majors and decided to move to my dormitory where others of the same major were living. Over the second semester we really bonded as bros. I didn’t have many opportunities to dress up but I would still sneak my panties and buttplug on for class. Besides that we ended up doing a lot together. Sports, studying, hanging out around campus, picking up girls together, all that good college stuff. We would go to the gym together and I really slimmed down. He hadn’t seen me naked but the results were coming out curvy and girly on my body lol. We ended up starting to go to the showers in the dorm together a lot just to hang out and talk more.

Being boys we would mess with each other. A lot. Throw cold water into our showers, scare each other in the echoey showers with loud noises. But then he started to pretend to look into my stall. It was playful and harmless I thought (kinda reminded me of how my two friends would play with me in high school) but I know he got a couple of good looks at me bent over washing my legs. And maybe he might’ve seen me shaving my ass pussy cause I always liked to stay smooth. One day he asks to borrow some shampoo and I said sure. I grabbed my shampoo bottle off the ground but as soon as I bent over I felt the cold air draft into my shower and there he was standing naked with my shower curtain wide open. He laughed and grabbed my shampoo from me and went back to his stall. He didn’t do it again but continued to jump up and look into my stall to mess with me.

The next year, we lived together in an apartment. I had my own room with a bathroom. You already know that I was so eager to be able to have my own space again. I got back to dressing up everyday. Except this time, I would tell my roommate that I was going to bed or studying but really I was locking myself in my bathroom and covering my mouth to keep my moans in while I rode my favorite dildo with my favorite thong pulled to the side. There were times when he would ask me what I do in the bathroom for so long but I would tell him I usually take a bath and read or play some games on my phone.

Later in the semester my roommate tells me that he’s going to go back home to visit his parents on their anniversary. As usual I was excited because I always got to dress up an entire weekend when he would go out of town. He left Friday after classes before I got back to our apartment. When I got home I immediately showered, grabbed my hidden sissy box from my closet, opened my new lingerie and clothes I ordered specifically for this weekend and got dressed up. I always feel so sexy dressed up. My sissy stick always gets hard and leaky as soon as I feel some nice lace panties trying to keep my bulge in. I went to the couch in our living room, set up some blankets, and had an amazing night playing with my toys and letting my sissy moans out freely. In a sentence: I really needed that.

The next morning I wake up from my night of girly sissy bliss. I know I have the whole day to myself. My plan is to make breakfast, shower, change into a mini skirt and crop top, try to fit in my biggest plug (fourth times the charm lol), then sit down to do homework all day. I also made plans to order a pizza and answer the door since I was getting good at applying my makeup. So I make breakfast in my lingerie, shower and moisturize my body, try out a few items of clothing until going back to my planned outfit, and I sit down to do my homework! Like a good girl.

A few hours pass by. I take breaks in between. Take pics for guys that I was chatting with on Reddit. A normal morning lol. So I order my pizza and continue working. I’m listening to music when I hear some noise from behind me. My heart starts racing cause I’m finally going to answer the door as a girly and I know the pizza guy is going to look me up and down. I’m thinking “should I let my cock and out? Or just keep it hidden for now?” I take my headphones off stand up and turn around and in the doorway to my room is my roommate standing there. We are both frozen. My heart is pounding and I don’t know if I should say anything. My immediate reacting is to run to the bathroom. So I hop in there and slam the door behind me. I’m vibrating at that point. I take my makeup off and all my sissy clothes. I get back into boy mode and sit down on the toilet for what seemed to be three or four hours. When I finally walk back into my room, my roommate isn’t there. I go into the hallway connecting our rooms and see him sitting at his desk on his laptop. I don’t say a single word and I sit back at my desk quietly reading my study material and quietly panicking. There’s a knock at the door and I go grab the pizza that I ordered. My roommate is in the living room at the point playing Xbox. The pizza is a whole hour late and when I answer the door the driver immediately apologized and offers us fifty percent off the price. While he’s fidgeting with change and receipts I could see the bulge on the college age guy through his pants. Might’ve been the perfect set up. My plans were ruined. I place the pizza on the table in the kitchen and ask my roommate if he wants some. He casually says yeah and then asks if I want to hop on the game with him. So I grab us some pizza and we play for the rest of the night. Quietly but still almost like normal.

A few weeks pass by and everything is actually pretty normal. I think at this point we both know it has to come up at some time but we are both non confrontational about it. So it just lingers in the air. We go to the gym, play video games, study, hang out with some friends, and everything. It’s like that for a while until one night we decide to have some drinks at our place and play video games all night for the first night in a while. We get some beers and order some pizza of course and get down to business on Xbox. A couple hours and a few beers in my roommate says, “you know you can dress however you want to here.” Immediately my heart starts pounding again. I don’t say anything. I’m processing the words that he just said to me. I’m unsure if he really said it or if I was just daydreaming again about him telling me he is okay with everything. The round ends on Xbox and I grab my beer and casually say “what do you mean? Like wear girl clothes?” I take a drink and glance at him out of the corner of my eyes but still avoiding his gaze. He said, “Yeah like that one time I caught you. I don’t mind but you have to keep it in our place.” We play a few more rounds and I tell him I have to go to the bathroom real quick. I decide to test him. So I put some panties on and a long shirt. I get my favorite cutest wig and put some lipstick on. Then I come back out nervous. My hands are sweating. My body is vibrating again. I come out and he looks at me. Then goes back to looking at the tv. I sit down on the other couch and we go back to playing games. That night I went to bed and came to the thought of my roommate railing me on the couch.

The next morning is a weekend. I take a morning shower to clear my head from a late night of video games. We stayed up longer than usual. I remember what he said about dressing up at our place. So I grabbed some cheeky lace panties, put on some thigh highs to stay warm and grabbed some cute silk pajama shorts with a crop top. I walk into the kitchen to start breakfast and my roommate is already in the living room watching morning television. I ask him if he wants some orange juice and pour him a glass when he says yes. I take it to him and realize he’s sitting on the couch in his boxers. It isn’t unusual. We would wear only our boxers around the apartment naturally. But this time I’m dressed as a girl and I can see his morning wood bulging in his boxers. He sees me looking at his cock and I hand him the orange juice.

I’m cooking and I say “You know you’re going to have to hide your morning wood better.”

He says, “why don’t you come do something about it.”

My heart is racing again. I look over at him and he’s smirking with his legs wide open on the couch and his hard cock teasing me underneath his boxers. I set the pan on a cold burner. I walk over to him and get on my knees. I reach into his boxer leg and start to caress his balls. He closes his eyes and lays his head back. Then I start to jerk off his cock in his boxers. I ask him if he likes it and he moans out yes. Then I pull his cock out and start to kiss it gently. His dick is hard and big. I knew it was big. We were really close guy friends and saw plenty of each other over the last two years. But it wasn’t like this. It wasn’t like me feeling so girly in my clothes holding onto his nice hard cock. But it also wasn’t usual to me. And I wanted so badly for him to ask me to suck his cock while I wear his girlfriends panties like I would for my two friends in high school. This time we were going to be a different level of close. And I knew it as soon as he came in my mouth that the next few years with him was going to be an amazing ride.