I tucked my little cock to the side without much difficulty, and immediately felt very feminine.
To my own embarrassment, I was fully erect when I slipped on the tight black thong, and I liked the way the strap felt against my butt. To be honest, hairless legs felt pretty good once I was done. It was a very slow process, and I scratched myself more than once. I took a shower, and shaved my legs for the first time in my life. It was probably just a prank by him, so he could get some embarrassing photos of me, but I could always get a new roommate if I had to. I couldn't believe Brian expected me to wear any of this! I was very turned on by crossdressing however, and something told me this was a chance to see how I liked it. Underneath these was a pair of high heeled shoes, a blonde wig, and a makeup box. There was a short black dress, with a white apron attached, a black thong, matching black bra, and fishnet stockings with lace at the top. I went to my room, and laid out the contents of the box on my bed. It was a while before I could collect my thoughts enough to actually make any kind of decision about this.
With that, Brian opened the door and left, leaving me standing dumbfounded with the box in my arms. I told him I would try, and he said he was glad. I saw nothing but honesty in his eyes, however, which made me trust him. I hesitated, wondering whether he was just making fun of me or not. I looked up at Brian in shock, and he smiled down at me. Not a real one, but one of those lingerie style fetish outfits. I opened it to look inside, and my jaw dropped. It was a shipping delivery, and had gotten in recently, probably while I was in class. "And also, I'd like you to use this," he said, handing me a big cardboard box. Laundry wasn't a very tedious chore, and I had my own to do anyway. I got this huge pile of dirty clothes in my room that I never got around to, could you be an awesome guy and do that for me? I'll make it up to you, I swear." I grabbed his jacket off the couch and went over to the door, where he was putting on his shoes. I certainly wanted to put it out of my mind forever. "Sure thing," I said, secretly relieved that he would be leaving for a while. Think you could grab me my jacket? It's on the couch." "Okay, your call," he replied with a smile. "Yes, I think I'd rather stay home today."
"Oh," I said nervously, the shakiness of my voice betraying my continuing embarrassment. "I'm asking if you wanted to come, but I guess you probably don't." "I'm going to the bar with some of the guys," he said calmly, with no indication that there was any awkwardness between us. Finally, Brian walked up to me while I was in the kitchen, making myself a sandwich. We didn't talk much over the next few days, which were the most embarrassing of my life. I couldn't look him in the eyes, but I could swear he was smirking at me. I went into the kitchen to find Brian eating a bowl of cereal. It was an hour before I dared leave my room again. Still chuckling to himself, Brian left the room, while I tried not to cry. Finally he sobered up enough to collect himself again, and apologized for entering without knocking. Not just a few giggles either he was doubled over laughing till tears came to his eyes. I was beet red, naturally, and was almost ready to cry when he suddenly burst out laughing. On my computer was a porno starring a very obvious transvestite getting penetrated by a man. It wasn't exactly a decently sized one, topping out at just under 4 inches. I had my boxers around my ankles, and my lotion covered hand wrapped around my dick. It wasn't a very confusing situation, and not many excuses I could come up with. On the other side of the doorway stood my roommate Brian, staring at me in disbelief. I stood in the middle of my room, frozen in shock and total disarray.