My Sweet Little Crossdresser

"You're gonna have to tell me about this eventually," I responded, winking at him slyly.

"It's your fault," he joked, waving his fork at me. We laughed a little bit, but finished eating in relative silence.

On the walk back to his dorm, I decided to probe him with questions. "Do you dress up often?"

"No, not especially. That was the first time I had a chance in a long time. That was also the most involved I had gotten."

"Who did your makeup and nails?" I queried, thinking that there simply had to be someone to pull off a look that well.

"I did," he replied confidently, "believe it or not. I have a sister, so I learned this stuff early on. Right before bathtime, she used to practice on me. Eventually, she even bought me a wig. It was great."

"My brother wasn't nearly that cooperative. It took a month of pleading to even get him to try on one of my skirts, much less makeup."

As we approached his hallway, the talk of childhood was toned down and he became rather quiet. When we got to his door, he invited me in. As he locked the door behind him, I noticed a particularly good sign. His roommate had gone home. I knew it would be just us. I sat down in his roommate's chair, and he sat in his. He then began to tell of his wet dream.

"Normally I don't dream about people, especially if I just met 'em," he began, "but for some reason, I had this dream about you. I was walking along and I saw you, but you were dressed differently than you were last night. Instead of that really long black dress, you had on a tight top and a skirt so short that I thought I'd see your pussy underneath it. I then realized that I would probably see your cock if it got hard enough. I started gettin' pretty hard myself when I realized that I didn't have any pants on, not even a skirt. I tried to run, but just froze. I then saw your cock gettin' hard and it was just below your skirt and I couldn't help but get turned on. You just pulled your skirt up and went to town on my butt, and I just about lost it when you came in me. Next thing I remember, I had to pee really bad. For some reason, instead of trying to hold it back, I let go. I then realized that I just creamed myself really bad."