My Sweet Little Crossdresser

Monday morning I woke up, still somewhat tired from the night before, asking myself if it was all real or just a dream. I then remembered that I had taken that cute guy's panties and put them on my neighbor's door, so I walked out into the hall and looked down to her door and, sure enough, there they were, still on her doorknob. Feeling a sense of obligation, I removed them, and decided to give them back.

I walked back into my room and fumbled through my purse when I found a piece of paper that had his name and contact info on it. Since he was also a freshman who lived in a dorm, I decided to see what he was up to that afternoon. I walked over to his dorm and cautiously knocked on his door. I was hoping that his roommate wasn't there, so I could have some time alone with him. He came to the door and opened it, somewhat surprised. However, I didn't fully realize it was him. I couldn't tell very well since he wasn't in drag anymore. I looked around to make sure nobody else was within earshot and whispered to him, "You look pretty cute as a guy too."

He smiled and blushed, seemingly proud of his ability to pass relatively well as a girl. Highly unlike the night before, he had almost no hint of girliness to him, with the possible exception of his Birki's, which were almost the same as the ones I had. I could tell that he had removed his nail polish which he had on the night before, and he was also wearing long pants, most probably to hide the fact that he shaved his legs. I decided not to ask him about that just yet, since I didn't want to make him feel uncomfortable. He appeared to be somewhat nervous, so I asked him out to lunch. He obliged, and we went to one of the dining halls to eat.

For some reason, we didn't hold hands on that walk. I'm not sure whether it was because we weren't that close yet, or perhaps because we somehow knew that the other wouldn't run away. While we were eating, he leaned over the table and confessed, "Last night was the first time I ever had a wet dream."

"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."

"It sounds like you had a wonderful dream there," I concurred, as I pondered the possibility of some more fun. Soon I realized that I had forgotten to give him his panties back. Reaching into one of my skirt's pockets, I pulled them out, then tossed them to him. "I just remembered. I figured you'd want those back."

"Hehe, yeah, I almost forgot what happened to 'em. I coulda sworn I wore panties up there, but when I came back here and didn't have 'em on, I figured you'd taken them off when you sucked my cock."

"That I did," I replied, seeing that he had moved his hand near his crotch, wanting to pull his cock out and stroke it at the thought. "Do you want some help over there?"

"With what?" he nervously queried, moving his hand away from his crotch.

"I saw you had your hand down there, and I figured that maybe your cock wanted to come out and play."

"Well," I could tell he was trying to figure a way out. "I reckon it does."

"Good," I happily replied. "Your butt will be spared, since I don't have any lube with me. Not to mention the fact that it's probably a little sore from last night, eh?"

"Yeah, just a bit," he responded. I could tell that I put him through more anal misery than I thought. I kinda felt bad for him, and I figured I'd try to make amends by letting him eat me out today.

I walked over to him and unbuttoned his pants, then unzipped them. I slowly pulled them off of him, along with his briefs, exposing his cock, which was already hard and somewhat wet. Seeing as how both of us were rather inexperienced, we got aroused easily. I laid him down on his back on the bed, and slipped out of my underwear. I pulled my skirt up, and said to him, "Take your pick, hun," then laid down on top of him, with my cock dangling right in front of him.

As I slid my lips around the shaft of his cock, I wondered whether he would return the favor and suck my cock, or slide his tongue into my moist pussy, or even eat out my butt. I was pleasantly surprised when I felt his lips slide down my cock. I honestly thought that he'd try to avoid the very thing that had invaded him the night before, stretching his butt and leaving a warm load of cum in him. No, he was enjoying himself. I could tell by how eagerly he sucked on me, trying to extract my gooey goodness by force. Closing my eyes, it was very easy to imagine that I had a girl sucking on me instead of a guy.

Nothing lasts forever, and our mutual sucking sure didn't. It was only a matter of time before he let go of his cum directly in my mouth and, shortly afterwards, I came in his. I quickly turned around, pinned him to his bed, and gave him a long, cum-filled kiss. For some reason, snowballs are so much fun, and with him they seemed to be even more fun since he was reluctant to accept them.

As I laid down beside him, I cautiously asked, "How in the world are we gonna survive the summer?"

"We can visit every day," he joked. After a brief pause, he theorized, "or we could just pounce random people at clubs who look cute."

"Hmmm, I reckon you're right. After all, we haven't known each other that long. And besides that, even if we do wind up hooking up with other folks, if we like each other that much, we'll be doing this again." We laid there in silence for quite some time, and he eventually put his underwear back on. "You'd look so much better in a skirt than in pants," I told him, hoping that he would eschew his pants in favor of a skirt, which would make him look so much sexier.

We saw each other every day that week, but didn't do anything more than kiss. This was probably good, since we weren't accustomed to getting sucked off every day. One evening, while we were talking about our lives and past love interests, he told me about the first time he had anal sex with a girl.

It was on spring break that he had his first anal sex, and it was that night when the girl had kicked him out of her house. As it happened, he was going to become part of a foursome, with him, her, and two other guys. Before they were going to have their fun, he came into the room just after he had shaved his legs. At that point, the girl kicked him out of her house naked, while the three of them opened the curtains and had sex where he could see it. As tears started to form, he told me of that night, "All I wanted to do was sit there and cry, but I just ended up stroking my cock to that sight and eventually came right there on the beach. Then, this group of drunk girls came along, and one of 'em felt sorry for me, and ended up letting me have her sarong to wear back to my room. I don't think she realized how much I actually enjoyed wearing it, but it was fun."

"So is that the girl you had anal sex with?" I asked eagerly.

"Yeah. Before we got back to the hotel, I stopped to pee. When I did, she walked over and watched me. When I finished, she took my cock in her hand and just started to stroke it. I was kinda baffled, but I didn't complain. I just sat down on the beach and she stroked me for a while, and then she started rubbin' her butt and she just pulled some lube outta her purse and smothered my cock and her butt in it, and she eventually just sat down on my cock, and just rode it with me in her butt. I came pretty hard in her, and then she came. After a few minutes, I felt something else wet on me. Evidently she found it proper to piss on me after all of that!"

I couldn't help but giggle a bit, pondering what that golden shower felt like. "I'll have to remember that next time we have fun," I remarked, winking at him. I could tell that I got under his skin a little with that remark, but there was potential to try it, the next time we were together. However, I knew that this would be the last time that we'd see each other for quite a while. As I got up to leave, I gave him a long hug, grabbing his butt lightly in the process, and reluctantly walked back to Lee, dreading the packing process and my last remaining exam, for which I hadn't studied much.