This is a story involving sexual content about a crossdresser. If you are offended by this, then please don't read. These stories are about my sexual experiences as a crossdresser. These stories are true with a few minor embellishments.
College Crossdressing Slut
Getting Set Up
Ok, I know that a lot of people are just reading the story for the sex parts, and I will get to that. The beginning of this story has some background information on me but don't despair, all my other chapters will have a lot of me getting sucking guys or getting fucked.
It's hard being gay guy in high school and its harder when you know you really want to be dressed as a girl for a hot guy. I began crossdressing about 14 years old and loved it immediately. My older sister had a ton of clothes and I loved trying them on during the rare occasions I was alone. When she left for college, she couldn't take all her clothes with her so I gradually started taking some of those clothes and hiding them in my room. I even bought a few clothes and a wig online during Christmas time. I told my family that a Christmas present for one of them was coming in the mail to make sure nobody opened it when it arrived. I fantasized about being with a guy when I was dressed up but was way too shy in the closet to actually pursue it. I knew I wanted that to change when I went to college.
When I graduated high school, I knew I wanted to get away from home for awhile. I was lucky my parents had some money and they helped me pay for an apartment when I went away. I was really glad about this because I knew I wouldn't have much opportunity to dress up in the dorms. My apartment wasn't too far from campus so it was convenient too. My first two days before classes started I spent almost all of it dressed up. I really loved the slutty/skanky look, like short skirts, thongs, short tops that showed off my stomach. I was tall for a girl, 6'1, and very very skinny. I loved that though because it made my legs longer and skirts naturally shorter on me. I'd usually fantasize about guys when I was dressed and one of my favorite fantasies was to be a prostitute. I loved to think about blowing a guy in his car for money or getting bent over in an alley while the guy paid me for sex. I didn't have any toys so I'd usually just use my fingers or sometimes I would buy something from the grocery store. At that time though, a carrot was all that would fit up my virgin butt.
After that weekend, I knew I really wanted to meet a guy and lose my virginity. I also knew I really wanted to lose it as a girl. I went to an online website and posted a profile and some pictures but was too scared to show my face. After seeing some of the responses I got back, I kind of figured that maybe wasn't the best way to go. I did have some fun with some dirty chat though at least. I really didn't want to come out of the closet yet though so I was in a dilemma. Walking on campus one day I saw the Gay, Lesbian, and Transgendered Coalition. It took me a couple days but I got the courage to walk in. There was an Asian guy sitting at the front desk and asked if he could help. I kinda lost my courage and said I was just looking and left.
The next day I was walking out of one of my big lecture classes and the Asian guy I had seen the day before came up behind me. He looked a little taller than I originally thought he was, about 5'10" and had a few extra pounds. He asked "Didn't I see you yesterday?"
A little flustered I replied, "Yeah, I think you did."
"Cool." He said. I'm Nick."
"Ok Nick, I'm Jason. Good to meet you." I replied, kinda glad to meet someone.
"I'm hungry. Come have something to eat with me." He told me. We went to a McDonalds and ate outside off to ourselves. We talked for about 20 minutes and he asked me a lot of questions.
Finally he came out and asked "You're gay too right?"
I stammered a little, "Ye-Yeah. Well sort of. I like guys but I haven't ever been with one." I was surprised at how straight forward I was with him. He was the first person I had known that was gay and truthful about it and it made me feel comfortable.
"I figured he said. It was obvious because why else would you go the Gay Student Union, but I also figured you were inexperienced since you left so quickly. Are you bi or gay?"
"I'm gay. I pretty much only think about guys." I informed him.
We went back to my apartment and talked for awhile and learned a lot about each other. He was a junior, had a boyfriend, was pretty active in the gay community, and was mostly a bottom. He was a pretty smart guy too. I told him I thought I was only a bottom, completely inexperienced, and still wanted to stay in the closet for a little while.
"Are you looking to meet a guy at all?" He asked.
"Of course. But I don't want to come out of the closet yet, and how am I supposed to meet a guy?"
"Hey, I know tons of guys. A lot of them are bi or in the closet and don't want people to know either. I can set you up with one of them no problem and they won't tell anyone either."
"Really?" I asked.
"Really." He assured me. "Just tell me what kind of guy you like and what you're looking for."
"Umm," I said. "I like taller, my age or a little older, not fat. I don't know."
"Are you looking for a boyfriend or just to get fucked?"
"Something in between I guess." I replied. "And... never mind."
"What?" Nick asked. "How am I supposed to find the best guy for you if you don't tell me?"
"It's something I want to try my first time, but it's embarrassing so never mind." I said extremely nervously.
"For my boyfriends birthday I let him fuck me while he was dressed as Batman and I was dressed as Robin. See now I told you something embarrassing so you can't be embarrassed. It's not like I'm going to tell anyone."
"OK," I said as I laughed. "As long as you don't tell anyone, but I really like to cross-dress." I told him with my face looking down. I was really surprised how open I actually was.
Nick exclaimed, "I know the perfect guy for you!"
"Really?" I asked quizzically.
"Yeah this guy Joey. He's about 6'3, pretty nice body, a senior, and he's bi and in the closet too. I hooked up with him a few times my freshman year and one time he brought panties and wanted me to wear them before he fucked me. He's actually a great fuck too. What do you wear when you crossdress?"
"That's awesome." I said trying to contain my excitement. I was already anticipating meeting him. "I actually dress all the way up. I have a wig, I'm a blonde, and makeup too. I'm not that great at makeup though."
"I think Joey will really like this." Said Nick. I'll let him know you crossdress so there are no surprises and I'll let him know you're a virgin too. He always liked to fuck pretty hard so I'll let him know to take it easy on you. Do you mind if I give him your number?"
"Go ahead and give him my number if you think he's interested." I said.
"I will definitely do that." And then said with a smirk, "And before I forget, I was just kidding about the Batman and Robin thing."
"Asshole." I said as I smiled. "I forgive you though since you're going to get me laid."
Nick stayed a while and answered some of my questions. He said buy some KY and to keep it close because, while Joey wasn't huge, his cock was definitely bigger than average. I asked him what positions are the best and he said they're all great but if it hurts to try riding on top. He also said to make sure I have condoms because Joey tried to pull the "I don't have a condom but we don't need one cause I'm clean" the first time they hooked up. He also said Joey loved to get head and gave me some tips. If you can't get it all in your mouth then use your hand too and don't forget to play with and lick his balls.
"Am I supposed to swallow?" I asked.
"Probably not." He told me. "Guys love it and it's actually the best part but its better not to take the risk. Honestly though I did swallow a couple times for Joey."
"What about anal? Is it messy at all?" It was good to have someone to answer my questions. Nick advised me it usually wasn't but I could give myself an enema beforehand if I was worried. That's actually what he did his first time just to make himself fell better. Nick left after we talked for awhile I went to sleep very excited and horny that night.