It was my first time crossdressing. I have no gender identity issues or anything, I just wanted to try it. But I also wanted to have a little fun since I was sure this would be the only time I'd do something like this and I hadn't gotten laid in a while. It probably wasn't the smartest idea, but if literotica had taught me anything it was that Craigslist was a place to find a quick fuck.
So I went on and posted an ad for myself. "First time cd looking to service a man in the area." Of course, I found out quickly that I had been misled on the usefulness of the site. The only replies I got back were from very shady characters and, honestly, not very attractive guys. If I was going to have gay sex for the first, and probably only, time I wanted the man to at least be a little attractive.
Thankfully after a week I got a hit that seemed promising. It was from a man who was visiting from out of town on business and he wanted to meet me for a "night of fun" in his hotel room. Attached were some pictures of a pretty fit guy in either his late twenties or early thirties with a nice tan. But I was still wary. I didn't want my body to show up on the 6 o'clock news and my family to know I was murdered by a psycho while whoring myself out in drag.
So I instigated a conversation between myself and the man, who said his name was Andrew, though I'm sure it wasn't his real name. I was able to confirm that the man in the pictures was indeed the man I was talking to, and a little image search brought up "Andrew's" facebook and twitter. By all accounts he seemed like a normal dude. Had a nice job, a hot girlfriend, and no red flags as far as I could tell, and I was able to gather that he was free of any nasty diseases.
So I agreed to meet him at his hotel that weekend. I went out to the lingerie shop close to campus and got a nice outfit, some sexy underwear, and a blond wig. I thought that getting one that was a different color than my normal brunet would help me hide my identity if I somehow ran into someone I knew. I also picked up some toys, for my alone time. A guy's allowed to treat himself a little now and then.
I'm somewhat ashamed to say that I was a little bit giddy that week. The thought of having sex with a guy for the first time was one I'd had for a while and now that the time had finally come I was nervous. But I was determined not to chicken out! This was an experience I was going to have! Even if it was only once, that'd be fine, but life is about experiences and I was going to do this.
I spent all day Friday shaving. Thankfully I was not naturally hairy, unlike a friend of mine. The guy was like a freaking bear. Of course, this shaving included what little facial hair I had and my crotch and even the hard to reach areas. By the end of it I was as smooth as a baby's butt. I then took some laxatives to clean out the system. What pornos and literotica stories never mention is all the work that goes into making this kind of thing, like, not really messy. As a guy about to be fucked in the butt by another guy I didn't want something obscene to occur in that hotel room. Andrew might have been into it but I certainly was not.
After cleaning and dressing myself I took a moment to check myself out in the mirror. I looked like a totally different person, which I suppose was the point. The wig didn't look terrible, the make-up I had put on did the job without making me look like a slut, and my outfit was a really sexy yet humble skirt and sweater ensemble. My figure wasn't too bad, either. I had never been a skinny kid, but for the past few years I had been using the college's gym to work off the fat around my stomach. I had left the weights alone, though, and the effect, with a little help, was that I could pull off a natural breast size between an A and B. If I hadn't known the girl I was looking at was me I would have definitely enjoyed a night with her.
The time had come. I put sweats on over the skirt, blouse, and sweater and set out with my equipment. Since I went to an urban school the hotel Andrew was staying at was only a 15 minute walk from campus, and as I arrived I tried to look as not-out-of-place as possible, so as to not draw attention. His room was apparently 7069 (the irony was not lost on me) so I made my way up to the 7
th
floor and found a bathroom to change in. I took my sweats off and stuffed them in my bag, which I then stuffed in a purse. Also in the purse went my shoes and out came a set of 1 inch heels. As a man, I had never had to master the art of walking in heels so I wanted some that would make me look more girlish, but that also wouldn't break my legs in two steps.
With wig adjusted and lipstick applied I walked out of the bathroom in my heels and with my purse over my shoulder and I can safely say I've never felt sexier. The confidence didn't last, though. I had butterflies building in my stomach as I walked down the hall. Standing in front of his door I wrestled with myself one last time. I decided that I wasn't going to let an opportunity like this go to waste so I psyched myself up and knocked.
He answered a few seconds later. He was just like in the pictures. He was tall, had short black hair, and was tan like he spent time in the Mediterranean. He had a dress shirt and some slacks on at this moment. "Yes? Can I help you?"
"Um... I'm looking for an 'Andrew?' Are you him?" I squeaked in the girliest voice I could muster.
A smile spread across his face as he shifted positions in the doorway. I had apparently found the right man. He had also apparently picked up on my sheepishness. "Aren't you a cutie? And what might your name be?"
"Um..." I hadn't really thought on it. I just chose the first name that popped in my head. "M- Meagan. Sir." It was my sister's name, which for me just made the situation hotter.
"Well, Meagan, why don't you come on in and make yourself comfortable," he said as he vacated the doorway and let me into the room. It was like all hotel rooms, a hallway with a bathroom leading to a central bedroom with a tv and windows. "I'm glad you agreed to meet me tonight, Meagan. Is this your first time?"
"Uh... yes, actually. It is."
"Well I hope I can make it an enjoyable one," and with that he grabbed me, brought me close, leaned down, and kissed me full on the lips. I was able to take in his musk and he definitely smelled like some kind of expensive cologne. His hands sought a place to be and found my butt, groping me under my skirt. Though that felt amazing I wasn't really ready for a make-out session, so I broke it off and kneeled down. This is what I was here for. "A little eager, are we?" he said with a smile as I unzipped his pants. Soon his flaccid cock popped out from behind his shorts. It wasn't pornstar sized, just as most men aren't, but it was big. I considered myself of average length and it was definitely bigger than mine. 7 to 8 inches, at least.
I looked at the head, transfixed. After a few absentminded strokes I took it in my mouth, licking the head and getting the length as wet as possible, even getting my tongue into his little hole. Down here I was enveloped in Andrew's smell. It was all musk and no cologne and it definitely got me all riled up.
