Hotel Night

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.

I continued to stroke the base as I sucked on the upper half of his meat. "Oh, yes. That feels amazing. Keep going," he was saying as he tucked my blond hair behind my ear and out of my face. I continued to stroke and suck for a few seconds after he had gotten hard, then stopped. "No," he whined, "Why'd you stop?"

"I have a little surprise for you," I replied. "Why don't you get comfortable while I get ready?" I picked up my purse and went to the bathroom in the hall. After admiring my reflection and how sexy I looked in it one more time I stripped and got the lacy lingerie I had bought a few days before. It was a set of black lace underwear with bra and panties (which my rock hard dick was sticking out of at the moment) and in addition I had gotten lace stockings with garter belt and gloves. After tonight, I thought, I will definitely have some fun alone time with this outfit.

He was sitting on the edge of the bed completely naked when I came out. I tried to strike a sexy pose and felt like I succeeded. "W-Well? Do you... see something you like?"

"Oh, yes," he said with that smile of his. "You are truly beautiful. The sexiest slut I have ever seen." He opened his legs, beckoning me. I walked over to him, swaying my hips like a woman who knew what she wanted, and took hold of his massive member as I kneeled down. Taking his cock from him, I stroked it with my gloved hand as I took one of his balls in my mouth and sucked. "Oh, god, this is amazing!" he moaned. I continued to stroke his rapidly hardening cock, loving on his sack all the while. He happened to be one of these guys who shaved his crotch, thankfully. This would not have been as enjoyable if I was getting a mouth full of pubes.

Taking the now hard and ready cock in my mouth I moved to massaging Andrew's scrotum with my hand. "Oh fuck! You're better than my girlfriend." That took me aback. It seemed rude to me to mention another girl when your cock was being serviced by someone else, and in response I doubled my efforts to make this man cum. When he was screwing his girl I wanted him to think about me and the great fuck I gave him.

"Oh- OH FUCK!" With a tensing of his balls and a flexing of his massive penis, load after load of hot cum shot into my mouth. The only cum I had ever tasted before had been my own, and Andrew's was definitely different. Thicker and sweeter.

His orgasm had caught me off guard, but I was determined to swallow every drop of the salty juice. After he had finished cumming into me I sucked on his beautiful member like a straw, trying to get everything I could. It was truly an amazing experience: the salty sweet taste in my mouth, the warmth in my stomach, and Andrew's moans of pleasure all added to my arousal, making me hornier than I had ever been before.

He fell back onto the bed, momentarily exhausted. "Wow. That was just... amazing," he said, though I didn't give him any time to recover. I began to stroke his wet meat again, trying to harden it back up. I was not done and I wanted to make sure he wasn't either.

When I was sure he wouldn't refuse some more, I stopped and climbed onto the bed kicking off my heels. I crawled up to the headboard and stuck my ass into the air. "Andrew, I would you be a dear and help a girl out?" I said with a little shake of the booty.

"You bet, you little minx." I could feel him position himself behind me, and after he pushed my panties aside he licked my ass hole. That was an entirely new experience for me and now I was definitely happy I cleaned earlier that day.

With his tongue in my hole I couldn't help moaning the cutest, girliest moan I had ever heard myself make. "Oooh, yes! That feels amazing. Keep licking my pussy; you're making it dripping wet." And he obliged. Not only did he wet my ass but also the underside of my balls and everything in between.

"Oh, oh please. Fuck me now!" I cried. I couldn't take it anymore. I braced myself and planted my face in the cheap hotel pillows, trying to relax my ass muscles. I felt his tip probing at my rosebud, then the pressure of his wet head pushing into me. I bit my lip, prepared for the point when his head entered me completely and the rest of the shaft slipped in.

It happened quickly. One moment there was a bulge pushing into me, the next it was traveling deeper into my bowels. I had never felt anything like it before: the sense of completely filling up thanks to the wondrous rod of a man, especially one as big as Andrew's. I didn't have much time to reflect on this, as Andrew started to pump almost immediately.

In and out, in and out. All I could feel was the head gyrating inside of me and the shaft rubbing on my asshole. "Oh-h-h-h my GOD! Fuck. Me! Yes! YesyesyesyesYES! Fuck me like you could never fuck your girlfriend. Make a woman out of me!" I undid my bra to let my breasts swing free and I couldn't keep my hand away from my neglected clitty. With my face buried in the sheets I started to masturbate as my ass was being serviced. The feel of my lace gloves did me in and I had never cum so fast and so hard. I could see trails of my jizz on the sheets under me as I screamed, "I'm cumming!"

I guess this pushed Andrew over the edge since he started to shoot his load into me for the second time that night, and this time I could feel the warmth actually filling me up. But he didn't miss a beat. After he had finished unloading his cream into me he picked me up and flipped me around, pivoting me on his penis, which was still inside me. I landed with my back in pools of my own cum and I could see this man furiously pounding into me, trying to harden back up. We locked eyes and he took the chance to start kissing me again. With my mind occupied by the meat in my butt I wasn't able to break away from the kiss and just went with it.

I lifted my legs to give him a better angle and wrapped them around his back, pulling him into me. He eventually broke off the kiss and sat back up, supporting my back with one hand and wrapping the other around my sore shaft. With a grin on his face he began to pump my penis vigorously. "Ow, I can't take it. My head's too sore." Thanks to my earlier orgasm my dick was hypersensitive to the attention Andrew was giving it. It seemed like only a few seconds had passed before a shudder ran through me and my balls constricted, retreating further into me than they already were, and load after load was launched from my hole.

Streams of my cum shot up my body, with most landing on my breasts and stomach, but some of the first few made it to my face. At feeling my juice on my face I opened my lips to try and get a few spurts into my mouth.

Andrew retreated out of me, leaving a cold, empty feeling in my ass, and laid down next to me, trying to catch his breath. I wasn't ready to be finished, but I was too sore to do anything fun, so I crawled down to his penis and started to clean the cum off his shaft with my mouth. After that was accomplished I snuggled up next to him and we laid there like that for a while.

I awoke in the same position an hour later. The lights had been turned off and I could feel Andrew breathing rhythmically beside me. I got up and looked out the window at the lights of the city below. The hotel was right on the edge of the financial district which, at night, was quite beautiful.

I didn't notice Andrew was behind me until he started touching me and sucking on my neck. I moaned, accepting his advances, and pushed my butt up against him. He accepted my invitation and shoved his dick back up my ass, pressing me up against the large glass window.

The mix of sensations was erotic: the heat of Andrew behind and in me coupled with the cold of the glass against my breasts, body, and erect penis. When I started to move with Andrew, the sensation of the window on my penis acted like a masterbatory effect and allowed me to orgasm. My load shot up, coating my stomach and the window in my cum. In all of this, the thought that this would be a bitch to clean up for the staff reached my head, and I sank down to my hands and knees and started to lick my own cum off the window in an attempt to clean it.

This gave Andrew perfect access to my hole, so he entered me, taking me doggie style. He reached around to grab my tits, grunting with every movement of his huge phallus inside of me. For my part I was moaning, tongue out and lapping up every stream of my cum that was sliding down the window.

"Mmmm... yes. Fuck my pussy. Shove your huge hot dick up my virgin pussy! Yes!" I was shouting between my licking of the cum on the window.

"Ooh yeah, you like that, you little slut? You like my dick up your ass?"

"Yes!" I couldn't take this anymore. I moved my arms to the window and shoved my face in my cum, preparing for what I wanted. "Will you stroke my clitty for me, baby?" I asked.

He didn't waste any time and grabbed my dick. He stroked it furiously, and I responded with violent thrusting back into Andrew.

"Oh- oh- OHHHHH!!" I screamed. Being taken furiously from behind like an animal and the scent of my own juices soaking me and the window filling my nostrils pushed me over the edge. More loads from my clit coated the carpet under me, as well as Andrew's stroking hand.

It was too much. I looked out over the city lights, a city that could probably see a little crossdressing slut in the window of a hotel laying in her own spunk after being taken like the bitch she was, and just rested. Andrew pulled out of me and went back to the bed.

I flipped around and just sat, my balls laying in pools of cum. This was the first chance I had gotten to reflect on the events of the night. I looked down at my sore and twitching penis and my cum stained body and decided that tonight had been a success, and that I should probably head out.

I got up and, trying not to fall thanks to my raw ass and weak knees, made my way to the bathroom and ran a bath.

After cleaning up I got my wig back on, bits of cum still in it. 'I need to find out how to clean this,' I thought. I also put some makeup back on. Despite just ingesting a lot of his cum, I didn't want Andrew getting a good idea of what my face really looked like.

Dressed in the skirt and blouse I arrived in, with my cum covered lingerie in a bag in my purse, I went up to the bed and told Andrew that I was leaving. He looked up and said, "Please wait a minute." He got up and jotted something down on a piece of paper, his now-flaccid organ swaying as he did. "This is my number. Get in touch with me and next time I'm in the city we can do this again," he said, with that mischievous smile on his lips.

"Will do," I mumbled, trying to suppress a smile of my own. With that I left the room and the hotel altogether.

I hadn't changed into my boy clothes before I left and on the walk back to my dorm I was getting stares from all the drunken guys leaving the bars. At this time of the night, or morning depending on how you looked at it, the only guys still out were those who went out looking for something and hadn't found it yet.

I passed this one guy coming out of a bar who noticed me and called out, "Hey, sexy. You looking for a good time?" I looked back at the guy, a young white stud who could barely stand, and decided in my cum-high that his was good looking enough.

"Sure. Why not?" I said and took his hand. I lead him to the ally beside the bar and got down on my knees.

I undid his belt, unzipped his jeans, and pulled his boxers down. His dick was already hard and I started sucking. "Holy shit, bitch. You're eager, aren't you?" I didn't want to talk to him, I just wanted his seed in my mouth.

I was startled to feel his hands on the back of my head pushing me down further onto his meat, which was smaller than Andrew's. In fact it was close to my size, though it was still bigger than my clit.

Gaging on his shaft I knew I couldn't do this for long. Someone could walk by, not to mention the difficulty I was having breathing with his penis down my throat. I grabbed his balls and began to massage and doubled my efforts on the cock. Moving quickly I bobbed my head up and down, using my tongue to clean the whole organ.

The guy couldn't take it and started to thrust into my face. "Sh- shit, girl. You're a re- real slut, you know that?"

I moaned into the guy's pelvis and that seemed to push him over the edge. Hot streams of his seed shot from his dick and into my eager mouth. I swallowed all of it, not letting one drop go. It tasted like alcohol.

With that I got up and left quickly, before the guy came to his senses. I was able to leave him dumb in the ally as I got back to my dorm. I was lucky that my roommates were out for the weekend. I did not want to explain to them why I was in drag at 2 in the morning.