Date: Fri, 15 Aug 2008 14:39:52 -0700 (PDT) From: Jenette LaSalle <jenettelasalle@yahoo.com> Subject: A Night In A Night In Copyright 2008, Jenette LaSalle As usual I'm a bit tardy in posting this story - it happened last winter and as usual I've been so busy I haven't had time to put it down on paper but I finally has a small break and decided I should finally write up my last adventure - especially since so many people have written to me after reading my first posting and asking for more. I'm your typical crossdressing guy - 30-something, straight, professional - but since I was just a kid I've always had a hankering to don a skirt and heels for fun and excitement. I only dress up and go out a few times a year but when I do it I really enjoy it! During my last outing while dressed I surprised myself by letting a complete stranger have his way with me in a darkened nightclub parking lot. I don't consider myself gay or even bi, but the combination of dressing in a mini skirt, heels, hose, too much to drink, and the thrill of seducing a guy ended up with me bent over the hood of a car with my skirt pushed up, thong pushed to the side and hard cock sliding in and out of my ass. And, much to my surprise, I truly enjoyed it and often found myself fantasizing about it for weeks after it happened. Fast forward now to the dark, cold and dreary winter months that makes up the weather here in Chicago. My days had consisted of nothing but work, school, and an occasional chat with an internet friend or two. One of these friends was a guy named John. He lived near me and after seeing my pictures online had expressed more than once how he was attracted to "girls" like me and that he would like to get together some evening. At first I wouldn't even consider the idea, but after getting my "cherry" popped a few months before I started to entertain the idea of having him over for an evening. From his pictures and self description John was an attractive man - in his late 30's, tall, fit, brown hair, and clean shaven. He was also polite (if not insistent), a professional, and engaged to be married. He informed me that he had always been attracted to t-girls and had dated a few in the past. He also stated that he desperately wanted to have a "fling" before tying the knot in the spring. We continued to exchange emails - benign at first and then building to a slow sexual boil as we described our experiences and fantasies to each other. Finally, in an email he stated that his fianc‚ was going out of town during the weekend and he was wondering if we could finally meet. I knew what he meant by wanting to "meet". I mean, I may wear a skirt and heels but I'm still a guy and know what a guy is going to want. I was nervous and excited all at the same time. It was one thing to have a few drinks and find yourself in an awkward (if not exciting) position, but to actually plan something out like this in the cold and sober light of day is quite another. But again that little voice kept whispering to me that I had had a lot of fun last time and what would be the harm in a little more experimentation. So I quickly sent a reply that I would be available Saturday night, added my address and suggested he should come over around midnight. His response was quick - about an hour later he replied to my email saying that he was very happy and would be there at the appointed hour. With my fate sealed I realized that I needed to do a bit of shopping to make sure I had the right outfit for the evening. Over the next couple days I scoured the stores looking for what I thought would be the appropriate attire for my planned tryst. John had let me know in the course of our email exchanges that he really liked my legs and particularly enjoyed them encased in thigh-high stockings with CFM heels. Being a people pleaser at heart, I was happy to acquiesce to his desires and bought a new pair of black pumps with four inch heels and a pair of nude-colored silky Victoria's Secret thigh-highs. I also picked up a black satin and lace chemise and a black mesh kimono robe. I would have bought more of an outfit but since we weren't planning on any public appearances and the purpose of the coming event was to let a stranger from the internet have his way with me I figured any clothing I bought would soon find its way onto the floor anyway. The weekend quickly arrived and by Saturday afternoon I was feeling a bit nervous. Was I really up for this? What if he didn't find me attractive? What if I didn't find him attractive? What if I couldn't go through with it? I wondered at that point if real women have these same thoughts before going on a blind date. Then another thought hit me -- what if his cock was so big that I couldn't handle it? Hmmm...I hadn't even asked him about "size". I'm not very big myself - just under six inches - but I've seen pictures of guys with massive slabs of meat between their legs and the thought of trying to stuff one of those into my tight little ass made me shudder slightly. I quickly dismissed the concern and figured I'd cross that bridge when I got to it. By early Saturday evening I was growing more and more excited about my pending adventure and decided I should start getting ready. I took a long and very hot bath to soak away any lingering concerns and to prepare for an all-over shave. Next, I lathered up and "veeted" almost everything south of the eyebrows. What I couldn't Veet I shaved - and I mean "everywhere". Once that was done I started working on the makeup - placing my hair in a net and going to work on my foundation, shading, eyes, and lips. It's a long process to go from "average joe" to "hot tranny" and the makeup alone took more than two hours. Then I fluffed out my blond wig and moved back into the bedroom to start getting dressed. The best part of the transformation process for me is, once the makeup and wig are in place, sliding on a brand new pair of stockings up my freshly shaved legs. There's just something so incredibly sexy about the feeling and the visual. When I started to put on my new thigh highs I instantly got hard. I looked over at the clock and saw that I had a couple hours yet until my mystery date arrived so I decided to take advantage of the time and take a little self pleasure. I slid on my heels and, dressed in nothing more than my stockings and heels I laid down across the bed and started to stroke my stiff prick. As I slowly stroked myself I rubbed my stocking covered legs together and imagined what would be happening to me in just a few short hours. The intensity of my fantasy and the feeling of lying there - my smooth scented skin, the smell and feel of my makeup, the sensations of the new thigh highs, and the sight of new CFM shoes on my feet with my legs parted and lifted high in the air brought me to a quick and intense orgasm that seemed to last for almost a minute. I lay there, panting and happy for a while until the "post orgasm glow" subsided, went back into the bathroom to clean up, and then finished getting dressed. The rest of my preparations were relatively simple - slip on and tighten the corset (gotta have one - too many cookies I guess), a black lace bra with silicone breast forms, a black lycra thong, slide the black satin and lace chemise over my head (carefully so as not to mess up the makeup or wig), wrap myself in the black mesh kimono robe, and as a final touch apply a set of fake nails with a French manicure finish. Time is a funny thing - when you're doing something you hate it seems to drag (no pun intended) on and on but when you're doing something you like it can pass in the blink of an eye - which it had done when I realized that the appointed hour for my internet booty-call was fast approaching. I quickly tidied up the bathroom and walked out to the kitchen to check on the drinks and snacks I'd laid out - all while acutely aware of the click of my high heels and the silky feel of my stocking-covered legs as they brushed against each other as I moved about. The doorbell sounded and I almost jumped. My prospective paramour must have been eager since he was about fifteen minutes early. Not a problem - I was ready. I hit the buzzer to open the entry door to the apartment building and moved to the front door of my flat, peering out the peephole just to make sure it wasn't an unexpected friend showing up. It would have been rather awkward had something like that happened since few of my "buddies" had any inkling that I occasionally wore a dress. Much to my relief I saw my internet friend on the other side of the door. I took a steadying breath - nervous and not really sure I was ready for what he was after - then plastered a smile on my lipstick covered mouth and opened the door. John was exactly like his pictures from the net - late 30's, tall, fit, brown hair, and clean shaven. He was a bit shorter than me, but then again I was teetering about in four inch CFM heels. I invited him in, trying to use a breathy whisper and not spoil the illusion with my rather deep masculine voice. I asked him to sit on the couch while I got us a couple drinks. I felt like slugging back a shot of bourbon but that would have been unladylike so I contented myself with a glass of wine. In our email exchanges John had indicated a penchant for scotch so I poured him a glass and moved to join him on the sofa. I wasn't sure who was more nervous. He smiled a lot and was exceptionally polite but I could sense an undercurrent of nervous energy. I wondered if he was disappointed in me and how I looked. I wondered if he was having second thoughts. I wondered if he might just get up off the couch and call the whole thing off. We made a bit of small talk as we sat next to each other on the couch. I asked if he had trouble finding the place and he said my directions were good. As he sipped his drink he looked over the rim at me and I caught his eyes wandering over my crossed legs. I took a chance and asked him if he thought I looked "o-k"? He smiled and said that I looked "amazing". I smiled at that. He must have taken my smile to as a sign to proceed since he set his drink down on the table and placed a hand on my thigh. "Well, here it goes" I thought to myself as he started to slide his hand up my thigh and into the V of my crossed legs. He leaned in to kiss me and I had to fight the urge to lean away. Years of enculturation against kissing a guy is not instantly overcome just because I happened to be dressed as a chic. I let our lips meet and felt him tentatively flicking his tongue across my lipstick covered lips. I obliged and parted my mouth a bit allowing our tongues to meet and dance together a bit. I was conscious of my lipstick and pulled away before it became a complete mess. He looked a bit confused by my retreat so I decided to let him know things were going well. I slipped off the couch and, while on my knees, moved in front of him and started to undo his pants. A few quick motions of the wrist and his buckle and zipper were undone. He pushed up slightly as I pulled his pants down to his ankles. He was already hard. A clean shaven and stiff prick met my eyes. My worries about his size were not completely unfounded. He was a good seven inches, cut, not too thick, and already oozing precum fluid. I figured it wouldn't take much to get him off. I wrapped a hand around his cock and held it tight while I let my tongue slide from the base of the shaft along the bottom to the tip. He moaned with pleasure, his eyes rolling back and he leaned back onto the couch. I repeated the move a couple more times and then slid as much of his meat into my mouth as I could. Again, I'm not what you'd call an experienced cocksucker, but I do know what I like and I tried to repeat some of the moves I remembered from past blowjobs I'd gotten. I made sure to pull my teeth back, let his cock slide in and out of my mouth as my hand pumped his shaft in rhythm with my mouth. I made sure the pad of my thumb was pointed up and that it rubbed the underside of the tip on each stroke. He seemed to enjoy it as he groaned and gripped the couch cushions. As I predicted, he didn't last too long and after about thirty to forty strokes he stiffened up, gave a half grunt half shout, and shot his load into my mouth. My first taste of cum surprised me. It wasn't "the nectar of the gods" that some stories will make it out to be, but it wasn't terrible either. It kind of reminded me of oysters on the half shell. I swallowed, smiled, brushed my blond wig hair back and looked at John. He sat there with a contented yet sheepish grin on his face. I asked him if he enjoyed himself and he told me I was "great". Hmmm...not bad for a beginning cocksucker. It had been fun but I wanted more now. I grabbed him by the hand and as he gave me a puzzled look I lead him into the bedroom. I'd taken the time to light some candles. Call me a sucker for romance, but I do love candle light. After leading him to the foot of the bed I worked to finish undressing him. Shoes, pants, shirt, underwear were all stripped away in short order and soon my internet friend stood before me naked. I was afraid my blowjob might have finished him for the evening but much to my pending enjoyment I saw the stirrings of another erection on him. I, of course, was hard as nails by now and I was sure John could see the bulge in my thong poking out from beneath my chemise and robe as I removed his clothes. John's body seemed to react before his mind did. He pulled me close to him and started running his hands along my body, stopping occasionally on my thighs, ass, and shoulders. He grabbed my silicone chest a couple times but didn't linger there. He untied the belt of my robe and pulled if off me letting it slide to the floor. Then he turned me slightly and pushed me back onto the bed. I lay on my back on the bed still wearing everything but my robe. My legs were spread with my heels dug into the edge of the mattress. John had started kissing and caressing his way up each leg from the ankle to the top of my thigh high stopping just before reaching my crotch. Much to my amazement he took his time and did this slowly several times, each time making me want to feel his hot breath on my rock hard cock which was now sticking clearly out of the elastic top of my thong. In my overheated delirium I realized he had stopped and I looked between my legs to see him standing on the side of the bed. He looked over at the night stand where a rather large and obvious bottle of lube was sitting. He grabbed the bottle and started pouring a generous amount onto his hand. "Easy there cowboy," I said as I realized what was about to happen, "nobody rides this cowgirl without a raincoat." He looked a bit crestfallen but eagerly took the condom I offered from the night stand. I helped him roll it on with a grin. I'd never put a condom on any cock other than my own. It was kind of fun. Once the he was properly sheathed I lay back down and watched as he dumped more lube onto his hand and proceeded to slather up his jutting cock. I grabbed a pillow from the head of the bed, shoved it under my ass and waited for him to take me. John climbed between my legs and, with the help of my guiding hand, positioned himself to enter me. Last time I'd had a cock in my ass I was drunk, bent over the hood of a truck, and didn't have much time to think about what was happening. Now I was a bit nervous. What if it hurt? What if it hurt a lot? Last time, which was the first time for me, it didn't hurt a bit. Now I was going to find out if this was something I really liked or if it had been just a one-time thing. I felt the tip of his cock start to slide into my ass. No pain at all, just a flush of excitement and feeling of fullness. So far I was enjoying it. I did feel a bit claustrophobic with him on top of me but that quickly passed as he started to pump his meat deeper into me. He started out slow, pressing all the way into me and drawing back till he was almost pulled completely out. My cock stuck straight up and his abdomen would brush it from time to time making me tingle. As he continued to fuck me his pace increased and I started to get into it. I grabbed his ass with my hands, digging my nails into the ass cheeks and pulling him deep into me on each thrust. When we first started to fuck he had been looking at me, now his eyes were closed and he had a faint sheen of sweat on his forehead. I knew that look, I'd had it plenty of times myself, and it meant he was getting close to cumming. I continued to urge him on, whispering for him to "fuck me harder" and "I want to feel you cum inside me". I still grasped his ass, digging my nails into him and pulling him into me with each stroke. His pace picked up even more and as he rammed his cock deep into me he let out a gasp as I felt his cock expand and stiffen. I held him in me, wrapping my stocking covered legs around him as he shot his load. He shuddered and collapsed on top of me. We lay together like that for a few moments. His breathing was hard against my ear. I savored the moment, my legs still wrapped around his body, my hands still on his ass, his cock still inside me. I'd done it. I'd let a man fuck me while I was dressed. This time it was planned and deliberate. And I had enjoyed it. It wouldn't be the last time if I had any say in the matter. As we lay there John shuddered a couple times with post-orgasm aftershocks and I felt his cock start to shrink and pull out of my ass. He levered himself up on his elbows and smiled at me. "That was fun," he said. I nodded agreement with a dreamy smile of my own. He pulled out of me with a quite "pop", stood up and peeled the filled condom off his cock. He reached for his clothes and said he had to get back soon. Typical guy, got his rocks off and out the door. It wasn't unexpected. I had done the same to plenty of women in the past, but it still kind of stung a bit. Besides, I hadn't gotten off yet. Damn. John finished dressing as I readjusted my clothes, checked my makeup, and put my robe back on. I could tell he was eager to get going - probably a nagging conscience about cheating on his fianc‚e with a guy in a dress. I walked him to the door and he glanced up and muttered, "uummm...thanks." I give this guy a great blow job and let him fuck me and all I get is "uummm...thanks." Nice. I locked the door after he left. It was about two in the morning, too late to get changed and head to the bar. So I just headed back into my candle lit bedroom, laid down on the bed and remembered the sensation of a hard prick riding my ass. And as I slowly stroked myself, legs in the air and my hands caressing my stocking covered legs and lace cover body, I brought myself to a mind-blowing climax.