Copyright 2008 by Jenette LaSalle
O-K, It's been about a year since this happened - I know it's a bit tardy but I had been planning on writing about the last time I went out and what happened. I know it's been months and months, but I finally sat down and described the night and what happened. Here's the story of the last time I went out dressed.
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. Last time I went out was last fall. I ended up going to a local TG bar and on this night it was packed! I was wearing a short black lacy skirt, cream and black corset top and a black velvet jacket, knee high black boots with a four inch heel ? and under it a black corset, black bra, black thong panties and a black garter belt with nude stockings (from Fredericks - they're great!). I also had silver hoop earrings, a cute little silver necklace, a nice set of fake nails and my favorite medium length blonde wig. When I got to the bar I parked in the lot next to the club and as I was walking in a car pulled up and a guy rolled down his window, looked me up and down and then asked me if I wanted to "fool around". I smiled, politely turned him down and headed into the club.
When I got inside the place was already packed. About a quarter of the people there were CDs or TGs. I headed over to the bar and amazingly I found a seat right away and ordered a beer (not too lady like but what can I do?). Sitting next to me on either side were some CDs and we all immediately started chatting and complimenting each other on shoes, outfits and overall look. I was looking for a CD friend I'd chatted with online and finally found her. We talked for quite a bit, sat back by the pool table and had a great time getting to know each other a bit more. As we chatted our stocking covered legs kept brushing against each other (not by accident either) and I was getting rather turned on at the prospect of some playtime with her. I think more might have developed between us since there was definitely some serious chemistry, but she had to leave so I ventured out to find more people to chat with. After a bit I got asked to dance and headed out onto the floor. After a couple songs I headed outside to the patio area to cool off, then back to the bar for another drink. Most of the night proceeded that way. At one point I headed into the ladies room and found a lot of GGs, TGs and CDs in there all chatting away. At one point a rather attractive GG took my hand, pulled me close and gave me a big kiss ? telling me how beautiful I was. I'm pretty sure she was really drunk :)
A bit later during the night a guy asked me to dance. There tends to be a lot of "tranny chasers" that hang out at the club and I've never been interested in guys (unless they look like a woman), but I figured what's the harm in a dance and headed out to the floor with him. The dance floor was really crowded, the music was incredibly loud and thumping, there were smoke generators pumping mist all around us - it was very surreal. There were mirrors on the walls all around the dance floor and I could catch small glimpses of myself and the guy who was leading me to the center of the floor. He was tall (same height as me in my heels), wearing jeans and a plain white button down shirt. When I saw our reflection we looked like just another couple getting ready to dance.
At first we just danced around each other but then he started to move in closer to me - turning me around and placing his hands on my hips. I was a bit weirded out by that but just kept dancing. The he moved in really close and started grinding himself against my ass. Again, a bit strange - but I had a few drinks in me and was kind of getting into it, so I started grinding my ass into his crotch. It wasn't long until I could feel a distinct bulge in his pants and, as much as I hate to admit it, it was kind of a turn on to know I could get a guy hot and bothered while I was dressed up. Then I figured I'd have a bit more fun so I spun around to face him, stared into his eyes and crouched slowly down to my knees while running my hands down his chest and stomach and finally giving a little squeeze on the bulge that was highly evident in the front of his pants. As I rose up again he gave me a huge smile, put his hands on my hips again and spun me around once more and started grinding his crotch into my ass in earnest. He was actually dry humping my ass so hard on the dance floor he almost knocked me over.
Then he started getting a bit bold - his hands moved from my waist down to my outer thighs and he slid one of them up over my stocking top under my skirt and started to grab my ass. With his hand firmly on my ass under my skirt he pulled me close and started to grind again against my front. Again, I'm not sure if it was the booze or the surreal surroundings but I let him continue and even wrapped my arms around his neck - staring into his eyes while he continued to fondle my ass under my skirt. By now he'd positioned me so that his leg was between my legs. His hand alternated between grabbing my ass and running up and down my stocking top and sometimes tugging lightly on one of my garter straps. I have to admit I was kind of enjoying the attention - playing the role and letting him try and seduce me. It was incredibly erotic for some reason. Soon he became a bit bolder and started moving his hand slowly around so that he started cupping me through my panties. I let him do it - and I was getting turned on too - I felt a twitch and then another as I started to get hard. I was just glad that my skirt flared out and would cover me. The music finally changed and I figured I'd better disengage myself from what was happening or I might just regret what was happening in the morning.
I made my way over to the bar and with a flush on my face I ordered a cold beer and plopped my thong-covered butt down on the nearest available bar stool. As I sat sipping my beer I crossed my legs, looked up at the mirror behind the bar and noticed my recent dance partner was standing behind me signaling the bartender. Not wanting to appear unfriendly I offered to buy him a drink (unladylike, but guy habits can die hard I guess). We chatted for awhile, me sitting with him standing next to me until the bar stool next to me became vacant and he quickly snagged it for himself.
We chatted for quite some time - facing each other and often leaning in close to each other to be heard over the music. He seemed to have lost the aggressiveness he'd shown on the dance floor before but I could tell he was still flirting with me. Finally he must have had enough liquid courage because during a lull in the conversation he slyly slipped a hand on the top of my crossed legs and let it rest lightly there. Much to my own surprise I didn't push him away. I guess I was still feeling a bit saucy and enjoying playing the role of seductress so we continued to drink and talk while he slowly started caressing my stocking covered leg - working his hand up and down the top of my thigh, reaching a bit higher with each slow stroke until he was touching me under my skirt and above the top of my stocking top. I don't know at what point I made the decision, and I'm not even sure if it was a conscious one or not, but it was then that I knew I was going to let him have me. I was nervous ' I'd never been with a man before and wasn't sure how I'd react when the big moment came, but I just felt a sense of inevitability about the whole thing (I'm sure the alcohol haze must have helped too).
We talked a bit more and as a slow song started playing my mystery man asked me if I'd like to dance again. I smiled, nodded "yes", and let him lead me by the hand like some schoolgirl out to the dance floor again. I let him pull me in close, my arms going up around his neck and his arms going around my waist with his hands resting at the small of my back. We started moving slowly together to the music and again I looked up at the mirror on the wall and saw what looked like just another couple dancing together slowly. I could smell his aftershave and feel the warmth of his cheek against mine. As we moved to the music his hands moved from the small of my back and he alternated between running a hand up and down my back to gently caressing my ass. Again I was glad that my skirt had pleats because my thong was doing a poor job of containing the hard-on I was getting while we danced. Finally the song ended and as I started to pull away he tightened his grip around me, pulled me close and kissed me. My first instinct was to pull away but after a flash of resistance I quickly started kissing him back. When he pulled away I started to laugh because my lipstick was all over his lips. At first he looked puzzled about my reaction but when I pointed to his mouth he quickly understood and started laughing too.
After wiping his mouth off with a tissue from my purse I started to move back toward the bar. But my new friend had other ideas. He took my hand with a knowing smile and started leading me toward the door. I froze for a moment - this was the moment of truth. Was I actually going to let this guy fuck me? With my heart pounding under my bra covered chest I started walking toward the door with him.
The night air was cool and I always enjoy the feel of a breeze blowing around my legs and under my skirt when I'm out en femme. Since I was a bit tipsy I asked him if he was going to drive. He gave me a devilish look and told me not to worry as he lead me over to a large SUV parked near the back of the bar's parking lot. The parking lot was virtually empty and is not very well lit. I noticed that this particular section was almost completely in shadow. As I moved toward the passenger door he continued to pull me around to the front of the SUV - next to a fence and even deeper in shadow - and proceeded to start kissing me again.
Our tongues met and his hands were everywhere while we necked and groped in the dark. As we made out in the shadows he whispered to me how much he wanted me. At this point I was just about ready for anything so I dropped down to my knees and quickly unzipped his pants. His cock was larger than mine and hard as a rock. I wrapped my fingers around the shaft and started to gently stroke him. He moaned with pleasure and leaned back against the SUV and I worked him up and down. After a few strokes I leaned in and slid my mouth down the head of his cock and started sucking on him, using my spit to lube my hand as I continued to slide my fingers up and down. Now, I've never sucked a cock before in my life, but I know what I like when it's being done to me so I just went from memory and continued to work his tool with my mouth and hand. I guess I was doing an O-K job since he was leaning there with his hands on my shoulders and his head back groaning softly. I felt him start to stiffen up even more and figured I was about to get my first shot of cum when he pushed me back and told me to wait for a second. He pulled a set of keys out of his pocket and unlocked the SUV with a loud beep. I stood back up, unconsciously smoothing my skirt down and straightening my jacket as he reached inside the cab of his vehicle and pulled something out of the glove box. When he closed the door I saw what he had in his hand - a condom and a small bottle of lubricant. Here it was - the moment of truth! Somehow I never figured I would get my cherry popped in some dimly lit parking lot - but then I've never really been a romantic and the whole exhibitionist thing was kind of turning me on. He moved behind me and I could hear the wrapper from condom being torn open. After a few seconds he pushed me toward the hood of the SUV and with a hand on my shoulder he had me lean over and place my hands on the hood of the vehicle. Bent over with my legs spread I felt him push my skirt up and pull my thong to the side. Then, balanced against his truck in my high heeled boots I felt him start to push his hard cock into my ass.
I'd expected it to hurt but there was no pain at all - only a feeling of warmth and fullness. He moved slowly at first, and then with his hands on my hips he started to stroke a bit faster. The sensations were intense and amazingly erotic. I could feel every inch of his cock as he slid it in and out of my no longer virgin hole, the tight pull of my garter straps across my ass as I continued to bend over, and the cool breeze on my thighs, legs and balls. It was incredible. I was hard again and as he continued to push his tool deep into my ass. I reached down with one hand and started to stroke my own cock. It felt amazingly good and I started quietly moaning, "Oh baby, fuck me...fuck me harder." I tried to pace myself but the excitement was too much and I came hard and quick with a force that almost buckled my knees shooting my load on the front bumper of his ride. When I came I cried out with a low moan of ecstasy. This must have been too much for my new friend since I felt his cock get even harder and he suddenly stiffened up, pulled my ass hard against him and I felt his cock pulse inside me as he came.
Still bent over with my legs spread I felt his cock softened quickly and he pulled out of my well-lubed ass. I turned around, adjusted my clothes and watched my new friend pull the condom off his withering prick and tuck his cock back into his pants. We both stood there in the shadows for a moment, smiling stupidly at each other, each feeling awkward because we both got what we wanted and it was now done. Not knowing what to do next, I leaned over and gave him a small kiss on the cheek and thanked him. He gave me a goofy smile and returned the thanks.
We walked back into the bar as the bouncer and several patrons gave knowing looks - maybe it was the disheveled appearance of my clothes or the self-conscious smiles on our faces but more than a few people at the club could guess that I'd just been banged in the parking lot. We parted ways at the dance floor. I wandered back to the ladies room where I fixed my makeup and make sure there weren?t any jism stains on my skirt. I spent the rest of the evening chatting with the other CDs and occasionally dancing. Later I saw my new friend on the dance floor with another crossdresser, his arms around her. I'd already been replaced. Fucked and forgotten.
As I drove home alone I stopped to fill my car up with gas. The wind once again swirled around my stocking covered legs, up my skirt, and around my slightly sore ass. And as I stood there in my high heeled boots I marveled at the fact that I'd just let a complete stranger bend me over the hood of his truck, push my skirt up around my waist and fuck me. Somehow, I knew it wouldn't be the last time.