Jenette LaSalle · Follow
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Another story from my adventures in crossdressing. I write these mostly to keep the memories fresh and not forget the details. If you are reading it, I hope you enjoy it.
The year was 2006. I was in my late 30’s and was beginning to really explore my interest in crossdressing including going out to clubs “en femme”. What happened that night was a first for me. A line was crossed that I never imagined would happen and it opened a door on a whole new and unexplored area of experience and enjoyment.
I should probably give a bit of “origin” story, so you understand how I got here. I’m a rather typical example of a crossdressing guy — or at least I think I am. I’m tall, slim, and keep myself in good shape. I don’t work out regularly, but I watch what I eat and am blessed with a fast metabolism that makes keeping slim easier. I also work in a high-profile profession therefore discretion is very important. As a result, I kept my crossdressing activities a closely guarded secret with only a few former girlfriends knowing of my penchant for skirts and heels. To my “vanilla” friends, family, and co-workers there is nothing that might indicate that I enjoy occasionally donning a dress for a bit of fun and excitement.
I have been attracted to women’s clothing for as long as I can remember. Can’t really say why, but the attraction has always there. My experiences with crossdressing were rather limited when I was younger. Growing up in a small conservative Midwestern town there were not many opportunities to indulge my interests beyond the occasional experimentation with clothing “borrowed” from female members of my family or the occasional sister of a friend. The topic was pretty much taboo. We didn’t have the internet back then up so my only exposure to the world of crossdressing came through stories in adult magazines and books. I devoured these stories, letting them fuel my fantasies of what it might be like to dress in the clothing of the opposite sex. But when I was 19 years old, I was fortunate to meet someone who helped me experience what it was like to dress fully as a woman and go out publicly for a night of fun. For me it was a dream come true (and another story).
Unfortunately, that first amazing experience of crossdressing in public was the last time I would get to fully explore my interests for almost two decades. Shortly after the events of that night I met a woman, got married, moved to a new state, and began a career. Those life events left little time or opportunity for indulging my penchant for skirts and heels.
Eventually my wife and I divorced, I changed careers, and moved from a small town to Chicago. I was new to the city with no friends or family nearby. I was single and not dating. As a result, there was no need to hide my expanding alternative wardrobe or explain my lack of body hair. All this combined to give me more freedom to explore and experience my long-subdued desires for crossdressing. Almost 20 years had passed since that first delightful experience of going out in public in a dress and heels. Now, for the first time, I found that I not only had the freedom, but the time and resources to explore my interest in crossdressing.
To make up for all that lost time I dove into my interest with a passion. I scoured the internet looking for articles, videos, and images. I purchased different outfits, both in stores and online, all with a critical eye towards women’s styles that would give me the most feminine look for my build. And I joined several online TG social sites including Flickr, URNotAlone, Adult Friend Finder and others where I could connect with people who shared my interests including other crossdressers and occasionally a few male fans.
I continued my exploration, discovering and then taking advantage of “transformation” services such as Jamie Austin’s “Angles”. I studied and learned how to do my own makeup and built up a sizable wardrobe and collection of wigs. As I got more comfortable with my skills, I developed a “style” and started going out to some TG-friendly bars and clubs where I met many wonderful people who, like me, enjoyed donning the clothing of the opposite sex.
I remember the first evening I ventured out during this time was in the spring of 2004. I was terrified and exhilarated all at the same time. I had read about a TG friendly club online and decided to try my luck. I dressed in a short tan suede mini skirt and black silk blouse with shiny tan pantyhose and three-inch black pumps. Underneath I wore a waist cincher, bra with breast inserts, and a gaff thong. I had done my makeup with smokey dark eyes and dark pink lipstick. My face was framed by a shoulder length blonde wig.
I was nervous when the bouncer checked my clearly male ID to enter the club, but he didn’t pay any attention as he waved me in. It was early in the evening, just after dark, so the club was rather sparsely populated. I sauntered up to the bar, took a seat on a stool, crossed my legs, and ordered a drink from the bartender. My heart was pounding in my chest as I sat there. Then I realized that no one was paying any attention to me. No pointing, no ridicule, no stares. I started to relax and realized that it was all ok. I only stayed for one drink, sipping it slowing and reveling in the sensations of being out en femme. As I looked around the club, occasionally glancing down to admire my nylon covered legs and heels, I noticed the song playing on the video system of the club, Christina Aguilera’s “Beautiful”. It made me smile. After my drink I headed back home, giddy with my small triumph of venturing out in a skirt and heels. I even stopped to fill my gas take, reveling in the feel of the breeze on my nylon covered legs. Eventually, the fear of discovery became less as I continued to venture out, replaced with the rush of experiencing the feel of heels and hose and makeup while being out in public.
It was fall of 2006 and I had decided to get dolled up on a Saturday night and go out to a TG-friendly bar. Work had been busy for me over the previous months leaving little time to indulge my interests and I felt it was long overdue for some fun. The bar, called “Hunters”, was in the western suburbs of Chicago. It was an accepting establishment for the crossdressing crowd, and I became a semi-regular at the establishment.
Naturally, I dressed for the occasion. My preparations consisted of soaking in a warm scented bath followed by a close shave everywhere south of my eyebrows. My ensemble was carefully chosen. It consisted of a short black lacy layered skirt that flared slightly giving the illusion of larger hips, a cream-colored corset top with black lace trim that helped give the illusion of narrowing my waist, and a black velvet jacket to de-emphasize my wide shoulders. Knee-high black boots with four-inch heels made me taller while making my legs and ass look shapelier. Underneath I had a black corset to narrow my waist, black bra with C cup breast forms, black satin “gaff” thong panties and shimmery sand-colored stockings held up by garter straps from the corset. I also had silver hoop clip earrings, a cute little silver necklace, bangle bracelets, and my favorite medium length blonde wig. My makeup, as always, was done up to perfection with dark smokey eyes, long fake eyelashes, flawless foundation, blush, and lipstick in shades of pink.
The process of getting dressed up for a night out is not an easy one. There’s a lot of shaving, plucking, taping things into place, tucking things away, adding padding to some places and cinching things down in other places. For me, it takes about two hours to make the transformation. When it’s complete it’s a total mind f*ck how different I look. Even after years of doing it I’m still amazed at the change in appearance.
There’s also another aspect of crossdressing that I enjoy. That’s the sensations of wearing the clothing of the opposite sex. Guys are pretty much restricted to the same old things — pants and shirts of mostly loose cotton, wool, or some blend. But dressing as a woman opens a whole new group of sensations including silks, satins, and my favorite, the feel of stockings and pantyhose. There’s something sensuous about sliding a new pair of hose onto freshly shaved legs and slipping into a pair of heels.
Once I was dressed, I did a final once over in the mirror, stopped to take a few selfies (I’m a total camera whor* when dressed up), tossed keys, wallet, and lipstick into a purse, and got into my car to drive to the bar.
When I got to Hunters the parking lot was crowded, but I managed to find a parking space toward the back. Walking in the cool fall air and feeling the breeze play across my stocking covered legs and up my skirt was exhilarating.
As I walked across the lot listening to the click of my heels, a rather beat up old car pulled slowly up next to me, and the window rolled down. Sitting in the car was a man who looked me up and down and then asked me if I wanted to “fool around”. Looking into the shadowy depths of his car I could see he was rather scruffy looking with a shock of wild dark curly hair. He had a scraggly patchy beard, pale skin, and dark circles under his squinty eyes. The smell of stale beer and pot smoke wafted up from the open window of the car. Nothing creepy at all about this guy. I smiled politely, declined his charming invitation, and headed into the club.
When I got inside the place was already packed. About a quarter of the people there were crossdressers or transgender. I headed over to the bar and to my surprise found a seat right away. I ordered a co*cktail and started watching the crowd. I was looking for a crossdressing friend of mine who I had met online. During one of our chats, she had mentioned that she might be at Hunter’s that evening and we could meet up. During our online discourses we had flirted a bit and indicated a mutual interest.
I had never been with another crossdresser before, and the thought of a possible rendezvous was intriguing. In the pictures we had shared online she looked to be a great beauty — always presenting with long raven locks, tall and slender, with a penchant for classic lingerie including full fashion stockings and corsets. I was hopeful that the night would lead to a new erotic experience with her.
As I waited, sitting next to me on either side were some other crossdressers. We all immediately started chatting and complimenting each other on shoes, outfits, makeup, and overall look. It’s amazing what having something in common with others can do to draw people out and put them at ease. We didn’t know each other, but because of our shared yet slightly taboo interest we were all chatting like old friends within minutes.
After about half an hour my friend from online showed up. She was dressed in a gorgeous black pencil skirt which came down to just above her knees, a wide black leather belt around her waist, and a dark green satin blouse. The blouse was unbuttoned at the top and brief glimpses of a black lacy bra peaked out of the opening. She had black leather pumps with 4-inch stiletto heels and black seamed stockings. Her hair, which I can only assume was a wig, was dark and came down in a cascade of curls past her shoulders. Her makeup was impeccable, and she was adorned with gold-colored rings, necklace, and dangly earrings. She looked like she was going for a Bettie Page vibe. She was succeeding wonderfully.
We moved into a quieter room of the bar, found a couple of unoccupied chairs near the wall. We had chatted online, but there’s nothing like a face-to-face conversation to get to know someone. As we sat, we shared stories about our lives and experiences.
She explained that she was married to a woman who did not approve of her penchant for crossdressing. However, they had worked out a sort of “don’t ask, don’t tell” agreement. She said it made for occasionally uncomfortable talks but the arrangement seemed to be working for them. I shared stories about my first time dressing in public many years before and my more recent journey of discovery since moving to Chicago.
As we chatted, our stocking covered legs kept brushing against each other and I could see the bump of garter straps outlined under her skirt. I was getting rather turned on at the prospect of some playtime with her. As we talked I started to think that there might be some chemistry between us and I was excited at the possibilities of what might happen.
More might have developed between us, but unfortunately, it was not to be. She explained that she had come to the bar with some other friends, and they were eager to leave. She didn’t feel right abandoning them so she apologized for the shortness of our time together and promised that we could meet up again soon. Naturally I was disappointed, but it was still early, and I was open to whatever the evening might bring my way. I ventured out to find more people to chat with.
I wandered around the various rooms and outside patio of the bar for a time. After ordering another drink, I found a seat near the juke box and took in the scene watching people dance on the dance floor and admiring the variety of people in the club. While sitting there, a rather aggressive guy with an unrecognizable foreign accent tried to chat me up and started pawing at me. He seemed to be under the impression that because I was wearing a skirt and heels he could get grabby with me. I forcefully removed his hand from my leg and told him to get lost. Later, I played a game of pool with a couple of guys who fell into the “chaser” group. These were guys who identified as straight but were still interested in connecting with, or “chasing”, crossdressers or transgenders for sex. I’d encountered more than a few online and there was always a healthy amount of these guys at the club looking to score with some hot crossdresser. I noticed many of them wore wedding rings — if only their wives knew what their hubbies were really into.
After a while I got asked to dance by another crossdresser and headed out onto the floor. She was cute, wearing black leggings and an animal print top, but not really my type. After dancing to a couple songs, I excused myself and headed outside to the patio area to cool off, and then back to the bar for another drink.
Most of the night proceeded that way. At one point I headed into the restroom and found a lot of women, transgenders, and crossdressers in there all chatting away. The restrooms at Hunters were always entertaining as a wide range of genders would frequent both the men’s and women’s rooms. It was not an uncommon sight to walk into the men’s restroom and see someone standing at the urinal in heels with their dress hiked up to relieve themselves.
While exiting the restroom a rather attractive woman 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. Leaving the restroom I returned to the bar, ordered another drink, and found a seat near the edge of the dance floor so I could watch the crowd move and sway to the heavy beat of the music.
While I was sitting, a guy approached out of the crowd from the bar area, stopped in front of me, and asked me to dance. I figured him for another “chaser” hoping to get lucky. I’d never been interested in guys unless they look like a hot woman. Sure, I’d flirted a bit with some admirers online, but this was something different. I considered his invitation for a moment and figured what’s the harm in a dance. I smiled, nodded ascent, and set my drink down on the table next to me. Then, my new paramour took my hand and started leading me out to the dance floor.
The dance space was really crowded, the music was incredibly loud and thumping, there were smoke generators pumping mist all around giving the space a surreal feel. Mirrors on the walls around the dance floor allowed me to catch small glimpses of myself and the guy who was leading me to the center of the floor. He was tall, about the same height as me in my heels, wearing jeans, a plain white button-down shirt, and black cowboy boots. He had short dark hair and was heavily built. Not fat, just stocky like someone who does a lot of physical labor. When I saw our reflection, we looked like just another couple getting ready to dance.
At first, we just moved to the beat dancing around each other. I’m usually not much of a dancer, but when I’m wearing a skirt and heels it just feels right. I was enjoying the sensations of the thumping music and the feel of my body moving to the rhythm. As we danced, I could catch glimpses of myself in the mirrors around the edge of the dance floor — a tall, beautiful blonde in a short skirt and high heeled boots dancing with a tall guy.
As the music continued my new dance partner started to move in closer to me. To be honest, I was absorbed in the rhythm of the music and the sensations of dancing in a skirt and heels and really hadn’t been paying much attention to him. I was surprised to feel someone take my hand and quickly realized it was my new dance partner. Holding my hand, he slowly turned me in a lazy half pirouette, so I was facing away with my back to him as we danced. Then, he reached out and took my other hand, effectively crossing my arms in front of me, pulling me closer as we continued to move with the music. I was a bit weirded out by our new position but decided to go with it and just kept dancing. Then he pressed in even closer until my back was against his chest. A few beats later and I felt him start 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 lightly grinding my ass back into his crotch. It wasn’t long until I could feel something poking me through the layers of my skirt. I realized that he was getting turned on.
I’ll admit, it was intriguing in a sexy sort of way. Knowing that I could get a guy hot and bothered while I was dressed up was something different for me. Of course, I had interacted with men online who commented on my photos. They had told me how beautiful and sexy I was, sometimes adding colorful descriptions of what they wanted to do with me if we ever met. I had even exchanged emails and chats with a few online admirers playing the role of seductress, describing what sexual encounters would be like if we ever got together. It was all done as a fun fantasy with never a thought that it would come true. Those text-based encounters were sexy in an abstract sort of way, like reading a story online, but now, on the dance floor with my new admirer, this felt very intimate. Much to my astonishment, I found I was enjoying it, so I figured I’d have a bit more fun.
As we continued to dance, I let go of his hands and spun around to face him. I stared into his eyes for a second and, while continuing to move with the music, crouched slowly down while running my hands down his chest and stomach. Keeping our eyes locked in a gaze, I made sure to run my hand across the front of his pants down the bulge that was highly evident. As I rose from my crouch, he gave me a huge smile, put his hands on my hips and spun me around once more. Pulling me back against himself again he started grinding into my ass in earnest. He was dry humping me so hard on the dance floor he almost knocked me over.
Then my new paramour started getting even bolder. He spun me around once again so I was facing him, pulled me in close, then moved his hands from my waist down to my outer thighs. As we continued to move with the music, I felt him slide one hand up under my skirt letting it rest on my thong covered ass. With his hand firmly on my ass under my skirt he pulled me closer and started to grind again against my front.
I’m not sure if it was the booze or the surreal surroundings but I let him continue. I was enjoying our game of seduction, so I wrapped my arms around his neck and stared 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. As we danced his hand alternated between grabbing my ass and running up and down garter strap holding up my stocking. I was enjoying his efforts at seducing me.
We continued to dance and he became a bit bolder, moving his hand slowly around so that he was cupping me through my panties. Again, I let him do it. To my surprise I realized I was getting turned on by his manipulations. I felt my co*ck twitch once and then again as he palmed me though the fabric of my panties. My gaff was doing a poor job of holding back my growing erection so I was 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. If I didn’t, I might regret it in the morning. My head was a mess of conflicting thoughts and the booze had lowered my inhibitions. So, when the song ended, I smiled at him, thanked him for the dance, and left the dance floor.
I made my way over to the bar and, with a flush on my face, ordered another co*cktail, settling down on the nearest available bar stool. As I sat sipping my drink, I adjusted my skirt and crossed my legs. Looking up at the mirror behind the bar I noticed my affectionate 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 a while, me sitting and him standing next to me. When the bar stool next to me became vacant he quickly snagged it for himself and sat down.
We continued talking for a short time, facing each other, often leaning in close to be heard over the music. He seemed to have lost the aggressiveness he had shown on the dance floor, 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. I didn’t push him away. I guess I was still feeling a bit saucy and enjoying playing the role of seductress.
We continued to drink and talk while he slowly caressed 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. 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 there was just a sense of inevitability about the whole thing. I’d like to blame it on the alcohol, but to be honest, I was curious and wanted to see what it might be like.
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 tilted my head down slightly, looked up at him with flirty eyes, smiled, and nodded “yes”. Then I let him lead me by the hand like some schoolgirl out to the dance floor again.
As he pulled me in close, my arms went up around his neck and his arms circled my waist with his hands resting at the small of my back. We started moving slowly together to the music. 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 warmness of his body. As we moved to the music, his hands moved down 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 layers because I could feel the gaff straining against my twitching erection.
When the song ended, I started to pull away. But my new paramour tightened his grip around me and pulled me close. Then he kissed me.
My first instinct was to pull away, but after a flash of resistance I quickly started kissing him back. I was really living my role now with a sense of submissiveness I had not experienced before.
It wasn’t a long kiss, but it was long enough. Not a deep French kiss. Just a lingering touch of our lips as he held me. I moved my lips slowly and put my arms around him again. We held that position for a few suspended seconds. When we separated, I let the tip of my tongue give a small flick across his top lip. For the briefest of moments, all sound and sights faded into the background as we shared our “moment”.
I felt flushed as I drew back, my arms still around him and his arms still around my waist. When I looked at him, 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.
As we moved off the dance floor, I offered him a tissue from my purse to wipe the lipstick off his mouth. I started to move 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 going to let this guy f*ck me? With my heart pounding under my bra covered chest I started walking toward the door with him.
As we walked out of the bar and into the parking lot the cool night air was refreshing after the stifling atmosphere of the club interior. I always enjoyed the feel of a breeze blowing around my legs and under my skirt when 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.
My new friend, still holding my hand, led me through several rows of parked vehicles toward the rear parking lot of the bar. The lot was filled with cars, but no people were about. It was very dark with few lights reaching this far back into the area. The sounds of the city at night were jumbled together like white noise. Traffic from the highway, aircraft from nearby O’Hare, and the muffled thumping of music from inside the club all blended into a background urban elegy. As we walked, I noticed that this section of the parking lot was almost completely in shadow.
We arrived at what I assumed was his vehicle, a large black SUV parked next to the outer fence of the parking lot. As I moved toward the passenger door, he continued to pull me around to the front of the SUV, next to the fence and even deeper in shadow. Then he started to kiss 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 crouched down and unzipped his pants.
His co*ck wasn’t large, maybe five inches and thin, but it was hard as a rock. My fingers seemed to move of their own volition, wrapping around his shaft and stroking him gently. He moaned with pleasure and leaned back against the front of the SUV as I worked him up and down. After a few strokes I leaned in and slid my mouth down the head of his co*ck 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 co*ck 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 back against his SUV with his hands on my shoulders and his head back groaning softly. I felt him start to stiffen up and figured I was about to get my first shot of cum when he pushed me back slowly and told me to wait for a second. He pulled a set of keys out of his pocket and unlocked the SUV with a flash of parking lights and a loud beep.
I stood back up, unconsciously smoothing my skirt down and straightening my jacket. As I watched I saw him open the passenger side door of the vehicle. In the dome light of the SUV, I saw him reach inside the cab and pull something out of the glove box. When he closed the door, I saw he had a condom and a small bottle of lubricant. I guess he was prepared. Probably not his first rodeo.
Here it was, the moment of truth. Somehow, I never figured I would get my cherry popped in some dimly lit parking lot, but you go with the opportunities you have. Besides, the exhibitionist thing was kind of turning me on.
He came back to the front of the SUV and turned me so that I was facing away from him. I could hear the wrapper from condom being torn open. After a few seconds he pushed gently 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 over my waist tucking the hem into the waistband. I was starting to think this guy might be more experienced than he let on. Next, I felt him pull my thong to the side. Then, balanced against his truck in my high heeled boots, I felt him slather lube on my ass. It was cool in the evening breeze, but the sensation soon passed as he slid two fingers into my ass.
I gasped with a sharp intake of breath as he stroked his digits inside me. I let a low moan escape my lips and felt my satin covered co*ck twitch and start to stiffen. After a few seconds he removed his fingers, and I heard him unzip his pants. I turned my head to look behind me, but hair from my long blonde wig hung down and blocked most of the view. The only thing I saw was the condom wrapper land on the ground. Then I felt my new paramour move behind me and start to push his hard co*ck into my ass.
There was a very brief flash of pain, but it quickly passed as he slowly slid his co*ck into my virgin ass. The pain shifted to a feeling of warmth and fullness. He moved slowly at first, sliding his co*ck inside me with a slow and steady motion. Then, with his hands grabbing my hips, he started to stroke in and out. The sensations were intense and erotic. Sort of a subtle feeling of being stretched or filled. I could feel every inch of his co*ck as he slid it in and out of my no longer virgin hole. I took in all the sensations. I saw the top of my head bobbing in time to his thrusts reflected in the windshield off the SUV, heard the sticky soft slap of his hips against my ass, felt the cool breeze on my exposed thighs, legs, and balls. It was incredible.
I was rock hard now. As he continued to bury his tool deep into my ass, I reached down with one hand and pulled my co*ck out from its restraining thong. Stroking myself in synch with his thrusts, I quietly moaned in a low breathy voice, “Oh baby, f*ck me…f*ck me.”
I tried to pace myself, but the excitement was too much. Within a dozen strokes my org*sm hit hard with a force that almost buckled my knees, shooting my load on the front bumper of his ride. As I came, I gave a shudder and a low moan of ecstasy. This must have been too much for my new friend. He quickened his pace. Then, still holding tightly to my hips, he grunted and pulled my ass hard against himself. I felt his co*ck throb as he came inside me.
We stayed in that position for a few seconds, each catching our breath and recovering from our org*sms. Still bent over with my legs spread, I felt his co*ck 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 co*ck 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. It had only taken a few minutes 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 across the parking lot in silence. I noticed that my new friend didn’t try to hold my hand anymore.
As we entered the bar 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 restroom where I fixed my makeup, cleaned the lube from my ass, and made sure there weren’t any cum stains on my skirt. I made a mental note to buy some leather miniskirts because I remembered someone telling me cum stains don’t show up on leather.
I went back out to the bar area and spent a bit more time chatting with the other crossdressers. Later I saw the man I had just let f*ck me out on the dance floor with another crossdresser, his arms around her. I’d already been replaced. Used and forgotten.
That night had turned out very differently than I had anticipated. I had gone to the bar looking to meet and possibly hook up with another crossdresser. Instead, I let a stranger bend me over the hood of his SUV and f*ck me.
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 the garish light of the gas station, I looked at my reflection in the window of my car. I was smiling. Somehow, I knew it wouldn’t be my last time letting a man f*ck me.
