A Couple for Coupling

I know what you’re going to say — not another Halloween crossdressing story. But Halloween is an opportunistic time for those of us who like to garb ourselves in the accoutrements of the opposite sex. For many crossdressers it’s like a national holiday! Anyway, I thought it might be time for me to share another adventure in crossdressing. It happened in 2009 and to this day it is one of my favorite erotic memories.

I should begin by saying that I’m a rather typical example of the crossdressing guy — tall, slim, and professional with nothing that might indicate that I enjoy occasionally donning a dress and heels for a bit of fun and excitement. I have been attracted to women’s clothing for as long as I can remember. I don’t know why, but the attraction has always been there. Perhaps it has something to do with my older sister and her friends playing “dress up” with me. Maybe something else. But whatever the root causes, a fascination and desire to occasionally dress as a woman has always been with me.

My explorations into crossdressing were rather limited when I was younger. Growing up in a small conservative Midwestern town didn’t offer many opportunities to learn about or indulge in my interests. 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. On that night I traveled to Chicago and was “transformed” by a professional drag performer. His skilled application of makeup, hair extension, along with a bit of padding gave me the appearance of a beautiful young woman. The sensations and feelings of that night were exhilarating. Unfortunately, that first wonderful experience of crossdressing was the last time I would get to explore my interests for almost two decades. Shortly after that evening in Chicago I met a woman, got married, moved to a new state, and began a career in a high-profile profession. These life events left little time for indulging my penchant for skirts and heels. My wife was not amenable to the idea. Possible discovery of my interest in crossdressing could jeopardize my career. So, like many crossdressers, I purged my wardrobe and buried my desires. During that time, I would dabble in crossdressing occasionally, usually on Halloween when it was easier to explain or an infrequent weekend when my wife was away. But for the most part I considered that part of my life to be done and over with.

Eventually my wife and I divorced, I changed careers, and moved to Chicago. All of these changes gave me more freedom to explore and experience my long-subdued desires for crossdressing. Almost 20 years had passed since that first wonderful experience of going out in public in a dress and heels.

To make up for all that lost time I dove into my interest with a passion, exploring the internet and connecting with others who shared my attractions. I was single with no attachments and my career had shifted, allowing me more free time and money. Over time, I found several transformation services including the legendary Jamie Austin. I flew to Boston and joined the ranks of Jamie Austin’s angels. Under his skilled ministrations the attractive crossdresser so long buried in me was reborn.

I continued my exploration, learning how to do my own makeup. I built up a respectable wardrobe and collection of wigs. As I got more comfortable with my skills, I developed a “style” and started going out to some Chicago area TG friendly bars and clubs where I met many wonderful people who, like me, enjoyed donning the clothing of the opposite sex. Eventually, the fear of discovery became less, replaced with the rush of experiencing the feel of heels and hose and makeup while being out in public. I still had a busy “normal” life with my full-time job and additional consulting jobs. I still socialized with my friends and family, none of whom had any idea that I liked to get dolled up short skirts and heels. I still dated desirable and charming women. My life was busy, but every few months I would feel the desire to don a dress and go out for an evening.

I’m pretty much only attracted to women. However, as I explored my interest in crossdressing, I found myself occasionally enjoying the company of men. Something about being dressed as a woman and immersing myself in the role seemed to make crossing that line not only acceptable, but in some ways desirable.

The first time I had sex with a man was really nothing more than a drunken tryst in a dark parking lot. A few too many cocktails at a local TG friendly bar, a few hot dances with a persistent admirer, and before I knew it, I found myself out in the parking lot bent over the hood of an SUV with my skirt pushed up, panties pushed aside, legs spread wide, and a cock stroking in and out of my virgin ass. Much to my amazement I found I enjoyed the experience.

The next time was a bit more deliberate. I had enjoyed innovia escort my first time letting a man have his way with me while I was dressed in a skirt and heels so I wondered if I would enjoy it a second time. Curiosity led me to an ardent internet admirer who wanted a last “fling” with a crossdresser before he got married. He was flattering and charmingly tenacious in his expressed desire to have sex with me. Eventually, I relented to his requests for a meeting, and I invited him over for an evening of carnal activities. It was another enjoyable experience which opened more possibilities for me.

Then I met a woman named Rita. She was a fiery raven-haired Latina with medium brown skin, perfect 36C breasts, a tiny waist, round full hips, shapely legs, and a full set of kissable lips. Her hair was glossy black and tumbled down in great curls past her shoulders. I admired how she dressed and presented herself with perfect makeup, impeccable clothes, and often wearing 4-inch heels. We started dating and after spending some time together I began to wonder if she might be the one for me. But, before things went too far, I needed to admit my penchant for putting on a dress. I was nervous to confess to her, but she had exhibited an open mind to erotic eccentricities, confessing her occasional fondness for other women and a love of light bondage. So, I figured if anyone would be accepting of a cross-dressing guy she would be. Much to my amazement and joy she was completely cool with the concept.

We’d been dating for about a month when I owned up to my alternative wardrobe activities. After I confessed to her, she smiled slyly and asked if I had any pictures. When I showed her the rather large collection of images of myself “en femme” she was speechless. She said I looked amazing. She had expected to see “a guy in a dress” and not some tall blonde hottie. She also admitted that she was jealous of how good my legs looked. I was flattered and happily surprised at her level of acceptance. I guess her being “bi” helped. She quickly urged me to dress up for her sometime.

I didn’t wait long. A couple of weeks later I got all dolled up and we went out to a local bar — both in short skirts and heels. It was a new experience going out with a “girlfriend” while dressed and we both received some attention from the guys at the bar. I briefly considered picking up a guy that both Rita and I could “share”, but I wasn’t sure how she might react to seeing me with another man, even if I was wearing a dress. The relationship was too new, so I decided to hold the idea for later and focus on being with Rita. After leaving the bar we had a great time back at my place. The feeling of our nylon covered legs rubbing together as we fucked brought back fond memories of the first time I had sex with a woman while dressed many years before.

A year passed. Rita and I continued to date, and we rapidly became a “couple”. But the demands of everyday life seemed to leave us little time to explore any erotic adventures. We managed to visit one of the sex clubs in the city a couple times and I even helped her pick up another guy at a bar and bring him home so she could enjoy a session of double penetration. But the opportunity for me to dress and play just didn’t seem to surface.

Finally, as fall approached, we decided that I should don a dress again for Halloween. We could do a theme costume we could both enjoy. After looking online for about a week we settled on a fun little combo of cop and prisoner.

Finding an outfit for Rita was easy. She selected a tight little prisoner costume dress in bright orange with appropriate numbers stenciled on the front. It was short, coming to just below her crotch, made form fitting spandex to show her curves, and low cut to allow ample cleavage. She accessorized the outfit with a wide leather corset belt, thigh high leather boots with four-inch heels, black fishnet thigh highs, and a black lace push up bra which was clearly visible. As was often her custom, she skipped wearing panties for the evening.

My outfit was a bit more difficult to find. I looked online at many different “law enforcement” style outfits but none of them looked like they would flatter my form. Finally, I found an outfit that I thought would work. It was a khaki colored “sheriff” mini dress with short sleeves and a short, pleated bottom which rode a good seven inches above the knee. I accessorized the dress with a wide black leather belt with silver buckles, black knee-high boots with three and a half inch heels, requisite badge and patches, and of course a sturdy pair of handcuffs. For under the dress, I chose a black lace bra, black lace camisole top, matching corset with six garters, tan full fashion stockings, black satin gaff panties, and a black lacy petticoat to fill out the pleated bottom of the dress.

Halloween quickly came and we rented a hotel suite that was ipsala escort near the bar we were planning on visiting. It was a nice set of rooms consisting of a small kitchen area, living area with couch, chairs, and a fireplace. It had a large bathroom and a spacious separate bedroom with two queen beds. We quickly settled in, stocked the kitchen with some drinks and snacks, and started to get ready.

Rita’s preparations were done in a short amount of time. She had a natural beauty so a bit of makeup, fluffing the hair, and donning her outfit was done with relative speed. That left her time to help me with my preparations.

My transformation from “average dude” to attractive crossdresser has always been a bit more time consuming. It takes full two hours to shave everything (and I mean everything), apply makeup, don the blonde wig, and get dressed. Rita helped lace me into my black corset, assisted with my chest tape to make convincing cleavage, and with snapping the garters onto stockings at the back of my thighs. Next, I pulled the satin gaff panty on and tucked my cock back between my legs before pulling it all the way on. One of the first lessons I learned is that the panties go on last over the garters. There’s nothing worse than having to unsnap all your garters to get your panties off — especially if you’re in a hurry to fuck.

For me, the dressing process has a strong sensual aspect. The smell of the makeup, the feel of the clothing, and most of all the sensation of sliding silky stockings up my freshly shaven legs is an incredible turn on. I can’t really say why, it’s just an amazing feeling that I never tire of.

The rest of my outfit went on quickly — bra with breast forms, lacy camisole, petticoat, and dress all slid into place with ease. The final step was pressing on the press on nails with a French manicure look.

Once I was fully dressed, I pulled on my high heeled boots, tossed a few things into my small shoulder purse, and we were ready to go. But before we headed out, I naturally wanted a few pictures. Like many of my cross-dressing counterparts, I’m a bit of a camera whore. I love posing for pictures while dressed, so Rita snapped a dozen shots of me on the bed and standing in front of the door. Then I popped the camera into my purse, and we headed out to the club.

The bar we were going to was called Hunters. It was in the western suburbs of Chicago and was a well-known gathering place for gay, straight, and transgender alike. This was especially true on Halloween when it became a mixing pot for everyone and everything. I had been frequenting the establishment for years, mostly in a dress but occasionally in straight attire.

When we arrived the parking lot was full, but we managed to find a place to park near the back. As we exited the car and started to head inside, I snuck a furtive glance toward the dimly lit back of the parking lot, remembering fondly, and with some chagrin, how not that long ago in this same parking lot I had let a perfect stranger bend me over the hood of his SUV, push my skirt up around my waist, and pound his meat up my ass. I’d never told Rita about that little adventure and had decided to keep that gem of a memory just for me. Focusing once again, I straightened my dress, and we headed inside the bar.

As expected, the bar was packed with a variety of folks in all kinds of costumes. There were plenty of transgender folks and a good mix of gay and straight. The costumes were a smorgasbord for the visual senses and covered everything from complex lighted costumes to funny outfits to slutty attire. It was entertaining and fun to look at.

Rita and I waded into the crowd and quickly made our way to the bar. We were lucky and found two unoccupied seats and ordered drinks. The music was loud, but not so loud you couldn’t converse. We marveled at the range of costumes. While we talked, I scanned the room for potential playmates for the evening. There were several attractive crossdressers in attendance, and I had a hankering to play with another like me. I had never been with another crossdresser and was curious to find out if I would enjoy it as much as encounters with men while I was dressed. As I ogled the crowd Rita downed her drink, grabbed my hand, and dragged me out to the dance floor.

Dancing in a dress is always fun. The sensations of the clothing while getting lost in the pounding rhythm of the music add to the feeling of femininity. While we danced, I could glimpse myself in the mirrors surrounding the dance floor. When I looked, I could see a tall, sexy blonde in a short khaki dress and knee-high black boots dancing with a hot little Latina in a short and tight orange dress. It was intoxicating. And there’s just something about wearing heels that makes it easy to shake your ass! Rita was getting her share of attention. She looked incredibly hot in her form fitting outfit and several times a random iskenderun escort guy would try to cut in on us or sneak a grope of her ass. But she’s well versed in fending off unwanted attention and deftly maneuvered away from superfluous suitors. We danced a few numbers and after some minor protests I finally convinced Rita that I needed another drink. She smiled and nodded, and I led her off the floor and out onto the outside patio to get some cool air and another cocktail.

The bar at the outside patio was less busy than inside and we quickly found a spot at a nearby table. Rita went up to the bar to order drinks. While she was gone, I noticed a rather tall guy dressed like a baseball player sitting at the next table who was checking me out. I was sitting facing him with my legs crossed and I realized his gaze toward my thighs where the hem of my dress had ridden up to expose my stocking top and garter. When he realized that I had caught him looking at me he quickly looked away. When he glanced back again, I gave him a sly flirty smile and recrossed my legs in a poor impersonation of Sharon Stone. I was rewarded with a smile in return. Just then Rita returned bearing a couple drinks.

As Rita and I chatted, I continued to catch Mr. Baseball looking over at me from his position behind Rita. He was with a petite Asian woman. She was pretty with a round figure but not fat. She had black straight hair down to her shoulders and was dressed in a French maid outfit with fishnets and black patent spike heels. As Rita and I conversed about random topics I furtively watched Mr. Baseball as he continued to sneak glances my way. I wasn’t sure where this was going, but I was rather intrigued at the possibilities. I decided to take things into hand, got up from the table, winked at Rita and asked her to follow me.

We walked up to Mr. Baseball and his hot little French Maid friend and all I could manage to come up with was an incredibly lame, “Have I seen you two here before?”

He looked rather taken aback but quickly recovered and said it was their first time at the bar. Rita quickly jumped in complimenting the woman on her outfit and we all started exchanging compliments all around. We introduced ourselves and they quickly followed suit — his name was Ken, and his wife was named Amy. They were both professionals, had lived in the area for several years, and had been married for about five years. Within minutes the four of us were chatting like old friends.

As the night progressed, we learned more about each other. Amy, like Rita, was bi (and they definitely seemed to be hitting it off). Ken confessed he had some bi experiences in the past and was open to almost anything. After talking for a while, Rita suggested we dance, so we all got up and headed for the dance floor.

We started out in typical couples’ fashion with me dancing with Rita and Ken dancing with Amy. Before long Rita and Amy started dancing with each other. As they danced, they began to get closer to each other, running their hands over each other and grinding into one another. It was an unbelievably hot show that they were putting on.

As the women danced with each other, Ken moved out of the way, stood awkwardly for a moment, and then he started dancing with me. He looked slightly embarrassed when he started to dance with me like he was unsure what to do. Trying to put him at ease, I leaned in close and asked him if he liked how I looked. “You look very hot!” he replied in a breathy whisper.

The girls continued to dance together, lost in their own sexual chemistry and oblivious to the rest of the world for the moment. Ken and I continued to dance together exchanging looks, smiling as we watched our women dance together, and occasionally brushing up against each other. At one point I leaned in close as though I was going to say something to him over the music. But instead, I put my face close to his neck and brushed my lips across his ear. As I did this, I felt him tense slightly and as we danced, I could see that he was getting an erection as his pants started to tent out a bit. We continued to dance, and he moved in closer. Then I felt him press his crotch against me. Slowly turning with my back to him, I wrapped his arms around my waist and arched my back to press my bottom against his crotch letting him slowly grind his stiffening cock against my ass. Feeling a flush of sexual excitement, I turned back around to face him and suggested we move to the bar for another drink.

As we sat next to each other we watched Rita and Amy continue to dance and grind with each other. I looked over at him and with a smile I said, “Looks like the girls have their evening planned. So, what do you think we should do?”

He gave me a quick smile and I felt his hand slide onto my thigh under the bar. His hand slid up my stocking covered leg and under my dress as he replied, “I think we’ll find something to do.”

I leaned in close to him, smiled back and said, “So what are we waiting for? Rita and I have a hotel room nearby. Let’s get the girls and go.”

We finished our drinks and headed out to the dance floor to get the girls. We got no argument from them. We left the bar and Rita and I piled into our car and Ken and Amy followed in theirs.

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