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 2014. I was in my late 40s and continuing to explore my interest in crossdressing. I’ve always figured I’m a typical crossdressing guy — tall, slim, and professional, with nothing outwardly indicating my enjoyment of occasionally donning a dress and heels. My attraction to women’s clothing has been lifelong. I’ve been told that I look rather attractive when all dolled up. I’m not sure I was ever completely passable, but there have been many compliments on my appearance when dressed. I was even offered a job as a crossdressing escort once. Flattering in a strange sort of way, but not a career choice I’d want to pursue.
Growing up in a conservative Midwestern town limited my crossdressing explorations. But when I was 19, I met someone who helped me fully dress as a woman for a night out in Chicago. A professional drag performer transformed me into what appeared to be a beautiful young woman, making it an exhilarating experience. However, life events, including marriage and a high-profile career, led me to suppress my crossdressing desires for nearly two decades.
After divorcing, changing careers, and moving back to the Chicago-land area, I had the freedom to explore my long-subdued interest. Despite a busy “normal” life with a full-time job, friends, family, and dating women, I would occasionally indulge my desires to dress up and go out.
I consider myself to be heterosexual, but when fully dressed “en femme,” I really like to immerse myself in the role and am open to the potential of erotic encounters with men. I’m not sure if that’s unusual; it’s just something that evolved over time with me. The first time I had sex with a man while crossdressed was really nothing more than a drunken tryst in a dark parking lot. Much to my amazement I found I enjoyed the experience.
The next time was a bit more deliberate with an ardent internet admirer who wanted a last “fling” with a crossdresser before he got married. I invited him over for an evening of carnal activities. It was another enjoyable encounter which opened more possibilities for me.
My third experience letting man fuck me was when I was dating a woman named Rita. We had become a serious couple, and she knew about my alternative wardrobe, going so far as to go out with me to frequent clubs when I was dressed as a woman. On one Halloween we dressed up together to go out to a costume party at a local club. I, of course, was wearing a dress and heels. While at the club we met another couple, Amy and Ken. After hitting it off at the bar, dancing and flirting, we invited them back to our hotel room for a night of erotic activity. Rita and Amy, who were both bi, quickly became entangled in a heated bout of licking a sucking each other. This left me the opportunity to engage in some amazing sex with Ken.
The memories of the evening with Ken, Amy, and Rita always brought a whirlwind of emotions. There was an intoxicating blend of exhilaration and trepidation. The novelty of the experience heightened every sensation, making it feel both forbidden and incredibly liberating. Each touch, sight, and sound had been electric, the fear of the forbidden mingled with an overwhelming sense of desire, creating a memory etched deeply in my mind.
That had been a few years earlier. Rita and I split a couple years after that, and we went our separate ways. The period following the split was one of intense reflection and solitude. Immersing myself in work helped to numb the loneliness, but the desire to reconnect with that small part of myself that enjoys donning a dress and heels grew stronger with each passing month. I needed the thrill and excitement again. I needed to get back into it. I needed another crossdressing adventure.
I took the first step and reopened an old profile on an adult dating site that catered to crossdressers and those who admire them. I wasn’t really sure what I was looking for or what to expect. It had been some years since I had used the site. Surprisingly, or maybe not surprisingly, a lot of the same faces were still there including a significant number of men I referred to as “tranny chasers”. These were the men who, while often married, straight, and in vanilla lives, occasionally sought out the company of a crossdresser or transgender for an erotic thrill.
Seeing the same faces on the dating site brought a strange sense of continuity to my life. It was as if time had stood still for this unique community, even as my own life had undergone significant changes. Each interaction carried a sense of familiarity, but also the bittersweet realization that some things remain constant in the ever-changing tapestry of life.
Reopening my dating profile came with mixed feelings, anticipation and “ennui” as I navigated through the familiar faces and profiles. I updated my profile page and posted new pictures of myself en femme. Soon after my ısparta escort inbox filled up rapidly.
Many of the notes were crude or banal with troglodytic expressions of “U R Hot” or “Wanna fuck”. Part of me felt objectified, part of me felt annoyed, but another part reveled in the attention. And while the attention was flattering, even from such crude expressions, I harbored a desire for a potential paramour with a bit more sophistication.
Within a couple of weeks, I received a note from someone who identified himself as “Anthony.” Beyond being impressed that he actually knew how to construct sentences and use punctuation, his note was straightforward, expressing appreciation for my well-constructed profile and my photos. I replied, thanking him for the compliments, and we started to have a regular exchange of messages, first on the dating site and then moving to regular email.
Over the course of our message exchanges, I learned that he lived near me in the suburbs of Chicago. We started exchanging messages regularly, including photos. From his pictures and self-description, Anthony was an attractive man. He was in his late 30’s, tall, fit, with brown hair and a clean-shaven face. He was also polite, educated, a professional, and married to an attractive professional woman of similar age. He said his sex life with his wife had diminished over the years of their marriage to the point of almost nonexistence. He didn’t blame his wife; she had a busy schedule and traveled much for her job. As a result, he had secretly opened an account on a dating site looking for a safe and discrete outlet for his erotic desires.
When I asked him why he had contacted me, he explained that he had always been attracted to crossdressers and had had some “experiences” with a few when he was in college. He also stated that he found my profile to be well-written, entertaining, and that my “look” appealed to him.
After exchanging a couple of dozen emails, he let me know that he would like to meet in person, suggesting a get-together some evening. When Anthony suggested meeting in person, a wave of hesitation washed over me. The thought of stepping out of my comfort zone after so many years was daunting. But as I reflected on my few experiences of having sex while dressed as a woman, I felt a renewed sense of courage. It was time to reclaim that part of myself and embrace the adventure. I decided it was time to dust off my heels and have some fun again.
We continued to exchange messages. Our emails gradually transformed from casual exchanges to intimate confessions. As we shared our fantasies and past sexual activities. I described several of my past encounters including my first sordid fling in the parking lot of a local bar. Sharing the stories with Anthony was both liberating and arousing. His curiosity and detailed questions about my attire, sensations, and emotions during the encounters seemed a good sign. I sent him some photos showing how I was dressed, describing in detail what I recalled from those evenings, the sights, the sensations, the feelings. In his next reply he stated that he found my descriptions and photos very arousing and confessed to masturbating while reading my stories and while looking at my pictures. Now it was my turn to be aroused. The thought of someone becoming sexually excited while looking at my pictures was definitely a turn on.
About a week after this exchange, Anthony sent a note letting me know that his wife was going out of town for 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 from time to time, 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. But what would be the harm in a little more experimentation?
With a deep breath, I crafted a reply letting him know Saturday night was good, pausing only a moment before hitting the send button. When Anthony asked where we could meet, I was a bit apprehensive about having a stranger come to my home. So, I suggested a nearby hotel where I could rent a suite for the evening. To give myself plenty of time to prepare, I offered that we should meet around midnight.
His response was quick — he replied to my email saying that he was thrilled we were finally going to meet in person and that he 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.
I had a pretty good assortment of clothing that would work for my rendezvous with Anthony, but it felt like something new, special, and sexy was needed. The idea of being with a strange guy while dressed as a woman was a turn-on, so I wanted to do everything possible to ensure that he liked what he saw.
Over the next couple of days, I scoured the stores looking for what I thought would be the appropriate attire for my planned tryst. Anthony had let me know in the course of our email exchanges that kadirli escort he really liked my legs and particularly enjoyed them encased in shiny pantyhose and wearing stiletto heels. He was also a fan of short skirts, so I went to work making sure I had the perfect outfit.
As I shopped, a mix of excitement and anxiety buzzed through me. “What if this is a mistake? What if he doesn’t like what he sees?” I questioned myself, but the thrill of anticipation kept me moving forward. Over the next few days, I searched the local discount fashion shops and quickly found an outfit I thought would please my potential paramour. It was a short black lace skirt that came down to about eight inches above the knee. It had a wide elastic band around the waist and a cascade of black lace and silky fabric that fell in layers. I thought it would look great with some silky tan pantyhose I had purchased. I also found a pair of black suede pumps with a half-inch platform and three-and-a-half-inch heels. These items, combined with a black silky blouse already in my closet, would do nicely for my pending weekend tryst. Once the shopping was complete, a small suite was booked at a nearby business-class hotel. All seemed to be falling into place nicely.
The weekend quickly arrived, and by Saturday afternoon, I was feeling a bit nervous. “Am I really up for this? What if he doesn’t find me attractive? What if I don’t find him attractive? What if I can’t go through with it?” I wondered at that point if real women have these same thoughts before going on a blind date. I looked in the mirror and took a deep breath. “This is it. No turning back now,” I thought, trying to steady my nerves. The reflection staring back at me looked confident, but inside, a storm of emotions brewed.
By early Saturday evening, I was growing more and more excited about my pending adventure and decided it was time to start getting ready. I gathered up my clothes, shoes, wig, and makeup case. I also packed a couple of bottles of wine, a bottle of whisky, some snacks, and a few other necessities. When it was all in the car, I drove to the hotel.
The hotel was located near the intersection of two interstate highways not far from O’Hare. It was within a cluster of similar business-class hotels and was part of a chain familiar to me. My job had me traveling often, so I had racked up a considerable number of award points. A few of them were cashed in, allowing me to upgrade to a nice multi-room suite.
The room was standard yet spacious and consisted of a sitting room with a couch, chair and ottoman, coffee table, and a scattering of end tables with lamps. At the end of the sitting room was a short hall with a large bathroom off to one side and a set of shelves with a microwave and small refrigerator on the other side. Through a doorway in the hall was the bedroom with a large king-size bed. The color scheme was neutral with cream-colored wallpaper and green carpeting. Non-descript “art” and several mirrors adorned the walls. All pretty bland. After unpacking, I took a long and very hot bath in the oversized hotel bathtub to soak away any lingering concerns and to prepare for an all-over shave. Next, lather and razor were applied, shaving pretty much everything south of the eyebrows. And when I say “everything,” I mean everything.
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. The process of transforming from “average Joe” to “hot tranny” was meticulous and lengthy. Each stroke of makeup brought me closer to the image I wanted to present. The makeup alone took more than two hours. I added some press-on nails and jewelry. Then I fluffed out my wig, shoulder-length blonde with dark roots, and gave a once over in the mirror. As I looked in the mirror, I saw a confident, beautiful woman staring back. She was older now with more lines on her face, but still attractive. With a nod of satisfaction, I moved back into the bedroom to start getting dressed.
First was the underwear — a sexy black lace bra stuffed with silicone breast forms. Following that, tan pantyhose were rolled up my freshly shaved legs and pulled up for a snug fit. I decided that a mid-cost control top pantyhose was best. I had a hunch they wouldn’t survive the planned activities for the night. I also decided to skip wearing any panties, hence the control top variety of pantyhose to help keep my cock tucked away.
The best part of the transformation process for me is, once the makeup and wig are in place, sliding a brand new pair of pantyhose up my freshly shaved legs. There’s just something so incredibly sexy about the feeling and the visual. As I slid the silky pantyhose up my legs, a shiver ran down my spine. The smooth fabric against my freshly shaved skin felt both foreign and exhilarating. My heart pounded in my chest, each beat echoing my growing anticipation. The sensations of the silky clothing and anticipation of the events to come were already stirring kadıköy escort an erection. I thought about masturbating, but I wanted to wait until Anthony arrived. So, I finished dressing, adding the skirt and heels and checking my makeup one last time in the mirror.
Time is a funny thing — when you’re doing something you hate it seems to drag (pun intended). But when you’re doing something enjoyable 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 main room of the hotel suite 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 nylon-covered legs as they brushed against each other while moving about.
A knock at the door 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.
Moving to the door of my hotel room, I peered out the peephole just to make sure it wasn’t an unexpected hotel maid showing up. It would have been rather awkward had something like that happened. Much to my relief, I saw my internet friend on the other side of the door. I took a steady 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.
Anthony 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 standing in three and a half inch heels. I invited him in, trying to use a breathy whisper and not spoil the illusion with my rather deep masculine voice.
Once inside, he looked around, seemingly unsure of what to do. He was a bit nervous, understandably so, since he didn’t know if the crossdresser he had seen on the internet was going to be the person answering the door. I asked him to sit on the couch in the main room of the suite while I got us a couple of 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, Anthony 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 there was an undercurrent of nervous energy about him. Was he disappointed in me and how I looked? Was he having second thoughts? Would he just get up off the couch and call the whole thing off?
But none of those things happened.
We made a bit of small talk as we sat next to each other on the couch, my legs primly crossed, and my skirt tucked neatly under me. I asked if he had trouble finding the place, and he said my directions were good. As he sipped his drink, I caught his eyes wandering over my crossed legs. Leaning in a bit towards him, I took a chance and asked him if he thought I looked “okay.”
“You look amazing,” he said. “Better than in your pictures.”
I smiled at that.
He must have taken my smile as a sign to proceed since he set his drink down on the table next to the couch and placed a hand on my thigh, slowly caressing it as his eyes continued to wander over me.
This was happening! I felt a mix of exhilaration, arousal, and fear. It was the same mix of emotions I always felt when crossdressed and about to engage in some erotic activity. His touch was gentle and a bit tentative, as though unsure of how to proceed. I decided to give him a signal on what to do next.
I uncrossed my legs and leaned back on the couch, parting my knees just enough for his hand to reach the hem of my skirt. As Anthony’s hand moved higher up my thigh my body responded to his caress, a tremor running though me as my cock twitched in response. I tried to appear calm, but my fingers trembled slightly as I reached for my glass of wine. He slowly rubbed his hand over the soft lace and silk, feeling the texture of the skirt and the smooth silky nylons covering my upper thighs.
As his hand stroked my thigh, I struggled to keep the conversation light. ‘So, do you have a favorite restaurant in the area?’ I asked, my voice barely steady.
“The Italian one near the corner is good,” he replied. His voice was distant, not really interested in conversation anymore.
A pause in the chat and our eyes met and locked for a moment. It was clear we were both very interested in seeing where this was going. Not knowing what to say, I lowered my head slightly, looked up at him through my fake lashes, and smiled. He took my look as a sign to proceed further since he set his drink down again and reached up, cupping my breast.
“Well, here it goes,” I thought to myself.
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. The taste of the scotch lingered on his tongue, mixing with the flavor of my wine and lipstick. I could smell his cologne. Nothing I could identify but it was nice.
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