One way to find out

One way to find out – a crossdressing story

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.

I have been attracted to women's clothing for as long as I can remember. I can't really say why, but the attraction has always been 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 family members or the occasional sister of a friend.

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).

After that I met and married a woman who did not accept my interest in an alternative wardrobe, so I buried my feelings and purged my closet. Later, I got divorced, advanced my career, and eventually moved to Chicago and began to explore my interest in crossdressing in earnest.

The year was now 2008. I was in my early 40's and was continuing to expand 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 remember the first evening I ventured out alone in public in a skirt and heels a few years prior. I was terrified and exhilarated all at the same time. My heart pounded in my chest, a mix of fear and excitement coursing through my veins. The sensation of the cool spring air against my bare legs and the click of my heels on the pavement were electrifying. Eventually, the fear of discovery became less, replaced with the rush of experiencing the feel of heels, hose, and makeup while being out in public. After that I started going out en femme every few months when time allowed. I'd even met some people and had a few erotic adventures in a skirt and heels.

Now it was December of 2008. Work had slowed down a bit, as was typical for my profession at this time of year. I was taking night classes toward another graduate degree, and my night classes were on pause until after the new year started. As a result, I had some spare time to indulge in my penchant for dressing up and going out.

Rather than trusting to chance that I might meet someone interesting to play with at a local bar, I decided to see if there was someone I could connect with online. I had profiles under my feminine persona on several hookup sites that catered to those with non-traditional sexual cravings. It had been a few weeks since I had visited the sites, and I found a plethora of messages waiting for me in the various inboxes.

I looked through the messages and quickly discarded most of them. There were the usual "wanna fuck" type messages. I rapidly deleted them. I had no interest in meeting anyone who didn't want to take the time to get to know me before trying to get into my panties.

There were some messages from other crossdressers looking to connect or chat. I hate to admit it, but I am kind of a snob about others who share my interest in donning dresses and heels. While I am always polite and supportive to all, I would never want to hook up with someone who looks like a hairy guy in panties. With a mix of guilt and relief, I politely declined several requests for connecting and moved on.

Then I saw a message from someone who called herself "Ms. Kathy." The message read:

"Hello Jenette. I like your profile and pictures."

Interest piqued, I scanned her online profile and liked what I saw. From her profile and photos, she appeared to be an attractive, petite woman, 5'3" tall, and 100 pounds. While her face was obscured in her profile pictures, I could discern other details about her appearance. Her hair was long and dark, her skin honey-toned, and she had a lithe, trim body with smallish breasts and shapely legs. She looked like someone who exercised regularly, probably a runner or swimmer.

A wave of curiosity washed over me as I pondered the message. The profile identified her as a woman, dominant, bisexual, and not into anything too extreme. This was unusual. I had never been contacted by someone like her and was curious as to why she would reach out to me.

I replied to her message, my fingers trembling slightly with a mix of excitement and nervousness.

"Hi Kathy. Thanks for the compliment. I liked your profile as well. Your pictures are beautiful. Are you interested in crossdressers?" I figured it was best to be direct.

I hit the send button and logged off to run some errands. When I returned home later that evening, I logged in and saw a reply from Kathy sitting in my inbox. A small thrill ran through me as I opened the waiting message.

"Thanks for the compliment. I've never been with a crossdresser but am interested in learning more. I saw on your profile that you are interested in women and other crossdressers."

I felt a rush of excitement and anticipation as I replied in the affirmative that I was indeed interested in women. I then suggested that we take our conversation off the site and sent her my email address. A short time later, a note arrived in my inbox from Kathy.

"Hi Jenette. Nice to meet you. I hope you don't mind that I reached out to you."

"No problem. I'm curious as to why you did though. You're a very attractive woman. I can't imagine you would have any trouble finding someone to play with."

As we continued our email exchanges, I learned that Kathy was a few years older than me, a military officer stationed near Chicago, and married. She explained that her husband was also in the military and stationed overseas. She and her husband had an arrangement while they were separated for their jobs; they had agreed to have an open relationship, which was why she was on the hookup site. She wasn't looking for anything serious or long-term, just some casual erotic exploration and enjoyment.

When she asked about my situation, I explained that I was divorced, unattached, predominantly heterosexual, and sometimes indulged in my penchant for crossdressing. I also told her briefly about my past experiences dressing up, even confessing to the times I had let men have their way with me.

She seemed intrigued by this and asked questions about how I did it and how I felt afterward. I relished the opportunity to express my thoughts and feelings freely to an attractive woman. It felt liberating to share my private world without fear of judgment.

When she asked if I had ever cross-dressed and had sex with a woman, I told her that I had, but the vast majority of women I had met had no interest in playing like that. The conversation stirred a mix of memories within me, reminding me of the complexities of human relationships.

When I asked her why she was interested in me she explained that most of her sexual experiences had been with men but had several encounters with women over the years. She had enjoyed both and when she came across my profile, she was curious what it might be like to have sex with someone that looked like a woman but had the "equipment" of a man.

We continued our email exchange for a few days. She asked me lots of questions about my crossdressing and my experiences. I answered her honestly and openly. Then she asked me to send her a new picture of myself dressed up en femme.

"Getting to know you through email has been fun," she explained, "But I've been fooled before by people using pictures that were not their own."

I replied that I understood and would be happy to comply if she would agree to reciprocate.

"Of course!" was her response, "Here's my request, I'd like to see a picture of you, full body length, wearing pantyhose and heels, fully made up, and touching yourself."

I thought about the request, and it seemed reasonable. Of course, I doubted she understood how much work goes into getting all dolled up, but I was beginning to become interested in the possibility of an erotic adventure with my new online friend. I agreed to her request, asking for a couple of days to make it happen, and sent my own request to see her, including her face, in a short red or black dress and heels.

She agreed, saying that she was enjoying our interactions so far and looked forward to seeing my new picture.

The next day, I started preparations for my little self-directed photo shoot. Filling my tub with hot water and scented soaps, I soaked for a bit and reflected on my recent interactions with my new online friend. The warm water enveloped me, easing my nerves and heightening my anticipation.

I wondered what she was like in person. Was she as pretty as her photos? Would she be able to handle the fact that I was a man who enjoyed dressing up as a woman?

After my bath, I began the process of shaving my body. I had learned through experience, sometimes painfully, what worked and what didn't. I used a razor and shaving cream to remove the hair from my face, chest, arms, legs, ass, and groin. Each stroke of the razor revealed smooth, sensitive skin beneath, enhancing the sensation of transformation.

Once done, I applied lotion to my freshly shaven skin. Moisturizing was important! The cool lotion against my bare skin felt refreshing and soothing.

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 almost two hours. I added some jewelry and fluffed out the wig I had selected, long straight blonde with bangs.

As I looked in the mirror, I saw a tall, confident, beautiful woman staring back. Her blue eyes sparkled under thick dark eyelashes and her painted lips were quirked up in a small smirk. I had passed 40 years in age recently, so the reflected image didn't show a youthful glow, but still attractive in a MILFish sort of way. With a nod of satisfaction, I started getting dressed.

First came a pair of nude pantyhose, sliding a brand new pair up my freshly shaved legs. For me there's just something incredibly erotic about the feeling and the visual. As I slid the silky pantyhose up my legs, a shiver ran through me. The smooth fabric against my freshly shaved skin felt both foreign and exhilarating.

Next, I slipped on a pair of black leather pumps with three-inch heels. I stood up and walked around my apartment, getting used to the feeling of walking in heels again. The tight embrace of the shoes and the height they gave me added a sense of elegance and power. I loved the feeling of the heels and the way they made my legs look. Looking into the full-length mirror in the room, I pondered what to do next. Kathy had said she wanted me to send her a picture wearing pantyhose and heels. Was that all I was supposed to wear?

I decided to err on the side of modesty and grabbed a black satin chemise and black boy-cut panties and put it on. I didn't want to send her a picture that was too revealing. I wanted to leave something to the imagination.

I set up my tripod and camera and adjusted the lighting in the spare bedroom of my apartment. The room had light-colored paint with a couple of small couches where I could watch television. I took a few practice shots to make sure I had the right angle and lighting. I tried a few different poses: sitting, standing, kneeling, checking the images after each to see if I liked them.

Finally, I found a pose I liked, laying down on a loveseat looking back up at the camera. Kathy had requested that the picture show me touching myself. Again, I didn't want to send anything too revealing, so I pushed my black panties down to my knees and reached under my pantyhose with my left hand, touching myself yet covering so as not to show anything too revealing.

I took a few shots and checked them out. A mix of pride and nervousness filled me as I selected the best photo to send to Kathy. Attaching the image to an email, I hit the send button and waited for a reply, eager to see how she would respond.

As I waited for a reply, I continued to lie on the couch. The combined effect of the silky material and the visual of my legs encased in shiny hose and high heels brought a stirring to my cock, a flush of arousal spreading through me.

Not being one to miss an opportunity for pleasure, I started to stroke myself through the thin fabric of the nylons. The sensation was exquisite, each touch sending currents of pleasure through my body. I ran fingertips over my pantyhose-covered cock, starting at the base and slowly working up to the tip, then moving back down again. The gentle friction was electric. My other hand roamed across my stomach and chest, feeling the warm satin chemise clinging to my body, its texture amplifying my arousal.

As I continued to stroke and feel myself, I raised my legs into the air, admiring the elegant curve of my calves and the black leather pumps on my feet. The sight was incredibly erotic, adding to the intensity of the moment. Erotic vibrations tingled throughout my body; a steady build-up of sensations. My breathing grew heavier, more urgent, as the warm rush of a rapidly approaching orgasm built inside me.

Pausing for a moment, I lowered my legs and pulled my throbbing cock free of the restrictive nylons, the cool air a stark contrast to the heat of my arousal. Curling my fingers around the shaft, I began to pump it in earnest, each stroke bringing me closer to the edge. A wave of orgasmic bliss washed over me, a powerful release that left me trembling. A moan escaped my lips as I shot a thick load onto my stomach, the warm fluid staining the silky chemise. The afterglow was sweet, a moment of pure contentment as I lay there, enjoying the aftermath of my pleasure.

After a few moments of basking in the afterglow of my orgasm, I went to the bathroom to clean up. As I washed up, I wondered what Kathy would think of my picture.

The next morning, I woke up to find a message from Kathy.

"Jenette, thanks for the picture. You look amazing! I'm curious, are you hard in the picture?"

I responded that I was and asked if she liked it.

"Yes, I did. It was very erotic. I liked seeing you dressed up and touching yourself."

A thrill of satisfaction ran through me as I thanked her for the compliment and asked if she had sent me a picture.

"I did. I hope you like it."

I opened the picture and gasped. There was Kathy, dressed in a short red dress, black hose, and black high heels. She was sitting on a chair, legs crossed and smiling at the camera. Her dark hair was pulled back into a ponytail, and she wore a light layer of makeup. Her face was beautiful, with high cheekbones and full lips. Her eyes were dark, hinting at a touch of Asian heritage. Her small, firm breasts pressed against the material of her dress, the outline of her nipples visible through the thin fabric.

She looked gorgeous.

A mix of admiration and excitement surged through me as I replied that I was very impressed with her picture and that she looked beautiful.

"Thank you. I'm glad you liked it."

"So, what do you think? Do you want to meet?" she messaged back.

I thought about it for a moment. The idea of meeting Kathy thrilled me. She was very attractive and seemed like a nice person. But I was also a bit nervous. What if she didn't like what she saw in person? What if she didn't like me?

Despite my nerves, I decided to take a chance and replied that I would like to meet the following weekend. We agreed to meet at a local bar for a drink. I explained that the bar, named Hunters, was friendly to gay, bi, and trans people and I was a semi-regular there.

The week seemed to drag on. I was excited and nervous about meeting Kathy. I spent a lot of time thinking about what I would wear and how I would present myself. I wanted to make a good impression.

Finally, the day of our date arrived. I got up early and spent a couple of hours getting ready. My anticipation was palpable as I carefully selected my outfit: a short black suede mini skirt, a gold-colored crushed velvet camisole with black lace inserts, a tan jacket, and black suede high-heeled boots. Laying the clothing out on the bed, I thought about what I should wear underneath. I chose a black lace bra that worked well with my silicone breast inserts, a black waist cincher to help give an hourglass figure, and a black satin gaff panty to keep things tucked away properly.

Kathy had asked me to pose in pantyhose for the picture she requested. I pondered the possibility but decided to go with a pair of gold-colored silky stay-up thigh-high stockings. Stockings were always a better choice in the event that things turned erotic.

To top it off, I picked one of my favorite blonde wigs. It was shoulder-length with a flip-out style that framed my face nicely. A few bits of jewelry and a lacy scarf completed the ensemble.

Later that evening, I began the ritual of getting dressed up. A hot bath, shaving, applying makeup, and wig. Each step heightened my anticipation and excitement. Next came the bra with inserts, cincher, and panties. I sat on the bed and rolled the thigh-high stockings up my freshly shaven legs, reveling in the erotic sight and sensation. The smooth fabric against my skin sent a shiver down my spine. I considered masturbating but quickly dismissed the thought. If I was going to have an erotic encounter with Kathy, I wanted to be fully "charged."

I quickly pulled on my top, careful not to disturb my makeup or wig, pulled up the skirt, and donned the jacket. The suede high-heeled boots came next, slipping them on over the silky thigh highs and zipping them up. They came to mid-calf and had a three-inch blocky heel. The toes were slightly rounded, making them very comfortable to wear. I love pointy-toed heels, but they can be painful to wear for long periods of time.

Finally, I added the jewelry and looked at myself in the mirror.

"Not bad," I thought to myself, feeling a surge of confidence.

I grabbed a small overnight bag and threw a few items into it. Always best to be prepared. Makeup for touchups, makeup remover towels, toothbrush and paste, deodorant, a set of guy clothes and shoes, and condoms and lube. As a final thought, I tossed in my black leather pumps and some lingerie.

Holding the bag, I grabbed my purse and headed out the door and to my car. My heart raced with a mixture of excitement and nervousness as I drove to the bar, eager yet apprehensive about what the evening might bring.

I arrived at the bar a little early. We had agreed on meeting at 8:00 pm, a bit early for the club crowd, which was one of the reasons why I had suggested the time. It was early enough that the bar wouldn't be too crowded. The other reason is if the meeting with Kathy turned out to be a dud I would still have time to try my luck finding a playmate at the bar later that evening.

Exiting my car, I walked across the parking lot, reveling in the feel of the chill December breeze on my stocking-covered legs. It had snowed a few days prior, and my high-heeled boots crunched across the scattered snow and ice patches in the lot, each step sending a little thrill up my spine.

Once inside, I found an unoccupied table in the back of the bar near the pool table and took a seat. Adjusting my skirt, I crossed my legs and flagged the server to order a drink. The low hum of conversation and the clink of glasses provided a soothing backdrop as I settled in, anticipation bubbling within me.

There were a few regulars in attendance that evening. I greeted a few, chatted with a couple that I had previously talked with, and waved at a few more. As I sat sipping my drink, a guy approached and asked if he could buy me a drink. He was younger, maybe late 20s, dressed in a clean button-down shirt and jeans. The bar always had a complement of what I called "tranny chasers," guys that were mostly vanilla but for whatever reason were seeking the company of a crossdresser for the evening. On another night I might have taken him up on his offer, but not tonight.

"No thank you. I'm waiting for someone," I replied, smiling politely.

He seemed a bit disappointed but moved on. I watched him move off toward the bar, seeking the possibility of a different conquest. I marked his look and, if my meeting with Kathy didn't work out, I might see if I could find him later.

A short time later, I spotted Kathy entering the bar. She was wearing a short black dress, black hose, black patent leather stiletto heels, and a black leather jacket. Her dark shoulder-length hair hung straight down, framing her beautiful face. She had a light layer of makeup, and she looked gorgeous. I felt a thrill run through me as I watched her scan the room.

I stood, waved to her, and she smiled and walked over to the table.

"Hi Jenette. It's nice to finally meet you in person."

"It's nice to meet you too. You look beautiful," I replied, pulling her in for a brief hug. Her body felt warm against mine, and I caught the intoxicating scent of her perfume.

"Thank you. You look great too. I like your outfit."

Pulling away from the hug, I was aware of the sweet, floral scent of her perfume. I didn't know what it was, but I liked it. I was also aware of our disparity in height. Without heels, I stand at slightly over six feet. Kathy, in her stiletto heels, only came up to a little over five and a half feet. Not a problem if we're both horizontal during sex I inwardly smirked.

We sat and chatted for a while, getting to know each other. As she sat, she crossed her legs, and I thought I caught a glimpse of a stocking top. I found myself hoping that I might get to see more of what she had on under the tight black dress. My pulse quickened at the thought.

Kathy told me about her job in the military and how she had met her husband. I told her about my job and my divorce. We talked about our hobbies and interests. We both enjoyed reading many of the same books and watching many of the same movies. Each shared interest felt like another piece of a puzzle clicking into place.

As we talked, I could feel what seemed to be a bit of chemistry developing. There was an electric tension in the air, a mixture of excitement and anticipation.

We ordered another round of drinks, and our conversation turned toward our erotic tastes. She told me she had discovered that she enjoyed being dominant in the bedroom, nothing too extreme, but she liked to call the shots. Maybe a little light bondage. She also confessed to a love of lingerie, including stockings, corsets, and vintage undergarments. Her eyes lit with enthusiasm as she spoke, and I found myself hanging on every word. I told her more about my affinity for women's clothing and about the first time I dressed up fully and went out when I was 19 years old. I tried to explain that I lived well over ninety-five percent of my life as a man, but there was something that drew me to occasionally dress as a woman. Sharing these intimate details felt liberating.

After our second drink, the pool table near our seats opened up. With a bright smile, Kathy asked, "Do you want to play pool?"

"Sure," I replied, feeling a thrill of excitement at the playful challenge.

We moved over to the pool table and started a game, racking the balls and selecting cues. As we played, I noticed that Kathy kept brushing up against me. At first, I thought it was accidental, but then I realized that she was doing it on purpose. Each touch sent thrilling shivers through me.

"Are you trying to distract me?" I asked, grinning.

"Maybe," she replied with a smile, her eyes giving a mischievous look.

At one point, when it was her shot, I asked if I could take a picture of her.

"Sure," she replied with a grin.

As she bent over to take a shot, her dress rode up slightly, giving a tantalizing glimpse of her thigh-high stocking tops. I snapped a few pictures, feeling a rush of excitement. She offered to do the same for me. I handed her the camera and posed with a goofy smile on my face as I bent down to take my shot.

As we continued to play, Kathy continued to brush up against me. At one point, she ran her fingers down my back as I prepared to make a shot. Even through my jacket, her touch sent a tingle down my spine and through my body. The sensation was both thrilling and distracting.

"Not fair," I said, missing the shot by a wide margin.

She just grinned and batted her long eyelashes at me, the playful twinkle in her eyes suggesting things to come.

After a couple games, we decided to take a break and get another drink. As we sat at the table, Kathy reached under the table and ran her hand up my thigh, her nails lightly tracing the line of elastic at the top of my stockings. Her touch made my skin tingle, and I felt my cock start to twitch.

"Do you want to get out of here?" she asked.

"Yes," I replied, feeling a rush of excitement and nerves. This was definitely happening!

We quickly finished our drinks and headed out to the parking lot.

"My place or yours?" she asked.

"Lady's choice," I replied.

She gave a snort of laughter, and I realized the irony of what I had just said.

"Your choice," I quickly amended.

"Let's go to my place. I have some ideas and might need some toys," she said with a devilish smile.

"What kind of toys?" I asked, a poorly disguised tremble in my voice.

"One way to find out," she said as she texted her address to my phone.

With that, she hopped into her car and started to drive away. I quickly followed her, my heart racing with a mix of anticipation and apprehension.

Her house was about half an hour away from the bar. As I drove, I thought about what was about to happen. I was excited and nervous. I wasn't sure what to expect. I knew that Kathy had experience with dominating men. I had no experience in being dominated by a woman, what was I in for?

"One way to find out," I said to myself as I followed Kathy's car.

A short time later we arrived at her home. It was a small bungalow-style house with a small front yard and a detached garage. She pulled into the driveway, and I parked on the street. Grabbing my bag from the back, I exited my car, locked the doors with a chirp, and moved toward the house.

As I walked up to the front door, I could feel my heart pounding in my chest. Each step felt heavier with the weight of my anticipation. Kathy opened the door and invited me in.

The house was small but neat and tidy. There was a living room, kitchen, and a small hallway that led to the bedrooms and bathroom.

"Can I get you something to drink?" Kathy asked.

"Yes, please. White wine if you have it," I replied.

"So, what do you think?" she asked, walking into the kitchen.

"It's a nice place. Very homey," I said, my eyes taking in the cozy decor.

"Make yourself at home," she said over the sound of a cork being pulled from a wine bottle.

I sat on the edge of the sofa and crossed my legs, the feeling of the smooth stockings brushing against each other giving me a small thrill. I gazed around the room. Books sat on shelves and small tables near comfortable reading chairs. On the mantle above the fireplace, there were framed pictures of what I could only guess were family and friends. Some of the pictures were of Kathy with a tall, dark-haired male that I assumed was her husband.

Kathy returned with two glasses of wine and handed me one.

"Thank you," I said, taking a sip and savoring the cool, crisp taste.

"You're welcome."

We sat and chatted for a while, enjoying our wine and getting to know each other. As we talked, I could feel the tension and anticipation building. Every glance, every smile seemed to carry a hidden promise.

"So, are you ready to have some fun?" Kathy asked with a mischievous smile.

"Yes," I replied, my voice trembling slightly with excitement.

"Good. I've been looking forward to this all week."

"Me too," I said, my sense of excitement growing, "What will we be doing?"

"One way to find out" she smiled rising from the couch. "I'm going to go get changed. I'll let you know when to come into the bedroom," she said.

"May I use your restroom to freshen up?" I asked.

"Of course. Down the hall, first door on the left."

"Thank you."

I stood, grabbed my bag, and walked to the bathroom. Closing the door behind me, I took a deep breath. I could feel the butterflies in my stomach. I set my glass of wine down on the counter and looked at myself in the mirror. I was excited and nervous. I could feel my hands shaking slightly.

"You can do this," I said to myself.

I took a few deep breaths to calm myself and then freshened up my makeup. I had brought some lingerie with me and decided that a change was in order before we started the evening's activities. I removed my jacket, skirt, and top, leaving only the bra, cincher, panties, and stockings. In place of the clothes, I donned a black silk chemise and a short, see-through kimono-style robe. Next, I swapped out my boots for the black leather pumps I had brought with me.

I looked at myself in the mirror. I liked what I saw. The black chemise clung to my body, accentuating my curves. The short robe provided a tantalizing glimpse of my lingerie-clad form. My blonde wig framed my face nicely, and my makeup was perfect. As I considered my reflection the feeling of astonishment at what some padding and paint could accomplish, the transformation into a beautiful woman always amazed me.

I heard Kathy's voice, "Jenette, I'm ready."

"I'm ready too," I said to myself, feeling a surge of confidence.

I picked up my glass of wine and headed to the bedroom.

Entering the bedroom, I quickly took in my surroundings. The room was smallish, with cream-colored walls and matching carpet that muffled my footsteps. A queen-size bed, wrought iron and canopied in gauzy linen, stood against one wall, its delicate fabric swaying slightly with the movement of the air. On the bed were clean crisp white linen sheets and extra-long pillows. A wooden dresser, polished to a soft sheen, lined an adjacent wall, and two high-backed chairs occupied opposite corners of the room, their upholstery a rich, deep red that contrasted with the pale walls.

As I walked in, I was greeted by the sight of Kathy standing in the middle of the room. She had lit several candles, their flames dancing and flickering, giving the room a warm and inviting glow. The soft light played over her features, casting delicate shadows that made her look even more alluring. The subtle scent of vanilla and sandalwood from the candles filled the air, wrapping around me like a gentle, intoxicating embrace, adding to the intimate ambiance. My sense of desire grew as I took in the sight, the anticipation almost unbearable, a knot of excitement tightening in my stomach.

She had removed her dress and stood, legs apart, dressed in a black silk robe, black stockings, and black stiletto heels. Her robe was unbelted and hung open, barely covering her small, perfect breasts. A "V" of honey-colored skin was exposed, and in the soft candlelight, I could see she wasn't wearing either a bra or panties. Her skin glowed, smooth and inviting, the black silk accentuating the delicate curve of her breasts. In the flickering light I could see a tantalizing glimpse of her sex.

The atmosphere was charged with a mix of desire and raw lust, the flickering candlelight casting playful shadows that danced across the walls. The warmth of the room, the soft glow of the candles, and Kathy's enticing presence created a heady mix of desire and intimidation. Every inch of my being was focused on her, the space between us charged with unspoken promises and palpable want.

Kathy's eyes met mine, and the intensity of her gaze sent a shiver down my spine. Her lips curved into a seductive smile, and she slowly ran her fingers along the edge of her robe, teasingly revealing more of her flawless skin. I took a step closer, the anticipation and longing almost too much to bear.

"Do you like what you see?" she asked, her voice low and sultry.

"Yes, very much," I replied, feeling a mix of awe and passion.

"You changed your clothes," she stated, a hint of approval in her tone.

"Yes. I thought you might like to see me in something different."

"I do. You look very sexy."

"Thank you," I said, feeling a rush of pride and excitement.

Kathy stepped back to a high-backed chair in the corner of the bedroom and sat down. As she sat, she let the robe fall open exposing her perfect small breasts. She crossed her stocking covered legs with a whisper of fabric, the shine on her patent leather stiletto heels glowing in the soft light. A small table sat beside the chair, and she set her wine glass down onto it. She raised her slender hand and made a beckoning motion. "Come here," she said, her eyes never leaving mine, the intensity in her gaze sending shivers down my spine.

I walked toward her; my heels almost silent as I stepped across the pale. Each step felt like a journey, my senses heightened by the anticipation. When I reached the chair I stopped before her, my legs modestly together, my hands clasped before me, and my head slightly lowered to gaze at her.

"Do you trust me?" she asked, her voice firm yet gentle as she looked up at me from her seated position.

"Yes," I replied, a tremble in my voice betraying my feelings of vulnerability and excitement.

"Good. I want you to have fun tonight. If at any time you want to stop, just say so. Do you understand?"

"Yes," I said, my voice steadier despite the fluttering in my stomach.

"Good. Now, put your wine down and kneel before me."

I set my wine down and knelt before her, the soft carpet cushioning my stocking covered knees. The act of kneeling made me feel both submissive and cherished, a heady mix of emotions.

Kathy leaned back in the chair and spread her legs wide, her swollen pussy lips glistened level with my eyes. "Now, I want you to worship my body. Start with my feet," she said in a voice made thick with lust.

I took her foot in my hand and gently kissed the top of it. The scent of leather from her shoes mingled with the faint, intoxicating aroma of her perfume. I ran my tongue along the top of her foot, tasting the smooth leather. The act was intimate and electrifying, each touch sending waves of sensation through me. I slowly worked my way up her leg, kissing and licking her stocking-clad calf. The texture of the stockings against my lips was a thrilling contrast to the smooth skin beneath.

As I continued my worship, the room seemed to shrink around us, the world narrowing to just Kathy and me. Each kiss, each lick was a declaration of desire, my willingness to surrender to the moment. The candles cast a warm glow, their flickering light dancing across Kathy's face, highlighting her smile of satisfaction.

As I reached her thigh, she placed her hand on my head and guided me to her pussy. I could smell her scent and feel the heat of her body as I pressed my lips against her wetness. I ran my tongue along her slit, tasting her juices.

"That's it. Worship me," she said.

I continued to lick and kiss her pussy, teasing her clit with my tongue. As I licked her, I ran my hands along her stocking clad legs, gliding up and down from ankle to thigh. I could feel her body respond to my touch, her hips moving in time with my movements.

"Mmmmmmm...yes, that's it," she moaned.

I increased the pressure of my tongue on her clit, flicking it back and forth. She lifted one leg and draped it over my shoulder, angling her hips so her pussy was at the perfect angle as I licked and sucked her clit. I felt her spiked heel dig into my back as I continued licking. I hooked my right index finger, slid it between her swollen lips, and began to lightly massage that special area inside. A gasp escaped her lips, and I could feel her body tense as she approached her climax.

"Oh god, of fuck, oh yes!" she cried out.

Her hands gripped the arms of the chair as her body shuddered with pleasure, her juices flowing freely. I licked and kissed her pussy, savoring her taste. She shuddered again and pushed my head away with a heavy gasp.

"That was amazing," she said, her breathing heavy.

"I'm glad you enjoyed it," I replied.

I continued to kneel on the floor in front of her, appreciating the sight before me. Kathy moved her leg from my shoulder and sat with her legs spread wide. They trembled slightly with post orgasm aftershocks. Her pussy glistened in the soft light and a wet spot darkened the upholstery of the chair between her thighs. Knowing I was directly responsible for her pleasure was extremely satisfying. Looking up at her from my kneeling position I saw her eyes flutter back to post orgasm awareness.

"Now, it's your turn to enjoy," she said with a wicked smile.

"What do you have in mind?" I asked.

"You'll see. Stand up."

I stood up, my cock straining against my panties.

"I see you're enjoying yourself," she said, reaching out and stroking my erection through the satin of my panties.

"Yes, very much," I replied, shivering at her touch.

"Good, now go stand by the bed" she said.

I walked over to the bed and stood, waiting for her next command.

"Now, I want you to take off your panties. Slowly."

I reached down and pulled the black satin panties down to my thighs, releasing them to slide down my legs to gather around my ankles.

"Now, step out of them and stand with your legs apart."

I did as she instructed, stepping out of the panties and standing with my legs apart, my heels dug into the soft carpet.

"Now, I want you to stroke your cock for me. Nice and slow."

I reached down and began to stroke my cock. As I looked down, I took in the sight, my hand wrapped around my hard cock, the gathered fabric of my chemise draped over my erection, the soft glow of the candles highlighting the shine of my golden thigh-high stockings, the faint reflections of light off my leather pumps. It was mesmerizing.

"Look at me," Kathy said with an edge in her voice.

Looking up, I locked eyes with her, continuing to stroke my rock hard cock.

"Mmmmm...that's nice," she purred.

"Now, lie down on the bed." she commanded.

I stopped stroking myself and lay down on the bed, my cock standing erect.

"I want you to stroke your cock for me. But don't cum."

I began to stroke myself again, a small moan escaping my lips. I could feel the pressure building as I neared my orgasm.

"Stop," she said.

I stopped, my hand lingering on the shaft.

"Now, take your hands and raise them above your head." she ordered.

I complied, my cock sticking straight up into the air.

She rose from her chair, a graceful, fluid movement that drew my eyes to her immediately. As she walked toward the bed, I couldn't help but marvel at the elegance of her lithe form. Her nipples, hard and erect, stood out clearly through the thin, almost translucent fabric of her robe. Her stocking-clad legs seemed to go on forever, each step accentuating the smooth, sensual curve of her calves. A shiver of anticipation ran down my spine.

She paused at the side of the bed, the room's soft light casting a warm glow on her skin, and let her robe fall to the floor with a delicate whisper of fabric. The sight of her standing there, her body now only clad in black thigh-high stockings and stiletto heels, was a vision of erotic perfection. Her gaze met mine, a mixture of desire and confidence.

The air between us seemed to crackle with sexual energy, every inch of my body attuned to her presence. As I gazed up at her, appreciating every flawless detail, my already hard cock stiffened even more, responding to the sheer eroticism of the moment. The intense desire I felt was almost overwhelming.

With a devilish smile, she climbed onto the bed and straddled my hips, her wet pussy hovering over my cock. Staring into my eyes she leaned to the side and pulled a pair of handcuffs from the nightstand drawer. She quickly snapped the cuffs around my wrists, securing them to the wrought iron headboard.

"Now, I'm going to ride your cock until I cum. And you're not allowed to cum until I say so. Understood?"

"Yes," I breathed.

"Good."

She reached down and gently grabbed my cock, guiding it to her wet pussy. She lowered herself onto me, her warmth enveloping me. She was wet but still tight.

"Mmmmm...yes," I moaned.

She began to ride my cock with slow, steady movements. She leaned forward, her breasts inches from my face. She continued to grind herself onto me, plunging down till my shaft was fully inside of her and then lifting herself up until the only the tip of my cock was touching her swollen pussy lips.

My toes curled as much as they could in my black leather pumps. I arched my back, not knowing if I could hold the building orgasm back.

Pausing her movements for a moment, my cock still buried deep inside her she asked, "Do you like this?"

"Yes," I replied, my voice strained with the effort of holding back my orgasm.

"Good," she said, leaning forward and kissing me.

Her tongue darted into my mouth, exploring every inch. She broke the kiss and sat up, her hands resting on my chest. Her fingers kneaded my breast forms as though they were real. Then she resumed fucking me, her hips sliding along my shaft in slow rhythmic perfection. As she moved, her hands slid across my chest and sides. Her caresses were electric through the silky fabric of my chemise.

The sensations were overwhelming. The curve of her face was highlighted by candlelight, her breasts bounced slightly in rhythm with her movements on my cock, the smell of her perfume mixed with the musk of her sex. I could feel our stocking covered legs rubbing together as she writhed on top of me.

Still riding me, she closed her eyes and dropped her head down so that her ponytail drooped down tickling my chest. I felt her stiletto covered feet shift position inside my legs and she pushed my legs wider apart.

I began to push my hips upward, driving my cock deep into her wet pussy, my thrusting almost lifting her off the bed. She moaned and gasped as I fucked her, her nails digging into my chest. Without warning her pussy clenched around my cock as she came, her body shuddered, and I felt her wetness flowing freely.

With a gasp and an inarticulate cry, she collapsed on top of me.

I lay there, still bound to the headboard by the handcuffs, my cock still hard inside of her. I was so close to orgasm I dare not move. I could feel her body tremble and hear the sound of her heavy breath as she came down from her orgasm.

After a few moments, she lifted her head and looked at me.

"You didn't cum," she said breathlessly.

"No, I didn't."

"Good girl. Let's do something about that now" she said as she reached up to unlatch the handcuffs.

Climbing off my still throbbing cock she sat for a moment as if deciding what she wanted to do next. Then she shifted to the edge of the bed, sitting up straight with her heels planted on the floor.

"Stand up," she said.

I climbed off the bed and stood in front of her, wobbling a bit in my heels from the intense erotic activity and sensations. Her hand reached out and lightly cupped my balls and with gentle pressure urged me to step closer toward her.

Without a word she closed her soft lips around my dick and started sucking me.

"Oh god," I moaned as her warm mouth enveloped my cock.

She began to work my shaft, her tongue swirling around the head. As she sucked, she began to explore my body, her caress light and gentile as she ran her fingers along my stocking covered legs, up my ass, and across my stomach.

I took in the sights, sounds, and sensations with a heightened awareness. Here I was, standing in three-inch heeled pumps with my legs spread and planted firmly on the plush carpet. I felt Kathy's hands caressing my legs through the thin, silky fabric of my stockings, sending shivers of pleasure up my spine. The soft touch of my silky chemise moved sensuously against my skin, making me acutely aware of every gentle shift.

Looking down between the rise of my black lacy bra, I watched a beautiful dark-haired woman sitting between my spread legs as she sucked my cock. Soft, warm light glowed off her honey-colored and flawless skin, giving her an almost ethereal appearance. Her legs, knees together and feet slightly splayed, were covered in the dark sheen of her stockings which shimmered in the light.

Watching her head bobbing slowly up and down my stiff prick, waves of pleasure and desire surged through me. Each movement sent electric jolts of ecstasy through my body. I could hear the faint slurping and sucking sounds as her wonderfully warm mouth worked my shaft, adding to the intense sensory overload. The room seemed to fade away, leaving only the overwhelming sensations and the building anticipation of release.

The sights, sounds, and repressed sexual energy came together and I could feel my orgasm rapidly approaching.

"I'm going to cum," I moaned.

She increased the pace of her sucking, her hand reaching up to augment the work of her lips and tongue.

"Oh god. Yes!" I cried as my orgasm hit.

My cock exploded, shooting my load into her mouth. My body shuddered, knees weak from the intensity of the orgasm, and I lurched forward almost falling.

Kathy caught me and guided me back to the bed. She lay down beside me and we both lay there, catching our breath.

"That was amazing," she said, wiping her mouth with the back of her petite hand.

"It was," I replied, barely able to speak.

We lay there for a while, enjoying the afterglow of our orgasms. After a few minutes, Kathy got up and went to the bathroom. She returned with a towel and a bottle of wine.

"Here, let's clean you up," she said, handing me the towel.

The towel was damp and cool against my flushed skin as I wiped the sweat and cum from my body.

"And here, let's have some more wine," she said, handing me a glass.

I took a sip of wine and lay back on the bed, feeling the coolness of the sheets against my skin. The wine was sweet and crisp, a perfect complement to the heady mix of spent lust and eroticism.

"So, how was your first experience with a dominant woman?" she asked, her voice filled with curiosity and a hint of mischief.

"It was amazing," I replied, my voice weak from the intensity of my orgasm. "How was your first experience with a guy in a dress?"

"It was great," she said, a satisfied smile playing on her lips as a fingertip traced a line down my stomach to the top of my stocking.

"I can tell," I said, pointing to the wet spot on the bed. The sight of it made me smile, a tangible reminder of our shared pleasure.

She laughed, a melodious sound that filled the room, and took a sip of her wine. The sound of her laughter was seductive, adding to the already surreal quality of the night.

We lay there together, holding each other, our stocking-covered legs entwined. The soft texture of the stockings brushing against each other was a constant reminder of the intimacy we had just shared. As we talked, the afterglow of our sex and the soothing effects of the wine began to take their toll on me, and I drifted off to sleep. As I drifted toward slumber, the events of the night replayed in my mind like a vivid dream. The night had been filled with new sensations, and a sense of discovery.

I awoke a short time later and sat up slowly, the world around me still steeped in the warm, comforting glow of the candlelight. The candles had burned lower, but still gave a soft, flickering glow within the room, casting gentle shadows that danced across the walls.

Looking down at the bed, Kathy lay sleeping. She was a vision of sensual beauty. She slept on her back, naked except for her black stockings. One of her stiletto heels had slipped off and lay on the side of the bed next to her. I noticed her toenails were painted a deep red, a small detail that seemed to capture the essence of her seductive allure.

Her chest rose and fell with the rhythm of her breath, and her face, relaxed in sleep, looked serene and beautiful. The sight of her like that brought the stirring of another erection. Moving slowly, I positioned myself between her legs.

Her pussy was still wet and glistening in the candlelight. I leaned in and began to lick and kiss her swollen lips. As I ran my tongue up and down her sex, she responded by spreading her legs.

"Mmmmmmm...that feels good. What are you doing?" she asked sleepily.

"One way to find out," I replied between licks.

Her chuckle morphed into a moan of pleasure as I continued my oral ministrations. I licked and sucked her pussy, savoring the taste. She moaned and writhed under my touch, her hips moving in time with my movements.

"Oh god that feels good," she moaned.

I continued to lick and suck a bit longer, flicking my tongue across and around her delicate bud, enjoying the sounds she made as my tongue worked her clit. Like before, I ran my hands along her stocking covered legs starting at her ankles and caressing up to her upper thighs, bringing my fingertips lightly to her pubic area. I stuck a finger in her again and started to massage inside.

She shuddered and said, "I want your cock inside of me."

I moved from between her thighs, crawling up till I was above her with my cock at the entrance to her pussy. I could feel the heat of her body as I pressed my cock against her wetness.

She reached down and guided me inside. I pushed my cock into her, feeling her wetness envelop me.

"Mmmmmmm," she moaned as I slid all the way into her.

I began to fuck her using a slow and steady pace. I could feel her body respond to my movements, her hips moving in time with my thrusts.

"Yes, yes, fuck me!" she breathed in a heavy whisper.

I continued to fuck her, my cock sliding in and out of her wet pussy. I reached up, grabbing her wrists and holding them above her head in a position similar to the one I was in when she had handcuffed me earlier. It was my turn to be dominant.

She kicked off her remaining heel and wrapped her stocking covered legs around me as we continued to move slowly together. A small gasp escaped her lips with each thrust of my cock inside her.

I slowed, wanting to pace myself and enjoy this moment. Here I was, dressed in lingerie, stockings, and heels, having amazing sex with a beautiful dark haired woman. I leaned back to see her face. We locked eyes as I continued to slide into her tight, wet pussy.

"Mmmmmmm...yessss," she moaned, "“I'm gonna. I'm gonna—ah!"

"Cum for me," I whispered looking into her dark beautiful eyes.

Her eyes lost focus and her head pushed back into the pillows as her pussy clenched around my cock. She came hard, her hands grasped the bed sheets on either side and her body shuddered as the orgasm rolled through her.

That was the trigger point for me. I couldn't hold back any longer. My balls tightened and I came with an intensity I hadn't felt in a very long time. My body tensed as I shot my load, my cock pulsing several times as I emptied myself deep inside her, each pulse sending waves of pleasure through me.

"Oh fuck, yes," I moaned, collapsing on top of her.

We lay there for a moment, our bodies entwined. I could feel her heart beating rapidly, her breathing heavy. The warmth of her body pressed against mine was comforting and exhilarating.

I rolled off of her and lay on my back, my chest heaving, trying to catch my breath. The room was filled with the lingering scent of our shared intimacy.

"That was amazing," she said, her voice a soft murmur of satisfaction.

"It was," I replied, a smile playing on my lips as I gazed up at the bed canopy.

We lay there for a while, basking in the afterglow of our orgasms. The silence between us was comfortable, punctuated only by the sounds of our slowing breaths. After a few minutes, Kathy got up and grabbed the towel I had used before and handed it to me. The cool touch of the towel was a stark contrast to the heat of our bodies.

As I cleaned up, she went into the bathroom to do her own cleaning. The sound of running water was a soothing background, but for some reason my thoughts had shifted to a whirlwind of self-consciousness. I moved to the edge of the bed, my movements feeling awkward in the three-inch heels that had once made me feel sexy. I looked down at my stocking-covered legs and heels, the sight of them now stirring a mix of conflicting emotions. The thrill from earlier was still there, but now overshadowed by a deep sense of vulnerability. This happened sometimes when I dressed up. Some long buried sense of guilt and shame tied to my desire to wear the clothing of the opposite sex. I knew it was meaningless, but the awkward feelings persisted.

When Kathy came back into the room, her eyes briefly met mine, and I quickly looked away, feeling my cheeks flush with embarrassment. I crossed my legs and pulled my chemise down, a futile attempt to cover myself. My feminine clothing suddenly felt more like an uncomfortable costume than an erotic statement. The initial excitement of crossdressing had given way to a feeling of vulnerability.

"What's wrong?" she asked, her eyes filled with concern as she approached me.

"Nothing, I'm just feeling a little awkward," I replied, my cheeks flushing with heat.

"Why?" she asked, sitting down beside me and placing a comforting hand on my knee.

"I don't know. I guess I just feel a little silly now," I said, my voice barely above a whisper, my hand making a sweeping gesture to my clothing.

"There's nothing to be embarrassed about. Tonight has been amazing. You're beautiful, you have an amazing body, and you look wonderful like this," she said, her voice firm yet kind, her words wrapping around me like a warm blanket.

"Thank you," I said, blushing slightly. Her words touched me deeply, filling me with a sense of acceptance and warmth.

We sat there for a moment, her hand still on my knee was warm through the thin fabric of my stocking, a silent connection passing between us. The night's events had brought us closer in a way I hadn't anticipated.

"And you're a pretty good fuck," she added with a grin.

"You aren't too bad yourself," I replied, also grinning.

"And your tongue! Wow!" she added.

"Yours too. Wow," I replied with a big smile.

"Now, let's get you out of those clothes and into something more comfortable," Kathy said, her voice soothing and kind.

She helped me out of my lingerie and into a pair of soft sweatpants and T-shirt that I surmised must belong to her husband. The soft grey fabric felt like a gentle caress against my skin, a comforting change after the intense sensations of the evening. I excused myself to the bathroom where I removed my makeup and wig, feeling a mixture of relief and melancholy as I wiped away the remnants of my femme persona. When I returned to the bedroom, we climbed into bed and lay there together, our bodies intertwined, the warmth of her skin against mine a soothing balm.

"Thank you for tonight," I said.

"You're welcome. I had a lot of fun," she replied, her eyes glowed with contentment.

"Me too," I said, feeling a profound sense of sexual satiation.

We fell asleep, our bodies still entwined, the rhythm of her breathing lulling me into a deep, restful sleep.

The next morning, I awoke to the smell of eggs and bacon. I sat up and stretched, my body feeling pleasant aches from the previous night's activities. The smell of the cooking food was a comforting reminder of the normalcy of the morning after such an extraordinary and usual night.

I climbed out of bed and walked into the kitchen. Kathy was standing at the stove, cooking breakfast. She was dressed in a pair of sweatpants and a sports bra, her casual attire making her look effortlessly beautiful.

"Good morning," she said, turning to me with a warm smile.

"Good morning," I replied.

"Did you sleep well?" she asked.

"I did. How about you?" I asked, taking in the serene expression on her face.

"I slept great. Here, have a seat and I'll get you some tea," she said, pouring me a cup and placing it in front of me.

I took a sip and sighed contentedly, the warm liquid soothing my throat and filling me with a sense of calm.

"So, how do you feel this morning?" she asked, her eyes searching mine.

"I feel good. A little sore, but good," I said, smiling.

"Me too. Did you enjoy it?" she asked, a hint of vulnerability in her voice.

"I did. It was incredible," I replied, surprised to see the dominant woman from the night before so vulnerable.

"I'm glad," she said, her smile returning.

We ate in companionable silence, the clinking of cutlery the only sound breaking the peaceful morning. When the meal was done, I helped her clean up and excused myself to the bathroom to change into my male clothing. As I moved into the bedroom to collect my things, I saw the remnants of our passionate night strewn across the floor—my chemise, panties, stockings, and heels mixed in with Kathy's robe, stockings, and heels. The sight made me smile, a tangible reminder of our shared adventure.

I put my things into the overnight bag and moved into the living room. Kathy sat on the sofa, her eyes following me as I approached.

"Well, I guess I'll be going," I said, feeling a pang of regret.

"Okay. Thank you for coming over last night. I had a lot of fun," she said, her voice tinged with something akin to sadness.

I paused and asked, "Do you think we can do this again sometime?"

She glanced at the photos on the mantle, her expression slightly crestfallen. "My husband and I have a deal," she explained while gesturing toward the photos on the mantle. "While we're apart we can have an open relationship. But one of the agreements is that we never have sex with the same person more than once. We don't want to get attached."

"Oh, okay. I understand," I said, feeling a mixture of disappointment and acceptance.

"I'm sorry. Last night was great. But I don't think it would be a good idea to do it again," she said, her voice soft but firm.

"I understand. Thanks for having me over," I said, trying to keep my tone light.

"You're welcome. Thank you for coming over," she said, her smile returning.

I turned and headed for the door, feeling the weight of the night's end settling on me. As I walked out into the cold and bright December morning, I smiled to myself. I had been in the mood for another adventure, and I had just had an amazing one. Maybe I could find another woman who was accepting of my desire to cross-dress from time to time. Maybe I could find one that was not only accepting, but actually encouraged it.

And eventually I did.

But that's another story.