Getting Back Into It
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 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 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 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.
Conscious of my lipstick and not wanting to smear it too much I pulled away before it became a complete mess. He looked a bit confused by my retreat, so I decided to let him know things were going well. I leaned in close to his ear and whispered, my breath tickling the lobe, and said, "Don't worry, everything's fine. Now why don't you slide your hand up my skirt a little further?"
His expression changed from confusion to lust, and he leaned in to kiss me again, his hand moving under my skirt and rubbing the smooth skin of my thighs.
"This is definitely happening!" I thought, a mix of excitement and nervousness swirling inside me.
His hand moved higher up my thigh, and I felt a shiver run down my spine. My skin tingled under his touch, and I could feel the warmth of his palm through the thin fabric of my pantyhose. I spread my legs wider, and his fingers brushed against my growing erection held close against me by the pantyhose. A shudder ran through my body and a small gasp escaped my lips. He paused and asked if he could remove my skirt. "Yes," I responded, "but leave the hose and shoes on. I think you'll like it."
Leaning back onto the couch and shifting my body slightly gave him the leverage to pull the skirt down. With a quick tug, he pulled it down and off, tossing it to the floor next to the couch.
I was sitting there on the couch dressed in a black silk blouse, a lace bra stuffed with breast forms, a pair of sheer tan pantyhose, and black stiletto heels. His eyes were taking in the sight before him, and it was clear that the visual was pleasing him. He reached forward and ran his fingers over the smooth nylon encasing my legs.
"You like my legs, don't you?" I asked.
He nodded.
"Would you like to see them from another angle?"
He nodded.
"Lean back a bit, I want to kneel on the floor in front of you."
I slipped off the couch and, while on my knees, moved in front of him. A few quick motions of the wrist and his belt buckle and zipper were undone. He pushed up slightly off the couch as I pulled his pants and underwear down to his ankles. He was already hard. A clean shaven and stiff prick met my eyes. He was a good seven inches, cut, not too thick, and already oozing precum fluid. I figured it wouldn't take much to get him off.
I wrapped a hand around his shaft and slowly moved it up and down, using his precum fluid as lubricant.
"I love how smooth your cock feels," I said looking up into his eyes as I ran my fingers over the taut skin.
"And I love what you're doing with your hand now," he responded.
"Well, I hope you'll like this too."
With that I leaned in and wrapped my lips around his throbbing member. I let my tongue slide from the base of the shaft along the bottom to the tip. He moaned with pleasure, his eyes rolling back, and he leaned back onto the couch. I repeated the move a couple more times sliding his stiff prick in and out of my mouth. I'm not what you'd call an experienced cocksucker, but I do know what I like, and I tried to repeat some of the moves I remembered from the many blowjobs I'd gotten. I made sure let his cock slide in and out of my mouth gliding my tongue around the head as my hand slowly pumped his shaft in rhythm with my mouth. Keeping the pad of my thumb pointed up so that it rubbed the underside of the tip on each stroke, I looked up at him from my kneeling position, making eye contact as I continued to suck and pump his shaft. He seemed to enjoy this as he groaned and gripped the couch cushions.
As I predicted, he didn't last too long. After about thirty or forty strokes he stiffened up, gave a half grunt half shout, and shot his load. It wasn't a big load; not like you see porn films. The taste wasn't terrible either. It kind of reminded me of oysters on the half shell. I swallowed, smiled, brushed my blond wig hair back and looked at Anthony. He sat there with a contented, almost dreamy smile on his face.
"Did you like that?" I asked with a sheepish smile.
"That was great," he said with unvarnished enthusiasm.
Hmmm...not bad for a novice cocksucker I thought to myself. It had been fun, but I wanted more now. Getting up off my knees I grabbed him by the hand and as he gave me a puzzled look as I pulled him up off the sofa.
"Would you mind taking a few pictures of me?" I asked while handing him my phone. "I hate to admit it, but I'm a total picture whore."
"Sure," he replied, "How about over there on the chair?"
"Give me a second to freshen up my lipstick," I said as I moved to the bathroom mirror.
I thought about grabbing my missing skirt and putting it back on for the pictures but decided to pose in just my blouse, hose, and heels.
After snapping a few pics, I took the phone from his hand and started to lead him into the bedroom. As we walked toward the bed his eyes were riveted on my legs and ass in the shiny pantyhose.
The bedroom of the suite was bathed in the warm glow of candlelight. I'd taken the time to light some candles. Call me a sucker for romance, but I do love candlelight. And sex is always better in the warm glow of candles.
After leading him to the foot of the bed I worked to finish undressing him. His shoes, pants, shirt, underwear were all stripped away in short order and soon my internet friend stood before me naked. I was afraid my blowjob might have finished him for the evening but much to my pending enjoyment I saw he was still hard. Thank you, Viagra!
I was hard too. My stiff cock was clearly visible through the translucent fabric of the pantyhose as I removed his clothes.
I sat on the edge of the bed and crossed my legs while he stood naked front of me, his cock sticking out toward me at eye level. I reached out and slowly started stoking his meat again, enjoying the anticipation of what was about to happen.
"So, how do you want to do this?" I asked.
He looked at me with a questioning look.
"You didn't tell me when we were exchanging email messages, what do you prefer?"
"What do you mean?" he asked.
"Well," I responded, "you said you wanted me. So, do you want me on my knees? On my back? On my stomach? How do you want to do it?"
A look of revelation spread across his face, and I could tell he was realizing that we were going to fuck.
"Does it have to be only one position?" was his response.
I laughed at his answer.
"No, we can do more than one," I answered. "Just depends on how long you can last," I added with a sultry wink.
With that, he pulled me up off the bed, and we started making out again, our bodies pressed close together. His hands ran up and down my sides, paying special attention to my legs and ass, feeling the shape of my body through the nylon covering. Mine were busy as well. As we kissed and caressed each other, I felt his fingers start to trace a path down my back to my ass. He gave a little squeeze and then a more forceful push on my butt. I could tell what he was asking for, and I didn't want to disappoint.
"You want me on the bed?" I asked, a tremor of apprehension combined with excitement in my voice.
He nodded.
"You want me on my hands and knees so you can take me from behind?"
He nodded again.
"You do like to watch, don't you? You like seeing the nylons on my legs and the heels on my feet."
He nodded a third time.
The room had a full-length mirror facing the bed. A plan started to form in my head. I stepped to the side and turned my gaze toward the mirror.
"How about a nice view?" I asked.
I climbed up onto the bed, my body parallel to the headboard, getting onto my knees, back arched, and resting on my forearms. The mirror was directly across from me, and I could see him standing there staring at my pantyhose-covered ass.
I wiggled it a bit, and he grinned.
A thrill ran through me, feeling the cool air on my exposed skin and the intensity of his gaze. I watched his reflection as he approached, his eyes locked on the sight before him. My heart raced with anticipation, the feeling of being on display both exhilarating and nerve-wracking. I could sense his excitement, his movements becoming more deliberate and eager.
Standing behind me and next to the bed, he placed his hands on my hips, pulling me slightly towards him. The pressure of his grip sent shivers down my spine, heightening the sensation of vulnerability and desire. He leaned down and began to lightly kiss my lower back, ass, and backs of my legs, his brushing lips and hot breath tantalizing me through the silky nylon fabric. The moment stretched, a blend of tension and passion that seemed to fill the room.
"You're incredible," he murmured, his voice thick with lust. Standing straight again he used his fingers and traced a slow, deliberate path down my spine, each inch sending ripples of sensation through my body. When he reached my lower back, he applied gentle pressure, guiding me into a deeper arch.
I smiled, feeling a surge of confidence. This was exactly what I had hoped for, the fulfillment of fantasy that now felt all too real. I arched my back a little more, giving him an even better view, and let myself get lost in the moment, savoring every touch, every sensation. Every caress from him seemed to amplify my awareness of my own body, the silky feel of the pantyhose, the tightness of the bra, and the slight pressure of the heels grounding me in the moment. My mind raced with excitement and a hint of nervousness.
Looking up and catching his eyes in the mirror I said, "Come and get it."
Anthony climbed up onto the bed kneeling behind me. I could see his eyes wandering from my legs and feet up to my backside. He seemed enraptured by the sight and was having trouble deciding what part of me he wanted to touch the most. As he moved his hand over my smooth nylon covered thighs, ass, and hips I could feel the head of his cock brush up against my ass through the pantyhose. He was stroking himself and running the tip along the crack of my ass.
I gave him a look over my shoulder and whispered, "Come on, stop teasing. Rip a hole in my nylons and put it in."
He pulled the waistband of the hose down a bit and reached in to rip them open. He seemed to be having a bit of difficulty, so I reached back and using one of my pointy fake nails I pushed a small hole through the fabric. This was all the help he needed as he pulled a wide tear from the crotch up about halfway to the waistband completely exposing my ass.
I turned back around and resumed a position on my knees with my legs spread, back arched, down on my forearms, and exposed ass in the air.
He moved in behind me again and began to run his hands over my ass and along my legs. As he moved his hand over my thighs and hips, I could feel the head of his cock brush up against my exposed ass.
"There's a bottle of lube and condoms on the nightstand," I said. I had planned for every contingency.
He smiled and reached over to grab the bottle and a square packet. After a moment of preparation, he slid the rubber on, squirted a dollop of lube onto his member, and climbed onto the bed behind me.
As he moved into position and the head of his dick pressed up against my ass. I felt a brief moment of panic. I wasn't sure how I was going to react. What if it hurt? What if it hurt a lot? I'd done this a few times before, but it had been years since my last encounter with a man.
I felt the tip of his cock start to slide into me. There was a brief flash of pain, but it passed quickly. After that just a flush of excitement and feeling of fullness. Anthony took his time. He slowly began pushing his cock deeper into my ass. As the head of his dick passed through the sphincter, he gave a little sigh and continued to move his hips forward, slowly, gently until his cock was completely buried inside me. I looked up into the full length mirror against the bedroom wall. In the candlelight I could see Anthony kneeling on the bed behind me, his dick buried balls deep in my ass, his hands gripping my hips and his eyes glued on the sight before him.
He looked up and our eyes met in the mirror.
"Are you ready?" he asked.
"I'm ready."
With that he began slowly pulling his dick from my ass. When only the head was still in, he paused for a second, looking into the mirror, and then slowly pushed his cock back into me.
I groaned.
"Like that?" he asked.
"Mmmmm hmmm" was all I could manage.
"Me too."
He began a slow rhythm, his cock sliding in and out, his hands squeezing and rubbing my ass, his eyes alternating between my legs, the look on my face in the mirror, and the sight of his dick plunging in and out of my ass.
I closed my eyes and leaned my head down on the pillow, taking pleasure in the sensations of being dressed as a woman while a man ravaged me. I was enjoying this more than I thought I would. Focused, I savored the feel of the nylons encasing my legs, the slightly pinched feel of the heels on my feet, the caress of Anthonys hands along my ass and legs, the fullness of his cock sliding into and out of me. And the sounds were savored too. The rustling sound of my silk blouse, the squeak of the bed moving in synch to Anthony's pumping, and the dull slap of flesh on flesh as his abdomen came in contact with my ass.
I could hear his breath coming faster and his grip on my hips becoming more insistent.
"Are you getting close?" I asked, lifting my head up off the pillow to look at him in the mirror.
"Yes," was his breathless response, "but I want to change position."
"What do you have in mind?"
"Turn over. I want to see your eyes when I cum."
"Ok, but you have to pull out first."
With a reluctant sigh he pulled his slick cock from my ass and moved back to give me room.
I flipped over, careful not to catch the stiletto heels of the pumps on the sheets and, leaning on the pillow, looked up at Anthony. His cock was throbbing and pointing straight out from his body. It was sheathed in the condom, which was slick with the lube. I laid back onto the bed, stuffing a pillow under my ass. I raised my arms above my head and lifted my legs slightly to spread them wide. That was all the encouragement he needed. He moved between my legs and, grabbing my thighs, pulled me toward him.
He aimed his cock for my gaping asshole and plunged it deep. Once he was balls deep, he leaned forward and grasped my wrists to hold them above my head. Then he started out slow again, pressing all the way into me and drawing back till he had almost pulled completely out.
My cock, rock hard, was pressed against my stomach by the fabric of my pantyhose and while he fucked me his abdomen would brush against it giving intense shivers of sexual excitement.
As he continued to fuck me his pace increased. I started to get into it and wrapped my nylon covered legs around him. When he released his grip on my wrists I grabbed his ass with both hands, digging my nails into his cheeks and pulling him deep into me on each thrust. When we first started to fuck, he had been looking into my eyes, now his eyes were half closed, and he had a faint sheen of sweat on his forehead. I knew that look, I'd had it plenty of times myself, and it meant he was getting close to orgasm. I decided to speed things along a bit.
I started whispering to him.
"Come on, fuck me. Fuck me hard. Fill me up with that big cock."
"Oh yeah, oh god, yes," was his response.
"You like fucking my tight ass, don't you?"
"Yes, yes!"
"I want to feel you cum inside me," I whispered into his ear.
His pace picked up and his breathing became ragged as he rammed his cock deep into me. Anthony gasped and went ridged as I felt his cock expand and stiffen. I held him in me, my nylon covered legs around naked body as he shot his load.
He groaned, shuddered, and collapsed on top of me.
I lay there under him, holding him, enjoying the post-coital glow and the feeling of his still semi-hard cock in my ass. We lay together like that for a few moments. His breathing was hard against my ear. I savored the moment, my legs still wrapped around his body, my hands still on his ass, his cock still inside me. I'd done it. I'd let a man fuck me while I was dressed again. And I enjoyed it.
We lay there, our breathing slowing, for what seemed like a long time. Finally, he lifted himself up, his softening dick sliding from my ass.
"That was great," he said as he lay down beside me.
"Glad you liked it," was my response.
As Anthony pulled the used condom from his deflated meat, I rolled off the bed. As he watched I made a show of stretching, my legs apart, high heels planted, and arms up, arching my back.
"God, I'm horny," I said, "You've gotten off twice and I haven't even gotten off once. That's no way to treat a lady."
He smiled and looked at me, then his eyes wandered down the length of my body. I could see he was looking at my cock, which was bulging at the front of my pantyhose.
"Well, why don't you take care of that?" he said.
I laughed.
"Oh, I will," was my reply.
With that, I started walking toward the other room in the hotel suite, my heels clicking on the tile floor of the short hall, my hips swaying seductively. I could feel his eyes on me, a gaze that was both heavy and thrilling. When I reached the door, I stopped and turned slightly, giving him a playful wink.
"Are you coming?" I asked, my voice a blend of teasing and invitation.
"You mean you want me to?" he replied, a hint of surprise and eagerness in his tone.
"Of course. I'll need your help."
With a deliberate sway of my hips, I walked into the living area of the suite and sat down on the couch. I positioned myself, one leg on the floor and the other raised so that the stiletto heel rested on the edge of the couch. Leaning back, I arched my back, making sure my fake breasts jutted out provocatively. My head rested against the back of the couch; my blonde hair fanned out like a halo.
"Now, are you coming?" I repeated, my eyes locking onto his as he rose from the bed and walked towards me, his gaze never leaving my body.
"What did you have in mind?" he asked, his voice thick with curiosity and desire.
"Come here and sit next to me," I instructed, patting the space beside me.
He walked over and sat down, his eyes roaming over me with an intensity that sent shivers down my spine. I began to caress my raised thigh with one hand, the other hand slowly moving down to run over the bulge in my pantyhose. My fake nails tickled my throbbing shaft through the fabric, sending waves of sensation coursing through me.
"You've gotten me all worked up," I said, my voice low and husky.
"Yes, I have," he responded, a satisfied smirk playing on his lips.
"Do you like the look of this?" I asked, my fingers continuing their teasing movements over the bulge.
"It's hot," he said, his voice barely a whisper, thick with arousal.
"Good. I want you to watch this. Watch me get off."
"Okay," he replied, his eyes gleaming with anticipation. "Do it."
I could see the smile on his face, a mixture of excitement and lust.
I closed my eyes for a moment, allowing myself to fully immerse in the sensations. My hand moved with more purpose, each stroke sending jolts of pleasure through me. The friction of the nylons against my skin, the pressure building within me, and the intense gaze of my partner created a heady mix that pushed me closer to the edge.
As my breathing grew heavier and my movements more urgent, I opened my eyes to see his reaction. His eyes were glued to my every move, his lips parted slightly as he watched me with rapt attention. The room was filled with the sound of our breathing and the soft rustle of fabric.
"It feels so good," I said.
I rubbed my cock faster and harder and could see his eyes moving back and forth between the bulge and my face.
The tension built; a coiled spring ready to snap. With one final, deliberate stroke, I felt the release building, a wave of pleasure washing over me, leaving me breathless and trembling. Then, with a shudder, I felt myself cum. My body tensed and jerked. I squeezed my cock, my hips bucking, as I shot my load into the pantyhose.
"Fuck. Yes. Oh."
I lay back, a sheen of sweat on my forehead and a big grin on my face.
"Did you like that?" I asked in a breathless whisper.
Anthony nodded, "Yes."
I reached down and ran my fingers over the now soggy front of the pantyhose and scooped up a gob of my cum.
"Open wide," I said as I moved my fingers to his mouth.
He hesitated for a moment, then opened his lips and I stuck my cum covered fingers into his mouth.
"Lick them clean."
He did.
"See, not bad."
He nodded his agreement.
I leaned back, catching my breath, and looked at him, a satisfied smile playing on my lips. "Was that good for you?" I asked, my voice a whisper.
He nodded, his eyes still locked onto me, a look of pure admiration and satisfaction on his face. "It was incredible," he said, his voice full of awe.
We sat for a moment in silence. The only sound that of my rapid breathing returning to normal after a mind blowing orgasm. I noted with some amazement that I hadn't cum that hard in a very long time. Seems exhibitionism agreed with me. I closed my eyes and basked in the post orgasm glow.
My reverie was interrupted by the sound of Anthony getting up from the couch. Opening my eyes, I saw him gathering up his clothes.
"I need to get back soon," he said. "Need to pick up my wife at the airport later today.
As Anthony finished dressing, I reached down to pick up my skirt, which was still lying on the floor where it had been tossed earlier. For some reason, I was feeling a bit exposed and vulnerable after my erotic performance. I pulled the skirt back up and into place and sat back down on the couch, crossing my legs.
I could tell Anthony was eager to get going, maybe a nagging conscience about cheating on his wife with a guy in a dress? As he started moving toward the door, I rose from the couch and followed him.
Pausing at the door he turned to look at me, giving me a once over with his eyes.
"You look like you had a fun night," he said with a playful smile.
Another mirror hung on the wall of the main room in the suite. What I saw in the reflection was an attractive middle aged woman, hair disheveled, clothing wrinkled, makeup smeared, and a large run down both legs of her pantyhose.
"I think the phrase is rode hard and put up wet," I responded with smirk.
We stood looking at each other for a moment. Then Anthony said, "I had fun tonight. Maybe we can do it again sometime?"
I thought about the possibility for a moment. It had been fun. Anthony had proven himself to be a capable, respectful, and considerate erotic partner. I didn't know what his vanilla life was like, but it seemed as though our lustful fling had given him something he needed. I couldn't see myself doing this on a regular basis, the possibility of another tryst with him was not out of the question.
"Maybe we can," I responded.
He left without saying another word. The door clicked shut behind him, leaving me alone in the suddenly too-quiet room. I sat back down on the couch, the events of the night swirling in my mind. A mix of satisfaction and a little sadness settled over me. Satisfaction from the physical release and connection, fleeting as it was, and sadness from the realization it was done now.
I glanced around the room, aware of the silence. The discarded wine and whiskey glasses, the crumpled sheets and tossed pillows on the bed, and the lingering scent of cologne and sex in the air—all reminders of the transient encounter
With a deep breath, I got up and began to tidy the room. I thought about kicking off my heels but part of me still wanted to play the role. The ritual of cleaning up helped ground me, piece by piece, until the room looked almost as if nothing had happened.
It was about two in the morning, too late to get changed and head to a bar. So, I walked back into the candlelit bedroom of the suite and sat down on the edge of the bed facing the full length mirror.
The reflection was the same as I saw in the other room. Staring back at me was what appeared to be an attractive woman, lit by candlelight, her blonde hair disheveled, her makeup smudged, her tan nylons torn.
Sitting there I replayed the events of the evening in my mind. The memories of sights and sensations from our carnal encounter brought the stirring of another erection. Laying down on the bed I shimmied out of my skirt and peeled my still sticky pantyhose down to my hips. With one leg up, stiletto heel dug into the bed, and the other leg extended I started to stroke my growing cock again. Turning to watch myself in the full length mirror next to the bed, I continued to stroke myself to another shuddering climax.
As I drifted off to sleep, I thought to myself that I needed to do this again sometime soon.