Dinner Date Dilemma

Dinner Date Dilemma

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 2015. I was in my late 40s, still exploring my fascination with crossdressing. I've always considered myself a typical crossdressing man — tall, slim, professional — nothing in my appearance hinted at my private enjoyment of slipping into a dress and heels. When fully dressed, I've often been told I look rather attractive. I'm not sure I've ever been entirely passable, but the compliments I've received I felt pretty good about the image I presented when dressed.

I identify as heterosexual, but when I'm fully "en femme," I like to lose myself in the role. In that role, I'm open to the possibility of erotic encounters with men. I'm not sure if that's unusual; it's just something that has evolved, a slow bloom of curiosity and desire.

My most recent experiences were with a man named Anthony, whom I met through an online dating service catering to those with non-traditional sexual interests. Anthony was trapped in a sexless marriage with a woman more devoted to her career than to him. His frustration had driven him online, seeking excitement to fill the void. We had met twice before over the past year, and each time had been intensely erotic, resulting in new experiences for me. Our last encounter had been particularly intense, leaving me trembling in the aftermath.

It had been several months since that last encounter. The daily grind of work and the demands of everyday life had kept me occupied, but the desire for another adventure in a skirt and heels began to stir within me once more. I found myself daydreaming about the possibility of seeing Anthony again. I hadn't heard from him since our last meeting, and the uncertainty of whether he would even be interested gave a strange mix of hope and apprehension.

Finally, unable to resist the pull any longer, I took the leap and sent him an email, the anticipation building with each word. When his reply came the next day, I felt a small thrill of anticipation as I read his words.

"Hey Jenette, Yes, I'm up for meeting again. Are you interested in doing something a bit different?"

What could he possibly mean by "a bit different?" My curiosity piqued, I quickly replied, asking him to elaborate. I waited for his response, my mind running through possibilities. When his answer came less than an hour later, it caught me completely off guard.

"Great. I was thinking we could have dinner together. Sort of like a normal date. Not that I'm complaining or anything — meeting in hotel rooms for sex is awesome. But it might be nice to spend some time talking and getting to know each other."

A dinner date? The idea was so unexpected it took a moment for me to process what he was asking for. I loved playing a female role when dressed, but the thought of doing something as conventional as going out on a "date" seemed both thrilling and terrifying. My mind raced with conflicting emotions. Could I really pull this off? The thought of venturing out during the day, into the public eye, was daunting. I'd never been entirely confident in my ability to pass as a woman in broad daylight, where every detail could be scrutinized.

I typed out a reply, expressing my reservations and fears. I worried he might lose interest or be disappointed by my hesitation. But when his response arrived almost immediately, it calmed some of my reservations. "You look beautiful. I'm sure it won't be a problem," he wrote.

It was a sweet compliment, one that made me wonder if he truly meant it or if he was simply trying to persuade me. I was about to decline his suggestion, but the more I thought about it, the more the idea intrigued me. I was still unsure of what he was suggesting.

Anthony had mentioned before that his marriage wasn't going well, and perhaps this desire for a more traditional interaction was fulfilling an emotional need for him. I recalled a phrase I had heard on a television show about escorts and their johns. It was called the "full girlfriend experience". As I recalled, the concept was to add an emotional connection between the sex worker and their client, thereby enhancing the sexual experience. Was that what he was seeking? Could I really give him the full girlfriend experience?

With these thoughts swirling around in my mind, I took a deep breath and wrote back, letting him know that I was game to give it a try. I hit send, a mixture of excitement and nerves coursing through me. This was new, uncharted territory, and I couldn't help but feel a thrill at the prospect of what lay ahead.

"Okay," I typed, my fingers hovering over the keys for a moment before hitting send. "But you'll have to be patient with me. Let's start with something easy. How about a small restaurant?"

"You got it! We can work up to bigger venues," came his quick reply.

What did he mean by "work up to bigger venues?" Was he envisioning us going out together more often, dressing up and stepping into public spaces that felt even more exposed? The idea of dressing up for him again, but in a public setting, sent a shiver of both exhilaration and trepidation down my spine. My mind raced, wondering what exactly he had in mind for us and just how far this might go.

"When?" I asked.

"How about next Saturday? I could pick you up."

A fresh wave of anxiety washed over me. I've always kept my regular vanilla life and my crossdressing life distinctly separate, never allowing them to overlap in a way that might expose me. Only once had I let someone from my crossdressing world come to my home, and that had been years ago. Now, in a new house, the idea of giving Anthony my address felt like a huge leap of trust.

And then there was the matter of riding in his car. Whenever I ventured out in a skirt and heels, I always drove myself, carrying a bag with male clothes in the event I needed to make a quick change. It was my safety net. Riding with him would mean relinquishing that control, that safety.

But Anthony had been polite and reliable in our previous encounters, and the more I thought about it, the more the concept of trying out the "girlfriend" role intrigued me. What would it be like to fully embrace that part of myself with someone who seemed genuinely interested in exploring it with me?

Taking a deep breath, I took the plunge and replied, "Sure. Let's give it a shot." I added my street address, a fresh surge of anxiety hitting me as I pressed send.

"Cool, I'll email you with more details," came his quick response.

In the days that followed, we exchanged more messages, ironing out the details of our upcoming outing. He asked what kind of food I liked, and when he suggested a small Italian restaurant not far from my house, I looked it up online. The place had a cozy charm, an old house converted into a restaurant nestled near one of the area's many forest preserves. It seemed intimate, a place where we could slip into our own little world.

When I asked Anthony what he wanted me to wear, his reply made me smile. "Dress sexy. Something that shows off your legs. You have amazing style, so I'm sure you'll look great." His compliment sent a warm flush through me. It's nice to be appreciated no matter what the reason.

As the date approached, though, nervousness began to creep in. The thought of being seen by the general public in a skirt and heels was intimidating, yet I couldn't deny the growing arousal that came with the idea. I'd been out dressed before, but always in the relative safety of bars or clubs that catered to crossdressers and those who ventured outside the social norms. This, however, was different. Going to a regular restaurant in daylight, where anyone could see me, where ridicule and discovery were real possibilities — this was a significant leap. The tension between fear and excitement wound tighter inside me as the day drew closer.

I was also feeling uneasy about what Anthony might be looking for. Our previous encounters, though intensely personal, had always been clearly defined. I dressed up, we met, we fucked, and then we parted ways. It was straightforward, no strings attached. For me, crossdressing was an escape, an erotic hobby where emotions, for the most part, were kept at bay. But now, with Anthony's suggestion of a "date," things felt different.

As I replayed his request in my mind, doubts began to surface. Was he seeking a deeper, more romantic connection? Did he see me as some kind of emotional or romantic surrogate to fill the void left by his distant wife? The thought made my chest tighten with anxiety. Or perhaps I was overthinking it. Maybe all Anthony wanted was to role-play a bit of seduction, to add a new layer to our encounters. That idea, I'll admit, was more appealing. The thought of being seduced while fully immersed in my feminine role sent a thrill of anticipation through me. Whatever the case, I was about to find out.

Finally, the day of our outing arrived. I spent the morning anxiously rummaging through my wardrobe, trying to find the perfect outfit. Most of my feminine wardrobe leaned heavily toward the slutty side, and I found myself at a loss for something that would be both sexy and appropriate for a dinner date. Anthony had specifically asked for something that would show off my legs, but I didn't want to dress in a way that would draw too much attention to myself.

I pulled out a little black dress with sheer sleeves and a high neckline, running my fingers over the soft fabric. I had worn it on an earlier adventure, and the memory of that night brought a mischievous smile to my lips. Thankfully, the cum stains from that encounter had come out during dry cleaning, and the dress looked as good as new. But as I held it up to the mirror, I hesitated. It was a stunning dress, but it seemed more suited for a nightclub than a quiet dinner date. I wanted to look sexy, but not too over the top.

I felt a wave of frustration bubbling up as I sifted through my options. The pressure of making the right choice was getting to me. Every outfit seemed either too revealing or not sexy enough. The thought of showing up in something inappropriate made my stomach churn with nerves. But I also didn't want to disappoint Anthony. I wanted to look my best for him, to play the role he envisioned, while still feeling comfortable in my own skin.

After much deliberation, I finally settled on a simple black leather mini skirt that hugged my hips and ended mid-thigh. The leather was soft yet firm, clinging to my body in a way that felt both comforting and daring. The high waist gave it a sleek look, and the thickness of the material provided some peace of mind, smoothing out any unsightly bulges if my tucking came loose.

Next, I chose a brown ribbed turtleneck. The fabric was soft against my skin, clinging just enough to accentuate my curves without feeling too tight. It offered a sense of security, wrapping me in warmth and confidence. I ran my hands over the material, feeling the slight ridges of the ribbed texture beneath my fingertips.

Then came the shoes. I stood before my closet, gazing at the collection of heels I'd accumulated over the years. Each pair held a memory, a story of a night out or a secret rendezvous. But tonight wasn't for a club date or a tryst in a cheap hotel room, so I dismissed some of the more outrageous heels, opting for something that would be sexy yet understated. My eyes fell on a pair of black leather high-heeled boots I had found a few weeks earlier. The boots reached just over my knees, the leather smooth and supple. They were undeniably sexy, but not so much that they screamed for attention. And since it was early autumn, they were perfectly in season. The boots paired effortlessly with the leather mini skirt, creating a look that was both confident and alluring.

For underneath, I selected more traditional undergarments. I had recently ordered a matching bra and panty set online — a soft brown color with black lace trim that complemented the darker tones of my outerwear. The bra was small, just a B cup, and with some inserts, it gave me just the right amount of shape without being too conspicuous. I then opted for a pair of simple taupe-colored pantyhose. The material was soft and sheer, like a second skin. I considered stockings — either the stay-up kind or the ones that required garters. Anthony had previously commented on how sexy my stocking-clad legs were, and the memory made me smile. But pantyhose felt more appropriate for the evening, given our plans for a public dinner.

I decided to forgo the waist cincher for the night. My recent efforts in the gym had paid off, and combined with small adjustments to my diet, I had managed to lose some weight and tone up. I was secretly eager to see Anthony's reaction, to see if he noticed the subtle differences.

The final touch was a long, straight-haired wig in a medium brown color that hung well past my shoulders. The hair was silky and smooth, framing my face perfectly, softening my features and completing the look I was aiming for.

I laid all the items out on my bed, the soft white comforter providing the perfect backdrop for the garments. I took a step back to admire the ensemble — the combination of leather, fabric, and color presented a polished yet subtly seductive image. I felt a rush of satisfaction, knowing that I had chosen well. This outfit would work — sexy, but not too flashy. With a deep breath, I turned and headed into the bathroom, ready to begin the transformation that would prepare me for the evening ahead.

I started with a long, very hot bath, hoping to soak away any lingering concerns. As I eased myself into the water, the heat enveloped me, caressing my skin and melting away the tension that had built up throughout the day. The bath's warmth enveloped me like a cocoon. It was a perfect place for letting go of the last vestiges of doubt. With each passing minute, my anxiety slowly dissipated. The steam rose around me, blurring the edges of reality and drawing me deeper into my own thoughts.

After a while, I reached for the razor, carefully lathering up. The ritual of shaving — the slow, deliberate strokes of the razor against my skin — felt almost meditative. With each pass, it was as though I was shedding not just hair, but layers of the everyday persona I wore. By the time I finished, my skin was smooth and soft, and I felt more in tune with the image I was about to create. Stepping out of the bath, I dried off with a fluffy towel and applied a fragrant moisturizer across my body, leaving me with an alluring scent.

Next came the makeup. I placed my short hair under a net, carefully tucking away every strand, and began the meticulous process of applying foundation. With each brushstroke, I felt myself gradually slipping into the character I wanted to embody for the night. The shading added depth to my features, the eyeliner and lashes accentuated the shape of my eyes, and the lipstick brought a color that made my lips look full and inviting. It was a slow, deliberate transformation, each step bringing me closer to the version of myself I wanted to present — self-assured, attractive, and feminine.

Once my makeup was done, I reached for the wig. The shoulder-length strands of medium brown hair were soft and silky, and as I secured it with bobby pins, I felt a sense of completion. The wig framed my face perfectly, softening my features and adding the final touch to my transformation. I gave it a gentle shake to ensure it stayed in place. Satisfied, I smiled at the reflection in the mirror. As I looked at the woman in the mirror, I couldn't help but wonder if this was the real me, or just another layer of the identity I've carefully crafted over the years.

As a last-minute thought, I decided to brush a quick coat of polish onto my nails. My nails weren't long, but the glossy finish added an everyday feminine touch — a small but significant detail that completed the look. I wiggled my fingers, watching the light catch the shine of the polish, feeling a sense of authenticity in my appearance. Everything was coming together, and with each step, I felt more assured, more ready for the evening that awaited me.

I looked at my reflection in the mirror. Staring back at me was a confident, beautiful woman. She was older but still radiated an undeniable attractiveness, with a hint of that MILFish allure. The makeup and wig had transformed my features, and for a moment, I marveled at the transformation, always astonished at how a bit of paint and padding could completely alter my appearance. With a nod of satisfaction, I moved back into the bedroom to begin dressing.

First came the bra and panty set. The satiny brown fabric with black lace overlays was both elegant and enticing. I slipped the bra over my chest, adjusting it until the small inserts nestled perfectly, giving just enough lift. The matching panties were next, snug enough to hold my "equipment" securely in place, the fabric smooth and comforting against my freshly shaved skin.

Then, it was time for the pantyhose. As I pulled the hose up my legs, the silky texture of the nylon glided over my skin, each movement sending tingles of pleasure up my spine. There's something incredibly erotic about the feeling of fresh pantyhose on smooth, freshly shaved legs — the way the fabric hugs every curve, the slight resistance as it stretches into place. A flush of excitement coursed through me as I slid the hose into position, savoring the way it made my legs look and feel.

I glanced at the full-length mirror on the wall of my bedroom and saw a trim woman with long brown hair standing in her underwear, her back to the mirror, her gaze thrown coyly over her shoulder. The sight made me pause. I knew it was a bit narcissistic, but damn, the woman in the mirror was sexy. The combination of makeup, hose, and lingerie worked together perfectly, and the sensuality of it all made my cock twitch in response. For a brief moment, I considered laying down on the bed and indulging in some self-pleasure, but I dismissed the thought quickly. I wanted to be "fully charged" for my evening with Anthony. Dinner was just the prelude; I knew there was a very good chance we would end up fucking afterward.

Glancing at the clock, I decided to finish getting dressed. I reached for the top — a ribbed turtleneck in a warm brown that complemented the color of my hair. The fabric clung to my body, revealing a flat tummy, a testament to my recent diet and exercise efforts. Tight and form-fitting, the top accentuated the bra underneath, creating the illusion of small, firm breasts. I slid it over my head, carefully, so as not to disturb the wig. The soft fabric brushed against my skin. The sleeves were long, and the bottom hugged my waist perfectly.

Finally, it was time for the black leather mini skirt. I pulled it up over my pantyhose-covered legs, and the soft hiss of the leather as it slid up my thighs was intoxicating. The sensation of the cool leather against the smooth nylon was almost too much, sending waves of pleasure through me as I adjusted it into place. The skirt fit like a glove, highlighting my ass in a way that was both flattering and undeniably sexy. I tucked the top into the high waist of the skirt and zipped up the back, the sound of the zipper a satisfying note in my transformation.

Next were the boots. They were tall, coming up over the knee and made of supple black leather that felt smooth and luxurious under my fingertips. The heels were five inches with a one-inch platform — high enough to give a "come fuck me" vibe yet balanced enough to make walking comfortable. The rounded toe made them more practical, unlike the pointed toe heels that often left my feet aching after just a short while. Those were more suited for wearing in bed than for walking through the streets.

As I tugged the boots up past my knees, the leather hugged my legs, the fit snug but comfortable. The sensation of the cool leather against my skin, especially where it brushed against the smooth nylon of my pantyhose, sent a delightful sensation through me. The way the boots paired with the skirt was perfect, the heels lifting me just enough to make my ass look even more accentuated and alluring.

I took a moment to admire myself in the full-length mirror. The woman looking back at me was polished, sexy, and self-assured. A small smile tugged at the corners of my lips — this was exactly the look I was going for.

To finish the ensemble, I added some basic costume jewelry. I draped a scarf around my neck, the soft fabric adding a layer of warmth and style and grabbed a small purse that was just big enough to hold my essentials: lipstick, wallet, and keys. At the last minute, I tossed an elastic hair tie into the purse, just in case I needed to pull my wig back into a ponytail later in the evening.

With everything in place, I returned to the bathroom for one final look in the mirror. It never ceased to amaze me how different I looked when fully dressed — how the combination of padding, makeup, and the right clothing could transform me so completely. It was truly mind-blowing. The woman staring back at me was mature and attractive. I just hoped the rest of the world would see the same thing.

I took a few moments to adjust my clothing, smoothing out any wrinkles, and made a few minor tweaks to my hair, making sure everything was just right. Finally satisfied with my appearance, I took a deep breath, feeling the anticipation build in my chest. I was ready.

Stepping out of the bathroom, I moved into the living room, the sound of my heels clicking softly against the floor. I settled onto the couch, crossing my legs. I smoothed out my skirt, my fingers trembling slightly with a mix of excitement and nerves. My heart was racing, my mind swirling with thoughts of what the evening might bring.

Sitting on my sofa, my mind swirled with a mix of anticipation and no small amount of worry. My chest felt tight, every beat echoing in my ears, reminding me that I was about to take the biggest risk of my crossdressing life. Was I really ready to take this step? The anxiety gnawed at me, thoughts spinning. What if I was outed at the restaurant? What if Anthony didn't like what he saw? I felt another flush of anxious energy, the cool leather of the sofa beneath me doing little to calm my nerves.

I was lost in these spiraling thoughts when the doorbell rang, the sound startling me out of my reverie. Taking a deep breath, I forced myself to stand, feeling the slight give of the leather boots against my calves as I rose. My legs felt a bit shaky, but I steadied myself, the familiar click of my heels on the floor grounding me as I walked to the door.

I opened the door, and there he was. He was dressed sharply, just as I had hoped. He wore a crisp shirt, and dark jeans tailored perfectly to his frame. His polished look was a calming contrast to the storm of nerves I was feeling. I smiled, the expression coming more naturally than I expected, and extended my hand.

"Hi, glad you could make it," I said, trying to keep my voice steady, offering him a genuine smile despite the butterflies in my stomach.

He took my hand, his grip warm and firm, and stepped inside. His presence immediately made the room feel smaller, more intimate.

"Wow! You look fantastic!" he said, his voice filled with genuine admiration. Then he lifted my hand to his lips and kissed the back of it.

I smiled, a warmth spreading through me that was both unexpected and welcome. His compliment and gesture sent a wave of relief through me, easing some of the tension in my chest.

"Thank you. You look nice too. And always such a gentleman," I replied, already slipping into the role, yet touched by the sincerity in his tone and action.

He paused, his eyes traveling slowly from my boots, up my legs, taking in every detail of the outfit I had so carefully chosen. His gaze was appreciative, almost hungry, and I could feel my cheeks growing warm under his scrutiny.

"Honestly, you look really great," he said, his voice lower, more intimate.

"Thank you," I repeated, feeling the heat of a blush creeping up my neck. I wasn't sure what else to say.

He stepped forward, closing the distance between us, and leaned in to give me a light kiss on the cheek. In my heels I was taller than Anthony, so he had to lift his head slightly to meet my cheek. I helped by angling my head down slightly to meet his lips, the brief contact sending a small jolt of electricity through me. I could feel the warmth of his breath as he pulled back, leaving a lingering sense of intimacy in the air.

"Shall we get going?" he asked, his voice smooth and confident, as if what we were about to do were the most natural thing in the world.

I nodded, and we stepped out onto the front porch of my house. I glanced around nervously, my heart quickening with each second, worried that one of my neighbors might catch sight of what appeared to be a strange man and woman leaving my home. The thought of having to explain to a neighbor that I like to dress up in women's clothing and occasionally have sex with men would be awkward at best and sent a wave of anxiety through me.

Anthony escorted me to his car, his hand gently guiding me by the small of my back. The pressure of his touch was reassuring, steadying me as we walked. I recognized the vehicle from our last encounter — a small, sensible Volkswagen. It was clean and well cared for, just like I remembered. As we approached the passenger side, he moved ahead to open the door for me, another chivalrous gesture that I appreciated, especially considering the challenge of getting into a car in heels and a mini skirt.

I focused on keeping my legs together. The heels added a layer of complexity, the tight leather skirt restricted my movements adding more difficulty. I concentrated on maintaining my balance as I lowered myself into the seat. The cool fabric of the car seat brushed against the back of my thighs, sending a subtle shiver up my legs.

Anthony slid into the driver's seat and started the engine, the quiet purr of the motor filling the silence between us. As he backed out of the driveway, I caught him sneaking a few quick glances in my direction. His gaze lingered on my legs, admiring the smooth, nylon-clad skin exposed between the hem of my skirt and the top of the boots. A small thrill ran through me at his attention.

We rode in silence, the only sound the steady hum of the tires on the road. I took a moment to revel in the sensations surrounding me. Here I was, sitting in the passenger seat of a man's car, fully dressed and made up as a woman, about to go out on a dinner "date" at a normal restaurant. This was something so utterly outside of my comfort zone. The reality of the situation was both exhilarating and terrifying, the duality of my emotions playing out in the pit of my stomach.

I stole small glances at my reflection in the glass of the passenger window — a pair of sparkling blue eyes, framed by thick, smoky lashes, stared back at me. The transformation was striking, and I found myself captivated by the person staring back at me in the reflection. The leather skirt, which had ridden up slightly during the drive, exposed more of my nylon-covered thighs. The tightness of the skirt against my waist was a constant reminder of the effort I'd put into my appearance. My high-heeled boots pinched a bit, but not uncomfortably so — just enough to remind me of the feminine allure they added to the ensemble. As the car moved down the road, my nylon-covered knees brushed together with each turn, the sensation deliciously accentuating the moment.

As we drove, my nerves slowly began to unwind, though the tension still clung to me like a second skin. I realized I had been holding my breath, my chest tight with anxiety, and let out a long, slow exhale, feeling a slight release as the air rushed from my lungs. Anthony noticed, his hand moving from the steering wheel to rest gently on my leg. The warmth of his touch seeped through the nylon, sending a small but electrifying tingle through me, grounding me in the moment.

"Hey, don't be nervous. It's just me," he said, his voice calm and reassuring. "There's no pressure here. We can just go and have dinner. If you're uncomfortable, we can leave."

His words were comforting, and I found myself glancing over at him, offering a small, appreciative smile. "Thanks. It's just, well, this is a big step for me. I've never really done anything like this before."

He nodded, understanding clear in his eyes. "Well, it's a big step for me too. You're the first crossdresser I've ever dated," he said with a smile that was both playful and sincere.

"Dated?" The word slipped out before I could stop it, the sharpness in my voice betraying my surprise.

"Yeah. We are on a date, aren't we?" he asked, his tone light but with an underlying seriousness.

I felt my mouth go dry, a wave of uncertainty washing over me. Why was I so unnerved by the idea of being on a "date" with him? It was just another bit of role-playing, right? But something about the way he said it made it feel more real, more significant.

"Um, yes, this is me... on a date... with you," I replied, my fingers fidgeting nervously with the strap of my purse, my eyes flicking between him and the road ahead.

"And you look absolutely amazing," he said, his voice dropping to a more intimate tone as he took his eyes off the road for a moment to give me a lingering, lustful look.

"Really?" The word came out softer than I intended, a mix of surprise and pleasure lacing my voice.

"Yes, really," he affirmed, his tone shifting to something more serious, more genuine.

His words made me feel better, a warm sensation spreading through my chest. I relaxed into the seat, the fabric cool against my back, the tension in my shoulders easing slightly.

"Okay, let's do this. Take me on a date," I said with a playful smile, using my fingers to make air quotes around the last word.

Anthony smiled back, his hand still resting on my leg. He gave my thigh a gentle squeeze, his fingers brushing lightly up and down the nylon-covered skin. His touch sent a jolt through me, a mix of excitement and arousal. I felt a twitch in my panties, a physical response that was both thrilling and slightly embarrassing.

The ride wasn't long, but it felt significant, each moment charged with anticipation. Soon, Anthony pulled the car up in front of the small restaurant and put the car into park, signaling the start of an evening that I knew would be unlike any other.

"Here we are," Anthony said, his voice cutting through the quiet serenity of the setting.

I looked around, taking in the scene before me. The small house-turned-restaurant looked just like the images I had seen online. It sat back from the road, nestled among heavy trees, with farm fields stretching out across the road in gentle, rolling hills. The light from the late afternoon sun cast a warm, golden glow over everything, giving the place a tranquil, almost ethereal atmosphere.

Anthony got out of the car first, the door closing with a soft thud. I watched as he walked around to my side, his movements purposeful and smooth. He opened the passenger door and extended a hand, a small gesture that made me feel both cared for and appreciative.

I accepted his hand, grateful for the assist as I carefully stepped out of the car. The fabric of the seat slid against the back of my thighs as I moved, the tightness of my skirt requiring me to keep my legs together. I made sure to avoid hitting my head, feeling a rush of relief as I straightened up, the gentle pressure of his hand steadying me.

Standing by the car for a moment, I took a deep breath, letting the fresh, earthy scent of the countryside fill my lungs. The air was cool but comfortable, a light breeze playing across my legs and up my skirt, just slightly and teasing the strands of my hair. The crickets trilled softly from the nearby woods, their song blending with the distant rustle of leaves. The lowering sun suffused the scene in a serene, golden light, making everything feel calm, almost dreamlike.

"Would you take my picture?" I asked, reaching into my purse and pulling out my phone. I couldn't help but laugh at myself. Yes, I was a total picture whore, especially when dressed up, but the moment felt too perfect not to capture.

"Sure," Anthony replied with a warm smile, taking the phone from my hand. "Lean up against my car."

I complied with his request, positioning myself against the car, feeling the cool metal of the door against my back. I tried different poses, turning, shifting my weight from one foot to the other, tilting my head this way and that, all the while trying to look sexy. The leather of my skirt creaked softly with each movement, the sensation of the fabric against my skin adding a subtle thrill to the moment.

My first actual dinner date in a skirt and heels. After about a dozen shots, Anthony handed the phone back to me. I quickly scanned through the pictures, a mix of anticipation and amusement bubbling up inside me. I couldn't help but laugh out loud at some of the more awkward poses I had tried. No matter how hard I tried to look sexy for a photo, I always seemed to end up looking awkward or weird. But there were at least a couple of images that I liked — enough to satisfy my inner picture whore.

Stepping away from the car, I slipped the phone back into my purse. I nodded toward the restaurant, feeling a renewed sense of excitement for what the evening might bring.

Anthony placed his hand lightly on the small of my back as we walked toward the front door of the restaurant. The warmth of his touch seeped through the fabric of my top, creating a comforting sensation that spread across my skin. I found myself instinctively swaying my hips a bit more, feeling the gentle breeze play against my legs, and the rhythmic click of my heels on the parking lot pavement echoing with each step.

As we approached the entrance, I caught sight of a few people sitting at the bar inside. They glanced at us briefly before returning to their drinks, their disinterest a silent reassurance. No one seemed to notice or care that I was a man in a skirt and heels — a small victory that boosted my confidence. I felt a sense of relief wash over me. Score one for me!

We stepped inside, and the change in atmosphere was immediate. The air was warmer, filled with the rich aroma of food and the soft murmur of conversations. A hostess approached with a welcoming smile.

"Hello, table for two?" she asked, her voice pleasant and professional.

"Yes, please," Anthony replied with a nod.

"Right this way," she said, picking up two menus and leading us through the restaurant. As we walked, Anthony's hand returned to the small of my back, guiding me with a gentle pressure that made me feel both secure and subtly excited. His touch, combined with the muted lighting and the click of my heels on the wooden floor, heightened my awareness of every sensation.

The hostess gestured to a small table tucked away in a corner, a bit secluded from the main dining room. "I hope this is okay?" she asked, holding the menus out to us.

"It's perfect," Anthony replied, his voice warm with appreciation.

We were shown to the table, and I couldn't help but admire the setting. The intimate corner, dimly lit by a soft overhead light, felt cozy and private — perfect for our evening.

"Your waiter will be right with you," the hostess added before placing the menus on the table and leaving us alone.

As I moved to sit down, Anthony quickly stepped to my side and slid the chair out from the table for me. Another chivalrous gesture. I could get to like this. "Wow, chivalry is not dead," I whispered quietly, careful to keep my voice low, aware that the wrong pitch or tone could out me.

I sat down gracefully, tugging my skirt down and crossing my legs under the table. I placed my purse in my lap, the familiar weight of it grounding me in the moment. Anthony smiled, clearly pleased, and chose to sit beside me rather than across the table. His closeness added to the intimacy of the setting, making the space feel even more private.

I took a moment to look around, taking in the ambiance of the restaurant. The soft, warm lights cast a gentle glow over everything, adding to the cozy and intimate atmosphere. The quiet hum of conversation and the clinking of silverware created a soothing background, making the space feel welcoming and comfortable. Much to my amazement, no one gawked or stared.

"Do you like it?" Anthony asked, his voice soft and full of genuine curiosity.

"Yes, I do. It's quite nice," I replied, keeping my voice low so as not to be overheard by others.

"I'm glad," he said, his smile widening, a look of contentment settling on his face as he leaned slightly closer, his presence a comforting anchor in the unfamiliar setting.

At that moment, the waiter approached our table, his presence both polite and professional.

"Hello, my name is Mark, and I will be your server this evening. Can I start you off with something to drink?" he asked, his voice smooth and practiced.

I opened my mouth to reply, but the words caught in my throat. A wave of anxiety washed over me, tightening my chest. I hesitated, suddenly unsure of how my voice might be received in this setting. The fear of sounding out of place, of being noticed in a way I didn't want, gripped me, freezing the words before they could form.

Anthony, always attentive, noticed my hesitation and stepped in smoothly. "Could we have a bottle of wine, please? Red, if you have something nice," he said, his tone confident and calm.

"Absolutely, sir. Will there be anything else?" the waiter responded, his gaze flicking briefly to me before returning to Anthony.

"Not yet," Anthony replied, his grip on my hand reassuring and steady under the table.

"Very good. I'll bring the wine," the waiter said with a nod, before turning and walking away, leaving us alone once more.

As the waiter left, Anthony reached across the table and took my hand, his thumb brushing gently over my knuckles. The warmth of his touch was strange yet comforting, grounding me in the moment, but I could still feel the remnants of my earlier anxiety swirling in my chest.

"Are you alright? You look a little uneasy," he asked softly, concern evident in his eyes as he leaned in closer, his voice low and intimate.

I hesitated again, feeling a little vulnerable as I tried to explain. "Well, it's just that, well, I have a male voice."

Anthony's gaze softened, and he gave my hand a reassuring squeeze. "Don't worry, I've got this. I'll order for you," he said, his tone filled with gentle confidence that made me feel instantly more at ease.

"Really?" I asked, surprised by how much his offer reassured me, a small smile tugging at the corners of my lips.

"Yes, it's no problem," he replied, his eyes warm and kind as they held mine.

"Thank you," I said, my voice barely above a whisper, but the sincerity in my words was clear.

"Anything for a beautiful woman," he responded, his voice dropping into an intimate, seductive timbre.

I felt the telltale warmth of an aroused blush blossoming across my cheeks as Anthony's compliment washed over me. A fusion of bashful embarrassment and undeniable pleasure tingled within me. It had been so long since anyone had made me feel this singularly desirable.

Perhaps indulging in this "girlfriend experience" thing wouldn't be so unnerving after all, I mused as Anthony leaned back, his intense stare lingering over my transformed figure. There was an undisguised hunger, an unapologetic lust blazing in his eyes that paradoxically made me feel both deliciously exposed yet powerful.

"So, tell me a bit about yourself," he prodded in a conspiratorial murmur that cut through the din of the cozy eatery, demanding my undivided focus.

I instinctively shifted, feeling the soft caress of my skirt's leather snugly tightening around my thighs as I needlessly rearranged my crossed legs. My mind raced, frantically searching for a way to respond as Anthony's burning stare.

Leaning in even closer, Anthony's expression settled into one of thoughtful seriousness. "Are you seeing someone else? Other men besides me, I mean?"

The blunt forwardness of his question momentarily stunned me into silence. I blinked rapidly, struggling to process the unanticipated boldness of his words before eventually regaining my composure. "No, not at the moment," I admitted with a subtle shake of my head.

A self-satisfied smile played across Anthony's lips as he gave an approving nod, clearly pleased by my response. "Good, because I was thinking that we could keep meeting up like this. You know, have some fun together and, I don't know...maybe get to know each other a little better?"

There it was — that weighted phrase dripping with unspoken hints from the moment he proposed this unorthodox encounter: "dating." The concept felt alien, dangerous yet somehow enticing as it fell from Anthony's lips.

"Like...dating?" I echoed tentatively, giving voice to the idea I had previously only allowed to flicker around the periphery of my subconscious. Speaking it into existence lent the notion a heavy, sobering sense of actuality that terrified me.

"Exactly," Anthony affirmed steadily, holding my gaze with an intensity that bordered on mesmerizing as he nodded once more in confirmation.

I looked at him for a moment, the silence between us thick with unspoken thoughts. I could feel the warmth of his hand still resting on mine, it's warmth still strange yet strangely reassuring.

Sensing my hesitation, Anthony softened his tone. "Listen, if it's a problem for you, we can forget about it. I don't want to pressure you or anything."

"It's just... well, this is a first and very different for me," I admitted, my voice faltering slightly as I spoke. "No man has ever asked me out before, not like this anyway. I'm used to being the male and dating women. I like being a male and dating women, having sex with women. I only sometimes crossdress, maybe two or three times a year. My experiences with men have been limited to a few times while I was dressed, and those have always been quick hook ups or one-night stands at most," I said, a blooming awareness of how tawdry I sounded as the words came out of my mouth.

The weight of my candid admissions hung between us, I searched Anthony's face for any sign of judgment or revulsion. But to my surprise, he simply looked thoughtful and intrigued, eyebrows raised in what seemed like genuine fascination.

"Really?" he asked, clearly keen to understand more of my unfamiliar dynamic.

Pushing past my lingering trepidation, I gave a resolute nod. "Yes...really."

An intense quiet fell over our table as the ambient noise of the restaurant faded into the background. Anthony and I simply looked at each other, both seeming to weigh the unspoken opportunities now hanging in the air between us.

Anthony considered for a moment before asking, "So you're bisexual then?"

I shook my head slightly. "No, it's hard to fully explain. It's different. I'm not interested in men when I'm in male mode, which is most of the time. But there's something about dressing up as a woman and inhabiting that role that really turns me on."

He raised an inquisitive eyebrow. "Role?"

I felt my cheeks flush as I tried to articulate my desires. "Yes, I get incredibly aroused by fully embracing the persona of a desirable, sexy woman. It's not just about the sex itself, although I won't deny how much that aspect excites me."

"I've noticed," he said with a knowing tone and a leer.

"Well, yes. We did twice before..." I stammered, feeling a rising blush at the memories of our slightly torrid encounters, the decadent memories bringing an involuntary twitch in my panties. I could tell Anthony was enjoying my slightly flustered response.

Clearing my throat quietly, I continued, Anyway, in a way dressing up is an escape, a chance to become someone else for a short time. And as someone else, in the role of a desirable woman, I find it enjoyable to be with a man."

I paused for a breath before continuing in a lower tone. "There's a powerful thrill in being the object of desire and succumbing to that dynamic. And the clothing and feminization itself is a huge turn-on, the sensations, the way it makes me look and feel. It taps into fetish territory for me. In my male role, I like the women I date to dress like I'm dressed now."

"I see," Anthony murmured, his expression unreadable. "Interesting."

The weighted silence that followed seemed to stretch for an agonizing eternity. I found myself unable to hold his appraising stare, instead dropping my eyes as mortifying self-consciousness washed over me.

"I'm sorry. I probably sound like a freak," I said, my voice dropping as I pulled back my hand and looked down at the table. A warm flush spread across my cheeks, and I could feel my skin tingling with embarrassment and vulnerability. The confession made me feel exposed, like I was peeling back a layer of myself that I'd always kept hidden.

Anthony's face softened as he noticed my discomfort. He paused, seeming to realize he had pushed into very personal territory a bit too forcefully. The heavy silence between us felt suffocating, and I could feel knots forming in my stomach.

No one had ever directly asked me to explain these complicated desires and feelings in such stark terms before. Sure, I had talked about my enjoyment of wearing women's clothing and embracing a feminine, sexualized persona. But I had never been prodded to dissect and analyze the confusing, conflicted emotions underlying those urges.

It felt like being thrust into an extremely intimate therapy session without any warning or preparation. I was forced to confront vulnerable parts of myself that I had instinctively shied away from until now. I felt stripped bare and exposed under the scrutiny.

I looked up from the table but was unable to hold Anthony's gaze, I dropped my eyes back to the table, the painted nail of my finger tracing a pattern on the tablecloth mindlessly. The earlier easy rapport between us had taken an awkward turn, leaving an uncomfortable tension that I didn't know how to dispel.

Anthony took my hand again — a reassuring point of contact amidst the swirl of self-consciousness. I focused on the steady pressure of his fingers, using that physical anchor to calm the storm in my mind.

After what felt like an eternity, Anthony finally broke the strained silence in a low, soothing tone. "Hey, you don't sound like a freak at all. You're just being open about who you are, and I appreciate the honesty."

I looked up at him, surprised by the gentleness in his tone, and felt a small flicker of relief. Maybe this wasn't so bad after all.

"I'm just interested in learning more about you. We've had some great times together, and the sex — wow! I didn't really know much about you beyond our..." He paused for a moment, considering his choice of words, "Our physical encounters."

I fidgeted with the edge of the tablecloth, nervous and not really understanding why. Stuffing down my confusion and embarrassment, I looked up and managed a smile. "Thanks, I guess I'm not used to this whole small talk on a date thing while dressed up."

"Well, you're certainly the most exotic date I've ever had," he said with a soft smile. "And the most beautiful."

"Flatterer," I replied, feeling the tension in my shoulders ease, my voice taking on a lighter, more playful tone.

"It's true. You look amazing," he said, his tone shifting to something more sincere.

"Thank you," I murmured, feeling a blush creep up my neck.

Trying to steer the conversation to safer ground, I took a breath and asked, "So, what about you? What about your wife? What does she look like?"

A shadow passed over his face, and his eyes softened with a hint of sadness. "My wife is beautiful," he said, his voice carrying a weight of resignation. "But she's so focused on her work that she really isn't interested in spending time with me. And she's lost all interest in sex or being sexy. I hate to say it, but she's sort of let herself go, putting on weight and not putting any effort into her looks. We haven't had sex in months. The last person I had sex with was you. I know that makes me sound shallow, and maybe I am."

There was a vulnerability in his voice that struct a note of empathy within me. "You're not shallow. And you're the last person I had sex with too," I replied, looking back up from the table into his eyes.

Anthony's face flickered with surprise before a small, grateful smile tugged at the corners of his mouth. We both chuckled softly as the lingering tension between us began to unravel like a loosening knot.

Feeling emboldened, I continued in a playful tone, "But just to be clear — you're cheating on your wife, and the other woman is me...a man in a dress." I gave his hand an affectionate squeeze and offered a warm smile.

Anthony blinked a few times as my teasing joke sank in before his expression melted into one of bemused acceptance. "Well, when you put it that way...yeah, I guess that's exactly what's happening," he admitted with a self-deprecating chuckle.

We both dissolved into laughter, bonding over the sheer absurdity of the unconventional situation we currently shared. As our amusement subsided into contented quiet, I was struck by the comforting realization that I wasn't so alone in navigating these strange, uncharted waters of blurred boundaries after all.

The waiter returned and set the bottle of wine on the table.

"Are you ready to order?" he asked.

Anthony looked at me, his eyes searching mine for confirmation.

I nodded.

"How about a pasta dish for an entrée?" he asked.

I nodded again, my throat suddenly dry.

As Anthony ordered our meals, I glanced quickly around the room and at the waiter. The soft hum of conversations and clinking of silverware filled the air. The waiter seemed disinterested, and no one in the restaurant was staring at me. Relief washed over me, and I felt a tiny victory settle in my chest. Another win for me.

As the waiter left to place the order, Anthony lifted his wine glass. "To an evening of great food and company," he said, his voice warm and sincere.

"Cheers," I replied, my voice soft and steady as I raised my glass.

We clinked glasses, the crystal producing a satisfying chime, and I took a sip. The rich, velvety wine flowed over my tongue, leaving a warm trail down my throat. As I set my wine glass back on the table, I noticed a faint lipstick impression on the rim — a subtle reminder that I was out in a normal restaurant, fully dressed as a woman, and on a date with a man. A small thrill of pride mixed with anxiety coursed through me.

Anthony put down his glass and asked, "What about your life outside of being a crossdresser?"

A familiar tightness crept into my chest. I was so used to keeping my vanilla life separate that revealing details to someone who knew me as my crossdressing alter ego made me nervous. I could feel my fingers fidgeting with the stem of my glass.

"Honestly, my life is pretty boring. I'm a government bureaucrat," I said, trying to keep my tone light.

"A government employee. Hmm, should I be worried?" he teased, leaning in slightly, his gaze soft but curious.

"Only if you are a terrorist," I replied, chuckling, feeling the tension in my shoulders ease just a bit.

"Good, because I would hate to see our relationship end that way," he said, a playful glint in his eyes.

"Our relationship, huh?" I asked in mock exaggeration, raising an eyebrow. "So, this is a relationship now?"

"You know what I mean," he replied, a bit flustered, his hand reaching out to gently brush against mine on the table. His touch was warm, sending a pleasant tingle up my arm.

"Sorry, just teasing you," I said, smiling as I felt the last remnants of my anxiety start to melt away.

"Oh, are you going to tease me later?" he asked, his voice dropping a notch, the hint of something more in his tone.

"Maybe. We'll have to see how the evening goes," I replied with a smile, "You're enjoying this, aren't you?" My voice soft, almost playful.

"I'm enjoying the company. It's a bonus that the company is dressed like you," he replied, his gaze lingering on the hem of my skirt. I felt the weight of his eyes, a mix of appreciation and desire.

"You like the skirt? It's a bit short," I asked, my hand instinctively reaching down to tug the hem lower, the warm supple leather brushing against my fingertips.

"You know from last time how much I like your legs," he said, his voice taking on a huskier tone that sent a shiver down my spine.

"I remember," I replied, the recollection of his lips on my skin springing to mind. The memory of his kisses and the way he had worshiped my legs flashed through my mind, leaving a warm, surge of erotic feelings.

"If I may ask, how did you find out that you liked to crossdress?" he asked, his curiosity evident, though his tone remained gentle.

I paused, the question pulling me back into memories I hadn't revisited in a while. I could feel a stubborn, lingering sense of shame as I searched for the right words to explain.

"I took a deep breath before replying, "It's been an interest for me as far back as I can remember. It started when I was just a kid, sneaking into my sister's closet or borrowing clothes from friends' sisters behind their backs." I let out a nervous chuckle and toyed with the tablecloth edge. "Pretty messed up, right?"

Pausing briefly, I continued, "But when I was 19, I met someone — an older man, about 10 years older than me who was my boss at the shoe store I worked at. Long story short, he found out about my crossdressing interests. He ended up taking me to Chicago, where he had a friend who performed in drag shows and offered feminine transformation services."

I felt my cheeks flush slightly at the memory as I went on, "They did my makeup, got me dressed up fully in a dress, pantyhose, heels — the whole nine yards. Then we actually went out to a bar, and I got to experience what it felt like to look and be seen as an attractive woman for a night. It was...intense, eye-opening in a lot of ways."

Meeting Anthony's gaze, I gave a small self-conscious shrug. "So yeah, that's how this exploration really took root for me. A pretty wild experience."

"Did you get laid?" he asked with a devilish grin, his eyes twinkling with mischievous curiosity.

I felt my face flush hotly as the vivid memories resurfaced. "Yeah, I did," I replied in a matter-of-fact tone. "Being all dolled up as a woman in that tight dress and high heels had me raging with horniness."

"There was this older woman at the bar, she was bi. She took a liking to me. She ended up pulling me into a bathroom stall before the night was over," I continued plainly. "I was sitting on the toilet with my panties and pantyhose pulled down. She hiked up her own skirt, ripped a hole in her pantyhose, climbed on top of me, and fucked me while I tried to muffle my moans."

Pausing, I gave Anthony a pointed look. "And later in my boss's car, I jerked him off to pay him back for setting up that whole experience. It was my first time giving a hand job, so I was pretty clumsy, and he ended up making a huge mess..."

I shrugged nonchalantly. "So yeah, it was a wild introduction into this whole world for me."

"Wow, what a night," he said, leaning back in his chair, his expression a mix of admiration and astonishment.

"It was," I said, a smirk playing on my lips as I leaned in slightly, feeling the rush of adrenaline from sharing such an intimate memory. "I've always been willing to try new things." The words left my lips with a mix of confidence and challenge.

"What about since then? Did you keep dressing up and going out?" he asked, his eyes fixed on mine, searching for more of my story.

I took a deep breath, feeling a subtle sadness as I recalled the years that had passed. "I didn't dress again for about 20 years. Oh, there were the occasional Halloween costumes, but I didn't really get back into it until about ten years ago. I had gotten married to a woman who didn't approve so I stopped. Later, I got divorced, moved to the Chicago area, and decided to explore my desires. I don't do it all the time, only once or twice a year." The words felt strange leaving my lips, like I was confessing a secret that had been hidden away for too long.

"Well, I for one am glad that you do. And I'm really glad we found each other online," he replied, his voice warm and genuine, sending a soft warmth through me. The way he said it, the sincerity in his tone, gave me a strange sense of ease.

The waiter returned then with our meals, breaking the moment. The aroma of the pasta filled the air, rich and inviting, as the waiter placed the plates in front of us. We ate in silence for a bit, the clinking of silverware and the quiet hum of the restaurant serving as the only sounds between us. I could feel the textures of the pasta in my mouth, the rich flavors mingling with the wine still lingering on my tongue.

As we finished our entrees, the waiter returned, efficiently removing the plates. "May I interest you in dessert tonight?" he asked, his professional tone breaking the comfortable silence between us.

Anthony looked at me, raising an eyebrow slightly, a silent question in his eyes. I shook my head no, dabbing my lips with the white linen napkin and leaving faint trace of lipstick, a subtle reminder my situation and how I was attired.

"Just the check, please," Anthony said, his voice calm and assured. I could feel a sense of conclusion settling over us, the evening beginning to wind down, but with a promise of something more in the air. The anticipation of what might come next sent a small thrill through me, the unknown of the night still holding its secrets.

As we waited for the check, I felt Anthony's hand slide up my thigh under the table. His touch immediately set off tingles of excitement rippling through me. His fingers crept higher along my inner thigh as I caught my breath, the warmth penetrating the thin nylon of my pantyhose. Fluttering my eyes closed, I savored the tantalizing sensations while fighting to maintain outward composure even as arousal wound tighter within me.

His fingers reached the hem of my skirt and lightly pushed the supple leather up, grazing the tops of my nylon covered thighs. I gasped softly at the intimate contact, hoping the other patrons remained oblivious to the surreptitious acts unfolding beneath the tablecloth, even as the taboo thrill of potentially being discovered only amplified my arousal.

Anthony's deft fingers continued mapping teasing trails along my sensitized skin in light, maddening circles. Then, with agonizing deliberation, his touch shifted over the concealed swell of my constrained cock, shamelessly fondling me through the thin barriers of panties and hose.

The electrifying jolt of sensation detonated through my nerve endings, making it increasingly difficult to smother the sounds of ecstasy threatening to spill from my lips. I had to grit my teeth against the overpowering urge to uncross and shamelessly spread my legs in wanton invitation for more sordid fondling.

"Do you want to go now?" he whispered, his voice husky with desire.

"Y-yes, pl-please," I stuttered, trying to keep my voice steady. "But if you keep this up, everyone will know what I have under this skirt."

Chuckling softly, Anthony withdrew his hand, leaving me breathless and trembling. He stood, his presence commanding, and walked over to my side of the table. He offered his hand, a silent invitation in his eyes.

I accepted his hand and rose, grateful for the tight fit of my panties that kept me discreetly tucked. Still, to be safe, I quickly grabbed my purse and held it low in front of me as we made our way toward the door. The soft rustle of the leather skirt against my thighs, the click of my heels on the floor, and the lingering sensation of his touch all combined to heighten my awareness of every movement. My body hummed with the anticipation of what was to come.

Anthony paused to pay the bill. I noticed he was a generous tipper. Nice.

As I stood at the register, I felt a sudden wave of self-consciousness, like all eyes were on me. My pulse thumped as I quickly scanned the room. I breathed a sigh of relief realizing that no one was paying any attention to us. My fears had been for nothing. Another win for me! I had successfully dined in a public place during the day, fully made up and dressed in a skirt and heels, and no one seemed to notice or care.

Anthony held the door open for me, and we stepped out into the cool evening air. I took a deep breath, letting the crisp air fill my lungs, trying to steady the mix of excitement and nerves still buzzing within me.

"Are you okay?" Anthony asked, his voice gentle.

Taking another deep breath, I replied, "Yes, I am now." The air felt refreshing against my flushed skin, and I could feel my pulse beginning to slow as I regained my composure.

Anthony's hand found its way back to the small of my back, the warmth of his touch reassuring as he guided me toward the car. "Are you still nervous?" he asked, his tone laced with genuine concern.

"No, not anymore. This was a very new experience for me. I wasn't sure how things would go, you know, going out to a restaurant dressed as I am," I said with a smile. The fact that no one had seemed to clock me crossdressing was a huge relief. The subtle thrill of going out feminized without getting exposed was both terrifying and exciting. I was slightly surprised at how good I felt about it, a sense of pride blooming in my chest.

As we reached the passenger side door of his car, Anthony paused, his eyes scanning the parking lot to ensure we were alone. With his hand still resting on the small of my back, he pulled me closer, the warmth of his body radiating through my clothes. I could feel his breath against my skin as he leaned in.

Then, his lips met mine in a soft, lingering kiss. His hand tightened slightly on my back, pulling me closer still, while my hands found their way to his chest, feeling the steady thrum of his heartbeat beneath the fabric. I fought the urge to pull back, decades of enculturation against kissing a man rising and then falling quickly. The kiss deepened, a slow, tantalizing exploration, the cool evening air contrasting sharply with the heat building between us.

When he finally pulled back, my lips tingled from the intensity. His eyes met mine, filled with a mixture of desire and lust, and I knew that this night was far from over.

"I want you. Right here. Right now," he whispered, his lips brushing against my ear, sending a shiver down my spine. His breath was hot, the words laced with a raw desire.

I pulled away slightly, trying to regain some semblance of composure. "Here? Are you crazy? What if someone comes out of the restaurant?" My voice was breathless, a mix of excitement and apprehension.

He smiled, a wolfish grin that sent another jolt of excitement through me. He didn't let go, his hands still pulling me against him, and I could feel the hard length of his cock pressing against me through his pants. I was acutely aware of my own cock straining against the tight confines of my panties and pantyhose, the fabric almost painful in its restriction.

"If someone comes out, we can invite them to join us," he said playfully, his voice a low growl.

"Take me somewhere," I whispered, the words barely audible. The idea of being caught was thrilling, but the need for more privacy won out.

Anthony didn't hesitate. He opened the car door with a swift motion, and I slid into the seat, feeling the smooth fabric cool against the back of my thighs where my skirt had ridden up. My breath came in shallow gasps as I settled into the seat, my thoughts a swirl of anticipation.

As he closed the door, the sudden quiet inside the car only heightened my awareness of every sensation — the delicious feel of my feminine clothing, the tightness in my chest from the suppressed excitement, and the unmistakable throb between my legs. The ride was short, but the tension between us made every second stretch out. A feeling of excitement mingling with the nervous energy that had been building since dinner filled me.

It had been months since I'd been with anyone, since that last encounter with Anthony in a hotel room. The memory of that night, the way his hands had felt on my body, the way he had looked at me with such hunger, the way he had pleasured me, flooded my mind, sending a wave of heat through me. I could feel my body responding, a slow flush creeping up my neck and settling in my cheeks.

As we pulled into a small, secluded park nestled in a wooded area, I glanced around, taking in the scene. The sun was setting, and the light was fading fast, casting long shadows across the grassy area dotted with picnic tables. A stone pavilion stood nearby, its roof slanted to offer shelter from the elements. The park was deserted, just us and the growing darkness.

Anthony parked the car, the engine cutting off with a finality that seemed to intensify the silence around us. He didn't waste any time, leaning over to capture my lips in a kiss that was anything but gentle. His lips were demanding, his kiss fierce and hungry, a direct contrast to the soft, teasing kisses from earlier. I moaned softly against his mouth, my body reacting instinctively, arching toward him. His hand found the hem of my skirt and wasted no time in slipping beneath it, his fingers grazing with deliberate slowness as they slid upward.

I leaned back in the seat, my breath hitching as his hand moved higher. I spread my legs in a wanton invitation to explore further. His fingers brushed the top of my thigh, sending a shiver through me. The thin fabric of my pantyhose did little to dull the sensation, each touch tingling with raw sensual energy.

His fingers danced lightly along the edge of my panties, each touch sending a wave of constriction through the already tight fabric. The nylon that hugged my legs seemed to amplify every sensation, making each stroke of his fingers more electric. As the pressure against my cock grew, I felt the fabric of my panties struggle to contain the growing arousal. My eyelids fluttered shut, and my breath became shallow, each inhale pulling in the scent of his cologne mixed with the subtle hint of desire.

"God, you are so sexy," he whispered, his breath warm against my ear. The words sent a shiver down my spine, my skin tingling in response. His hands, now bolder, moved between my thighs, caressing with a deliberate slowness. When his lips found the sensitive spot on my neck, I couldn't help but gasp softly, my body arching slightly toward him, craving more.

His fingertips continued their exploration, brushing over my cock, still restrained by the layers of silky fabric. The friction was almost too much, yet not enough, the teasing touch driving the heat inside me. Each movement of his hands, each press of his lips, sent my senses spiraling further into a haze of want.

It had been years since I had experienced anything like this, the thrill of being touched and desired inside of a parked car. A flicker of a memory surfaced, the excitement of my first time going out dressed as a woman, the rush of being seen and wanted. That memory sparked an idea.

With a gentle but firm push, I guided his head back, locking eyes with him as I whispered, "Lean back in your seat. I want to do something." My voice was low, laced with the promise of what was to come.

Anthony complied, leaning back, the seat making soft mechanical ticks as it reclined. As he settled back, I felt a surge of anticipation.

I shifted position in the passenger seat, pulling my legs up onto the seat so I was kneeling toward Anthony, the windshield on my right side now. The way my skirt had ridden up as I moved into a kneeling position exposed the smooth nylon of my thighs to the cool air in the car, heightening the sensitivity of my skin. The texture of the seat beneath me contrasted with the delicate fabric of my nylons.

I leaned forward, placing one hand on his chest, feeling the steady rise and fall of his breathing. My other hand rested on the seat beside his head, steadying myself as I hovered over him. The position made my skirt slide up further, and I felt the cool air kiss the tops of my nylon covered thighs.

His eyes darkened with desire as they roamed over my exposed legs, and he reached up, his fingers brushing the back of my neck, pulling me closer. The heat of his body seeped through his clothes, mingling with the warmth radiating from my own.

I shifted my weight slightly, feeling the heels of my boots press into my ass. The sensation was a mix of pleasure and pressure. As I leaned in, my breath mingled with his, close enough to feel the warmth of his exhale on my lips.

My hands moved to the belt and zipper of his pants. With quick motions I undid the belt and unzipped his pants. His hard cock was outlined by his underwear. Grabbing the waistband, I pulled the undergarment down, his cock sprung free, standing upright.

I wrapped my hand around his hard shaft and stroked the silky smooth skin.

A memory flashed across my mind of a time long before, when I was only 19, out for my first time in a dress. I had done this exact same thing to a man who had been kind to me, a sort of sexual "thank you" for introducing me to the world of crossdressing in public. Now, I was in the same position again, on my knees in the passenger seat of a car, giving a hand job. The memory brought a smile and a flush of excitement

Anthony's groan of pleasure brought me back to the moment. Pausing in my manual manipulation, I reached for my purse. Snapping it open, I pulled the elastic hair tie our and deftly pulled my long wig hair back into a loose ponytail, a better hair style for what I was about to do.

Leaning over, I kissed the tip of his cock. My tongue flicked out and tasted the salty fluid that had gathered there. I could feel him shudder slightly. I licked the head again before running my tongue along the underside, savoring the feeling of the throbbing, hard shaft against my tongue.

"Fuck," Anthony moaned.

I smiled, enjoying the sensation of giving him pleasure. Opening my mouth, I let his hard shaft slip between my lips. My tongue slid over the smooth head and teased the hole.

"God that feels good," he said.

I began bobbing up and down, sucking the hard length into my mouth while continuing to stroke him with my hand. He shuddered again, his body trembling. His hand reached over and gripped the skirt, pushing the hem upward. My eyes flickered up, seeing his eyes focused on my legs.

I lifted my mouth off his cock and let my hand continue to stroke him.

"You like these, huh?" I said motioning with my free hand to my legs, now folded under me as I kneeled in the seat.

"Yeah, a lot."

I smiled, leaned forward, and resumed sucking his cock. After a moment he released his grip on the hem of my skirt. I could feel Anthony's hand under the skirt, rubbing my pantyhose covered thigh, lightly caressing up and down. I continued to work his shaft, my mouth and hand moving in tandem.

"Oh god," he moaned.

I knew the signs, he was close. I sucked and stroked harder, my head bobbing up and down, my tongue working the sensitive underside of his shaft. With a groan and a buck of his hips I felt his cock pulse, a warm rush filling my mouth. He grunted, his hips jerking as he came. I swallowed and kept sucking, milking him with my mouth and fingers.

I couldn't resist flicking my tongue over the sensitive head of Anthony's cock one last time as he shuddered through the aftershocks, finally releasing him from my lips with a wet pop. Leaning back, I smoothed down my skirt and grinned at the deliciously debauched sight he made.

Anthony reclined bonelessly in the driver's seat, pants and underwear shoved down his thighs, chest heaving as a glistening mix of saliva and cum coated his spent cock in the shadowy interior light of the car.

"Thank you," he panted out roughly.

"You're welcome," I replied, undoing the hair tie to let my long wig tresses spill freely over my shoulders.

"Just...give me a minute, then I'll return the favor," Anthony rasped out.

"Don't worry about that right now," I dismissed with a casual wave as I shifted back from my kneeling position to sit facing forward in passenger seat.

I watched idly as he tucked his softening cock away and zipped up, noticing how the windows had fogged up with condensation from our heated exertions. We were like a couple of horny teenagers fooling around in a secluded parking lot. Waving a hand in front of my face, I stirred up a slight breeze to dispel some of the hazy residue.

After a beat, Anthony's warm palm found my thigh, his deft fingers skating teasingly along the sleek nylon as desire rekindled in a slow burn under my skin. The silky fabric seemed to amplify every caress, waves of sensation radiating outward from his exploratory strokes.

"Would you do something for me?" Anthony's voice was low, thick with anticipation.

"Sure," I responded, feeling curiosity mixed with hesitation. "What did you have in mind?"

"Take off your clothes," he said frankly, desire undisguised in his tone. "I want to see what you've got underneath."

"Really?" The request caught me slightly off guard, shyness and arousal mingling.

His eyes stayed locked on mine. "Yeah. I love those stockings on your legs, and the boots are so hot."

A small smile curved my lips as a thrill of nervous excitement rippled through me at his admissions. "Okay, then."

"Thank you," Anthony murmured, raw appreciation lacing his words.

I shifted positions, the confined space of the car's interior making it challenging to disrobe fully. For a fleeting moment, the idea of getting out of the car to disrobe crossed my mind, but the tantalizing thrill of potentially being discovered kept me inside.

Planting my high-heeled feet firmly on the floorboard, I leaned back against the seat and reached behind to unzip my skirt. The clinging yet supple leather hugged my hips snugly, requiring some shimmying and wriggling before I could finally peel it down over my thighs and past my boots. Stepping out of the skirt, I folded it neatly and placed it on the dashboard, keenly aware of Anthony's intense, hungry gaze burning into me.

I quickly pulled off my scarf, setting it on my skirt on the dash. Then turning slightly, I hooked my fingers under the hem of my top and smoothly drew the thin, soft material up and over my head to join the steadily growing pile of discarded clothes. Now I was left in just my lacy bra, sheer pantyhose, thigh-high boots, and barely-there panties. The air of the car's interior raised goosebumps along my exposed skin in stark contrast to the scorching weight of Anthony's roving stare as he drank in every inch.

"You're so beautiful," he murmured, raw sincerity underpinning the husky words.

"Thank you," I replied, feeling both shy and flattered.

"Can I take a picture of you like this?" Anthony requested, his tone gentle yet filled with unmistakable yearning. "Just for me to keep — I swear I won't share it with anyone else."

I hesitated for a moment. Then, nodding consent I said "But you have to use my phone. I'll pick which ones to send to you." I pulled my phone out of my purse and handed it to him.

"Climb into the back seat so I can get a better angle," he suggested, his eyes glinting with anticipation.

I did as he requested, maneuvering into the back behind the passenger seat. "Anthony, be a dear and move the seat forward for me?" I asked in a honeyed tone.

He grinned and reached over, adjusting the front passenger seat to give me a bit more room. The space was tight, but I shifted until I found a comfortable position.

Anthony started snapping photos as I tried different poses, showing off as much leg as possible. Feeling brazen, I moved my hands to the waistband of my pantyhose. With excruciating leisure, I started inch by inch to peel the sheer nylon downwards, offering tantalizing glimpses of newly exposed skin as Anthony watched with undisguised hunger, the digital shutter of the phone working furiously to capture every sultry reveal of my impromptu private strip show.

Once my pantyhose were rolled provocatively low on my hips, I shifted my attention lower. My fingers traced featherlight, teasing paths along the thin fabric of my panties, unabashedly fondling myself through the sheer material as lust-darkened eyes followed every stroke, every caress.

"Pull your panties aside for me — let me see your cock," Anthony commanded, his voice thick and molten with lust.

I flashed him a coy smile. "Only if you put that phone down first. No X-rated pictures allowed."

He didn't hesitate, immediately setting the device aside atop the pile of my discarded clothes. Holding his stare, I hooked my thumbs into the clinging fabric of my panties and shamelessly pulled the gusset aside, exposing my rigid length to the cool rush of air — the delicious thrill made me shudder.

"Play with yourself," Anthony growled. "Jerk off for me."

Wrapping my fingers around my stiffened shaft, I began to stroke with tantalizing leisure, reveling in the exquisite friction. Sensations sparked along every nerve, each caress sending tendrils of pleasure through me. The soft lace of my lingerie clung snugly, while the thigh-high boots lent an undeniable edge of wickedness.

I was keenly aware of Anthony's gaze hungrily following the glide of my fingers, the whisper-soft drag of satin and lace only amplifying the blissful sensations. The mental aspect alone was almost overwhelming — knowing he desired me like this, knowing I was putting on such an unabashedly lewd show just for him.

The combination of physical rapture and that intoxicating rush of being so keenly wanted quickly stoked my desire. I could feel the tension rapidly coiling tighter with every stroke, every breath, every lustful brush of material against overheated flesh bringing me ever closer to climax.

I soaked in the dizzying power I felt under his rapt stare as I shamelessly exposed myself to him. Some deeply voyeuristic part of me reveled in being so brazenly exposed for his viewing pleasure. I was raw, unfiltered sensuality incarnate. I fucking loved it.

"That's so sexy," he breathed.

His words stoked the fire.

I caressed myself faster, feeling the tension build.

"Come for me. Come for me, baby."

"Oh fuck," I groaned, sinking deeper into the seat, my left leg stretching out between the front seats. The sensation of the cool fabric beneath me contrasted sharply with the heat building inside.

Anthony reached a hand to my outstretched leg, his touch electric as his fingers trailed over the nylon of my thigh, just above the top of the leather boot. The smooth glide of his hand against the fabric amplifying the tension within me. I bit my lip, trying to stifle the moan threatening to escape.

"Come on," he whispered, his voice low and filled with desire. "I want to see you cum."

I locked gazes with him, looking into his eyes and seeing the raw lust smoldering. The intensity of his gaze, the way his eyes drank in every movement, pushed me to the brink. The combination of his touch and his gaze sent me spiraling over the edge, my body shuddering as I surrendered completely to the moment.

"Oh... yes...," I moaned, a low and shuddering sound.

My eyes never leaving his, I bucked my hips as I came, shooting cum onto the car seat. Several drops shot past and landed on the back of the passenger seat as I surrendered to the throes of ecstasy ripping through me. My body shook with the intensity of my orgasm. It had built quickly, and the release was powerful.

As the last tremors finally subsided, I sank back against the rough fabric of the seat with a deeply satisfied smile curving my lips. An intoxicating warmth still thrummed through every nerve ending, the lingering remnants of my orgasm.

After a few moments of basking in the afterglow, I reached out, opened the car door, and stepped out into the night. The cool air brushed against my bare skin, a refreshing contrast to the heat that had enveloped me moments before. I reveled in the sensation, the coolness welcome after such an intense release.

I glanced around the dark, empty park, feeling a sense of liberation in the quiet solitude. I realized how I might look to anyone that might be concealed in the darkness of the park, stumbling out of the back seat of a car, its windows steamed up, standing shakily, unclothed with panties and pantyhose rolled halfway down my thighs. The image made me smile.

Reaching down, I pulled the smooth fabric of my panties back into place over my sensitized flesh before adjusting the sheer nylon hose, reveling in the whisper-soft glide over my tingling thighs and the lush curve of my backside. My limbs felt deliciously leaden, faintly unsteady as the aftershocks of such a fierce orgasm still left me trembling slightly.

A few slow, wobbly steps in my heels and I made my way to the front passenger door, the slight breeze teasing my skin as I moved. Opening the door, I retrieved my skirt and top from the dashboard, the interior light casting a soft glow that guided my hands as I dressed. The fabric felt familiar, comforting as I stepped into the skirt and pulled it up over my hips. I slipped the top back on, restoring a sense of normalcy to the surreal erotic moment I had just experienced.

Bending down to look inside I saw Anthony using a napkin to clear the cum stains from the seat.

"Sorry for the mess," I said, still catching my breath.

"The show was well worth it," Anthony replied, his voice carrying a hint of satisfaction.

I slid back into the front passenger seat, the fabric cool against my skin as I closed the door and rolled down the window. The night air rushed in, crisp and refreshing, gently caressing my flushed cheeks and easing the lingering heat from our earlier encounter. The silence between us was comfortable, almost serene, as we sat in the darkness, the only sound being the soft rustling of the wind through the trees outside and the trill of crickets.

After a few moments, Anthony broke the quiet. "How about some dessert?" he asked, his tone light and playful.

"What do you have in mind?" I replied, curious.

"Ice cream?" he said, a smile in his voice.

"Sounds great," I agreed, the idea of something cool and sweet appealing after such an intense moment.

"There's a place a few miles up the road," he offered.

"Ok," I said, settling into my seat and buckling the seat belt as Anthony started the car.

We drove in silence, the night enveloping us as the car glided down the empty road. The hum of the engine was soothing, and the promise of something as simple as ice cream felt like the perfect way to punctuate our carnal activities.

We rode in silence, the car's gentle hum filling the space as my thoughts replayed the events of the evening. The ice cream shop was a welcome sight, its soft glow drawing a light crowd savoring the night and their treats.

I stayed by the car as Anthony went up to the window of the shop to buy the ice cream. After handing me a cone, we strolled out into the shadows of the parking lot.

"Want to sit on a bench by the river?" Anthony asked, his voice warm and inviting.

"I'd like to watch the river," I replied, the idea of the calm water appealing.

"Me too," he said.

We found a bench in a park near the riverbank, the cool evening breeze brushed against my legs, sending a slight shiver up my spine. My long wig hair swayed gently, occasionally threatening to stray into my ice cream cone.

I sat, instinctively tugging the hem of my skirt down and crossing my legs. The lights from the shop provided just enough illumination to see, but not enough to disturb the tranquility of the water. Anthony sat down next to me, close enough that our hips touched.

"What do you have planned for the rest of the weekend?" he asked, his tone light.

"Laundry and shopping," I replied.

"Shopping? For what?"

"New panties and pantyhose. I think these may be stained," I said with a playful smirk.

Anthony grinned and nodded, his expression softening as he reached out to place a hand on my thigh. The touch was gentle, not meant to ignite, but to connect. It was comforting, grounding. After finishing our ice cream, we walked back to his car, his hand once again finding its place on the small of my back, guiding me with a subtle, protective pressure.

"What do you want to do now?" he asked, his voice a soft rumble in the darkness.

"I... er... would you like to come back to my place?" I asked, my voice tinged with nervous anticipation.

"Yes," he replied quickly, his tone firm and reassuring.

"Are you sure?"

"Very sure. Yes. If you'll have me. But I can't stay too late," he said, glancing at his watch.

"Ok. Let's go. It's not far," I replied, walking to stand next to the passenger door of his car. He opened the door, holding his hand out to help me sink into the seat. As before, I was grateful for the assist.

We arrived at my place, parking in the driveway. I glanced around, checking the surrounding houses to ensure no neighbors were out who might see me. The thought of explaining why I was dressed as a woman bringing a man home sent a pang of unease through me.

Anthony repeated his routine, getting out of the car and assisting me out of my seat. We walked up the drive to my front door, my heels making a pleasant clicking sound on the concrete. Pulling the keys out of my purse, I unlatched the door and opened it.

"Do you want anything to drink?" I asked, shutting the door behind us and flicking on the lights.

"Beer if you have it."

I sauntered into the kitchen, my footsteps muffled by the deep carpeting of the living room. The sensation of my nylon covered legs brushing together as I walked heightened my awareness of every movement.

Grabbing two beers, I returned to the living room and found Anthony sitting on one of the sofas. The room was cozy, with two leather sofas facing each other across a small coffee table in an alcove, the larger part of the room filled with dining table, comfortable chairs, and shelves with books and curios. I handed him a beer and sat beside him, crossing my legs and leaning back against the cushions. The leather was cool against the back of my thighs.

We sipped our drinks, making small talk, but I could feel Anthony's eyes drifting over my legs, the length of my skirt.

"Are you okay?" I asked, noticing the slight distraction in his gaze.

"Yes," he replied, though his voice was distant.

"Would you like to see the rest of the house?" I offered, trying to break the tension.

"Sure," he said with a smile.

I led him through the house, showing him the other rooms before finally reaching the bedroom. I flicked the light switch, and dim light bathed the room in a soft glow. The queen-size bed, with its simple Mission style wooden frame, stood as the centerpiece, the headboard and footboard unadorned, a simple white cotton comforter with matching pillows covered the top of the bed. The dresser against the opposite wall was equally understated, practical but without flair. Two matching nightstands flanked the headboard of the bed, the wood a match for the bed and dresser. The nightstands had matching lamps of stained glass that gave a soft golden glow. Two cream colored fabric chairs took up space in opposite corners of the room. A full length mirror adorned one wall, angled toward the bed. An open door on a side wall led into the master bathroom, now dark save for the glow of a small nightlight in the back of the bathroom.

Anthony followed me in, moving to sand beside me in the center of the room, his presence close and warm. Taking a sip of his beer he looked around, his eyes taking in the details in the dim light.

"Nice," he said, his eyes meeting mine.

"Thanks."

"You have a nice place," he said.

"I like it," I replied, stepping toward the dresser.

"Have you lived here long?" he asked, but his voice had a distracted quality, as if his thoughts were elsewhere.

I set my beer down on the dresser and stepped closer to him. He hesitated, watching me as I reached out, gently taking the beer from his grasp and placing it next to mine. I could see the desire in his eyes, a hunger that made the air between us feel charged. Without hesitation, his hands slid around my hips, pulling me closer until our bodies were almost touching.

"Would you like me to model some lingerie I bought recently?" I asked, feeling a wave of warmth spreading through me.

"No," he replied, his voice low and thick with need. "I want you just like this."

Our eyes locked, the intensity between us growing. "Are you sure?" I whispered.

"God, yes," he breathed.

Leaning forward, he kissed me. The first touch of our lips was gentle, a tentative exploration. But the spark quickly ignited into something more. Our kisses deepened, tongues meeting in a heated dance. His hands roamed over my sides and hips, eventually finding the zipper at the back of my skirt. Pulling the zipper down, his hands moved to the waist of the skirt, shoving it down. As the skirt began to slide lower, it caught on the tops of my thigh-high boots.

"Damn boots," I muttered, reaching down to free the skirt, letting it fall to the floor.

"Leave the boots on." Anthony's growl resonated with unrestrained lust.

Flashing a wicked grin, I shifted my weight from one heel to the other in a subtle, teasing sway. "But this has to come off then."

Without ceremony, I peeled the clinging top up and over my head, letting it puddle unceremoniously on the floor next to the skirt.

Standing there in just my bra, panties, hose, and boots, I felt the cool air brush against my bare skin. The bra pressed lightly against my chest, a small reminder of how exposed I was. The nylon of my hose slid smoothly against my legs, creating a slight, tingling sensation with each movement. My panties clung to my hips, the fabric thin and barely there, the outline of my erection clearly visible in outline. The boots gripped my calves, providing a solid anchor in the moment. His eyes moved over me, taking in every detail, and the space between us felt charged.

I could feel the unmistakable swell of my arousal tenting obscenely against the clinging lace front of my panties, the desperate head already peeking over the waistband to leave a small glistening streak of need against the hosiery's sheer fabric. Anthony took in the sight with ravenous eyes

His gaze traced the contours of my body, taking in every detail. "You're gorgeous," he said softly, his voice laced with admiration as he took my hand and guided me to the side of the bed.

He sat down, and I stepped closer. His hands found their way to my ass, gently squeezing through the sheer fabric of my nylons and panties. The fabric stretched slightly under his touch, heightening my awareness of his grip. I tangled my fingers in his hair, pulling his head toward me.

I could feel his breath warm against the delicate fabric of my hose. The heat of it sent a subtle, electrifying sensation through me as his face hovered just inches from my crotch, his touch both possessive and tender.

He leaned forward and planted a soft kiss on the tip of my cock through the sheer fabric. A shiver ran up and down my spine. The touch of his lips was electrifying.

My fingers tightened their grip in his hair, holding him there, his lips against my cock. He pressed another kiss against me. A soft moan escaped my lips as he nuzzled me through the fabric, the warmth of his breath sending shivers down my spine. His hands roamed over my ass, fingers pressing gently into the nylon before sliding down my legs to the tops of my boots.

Anthony paused, lifting his face from me but keeping his hands firmly on my ass. "Get on the bed. On all fours," he ordered, his voice low and commanding.

I stepped back, the cool air brushing against the parts of my skin now exposed. Crawling onto the bed, I positioned myself on my knees and hands, legs spread, presenting myself to him. The anticipation buzzed in the air as I waited, feeling every inch of the fabric against my skin.

Standing beside the bed, Anthony reached out, his fingers tracing a deliberate line along my thigh and over the top of my boot. The sensation was a teasing touch that made me tense in expectation. His hand moved up, finally resting on my ass, where he squeezed and kneaded, the pressure firm and deliberate.

"You're so hot," he murmured, his voice dripping with desire as both hands explored my body, his touch both possessive and admiring.

"Thank you," I whispered, my voice barely steady, each word carrying the weight of the moment.

I could hear the sound of the zipper on his pants as he removed them. Turning to look behind me, I saw him standing beside the bed. He had removed his shirt, kicked his shoes and socks off, and was pushing his pants and underwear down, exposing his erect cock.

The bed jostled underneath me as Anthony climbed up behind me. On his knees and naked, he moved behind me between my spread legs and pressed his firmness against my ass.

I could feel the heat of his hardness pressing into me. His fingers roamed my body, trailing across my ass, up my back, and along the straps of my bra. After a moment of exploring my body, he moved his hands back to my ass and began rubbing and stroking it.

"You're so beautiful. So sexy," he said, his voice thick with lust and intention.

"Thank you," I moaned, enjoying his attention.

His hands found their way to my hips, and he pulled me toward him, his rigid cock nestled in the crack of my ass against the fabric of my hose and panties. Then he started to slowly hump me, rubbing his cock along my ass against the silky fabric of my pantyhose.

One of his hands left my hip, reaching up to grasp my shoulder, giving him more leverage to pull me harder against him. I felt his cock throb against my ass crack.

"Oh, fuck," he groaned.

I could feel the pressure building as he humped me. He let go of my hip, reaching a hand forward to grab the back of my neck. With gentle pressure he pushed my head down onto the soft cotton of the comforter, my back arched wantonly, my ass still elevated as he stroked up and down against it.

His thrusting was getting faster and harder, his breathing more erratic. He was getting close.

"Oh fuck," he said, intensity and urgency in his voice.

His hand tightened on my shoulder. I could feel his body tensing.

"Come for me," I said, wanting to feel him shoot his loan onto me.

His hips pressed against my ass. I could feel his hardness through the thin fabric of the panties and pantyhose as he slid his cock up and down along my ass crack. A strangled moan escaped his throat, and I felt a splash of warmth on my ass as he shot his load on me.

"Oh, fuck yes..." he panted harshly as his hips pistoned in sharp, erratic jabs, each maddening grind milking out another gush of his cum to soak through the sheer nylon. The sloppy, wet sounds of his cock sliding through the rapidly blooming mess only seemed to spur him into a more fevered frenzy. By the time the last shudders finally subsided, a sizable damp patch marred the stretched fabric, lurid evidence of his violent climax trickling down my ass. Unthinkingly, I shifted my position, the subtle movement causing the soiled material to cling against my sensitized skin in a glaring reminder of how utterly wicked I looked in that moment.

"Oh god," he murmured, his grip on my shoulder loosening as his other hand moved from the back of my neck.

He collapsed forward, pushing me down onto my stomach, his body heavy against mine. The warmth of his skin pressed into me, his ragged breaths brushing the back of my neck, each exhale a soft, heated whisper against my skin.

We stayed like that, tangled together, the rise and fall of his chest a steady rhythm against my back. Eventually, Anthony rolled off me, settling onto his back beside me. His hands found their way to my body again, resuming their gentle caresses, tracing the contours on my skin with a languid, almost possessive touch. Each stroke of his fingers sent a lingering warmth through me, grounding me in the quiet intimacy of the moment. I could feel a cool spot where his cum had soaked through the wet fabric of the hose and panties.

"That was amazing," he breathed out, his voice still heavy with exertion.

"I'm definitely going to need new pantyhose," I replied with a playful smirk.

"Sorry about that," he said, a hint of amusement in his tone.

"It's not a problem," I assured him.

He reached over, wrapping his arm around me and gently pulling me onto my side so that my back pressed against his chest. His hand began to roam over my body again, his touch warm and comforting against the coolness of the room. The rhythmic motion of his fingers tracing lazy patterns on my skin was soothing, each stroke lulling me further into a state of relaxation. The heat of his body was a comforting presence, and I felt my eyelids grow heavy, the world around me fading as I drifted into that blissful in-between state of half-sleep.

Time slipped away, the minutes blending together in a haze of warmth and contentment. At some point, I felt Anthony shift beside me, moving closer, his hand finding its way to my side. The soft pressure of his touch brought me back to awareness. I could also feel his half hard cock pressing against the wet fabric where he came on my ass.

"Mmmmm," I moaned, feeling his hand gently glide over my hip, sending a small tingle through me, "Is someone ready for round three?"

"Do you mind?" he asked, his voice low, the heat of his breath grazing my ear as his hand continued its slow exploration, fingers tracing delicate patterns along my skin.

"No, not at all," I replied, the words barely more than a whisper as the anticipation built.

"I want to enjoy this while I can," he murmured, his touch growing more insistent, the warmth of his body pressing against mine, each movement sparking a new wave of sensation that spread through me like a slow burn. His hand moved forward, his fingers brushing across my crotch.

I gasped as his fingertips brushed over the head of my cock. It had deflated somewhat as I had started to drift off to sleep but his gentle caress quickly made me hard again. He kissed the back of my neck, his hands continuing their caressing.

"That's so sexy," he said, his finger tracing the outline of my shaft. I shuddered as his fingers brushed against the thin fabric of my hose and panties, the sensation electric. His touch lingered at the waistband of the pantyhose, tracing the edge slowly, teasingly.

"I like these," he murmured, "but they have to go."

He grabbed the waistband firmly, and I instinctively lifted my hips to help. The fabric slid down, the cool air replacing the warmth as he pushed them down to mid-thigh. The contrast between the exposed skin and the still-covered areas heightened the sensitivity, every touch now sharper, more intense.

"This is better," he said.

His hand returned to my erection and began slowly stroking it, the head now clearly poking up over the waistband of my panties. The sensations were amazing. The gentle touch, the feeling of his warm breath against my neck.

As he continued stroking, his kisses grew more intense, his mouth sucking and licking the sensitive flesh of my neck.

"You got one more round in you?" I asked, my voice trembling slightly as his hand continued to lightly stroke my cock through my panties.

"Yeah. Maybe two."

I chuckled lightly and said, "But you already came twice tonight."

"You inspire me," he replied, his lips starting to kiss their way down the exposed flesh of my back, "And I took a little blue pill just in case I might need it."

"Better living through chemistry," I responded with a grin, "Thank goodness for little blue pills."

I let out a contented sigh as his lips brushed over my bare skin, leaving a warm trail from my neck, down to the curve of my back, and finally to my ass. Each kiss sent a ripple of sensation through me, my breathing growing shallow and uneven.

When his mouth pressed against the soft curve of my ass, his lips alternating between kisses and teasing licks, I could feel my body responding, the sensation electrifying.

"You have a beautiful ass," he murmured between lingering kisses.

"Thanks," I managed, my voice barely more than a breathy whisper, "The squats must be working."

He continued his path along the curve, his touch both firm and gentle, building a slow burn of anticipation.

"I've been thinking about this all night," he whispered, his grip shifted, hands now firmly on my hips as he rolled me onto my stomach.

I felt him hook his fingers into the waistband of my panties. He tugged them down, the fabric sliding effortlessly to join my already lowered pantyhose at mid-thigh. Kneeling behind me, he gently took hold of my ankle, spreading my legs wider, his movements deliberate and commanding.

"God, you're hot," he said, his voice thick with desire.

"Thanks," I replied, a tinge of self-consciousness creeping in, unaccustomed to the intensity of his admiration. I looked back over my shoulder and saw Anthony kneeling behind me between my legs. His cock was hard again and stuck out straight from his body. His hands reached out, grabbing my hips and pulling me back into a kneeling position. Once again, I was on hands and knees, ass up and head down, ready to be fucked.

"Wow. You really are hard again?" I teased, "Color me impressed!"

"Like I said. You inspire me."

"Well, let's not waste it. There's lube and condoms in the draw of the nightstand," I said, gesturing with one hand to the side of the bed.

He quickly leaned over and rummaged around, emerging with a condom and bottle of lubricant. He rolled the condom onto his erect cock and flipped the lid open on the lube.

"Lots of lube," I cautioned, "It's been a while."

He nodded his head and poured a generous amount onto his sheathed cock, slathering it up and down the length. He moved closer, his legs resting against the back of my legs, his hands rubbing up and down my back, his fingers tracing the straps of my bra. The pantyhose and panties tugged at my thighs, the tension making it harder to spread my legs as wide as I wanted. I could feel the fabric biting into my skin, a blend of discomfort and arousal.

"Should I take these off?" I asked, my fingers brushing over the bunched-up lingerie, feeling the slight indentation it left on my skin.

"No. It's sexy," he replied, his voice low and firm.

"And the boots?" I couldn't resist toying with him, delighting in the naked yearning dripping from his tone.

"No, leave them on. It's sexy as hell." Anthony's growl brooked no argument, pure unadulterated lust roughening his timbre.

Peering over my shoulder, I flashed him a sultry, conspiratorial smile. "You really like the boots, don't you?"

"Fuck yes, I do..." Anthony groaned, shamelessly dragging his hungry stare down the sleek leather and sheer nylon encasing my thighs.

A heady rush of satisfaction blazed through me at how utterly captivated he was by every detail. "Good," I purred, arching my back in a subtly wanton stretch that further emphasized my lustfully compromised state. "Are you ready?"

"God yes." He growled. His hands moved over my ass, the warmth of his touch sending a shiver through me.

Anthony's deft fingers sought out my entrance, one blunt digit entering me with delicious ease. I jolted at the white-hot spark of initial penetration, a strangled gasp tumbling unburdened past my lips. "Ahhhh..."

"Fuck, you're tight," he rasped in reverent appreciation, that lone digit steadily pumping in languorous strokes to gently work me open.

I keened shamelessly at the smoldering friction, whole body arching. "Mmm...yesss..."

Seemingly spurred on by my blatant responsiveness, Anthony twisted and pumped the snug channel with increasing fervor, stretching the clinging rim wider and wider in lewd preparation.

"M-More lube," the breathy demand slipped out before I could rein it in, the searing drag quickly skirting the edges of discomfort despite how my body instinctively clenched around the invading digits.

"Yeah, good call..." With deft urgency, he drizzled a fresh, liberal stream of lube directly over his knuckles before those questing fingers slid back inside with obscene ease.

A low, lascivious moan spilled from my lips as I surrendered to the unhurried rhythm, my eyes drifting shut in ecstasy. Every dexterous pump and curl seemed to ignite tendrils of pleasure. I could feel myself rapidly becoming undone, the ring of muscle loosening in increments until it felt deliciously spread, exposed, primed for more..."Are you ready?" he whispered into my ear.

"Yesss," I hissed, a note of impatience creeping into my voice. I wanted him. I wanted him now.

He leaned over and kissed the back of my neck and shoulders, his lips moving along the length of my spine.

"Oh," I moaned, "I'm ready."

He pulled his fingers free and shifted his position. The head of his cock pressed against me, and he pushed. My body resisted.

"Just relax."

"Okay," I replied, taking a deep breath, letting the tension leave my body.

The pressure grew as he pressed harder.

"Relax," he said again, his hands rubbing along my back.

The head finally popped in.

"Oh, fuck," I exclaimed. There was a flash of pain that started to subside almost immediately. We held that position for a moment, my body growing accustomed to his cock inside me.

"You're so tight," he moaned.

"It's been a while," I said, the words sounding slightly defensive.

"Well, we're going to have to remedy that," he said as he slowly pushed in, giving me time to adjust, "You good?"

"Yesss..." The soft moan flowed from my lips, "Don't stop..."

He pulled his hips slowly back, almost pulling completely out but leaving the head still in me. Then he slowly reversed and pushed back in until he was balls deep.

"I've wanted this all night," he murmured, his voice thick with desire.

He began to establish a slow, deliberate rhythm, each thrust almost completely withdrawing before sliding back in. Sometimes he would pause, his cock buried deep inside me, allowing the tension to build. His hands traced a path over my skin, exploring my back, skimming over my ass, and sliding down my legs. My head dropped lower, my arms growing weaker with each thrust, trembling as he continued his slow and methodical pace.

I was immersed in the sensations, every nerve ending responding to his movements. Suddenly, his hands shifted, releasing their gentle caresses and moving to grip my ankles. He lifted them slightly, altering the angle of my ass, and I could feel the subtle change in pressure.

When he pushed in again, it was slow and controlled, every inch of his cock deliberately grazing over sensitive areas. My body tightened instinctively, and a moan escaped my lips as the head of his cock brushed against that tender gland, sending waves of pleasure radiating through me. The intensity of the sensation made me arch my back, lost in the overwhelming physicality of the moment.

"There it is," he said triumphantly.

"Oh god..." I moaned as waves of pleasure radiated through me. I arched my back, overwhelmed by the intense feeling.

"Found your sweet spot," he said proudly.

He pulled back and thrust in again, hitting that sensitive bundle of nerves once more. My ass instinctively clenched around his cock.

"Oh my god!" I cried out, shivering with primal ecstasy as he nailed my prostate over and over.

He let go of my ankles, leaning forward to grab my hips, pulling me back toward him as he thrust deeper inside. His pace remained steady, each stroke unhurried, each thrust angled perfectly to hit that sensitive spot inside me. Waves of pleasure cascaded through my body with every movement, intensifying as he continued.

I was completely absorbed in the sensations, every detail heightening the experience. The tightness of the bra across my chest, the silky caress of the nylons clinging to my legs, the pressure of the bunched-up panties around my thighs, and the firm grip of the high-heeled boots on my feet — all contributed to the intoxicating mix of pleasure. Fabric rustled softly beneath us as we moved on the bed, Anthony's hands holding my hips firmly, tethering me to the present.

The sensation of his cock sliding against my prostate was electrifying, sending waves of ecstasy through me that made my whole body respond. My world narrowed to the intensity of the moment, to the feel of his body against mine, the rhythmic thrusts, and the raw, physical connection between us. Every nerve ending was alive, attuned to the pleasure he was giving me, and I was utterly lost in it.

"Shuddering in primal delight, I stammered out, "Gonna... make me... cum..."

"That's the idea," he replied, a note of self-satisfaction in his voice.

He thrust forward again, slowly driving his cock deep.

I was rocking back to meet his thrusts, my knees and legs spread, bound by the waistband of my pantyhose and panties, my hips pushing back against him. The pressure was building. And I hadn't even touched myself. The muscles in my thighs started to quiver, the sensation moving out to engulf my entire body. I had never felt anything like this. The intensity and completeness of the approaching climax took my breath away. My entire body started shaking, driven by slow building waves of pleasure as Anthony's cock rubbed across my prostate.

"Aahhhhh... Uuhhhhh..." I moaned inarticulately, words were far beyond me as the crashing wave of pleasure built to crescendo.

"Come for me," he coaxed.

I gasped, pushing my hips back, clenching as the orgasm surged through me. My entire body trembled, muscles tightening uncontrollably as the intensity of the climax overwhelmed me. My hands gripped the soft fabric of the comforter, my toes curled tightly inside my boots. Cum dripped from my cock onto the bed, and I marveled at the electric charge that seemed to course through every nerve.

My arms gave out, and I collapsed onto the bed, Anthony following close, his cock still embedded deep inside me. I moaned, low and inarticulate, the sound drawn out as another wave of pleasure rolled over me.

We stayed like that for a moment, his body warm and solid against mine, grounding me as the intense waves of pleasure slowly started to recede. I trembled again and again as aftershocks of pleasure hummed through my entire body. Never, in my entire life had I experienced an orgasm this blissful or that lasted this long.

As some semblance of awareness returned, I realized Anthony's cock remained inside me. He had remained unmoving as I trembled underneath him. But as I began to come back to myself, I felt him shift slightly, his weight easing off me as he started to move once more, sliding in and out of my ass with a deliberate slowness.

I shuddered, my body still buzzing from the blissful waves of the orgasm that had just racked me. The sensation of him moving inside me, even now, sent ripples of lingering pleasure through my already sensitized body. The softness of the bed beneath me, the warmth of his touch, the weight of his body on top of me, and the lingering throes of release all melded together, leaving me in a state of pure, exhausted satisfaction.

"God, you're so fucking sexy," he whispered as his thrusts built in speed and intensity.

I felt his cock start to jerk and twitch as the orgasm washed over him. He pumped several more times and then fell forward onto me.

After a few moments, he exhaled heavily, "That was fucking amazing."

"Mmmm Hmmm," was all I could manage, my body still purring from the intensity.

He shifted, rolling off me, and settled on his back beside me. "Sorry," he murmured, "I didn't mean to crush you."

"No problem," I replied, my voice dreamy and muffled by the comforter beneath me, still floating in the lingering sensations.

"Fuck, I needed that," he said, his tone laced with deep satisfaction.

"Me too," I mumbled, feeling a similar contentment settle over me.

We lay there together for several minutes, the warmth of our bodies gradually cooling as the sweat dried on our skin. My thoughts wandered, the physical pleasure ebbing into a tranquil calm. The room was quiet, save for the soft sound of our breathing.

"I can't believe how lucky I am," Anthony said quietly, breaking the silence.

"Huh?" I asked, the words pulling me back to the present, my mind still fuzzy.

"You're amazing. Beautiful. Sexy. And you might be the best fuck I've had in years."

"You already fucked me, you don't need to flatter me," I said, a light laugh escaping as I turned my head to look at him.

"I mean it. I really do."

"Thank you," I replied, suddenly feeling a warmth in my cheeks that had nothing to do with our earlier activities.

"This has been an amazing night. I never imagined I'd meet someone willing to do all the things we did tonight."

We lay there a while longer, our bodies close but relaxed, basking in the afterglow and the quiet intimacy of the moment.

"Well," he finally said, breaking the comfortable silence, "I should probably get going. You're probably tired and all."

"Oh, okay," I replied, an unexpected note of disappointment in my voice.

He sat up and began gathering his clothes, turning his back to me as he dressed. Watching him, a sudden wave of self-consciousness washed over me. I became acutely aware of the state I was in — my makeup smeared, hair tousled, panties and pantyhose still bunched awkwardly around my thighs. The vulnerability of being so exposed, both physically and emotionally, weighed suddenly on me. Feeling exposed and vulnerable, I grabbed the comforter and pulled it up to cover myself, the fabric offering a small comfort.

When Anthony was fully dressed, he turned to look at me. "Can I use your bathroom to clean up a bit?"

"Sure. It's through the door," I said, gesturing towards the bathroom.

As soon as the door closed behind him, I slid off the bed, the cool air hitting my skin as I tugged my hose and panties back into place. I grabbed a robe from the closet and slipped it on, the soft fabric brushing against my skin, giving me a semblance of modesty. I sat on the edge of the bed and pulled off the leather boots, letting out a sigh of relief as my feet were freed from their tight confines. The coolness of the carpet against my stocking covered feet a small comfort as I began to gather my thoughts.

Anthony emerged from the bathroom, the sound of the door clicking shut jolting me slightly. I followed him into the living room, the cool air brushing against my skin where the robe parted slightly as I moved. I found him sitting on the edge of the couch, putting his shoes back on with deliberate motions. Each movement felt like a small barrier being erected between us.

"You could stay here if you wanted. It's late," I said, my voice laced with hesitation.

"I wish I could." he replied, his tone practical, almost distant. "But my wife gets back tomorrow. I need to get showered and make sure all the cum stains are off the car seats."

The casual mention of his wife was a cold reminder of reality. The realization that my time roll playing as his girlfriend was at an end. "Oh, yeah, right," I replied, trying to keep my tone light, but there was no hiding the sheepishness that crept in.

He stood up, smoothing down his clothes, and I couldn't help but feel a pang of discomfort at how quickly he seemed to be pulling away from the intimacy we had just shared.

"Well, it's been amazing. You're incredible," he said, his words kind but somehow feeling a bit formal, like the ending of a pleasant meeting rather than the conclusion of something deeper.

"Thank you," I responded, the words feeling small.

"Email me if you want to get together again sometime. Maybe we can go on another date?" he offered, his tone suggesting more obligation than genuine interest.

"Sure. Of course," I answered, forcing a smile. The room felt colder, the space between us widening even as he stepped closer.

"And send me those pictures, please. I really want to see them," he added, a note of enthusiasm in his voice.

"I will," I said with a small smile that didn't reach my eyes.

He leaned forward and gave me a quick kiss, his lips brushing my cheek with the faintest pressure. The contact was brief, almost mechanical, leaving behind a ghost of warmth that evaporated the moment he pulled away.

"Alright. Well. I better go," he stated flatly, glancing at his watch.

"Okay," my voice small and soft, "Thanks for the date."

"Well. Goodnight. Thanks for a great night."

With that, Anthony opened the door and stepped out into the night. I watched him walk down the driveway, his figure becoming a silhouette against the dim streetlights. The night air brushed against my skin as I stood in the doorway, feeling the coolness seep through the thin fabric of my robe. As he reached his car, I quietly closed the door, the soft click of the lock echoing in the quiet house.

I listened for the sound of his car starting, the engine's hum cutting through the stillness, before it faded away as he drove off. The silence that followed felt heavy, almost smothering. I lingered for a moment by the door, feeling the coldness of the floor under my stocking-covered feet, the plush carpet of the stairs beckoning me back to the warmth of my bedroom.

I made my way upstairs, each step slow and deliberate. My body ached, but it was the kind of ache that reminded me of everything that had happened, a lingering ache from a night of intense sex. My muscles felt heavy, fatigued in the most satisfying way.

Back in the bedroom, I let the robe slip from my shoulders, the fabric whispering against my skin as it fell to the floor next to where my skirt and top lay. I stood there for a moment, feeling the air on my bare skin, the tightness of the bra across my chest, the delicate sensation of the panties and pantyhose still clinging to my legs, the cool spot where Anthony's cum still soaked my pantyhose and panties. The room was dim, shadows playing across the bed, the scent of sex still faintly lingering in the air.

I glanced at myself in the mirror, the reflection showing a woman who had just been thoroughly ravished, makeup slightly smeared, hair tousled, but there was a glint in my eyes that spoke of satisfaction, of having been fully in the moment. The night had left its mark on me, and the sensations still hummed beneath the surface, a reminder of the passion that had just been shared.

But now, the room felt emptier, the warmth of a human connection replaced by the solitude of the night. Taking a deep breath, standing in the silence, I let the memories wash over me. My mind drifted back to the events of the evening.

It had been another night of firsts for me. The thrill of going out to a "normal" restaurant while crossdressed had been both exhilarating and nerve-wracking. I could still feel the tight pull of the leather mini skirt brushing against my nylon covered legs as I walked into the restaurant, the slight tension in my muscles as I waited for the reactions of others, the comforting weight of Anthony's hand on my back, guiding me through the evening with confidence. Role playing the girlfriend experience with Anthony had made me feel both powerful and vulnerable in a way I hadn't expected. The experience left a lasting impression on my mind and body.

Then, there was the unexpected excitement of my impromptu strip tease and masturbating in the car, the rush of sensation heightened by the fear of being caught, the tightness of the lingerie and the rough fabric of the car seat against my skin. The memory of that intense, secretive pleasure lingered, a mix of shame and satisfaction that still made me flush.

Looking at the bed it was obvious a change in bedding was needed. Padding silently, I reached the side of the bed, my hand running over the soft fabric of the white cotton comforter that only a short time ago had been the stage for our carnal activities. Looking down, I saw clear evidence of our passion. Streaks of smeared makeup stained the once pristine fabric — lingering evidence of where my face had been buried amid the throes of ecstasy, and dark stains of my cum in the spot where I had experienced the most powerful orgasm of my life.

Just the memory of that mind-blowing climax made me shudder with arousal again. It was the most raw, intense orgasm I've ever felt — triggered not by typical genital stimulation, but from Anthony's cock massaging that sensitive spot deep inside with each thrust. I didn't think it was possible to orgasm from anal stimulation alone, but clearly, I had been wrong. That had been yet another first for me. My body shivered slightly at the memory as I began to strip away the soiled bedding.

I shook my head in amazement, a small smile playing on my lips as I wondered what new firsts lay in store for me. The night had left me satisfied, sore, and yearning for more, the physical sensations still humming under my skin, a reminder that there were still so many experiences waiting to be had.