Close Encounters of the Femme Kind: Caught Crossdressing at the Bar

By Jessica Cockburn

Dan, a man with a hidden desire for cross-dressing, meets Mark, a man who helps him embrace his feminine side and explore new sexual experiences. When Dan's wife, Sally, discovers his secret, their relationship takes a surprising turn as they navigate their desires and encounter new friends who join them on a journey of sexual exploration and self-discovery.

• Language: English
• Publisher: Jessica Cockburn
• Release date: Sep 30, 2023
• ISBN: 9798215407653

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Close Encounters of The Femme Kind

Caught Crossdressing at the Bar

Copyright 2023 Jessica Cockburn

Published by Jessica Cockburn at Smashwords.com

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Table of Contents

Prologue

Chapter One

Chapter Two

Chapter Three

About the Author

Connect with Jessica Cockburn

Prologue

Author's note: All characters depicted in this work of fiction are 18 years of age or older.

I perched on the tall stool, clutching the bar for support as I reached for the ashtray. There I sat, engaging in conversation with Jacob, my dinner companion. Our evening had been quite indulgent, with a hearty meal and numerous beers both before and after. We capped off the night by watching a rather seedy striptease. The effects of the copious amount of alcohol were beginning to hit me, and I was more than relieved to let Jacob take over the driving duties for the final stretch of our journey.

As I sipped on yet another beer in the hotel bar, knowing that my room was just a short elevator ride away, my mind began to wander to the tranquility that awaited me. I envisioned myself reclining in my room, engrossed in an intriguing TV program, surrounded by my carefully-packed suitcase of attire.

Now, this was no ordinary suitcase. I harbored a secret love for donning women's clothing, but only in the utmost solitude, never for any other purpose. The suitcase contained a treasure trove of lace, frills, satin, and an array of colors, along with lipsticks and nail polish. All these items were reserved purely for my personal enjoyment.

As the fatigue of the day weighed heavily on me, I yearned for the comfort of my room and the intimate pleasure it held.

That gal, the petite one with the boots and lasso, really stood out, remarked Jacob, seated beside me. I recalled the vibrant, statuesque blonde teetering on her high-heeled cowboy boots, twirling a pre-made lasso that hardly captured anyone's attention. In fact, all eyes were mostly fixated on her leather vest, offering glimpses of her small yet immaculate breasts as she spun to the music. Then there was that short fringed skirt she defiantly hiked above her waist, revealing her unshorn front. The audience collectively flinched as she dragged a spur through her tresses, eventually tracing it down through her exposed nether lips.

Yeah, I nodded in agreement, but the most captivating was the petite one in black. I could still picture her in my mind's eye - dark-haired and delicately built, with a flawlessly youthful figure. She had been clad in the tiniest leather skirt, a translucent black blouse, black crotchless pantyhose, and sky-high heels.

Oh, absolutely, Jacob chimed in with enthusiasm. I was certain his thoughts weren't veering in the same direction as mine, for my mind was preoccupied with thoughts of how her attire might look on me. The mere notion ignited a pulsating sensation in my pants, accompanied by a fantasy of having her in my room, witnessing and patiently waiting as I transformed into her.

I had been utterly entranced as she shed her skirt and blouse, skillfully manipulating her nipples to stiff peaks. She leaned back near us, unveiling her adeptness as her vagina rhythmically contracted to the music, manipulating her clitoris within the parted folds of her lips.

The bar was buzzing with patrons, yet several vacant seats dotted the counter - two on Jacob's side and three to mine. As I daydreamed about the girl and eagerly anticipated a bit of solitude in my room, I surveyed the bustling bar.

As I glanced around the U-shaped bar, I noticed a striking man across from me who seemed to be stealing glances in my direction. His attention quickly shifted to his drink and the cigarette in his hand as our eyes briefly met. I looked away, suddenly realizing that I had been staring at him.

Finishing my beer, I decided to make a quick trip to the bathroom. While standing at the urinal, I heard the door open and someone occupy the stall beside me. Ignoring my surroundings, I washed my hands and tidied up my appearance. As I turned to leave, the man in the pinstriped suit passed by without a word.

Upon returning to my seat, I noticed that the man had taken the spot next to mine, still enjoying his drink and cigarette. I sat back down and continued my conversation with Jacob, completely forgetting about the man's presence. We chatted, drank beer, and smoked cigarettes, and I had completely pushed the man out of my mind. Every now and then, I would catch a glimpse of him engrossed in his own world, meticulously examining the bottles that adorned the backbar.

Then, as I was deep in conversation, I felt the man's knee touch the side of my leg. Startled, I instinctively moved away. It felt as awkward as accidentally witnessing someone in a compromising position in the men's room.

A few minutes later, I turned to grab another beer and once again felt my leg make contact with the man's knee. Curiously, he seemed unfazed by the accidental touch, while I couldn't help but notice it. This time, instead of moving away, I decided to stay put and observe his reaction. I continued talking to Jacob, smoking, and drinking, but my mind kept wandering back to the sensation of his knee against mine. Each time I thought it was a mere accident, he would subtly shift as a reminder of his presence.

Then, I turned slightly away and his leg also moved away from mine. When I turned back, I felt the side of his leg pressing against mine. Perplexed, I took a closer look and noticed the rather peculiar way he was sitting in his chair to allow this contact. It was hard to believe that he could be doing it unknowingly.

Despite my attempts to forget about the contact, he would readjust himself, instantly grabbing my attention again. I sensed a change and turned to fully face him, curious to see his next move.

He sat next to me at the bar, his left arm extended, his hand resting on his knee. Due to our proximity, his hand also grazed against my leg. He nonchalantly smoked a cigarette and drank his beer with his right hand, never once averting his gaze from across the room. Then, as if my stare triggered something within him, he slowly turned his head and locked eyes with me. A faint smile tugged at the corners of his mouth before he looked away again.

Jacob and I engaged in conversation, savoring our beers. Suddenly, his hand ventured between our legs, gradually moving up our thighs before retreating. I felt a surge of tension course through my body, but I managed to relax as his hand rested on his knee.

Moments later, the movement repeated. This time, I didn't instinctively react. My attention fixated on his hand, curious about its recurring motion. Again, it happened. And again. I couldn't fathom if it was mere accident or intentional, surely, it must be a coincidence.

Then, his fingers caressed the top of my knee. It wasn't a mere brush beside it, but a deliberate touch. Uncertain, yet sensing his intention, I stiffened again as his hand repeated the earlier journey from knee to thigh and back again. Disconcertingly, this time his hand settled on top of my thigh. But still, doubts lingered.

However, all doubts vanished when his grasp enveloped my knee, exerting a gentle pressure. Once more, my body tensed, but I refrained from moving away. Anxious, I finished my cigarette and ordered another beer. Before doing so, I glanced over my shoulder to ensure no one was observing our exchange. Then, I met his eyes with a secretive smile before resuming our conversation with Jacob.

My throat tightened as his open hand ventured higher up my leg, alternately squeezing and releasing with each upward movement. And just when I thought the sensation couldn't escalate any further, he reached the pinnacle of my leg, paused, and squeezed. As his fingers resumed their advance, my arm instinctively descended to shield my vulnerable space. It was then I realized just how urgently I needed to use the restroom. Informing Jacob of my predicament, I slipped off the stool, distancing myself from the mysterious man.

Hastily, I found relief in the solace of the bathroom, my eyes closed tightly, slipping into a euphoric state. I was vaguely aware of the door opening and closing, but it didn't register until I heard his voice. He stood at the adjacent urinal.

You got turned on, he stated matter-of-factly. Only then did I realize the obvious arousal I concealed with reservation.

What are you doing? I whispered nervously, my gaze fixated on the bathroom door.

I'm interested in getting to know you, he said in a similar tone.

Why me?

You seem attractive. You give off a pleasant vibe. There's an equilibrium about you.

Thanks, I guess. He responded with a smile. Get to know me how?

Well, I'd like to spend the night with you. My mind raced. I had never considered this possibility. I'm not homosexual. It's never crossed my mind--

Would you? he asked, interrupting my thoughts. Suddenly, I realized I had forgotten about my original purpose of going to the restroom, and the discomfort in my bladder had vanished. I quickly adjusted myself, moved to the sink, and began washing my hands. It will bring you satisfaction.

My thoughts continued to whirl. It felt so bizarre. I became aware that a part of me desired it, despite the clash with my upbringing and society's expectations. I met his gaze in the mirror as he stood behind me. In a swift motion, he reached around and gently rested his hand on the bulge in my pants. With a slight movement, he smiled.

You're still aroused. You want it, don't you?

Yeah, I whispered, before fully comprehending my words and realizing that I did, indeed, desire it. Then my determination solidified. Yes, I do.

Your place or mine? he inquired. I had to think quickly.

Mine, he claimed.

Fine, I'll quickly grab my things from my room and meet you. What room are you in? I informed him, until Jacob suddenly came to mind. Wait, I have my friend with me.

He reassured me, That's not a problem. Just tell him you're tired or want to watch a movie. You need your beauty sleep. I'll wait a few minutes and follow you. His hand gently caressed the bulge as he spoke, intensifying my arousal.

With trembling hands, I grabbed the door handle and made my way back to my seat, slightly shaky. I chose the barstool farther away from Jacob and swiftly finished my beer as soon as I settled.

Jacob, I'm exhausted, I think I'll call it a night, I informed him, and he decided to stay a little longer since it was early. Exiting the bar, I noticed Jacob engaging in conversation with the two girls sitting next to him, just as he had been for the past half an hour. I knew his efforts weren't going to lead anywhere, but I couldn't blame him for trying. Simultaneously, I observed the man returning to his chair, leaning his elbows on the bar, leisurely finishing his drink.

Upon reaching my room, I realized the sudden need to use the bathroom once again and hastily relieved myself. As I finished, I heard a soft knock on the door. My heart raced like it hadn't since high school, for reasons unrelated to this situation. My hand trembled as I zipped up my pants and flushed the toilet, before turning and heading towards the door.

I opened it, causing the concern on his face to transform into a smile. Hi. I thought maybe... I don't know. You weren't really going to stay here, or maybe you changed your mind?

Would that have been so terrible?

Yeah, it would have. We're going to have a great time, he grinned, radiating excitement.

Take a seat. Is there a specific show you'd like to watch on the television? I offered.

No, no. But you can turn on the radio. I think the good station is at 99.5 FM, he suggested. I followed his advice and tuned in to the easy listening station, but I noticed he hadn't settled into a chair.

Would you like a beer? I have a cooler right here, I offered.

"No, thanks. What I