Tales From The Strip

To the dominatrix sitting in the corner… your Fantasy Cowboy awaits.

Fantasy Cowboy

The cheap, dusty radio next to me was playing some old show tunes, and with the bass blown out and the vocals muffled, it was no wonder that my eyes were steadily closing in for the count. I’d been waiting for the past three hours for my superior to make an appearance, and I sensed as if she was standing me up. The rundown motel I was staying at was the most affordable place I could find, given as how I hadn’t made a ton of cash that evening, and the four-hour train ride up had taken a sizable bite out of my wallet. I was a young gun, and times were tough.

To put this story into context, an old buddy of mine had offered me a stripping gig at a country bar in Santa Maria, California. The ladies in town were celebrating their annual ‘cowgirl’ event, and a male stripper seemed like a safe bet for a wild night. The women were only offering three hundred bucks cash plus tips, and living down in Hollywood at the time, the gig was close to two hundred miles away. After paying for a roundtrip train ticket, plus tacking on sixty bucks to crash at some sleazy motel, I’d be lucky to walk out of the joint with a few bills to help pay rent. I was desperate at the time, and pulling in extra side cash on the weekends through stripping was just what the doctor ordered. The exotic dancing bug had bitten me hard, and I was starving for the attention, practically salivating over it.

The event itself was pretty underwhelming, to say the least, and given that the place was a hole-in-the-wall, the dozen or so women who even bothered showing up practically filled the joint. Reggie’s Hole was a dingy smoke-staled bar, with dim lights and strong drinks, hoping to mask all of its imperfections.

I ended up being the only dancer there to perform that night, seeing as how the other guy bailed. He must have googled the place and seen what a shit show he was in for. I can’t say that I blamed him, not showing up and all, it probably wouldn’t have been worth his time. Regardless, I always made it a point to stick to my obligations, for better or worse.

The gig at Reggie’s Hole was happening back in my early days when the only costume I owned was a cheesy ‘Frank Sinatra’ look; black dress pants, white suspenders, and a fancy red shirt. As I approached the bar, you can imagine that this hundred and fifty-pound Magic Mike wannabe must have come off like a real asshole to the cowboys that were smoking cigarettes out front.

“Be careful,” a gruff hillbilly warned me as I was carrying in my bag, “That’s my wife and sister you’re dancing for in there.”

“I got you,” I affirmed, never one to cause trouble.

“Just cause you here, don’t mean we gotta like it!” A short, paunchy dark-haired man wearing oversized burgundy boots called out behind me as I entered Reggie’s Hole.

Those boys were trouble, but thank God for alcohol. I shot back a few whiskey sours and let the sweet liquor take control over my nerves. The women were extra friendly, accommodating me as much as they could. One kind lady even walked up to me before the show and placed a leather cowboy hat on top of my head.

“There you go, fantasy man,” The middle-aged woman flashed me a genuine smile and I noticed a toothless grin.

All the ladies at the bar that evening were beautiful, generous, and kind. Within an hour, I was happy I’d come, and being their only form of entertainment, I was the star of the show. The spotlight fell on me, and the gypsy came alive.

Reggie’s Hole was far too small to have a stage, but the manager had cleared out the middle area and placed all the bar stools along the edges of the room. Most of the guests were in their fifties and up, not that I minded in the least, as they all brought stacks of cash to wave around while they hooted and hollered.

Maybe tonight wouldn’t be such a bust after all.

At the start of my routine, I made sure to go by and personally introduce myself to each and every woman in the circle, and when I reached the far end of the room, I spotted her for the first time.

Tink looked to be in her twenties, with short blue hair, bright eye shadow, and a pierced lip. She had more spunk than most girls in Los Angeles, let alone this small town. The young lady moved like a trained dancer, and the see-through thin mess dress she wore left little to the imagination. For a novice stripper such as myself at the time, I completely lost focus of the task at hand, and it wasn’t long until I was entertaining Tink more than I should have.

Looking back at it, I had just committed a classic mistake that many strippers fall victim to. Whenever I do a show, I take pride in providing the same level of attention to everyone. Sure, some women I find more attractive than others, and vice versa I’m assuming, but the job of the performer is to conceal all that, allowing the suspension of disbelief to take over.

Sadly, the man inside of that lowdown hole-in-the-wall that night wasn’t a seasoned dancer, but rather a young lustful boy, hungry for acceptance. My indiscretions quickly took over, and the whiskey sours did their job, numbing me of common courtesy.

Since the other stripper was a no show, I just danced around the entire two hours in my thong, grinding against whomever I felt appropriate. The cowboy hat was helping out a ton, giving me something to play off of, and I made a mental note to provide the woman who gave it to me a special lap dance as a thank you.

“How much for the night, babycakes?” An older, heavyset blonde lady inquired as I circled around collecting tips.

“How much you got?” I asked back with a sheepish grin.

The woman smirked and pulled out a crisp fifty-dollar bill.

‘Dollface,” I bluffed, “I’m at least worth double that.”

“I’ll give ya eighty, but I wanna eat your ass, too!” The weathered blonde licked her thin lips. She appeared old enough to be my grandmother, but hell, the lady was talking money.

“I’ll consider your offer,” I slurred, reaching across her table to grab a dry napkin, which happened to have a picture of Mighty Mouse punching his arch-villain in the face, “Got a pen?”

I jotted down my number and handed it to the lustful lady, spectating as she gingerly placed the piece of paper into her overstuffed brazier.

I had yet to have ever provided any sort of sexual services for money up until this point, and while the thought terrified me in some ways, I had to admit I was turned on and intrigued.

Maybe I could get this lady to pay for my hotel room as well?

“Make sure you call me after the show,” I winked while waltzing away.

“Don’t shower!,” The giggling woman shouted from behind.

I spent the final half-hour at Reggie’s Hole dry humping the seductive goth girl, Tink, in the corner.

“You’re so smooth,” I complimented her as my hands glided up and down her sultry physique.

“Brazilian waxed,” she whispered into my ear, right before playfully biting my lower lobe.

Other than the sheer, flowy dress Tink had on, the only thing she wore was a lace thin g string, accompanied by six-inch stilettos. My mind was on overload. I had never been captivated and controlled so thoroughly by somebody before.

“You’re the most beautiful woman in the world,” I told her while we continued grinding. My attraction was obvious, with my throbbing cock trying it’s best to bust through the tiny mesh thong that was holding it back.

“You got that right, Stripper.” Tink moaned as she reached down and grabbed ahold of my penis with a firm grip, “I wanted to get all done up for you tonight.”

“For me?” I could barely get my words out, as the lust had me mesmerized and overcome with sensation.

“A huh,” She motioned over to the small print out sheet of paper stapled to the back of the entrance door.

‘Fantasy Cowboy Strippers!’ the sign read in big bold letters. There was a photo of a buffed up fitness model holding a bullwhip and wearing assless chaps. The guy was massive, with every tanned muscle oiled to perfection, in short, he looked nothing like me.

It appeared as if Tink had planned to show up scantily clad and seduce the annual stripper that evening, maybe it would make for a good story and something she could gloat about to her friends the next day.

“Are you staying in town after the show?” She asked while lightly pinching my nipples.

“I, I am.” I stuttered. The more I stared at the short-haired vixen, the more control she seemed to gain over me.

“That’s what I thought. Take my number… I’m gonna fuck your stripper brains out tonight.” She teased.

“Whatever you say.” I was being completely dominated, and loving every second of it.

Out of nowhere, Tink jumped into the air and wrapped her legs around my waist, forcing me to hold her weight. She may have been fit, but she was meaty, so thank God for all those leg workouts I’d been doing at the gym, or that could have ended badly. Once I managed to wrangle myself free, I raced over to my phone to take down her digits.

“Thanks so much for coming tonight,” I tipped my hat to some ladies as they walked toward their cars once the gig was over.

Luckily for me, I’d heard of a cheap motel I could stay at down the street, so I stuck around the bar after performing to consume some more alcoholic beverages.

“You were great in there,” A tiny voice squeaked. I turned around to see a shy, awkward woman in her late thirties smiling back at me.

“Thank you so much,” I embraced her with a warm hug and escorted her across the street to her car, “I’m so glad you enjoyed the show,” I said along the way.

“My friends and I have been looking forward to you coming for months, there ain’t much to do in Santa Maria,” She blushed.

“Yea seems desolate,” I scanned over the barren, dry landscape, “I wish I could have spent more time with you and your friends during my act.”

“It wasn’t your fault, only if that girl hadn’t come and distracted you from the rest of us.” She seemed disappointed.

“I wasn’t distracted, I promise. I loved all you guys!” I lied.

“It’s OK, I understand, none of us look like her. She knew what she was doing alright,” The sweet lady smiled, “Thanks for walking me,” We hugged one final time before she got into her car and drove off.

Even being in a drunk and anxious state, I couldn’t help but stare off contemplating into the distance, severely disappointed in my performance. Those girls had been excited about my show for months, and I had squandered the opportunity to live up the hype. To this very day, I’ve never forgotten how that made me feel. The reason I love stripping so much is because of the way it brings joy to my audience, empowering these women in a sexy, yet comfortable way. I create a space that is very sexually charged but also filled with love and non-judgment. Everyone is treated the same and encouraged to be their sensual, fun self, but inside of Reggie’s Hole that night, I had done the exact opposite.

Instead of enchanting my audience into a fantasy land of acceptance and silliness, I had managed to magnify the coldness of the real world we live in, vain flaws and all. That night, I made a solemn vow to myself that never again would I let my penis do the thinking for me during a show, and while I may have slipped up once or twice since, the Fantasy Cowboy gig left a lasting impression on my ‘stripper’s code of ethics.’

Thank you, mysterious shy lady, you taught me a valuable lesson that I am forever grateful for.

“Hello?” I answered my phone, curious as to who was calling me from the local area code.

“Hey Fantasy Cowboy, you wanna come over here tonight?” I recognized the blonde woman’s scratchy voice from the bar.

“I would, but I need to rent a room around here babe,” I didn’t want to spend the night at this strange lady’s house if I didn’t have to.

After some muffling on the other end, the older woman finally spoke, “I can rent you a room, but then I can only pay ya forty.” She counter-offered.

As bad as I wanted to save the bills I had just earned, I chickened out at the last second, “I’m sorry, I can’t do that.”

“Oh Daddy, come squat on my face and make an old gal proud. You’re so fucking hot!” I could tell by the way she dragged her words that this woman was heavily intoxicated and possibly quite sloppy.

While it sounded like a wet and wild night, my intuition was telling me that it wasn’t something I wanted to get into. Making forty bucks and scoring a free hotel room seemed fun, but naked wrestling with this lady in order to get it didn’t. Regretfully, I decided to pass.

“Dagnabit! Well, hell, maybe another time, Pedro. My husband’s lurking around anyways, it’s probably for the best.” The elder woman croaked before hanging up.

I couldn’t help but feel like I had just dodged a bullet as I made my way down the street toward the cheapest motel in town.

“Hey, you that cowboy stripper?” Someone shouted out at me as I approached the motel lobby. I heard a loud muffler and numerous voices behind me in the street, but I made a conscious effort not to look back.

“Guess who?”

The mysterious text message came through right as I was bringing my suitcase into the room I had just secured. When I noticed another local area code, my heart (and penis) leapt with joy.

“Tink?” I measly replied.

“Mistress Tink!” She messaged back instantly.

I was sitting on the edge of the bed in anticipation, as I had never desired anything as much in my life as I did at that moment, wishing that Mistress Tink would grace me with her presence.This woman had me by the balls.

“Yes, sorry. Mistress Tink.” I responded.

Her messages were direct and to the point, so much so that I thought she might be playing with my emotions. I wanted to write to her again, asking what time I should expect the gorgeous goth, but I restrained myself. It would have looked weak. I must have stared at my phone for close to an hour until it finally lit up again.

“Hotel? Room number?” The Mistress simply inquired.

After sending back all the necessary info, the level of anticipation building within me was insatiable.

“Excited?” My blue-haired superior added a smiling devil emoji at the end of her question for added emphasis.

“Fuck yes, Mistress Tink,” I answered impulsively.

“Good… wait!” She shot back.

Several long, quiet hours passed, and I was almost certain that the beautiful vixen had led me on. Checking the twelve dollar alarm clock sitting next to me on the bedside table, I was shocked to discover that it was past two a.m..

Mistress Tink had played me for a fool…

“Are you still coming?” I finally mustered up the courage to message the girl my plea for attention. When she didn’t respond, I knew it was a lost cause and decided to go to bed.

Around three-thirty in the morning, a loud knock on my door startled me awake. At first, I was too frightened to answer, worried that some of those angry hillbilly husbands had tracked me down to wreak vengeance. As I carefully peeked out of the window, I could tell that it was just a single female waiting outside.

When I opened the door, Mistress Tink was standing in the archway, her body was covered by a long black trench coat that went past her ankles, all the way down to the floor. She smirked when she noticed that I was in my pajamas and had just woken up. After casually strolling into the room, she twirled around, flinging her coat off in the process, revealing a latex-laced bodysuit that somehow managed to cover up her bare essentials. The dominant woman also wore thigh-high latex boots. She allowed me a moment to stare and bask in her beauty, and I noticed several colorful tattoos on her pale white skin, especially the twin smoking pistols adorning each of her curvy hips.

“On your knees, stripper.” She ordered with authority.

I kneeled immediately, giddy with an

excitement that was unknown to me. Here I was, face to face with my gothic goddess.

“Look at me,” She commanded, and when I gazed upward, she smiled back approvingly, “Are you happy I came to see you?”

“Very happy, Mistress.” I began kissing her stomach and thighs, but she grabbed my face with intensity, “Show me,” she snarled while staring deep into my eyes, “Lick my boot, you worm.”

I didn’t even bother responding, instead, I just instantly began the process of polishing her boots with my tongue. I had never found myself so submissive to anyone before and was loving every second of it.

Mistress Tink then ordered me to get onto the bed, where she stripped me naked and proceeded to tie both my hands to the corners of the bedpost with strong fabric. The dominatrix then laid a leather bag onto the bed between my spread legs, unveiling her set of pleasure toys. Safe to say that the next hour or so were the kinkiest moments of my life, as nipple clamps, ball gags, and hijinks ensued.

After stuffing an oversized jawbreaker into my mouth, Mistress Tink began tingling my tits with electric nipple clamps, but not before squeezing my genitals into a raging bull cock ring. Within seconds, my dick and balls were so rock hard they were ready to burst.

“Someone seems to like that,” She started jerking off my swollen penis with such ferocity, I was terrified it was going to explode, like a balloon filled with too much air.

I would have screamed, pleading for her to stop, but the ball gag was doing its job. The worst part was that I had to keep my neck arched up because if I didn’t, none of the saliva building up in my mouth would be able to slide down the back of my throat, and I would gag on my own spit. There I was, forced to watch as Mistress Tink had her way with me.

The nipple clamps were titillating, and while at first, I had felt the sensation intensely, a few minutes into the festivities, I barely remembered they were even hooked up. It was at that moment when Mistress Tink took them off and pinched them onto my nutsack, while also managing to jam a small, vibrating bullet into my anus at the same time. As bad as I wanted her to stop, another piece of me prayed that she would continue.

The ball gag was forcing me to breathe through my nose this entire time, and even though I wasn’t on any drugs, the loss of oxygen to my brain had caused a euphoric high that made this whole experience seem surreal and foggy, almost like a lucid dream.

Pain mixed with pleasure, what a deadly combination.

After untying me from the bedpost and freeing my genitals of their devices, The Mistress ordered me to lick her vagina. It was the first time I had ever encountered a pierced clit in my life and was nervous to engage, fearful of hurting such a sensitive area.

“Don’t be a bitch and suck on that cunt! Your Mistress commands it,” She ordered, at which point I obediently dug in with reckless abandon.

Mistress Tink was right, a woman’s clit is very stretchy, and the more I sucked and pulled on that ring with my tongue, the more it drove my Dominatrix wild.

“Enough!” She screamed over the pandemonium. Reaching down, she grabbed me by the throat and pulled my face up to meet hers, “I’m ordering you to fuck me, stripper!”

Instantly, I mounted her on the bed and began thrusting with a passioned fervor, as all of Mistress Tink’s taunting and teasing had awakened a beast inside of me that I never knew existed. As I plowed her from the missionary position, she continued with her instructions.

“Choke me!” She yelled out.

I gripped her pale throat with my right hand and squeezed as hard as I thought was appropriate, because we had never set any boundaries, and it was my first time doing this, I leaned on the side of caution.

“Harder!” The words rattled in my head, mostly due to the hard slap across the face she gave me while simultaneously screaming, “Your Mistress commands it!”

I usually hate pain, and the left side of my face was now radiating from the smack she had just delivered, yet I found myself extremely turned on by the whole thing. Mistress Tink had brought me into this world, and I trusted her to steer me along the righteous and pleasurable path. I was completely bought in, as this was definitely the wildest sexcapade of my life.

“That’s good,” The words barely managed to escape her vocal cords, as my choke was pretty hardcore, “Now… spit in my mouth,” She uttered.

My Mistress ordered, and I obeyed. Surprisingly, watching her struggle for air was bringing me a sinister delight. We were playing her game, and her game was dangerous.

It wasn’t long until she told me to flip her over so that I could mount her from the doggy style position.

“Didn’t I embarrass you?” She turned back around and taunted me, right before I entered her, “Aren’t you ashamed? Take it out on me, punish your Mistress for humiliating you!” She squealed in sheer delight. I could tell how much fun she was having.

“Yes, Mistress. Whatever you say.” I brainlessly replied in a monotone voice. She had successfully turned me into her personal fuck zombie.

“Wait!” She screamed out after a few seconds, “Put this on,” The Mistress leaned over and snatched the leather cowboy hat off the TV stand.

“As you command,” A sense of manliness crept over me as I put on the hat.

“Ride me, Fantasy Cowboy! Tame this wild mare!” She gleefully exhaled.

For the next phase of our night, The Mistress ordered me to pull her hair and spank her ass while pounding away from behind, there was even a point when she made me roughly step on her head. She continuously ordered me to tell her how angry I was for suffering all that humiliation.

“Bad Mistress!” I yelled out constantly, “I’m so ashamed!”

The night continued this way until she finally instructed me to ejaculate, at which point Mistress Tink had me stand up on the bed and cum on her face while she kneeled in front of me. In my hypersexualized state, I didn’t ask questions and obeyed. This was my first time ever finishing on a girl’s face before, and I have mixed feelings about it, but if it made The Mistress happy, then I was all in.

After blowing my load, I must have passed out on the bed, completely exhausted. The four-hour train ride up that morning, mixed with the stripping gig, and now all of this, I fell into such a deep sleep that it seemed like a dream when Mistress Tink awoke a few hours later. I loosely remember her getting dressed and storming out without saying goodbye, slamming the motel door with authority behind her.

When the next day rolled around, I suddenly woke up in a sort of panic. Glancing across the room, I noticed no sign of any of my belongings, including my wallet, keys, and phone.

“Such a fucking idiot,” I muttered to myself as I frantically jumped out of bed.

How would I ever get home? I didn’t panic long, however, as I soon noticed all my stuff piled up in the corner of the room, with the worn cowboy hat placed on top. When I picked up the hat, I noticed a single red rose underneath. Nothing was missing, The Mistress was just playing one final trick on me. I lifted the rose and smelled its fresh petals. This woman had class.

As I sat at the train depot, waiting for my departure, I couldn’t help but relive the incredible night over and over. This was the kind of stuff you hear about in stories, or see in a late-night movie. The blue-haired girl had empowered me in ways that have stuck with me to this day, and while BDSM isn’t something I regularly engage in, I have a deep fondness and appreciation of it now.

To my next Mistress reading this story… your Fantasy Cowboy awaits.