Tranny Glory Hole Surprise

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Home Cuckold How I Unleashed a Tranny Gloryhole Surprise in Adult World, Las Vegas
A self-confessed sex addict, Catherine started Whoreuro magazine to connect with like-minded people, share her sexual journeys, and provide an insight into the sleazy side of Europe and beyond. Originally from Northern Ireland, she adores writing, travelling, great food, and sexual exploration.
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This frankly debauched little tale of a tranny Gloryhole surprise occurred just before the madness of 2020.
To celebrate a friend’s hen do/bachelorette party, I found myself on the way to the original city of sin: Las Vegas.
Due to work commitments in Europe, I had to miss the debauched hen party flight with my friends. I arrived in Vegas a few days before them.
This left me with a lot of time to explore and revel in its notorious debauchery. Like any new city, I logged onto Adult Friend Finder sleazy hookup sites like Adult Friend Finder to see what local sleaze was on offer .
As you all know, I adore the feminisation fetish. So my bio on my profile had a blurb to attract any sissies who desired me to turn them into a dribbling cock whore.
I updated my Adult Friend Finder location and status in my hotel room in Vegas. Like a cock-addicted lioness searching for her prey, I sat back and waited for the messages.
It didn’t take long, with my slit and tits blatantly advertised on the site.
I had a couple of days here. This meant I could plan a few cock appointments with my online hookups. Lying back in bed, fighting the urge to rub my clit rather than respond to messages, I was amassing an assortment of kinky meets for the next few days.
But then came a message that stood out from the rest of the throbbing Alpha’s looking for an easy hole to bury their cock into. The username read ‘Stacey’, and the message read as follows:
“Dear Catherine, firstly I would like to say that I and my long-term girlfriend are adoring fans of your blog. We’re an open-minded couple and you’ve provided us with so many new avenues to explore over the last few months. In particular, we’ve fallen in love with sissification.
My other half loves nothing more than dolling me up like a bimbo fuckdoll and ruining me with a strap-on. Following your tips online, we’ve progressed to even more hardcore play, from hotwifing to forced bi-play.
We use AFF to arrange our fetish hookups, and we were both nearly floored to see you in Vegas. We were wondering if you would be interested in meeting us to show us some of your sissification techniques in person and humiliate me in front of her?”
If there’s one thing I love, it’s a thoughtful and well-written message on hookup sites (hint-hint). I hadn’t considered any sissy sessions for Vegas, but now one had seemingly dropped onto my lap.
The pictures on his profile were divine. He seemed to have perfected the bimbo slut look and wasn’t shy about showing off his humiliating escapades for all of the online hookup world to see. We agreed to meet for a few drinks that evening.
For the social meet, I opted for a discreet bar away from the tourist strip. I got there first and found a discreet booth away from prying ears. I ordered a Jameson and coke to relax. Then, I saw them arrive.
She was in her mid-40s, slightly curvy and sporting a mishmash of tattoos and blonde curly hair. Her high-speed entrance and body language showed she was in control. This was reinforced when her man appeared behind her.
He was in his mid to late 20s, obviously with a taste for older women. He was not much more than 5 feet tall, slim, and looking very nervous. He was almost too nervous to look around the bar, but his girlfriend did that for him.
Greeting them with a discreet wave, they came toward me, and we hugged. She gripped me in a tight hug and kissed me on the cheek.
With minimal eye contact, he offered to shake my hand. But I laughed it off and gave him a cuddle with a kiss.
Over drinks, we talked about our backgrounds, how I liked Vegas and all that jazz. But after a few drinks, his confidence grew, and the conversation soon turned to sex.
The pair had been ardently following my various sissy school articles online. I was immensely proud as they detailed their subsequent journey into sissification and how it had transformed them.
His girlfriend proudly confessed that her discovery of ‘Hotwifing’ and sissification had been the perfect match for her insatiable sex drive and her man’s desire to be fucked like a woman and humiliated.
He had grown in confidence and developed quite the taste for alpha male cum. Whether it was sucking it from his girlfriend’s freshly fucked orifices and slurping it out of used condoms, there was no going back from his spunk addiction.
Sadly, his girlfriend was completely straight. Although she was very much my type, I respected her boundaries. Her desire was for me to take ‘Stacey’ away, sissify him, and humiliate him as I saw fit.
I was to record everything on his phone. She would then pick him up when I was done, and they would play together whilst watching the footage.
I was more than keen. I felt like a sleazy godmother being asked to grant the kinky wishes of this couple.
The deal was done. Stacey was to meet me at my hotel the following afternoon and bring a bag full of sissy gear.
His girlfriend would only discover what had happened when she picked him up. Safeword? Bingo!
Before he arrived in my room, I’d already sandwiched in three meets off of AFF. Nothing exotic, just an attempt to put out the perpetual aching lust in my slit with a hearty injection of cock.
Nevertheless, the trash can was full of spunk-filled condoms and tissues stained with my pussy grool.
With another hour to spare, it was time to make the finishing touches on the humiliation I had in store for the incoming sissy slut.
I had planned on a tranny Gloryhole surprise. As a bastion of porn cinemas, the United States rarely disappoints when it comes to glory holes.
I found a nice little gem online called Adult World, Las Vegas. It was here that I would be putting Stacey to work.
Drenched in a mixture of my own and other men’s sweat and various other love-making juices, I took a quick shower to freshen up.
I then slipped into black heels, stockings, a pencil skirt, and a white shirt that left my nipples poking through.
At 11 am on the dot, there was a knock at my hotel door. I do love a punctual whore! Dressed in a tracksuit and holding a gym bag, I invited him in and offered him a drink. As he sipped on his coffee, I delved into what was in the bag.
It was a fucking treasure trove! Wigs of various colours, stripper heels, outfits that could drain any man’s balls, and enough sex toys to endure countless orgasms. We were going to have fun!
“Before the internet, there used to be monthly guides sold at adult bookstores that enumerated and gave the addresses of every known glory hole in America.”
Of course, I wasn’t planning on parading Stacey through the lobby in all of her slutty fineries, so we opted for her to don the lingerie in the room, cover it with the tracksuit and finish the rest on the way.
Her petite, feminine, freshly shaved frame looked divine in black fishnet holdups. I ordered her to bend over and promptly inspected her shaved asshole like a farmer inspecting livestock. I spat on her open hole with approval before sliding a lubed-up butt plug inside.
Getting Stacey’s erect cock into a sissy chastity cage was a bit of a task, but I managed. Before we left, I grabbed the used condoms and tissues from the trash can beside the bed.
That’s a surprise tool that’ll help us later, I thought.
“Now get your shit and let’s make a move, you disgusting little tart”, I barked at her. Her obedient eyes, tinged with apprehension about what was coming next, flicked to the ground as she followed me like a dog.
We hopped in Stacey’s car and began the drive to Adult World, Las Vegas. I controlled her phone and kept his wife updated on everything. It was incredibly horny.
The entire drive, I was taunting her about her plugged ass and caged cock, reminding her that she exists only to serve real men’s dicks.
I was beyond excited when we finally pulled up in the parking lot of this sex store and adult theatre.
Stacey slipped out of her tracksuit, did her makeup and slipped into a pink latex mini skirt, and high heel outfit topped off with a white crop top that read: “Mummy’s little cumslut”.
Caked in makeup with red puffy lips painted with lipstick, she was wearing a pair of silicone breasts underneath her audacious shirt.
Trust me; she looked like a magnet for cock. I was only too proud to put the blonde pigtailed wig on her head. It was like crowning a princess!
As we made our way to the porn theatre, the sound of our high heels resonated across the sun-baked parking lot.
A loud buzzer welcomed us into the air-conditioned world of sleaze. The quintessential smell of sex toys, lubricant, and an odd candy-like smell filled our nostrils.
I made the slut pay our entrance fee, and the female cashier didn’t bat an eyelid at the sordid sight in front of her. That’s just Vegas, baby!
We ditched the well-lit sex shop and soon transferred into the darkness of the sex cinema.
The sound of the radio in the Vegas sex store was now drowned out by the artificial orgasmic screams coming from the various porn cinema rooms. Amidst it, were the non-artificial moans of people fucking in the dark corners of the cinema.
Stacey clung to me as though we had just entered a pit of lions. As far as she was concerned, we might as well have been. Her bright pink outfit had attracted many men furiously wanking to come out of the shadows.
These horny men of varying ages and sizes were keen to replace their spit-soaked palms with the inside of Stacey’s willing mouth and ass, and I knew just how to do it. We set out to explore, and the men followed close by.
“Take a good look around, whore. This is what you call real men. This is the best place to be if you want to feed your cum addiction”, I said to Stacey loudly. I ensured all the men could hear to identify that I was in charge.
Finally, we found it. In a particularly sleazy corner of the cinema was a series of Gloryhole booths.
The smaller types fitted with a porn screen and a sucking bench led towards a larger booth at the end.
The latter featured around six holes on two walls facing out onto the largest porn cinemas in the complex.
The idea of Alpha men watching hardcore porn whilst having their cocks serviced by Stacey sent lightning bolts to my clit.
“Feeding time, boys! If you want to feel how good this whore can suck cock, line up and see how long you can last. No holes barred, just let us know which one you want!” I shouted at the men waiting in the darkness.
We both slipped into the booth and locked the door. I reaffirmed Stacey was comfortable and reminded her of the safeword in case she wanted to stop.
But who was I kidding? This insatiable bimbo whore quickly confirmed that she wanted nothing more than an endless supply of cock entering her body.
The first cock that appeared through the tranny Gloryhole was flaccid and underwhelming. Regardless, Stacey needed no instructions and promptly wrapped her lips around it.
Suddenly, the limp worm in her mouth began to grow. I was so entranced as this white cock in her inflated like a balloon that I almost forgot to start recording this tranny whore.
Within seconds, her ruby red lips glided up and down this slick length as she unleashed involuntary moans.
I sat on the sticky stool in the corner of the tranny Gloryhole booth and recorded this slut in all of her sleazy glory.
Suddenly, a sharp knocking sound chapped on the wall. Stacey started coughing, and spluttering as ropes of salty cum sprayed her throat.
The cock withdrew. Stacey looked at me for approval like a dog that had just learned a new trick.
I held her cheeks and admired her. Her makeup was already starting to run down her spunk-stained lips.
“This is what you were made for, slut. Get back to work, ” I muttered to her as two new cocks slid through the wall almost simultaneously.
The sight of the spit-covered cock on the first guy to pioneer the tranny Gloryhole had affected the others.
These guys weren’t flaccid. One white cock and one black. Two twitching members keen to be engulfed by a sissy slut’s mouth. Squatting beneath them, Stacey alternated her mouth between both.
One by one, she emptied the ballsacks. Whether it was on her face or deep in her throat, her lust for cum was insatiable. After sucking six or so cocks, I rested the phone on the stone to keep recording as I moved closer to her.
The booth was now engulfed by the sound of loud gagging and horny moans from the other side of the wall. With her stocking-clad legs spread, her sissy clitty was dangling beneath her.
I lifted her skirt and began gaping her ass with the butt plug by removing it and sliding it back in, causing her to release cum-drunk moans from her meat-filled gullet. Stacey was heading full speed towards true sissification.
Removing the butt plug, I inserted my fingers one by one until I had three stuffed inside her pink hole.
When another rapid knock on the wall was heard, I used my other hand to push her head down onto the anonymous cock as it erupted in her mouth.
Stacey’s body convulsed with the unexpected deepthroat and throatpie. As she gagged, her slutty sphincter gripped my fingers with intense tightness. I could feel my slit leaking from the sensation.
I released my grip from her head, causing her to gasp for air and cough out spunk. As she took a breather, more cocks appeared. I was insanely horny at this point and sucked her sissy lube off my fingers.
“Her features melted into the O-face as I admired her ruined makeup and smelt her cum breath.”
“Please, Mistress. Can you put my pussy to good use?” Stacey asked me, out of breath. I nodded to confirm.
Following Gloryhole etiquette, I lightly tapped the largest cock on the tip. When it retreated, I pushed a handful of condoms through the hole.
Anyone who put the condom on wanted to fuck; any who didn’t were happy with a blowjob. In a few seconds, some pretty large cocks were glistening with latex. Thankfully, Stacey had been stretched in preparation.
I got to work lathering two cocks with an abundance of lubricant whilst I ordered her to keep fluffing up other cocks keen for a suck.
Then, I stood her up and guided her pretty pink hole back onto a Latino-looking dick with a thick bulbous head.
“That’s it, baby. Let that cock explore your love tunnel. This is what you were made for”, I said whilst looking into Stacey’s eyes. Her features melted into the O-face as I admired her ruined makeup and smelt her cum breath.
The crinkle of the condom came to an end as her s
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