When it comes to pleasure, I’m very open-minded. Which is what led me to a role with Whoreuro magazine. As much as I love pussy, I’ve developed quite the taste for shemales, femboys and sissies over the years.
But today’s extreme sex story isn’t going to be about me plunging my throbbing cock into the willing holes of beta sissies. Quite the opposite. It’s a confession of when I bit off a bit more than I could chew with the self-described ”Shemales From Hell”.
Shemales From Hell was their username on Adult Friend Finder. A duo of Brazillian shemales, they were stereotypical of the South American country’s transsexual population.
We’re talking ass implants, enormously enhanced breasts, and gorgeous ebony skin. I was on a winter work trip to London and was browsing AFF in the evenings back at my hotel looking for local sluts and submissive sissies.
Despite my search intentions, this dominant pair of ”Shemales From Hell” immediately grabbed my attention. Their profile made my cock twitch on sight, so I dropped them a message with a photo attached that went as follows:
“Olá girls! I hope you’re enjoying everything London has to offer. I’m Karl, a local professional visiting the city for work. I’ve been a lover of transsexuals for a while, and your photos caused my cock to quiver. I’m curious as to why you’re called ‘Shemales From Hell’, too. The weather is awful, so why don’t we meet up and keep each other busy?”
About twenty minutes later, my AFF app pinged. It was them. Their messages were rather blunt, which I assumed was just the language barrier. They asked if I was a sub or a top and when I was free.
Honestly? It might have been blunt, but it was better than ping pong messages all night. In minutes, I was given their address in North London. I was to be there within an hour at 15:00.
I had told the girls I was versatile. Truthfully, I’d been fucked by shemales before. But they were all Asian transsexuals and far from hung. But always down for an adventure, I anally prepared in the shower and jumped on the tube to their address.
As I sat on the tube surrounded by Londoners, I wondered what everyone around me would think of my final destination: Meeting two Brazillian transsexuals for what would, hopefully, be a sordid shemale threeway.
Meeting the local shemale family
I reached the address: A 1970s block of flats stereotypical of North London. I have to admit that I was slightly nervous at this point. I had no idea how hung these girls were, how dominant they were, or where they got their ”Shemales From Hell” nickname.
As I rang the doorbell, I heard the pitter-patter of bare feet approaching on laminate flooring. Opening it to greet me was a petite mid-20s girl scantily clad in pyjamas. She was staring at me with a slightly aggressive and confused look.
Fucking Hell, I thought, I’ve been taken for a ride here. “Have you made an appointment?” She asked me in a Northern English accent. I couldn’t think of a reply. “Are you here for some business?”
Now, ”Business” is British escort slang for paid sex. Feeling a little less awkward, I discreetly explained that I’d arranged to meet two Brazillian girls at this address. The girl rolled her eyes and beckoned me inside whilst calling out the name of one of them.
Then, one of them appeared at the end of the hallway. Her name was Ana, and she hurriedly greeted me with a hug and a deep kiss leaving me with the taste of lipstick in my mouth and feminine perfume in my nostrils.
Standing at about five foot six inches, she was gorgeous. Long black hair ran down her dark skin to her enhanced Brazillian ass. Her giant fake tits drew the eyes down to a slim waist with a prominent bulge hidden behind a pair of classy panties.
I still had no idea who the girl at the door was, but the atmosphere was awkward. Especially as she was mildly reprimanding Ana about inviting ”fuck dates” over to the house unannounced.
Sensing the atmosphere, Ana brushed her off and made me a drink before inviting me into her bedroom. We sat on a large Queen size bed and chatted a little.
From her life back in Brazil to how she was finding life in London, the conversation flowed well. With curiosity getting the better of me, I had to ask who the English girl was and why she was sharing a flat with two transsexuals from Brazil.
“Her name is Sarah. She’s a slut, just like us, honey!” Ana said with a wink. It dawned on me. It seemed that she was a working girl, as were they, and sharing the flat as a shared knocking shop. Thankfully, this meeting was on the house.
Suddenly, I heard another set of footsteps approaching the bedroom door.
Our shemale party begins
In walked Francisca. She was Ana’s partner in crime, and her arrival meant the Shemales From Hell were now complete. Ana had already taken my breath away, but Francisca made an even more memorable first impression.
The taller and darker of the two, Francisca’s black shemale skin was glowing with the wetness of the shower she’d just stepped out of. As she began drying herself with the towel around her waist, I nearly choked on my drink.
A flaccid black shemale cock was between her smooth thighs that must have been seven inches. I had to remind myself I wasn’t watching porn here. Now dried off and in her underwear, she playfully jumped next to us on the bed and shared a deeper introductory kiss than Ana did.
The girls were a lot more fun in person than their online attitude. Both shared Brazilians’ fun and outgoing personalities, and I was content chilling with two gorgeous shemales sipping strong Caipirinha’s and listening to Funk music.
As the sunset, we drank more, laughed, and danced around the bedroom. As the night went on, the Caipirinhas kept us warm from the cold weather outside. And the atmosphere grew increasingly hornier.
Watching their asses bounce to the aggressive beat of Brazillian Funk was intensely erotic, especially when combined with their bulging cocks under their panties. Then, Francisca pumped it up a notch.
She stared me dead in the eye, stuck her long tongue out, and flashed her perfectly round tits at me. I responded with a drunken and deeply approving look. “They’re perfect, right?” she asked in rolling broken English.
I nodded in agreement. “Then how can you stand there and stop yourself from sucking them?” She asked dominantly whilst pushing her left breast into my face. I took the bait and wrapped my wet mouth around her tit as Ana cheered enthusiastically.
The drinks, the music, and the pure sexual energy sent me over the edge. I lost control and began burying my head between her tits and sucking them wildly and only stopping to kiss her in between deeply.
“Don’t forget me!” Shouted Ana, who already had her hands all over my body. I switched and hungrily swallowed her erect nipples as my hands wandered down to their now semi-erect cocks.
Suddenly, I felt my alcohol weakened legs being pushed back to the bed from the impromptu dancefloor by the girls. Soon, I was about to learn how they earned their Shemales From Hell nickname.
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Softly falling back on the bed, I noticed that both of the girls had slipped out of their panties and now had their big black cocks swinging free. I then felt the soft hand of Ana guide me towards her shemale dick.
Not wanting to stop the momentum, I spat on her quivering black length and began to work it into my mouth. Now, I knew it was huge. But it’s only when it’s in your mouth that I start to appreciate its size truly. Primarily due to my inability to breathe.
Just as I began getting a handle of swallowing her cock, my head was rudely pulled off by Francisca, who plunged my still open mouth deep down on her considerably larger dick. Tears rolled down my face as I struggled with Francisca’s far more aggressive sex drive.
She used my throat like a Fleshlight and had a firm grip combined with powerful thighs that ensured the tip of her cock and my Adam’s Apple got well-acquainted.
With one hole occupied, I soon felt the cool kiss of lube on my exposed asshole. Ana had taken the initiative and began using an array of toys on my ass. From plugs to dildos, I could feel my whole being stretched out.
Even if I wanted to object and chicken out, it would have been hard to express myself. The room was now filled with lust-fuelled roars of the Shemales From Hell as they abused my holes.
Francisca pulled her cock out of my mouth to give me air, and it honestly felt like minutes passed until I finally saw the head of her cock leave my lips. Before I had time to think, I heard the tear of a condom wrapper behind me.
Then, the two conversed in Portuguese about something as I struggled for air and lay, somewhat humbled, partially on my front with a sex toy left in my ass. The conversation then became playfully heated, causing me to ask for some translation.
“We’re arguing over who gets to fuck your ass first because you’re so tight,” Francisca bluntly replied with a smile. I was genuinely concerned that they’d split me in two and seriously doubted that I could take either of them.
Ana won the debate and began sliding the glistening condom over her throbbing length before coating it in a generous coat of lube. The sex toy in me was rudely pulled out, and she parted my ass cheeks, spat inside my hole, and laughed mischievously to herself.
A big shemale on top puts me to the test
As Francisca resumed her position with her she-cock in my face, she took mercy on me and let me worship her length at my own pace. Probably because she could see the apprehension in my face as the first cock of the Shemales From Hell duo came closer.
Ana’s latex-wrapped cock teased my asscheeks and began pressing rudely against my gaped sphincter. Both girls were silent with their eyes fixed on my ass. The start of the tip was ok, but when the girth of her cock hit my sphincter, I began to chicken out.
I pulled off her cock quickly. It felt like a small truck reversing up my inexperienced hole. I explained to the girls that I didn’t think it would work. But I was met with disappointment and slightly annoyed looks from both.
I felt like I had given up on the first hurdle and let everybody down. Of course, it’s going to hurt at first, Karl. I told myself. I also didn’t want to ruin the intense sexual atmosphere in the room.
”I just think I need more lube, girls”, I explained. A new wave of optimism washed over their faces, and Francisca quickly handed Ana the lube. My hole was freshly lubricated, and the foreboding cock began its second charge into me.
I have an alpha male appearance in real life. But I’ll admit, the extreme sensation of that Brazillian shemale cock violating me made me squeal like a pig. Sensing I might try and back out again, Francisca plugged my mouth with her cock.
“Focus on my cock. Your ass belongs to us now!” She shouted down as both of my holes were violated. I was overcome with sheer pain and sheer pleasure when I felt the soft skin of Ana’s crotch kiss my asscheeks. She was entirely inside me.
Despite their ruthless sex drive, the Shemales From Hell had some mercy. Ana remained still with her throbbing cock plugged into my ass. This way, I could grow used to it. But this anal amnesty didn’t last for long.
Her cock was soon slowly sliding out and slithering back in at an increasing speed. I moaned like a bitch beneath this formidable Brazillian shemale as her partner’s meaty cock stifled my cries.
In the space of minutes, I was now a pincushion between the two of them. As the thrusts from the cock behind thrust me forward, those from the cock in front forced my body back. There was no respite. There was no mercy.
My face was a mass of spit and pre-cum. My ass was undoubtedly a sloppy mess of lubricant and meat. I’d be lying if I said I didn’t adore the humiliation, and my erect cock would have contradicted me if I said otherwise.
But what happened next put my humiliation kink to the ultimate test. Amidst the lustful shemale moans and my cries, the bedroom door flung open. Instinctively, I pulled myself off the cock in my mouth to see who it was.
Standing there was Sarah, the petite English girl who opened the front door to me earlier that day. She looked me in the eye, relatively unphased in fact, then looked up to Ana. My vision of her was shaky as Ana didn’t let the unexpected visitor interrupt her rhythm.
“Hey, what are you guys doing for dinner?” Sarah asked whilst sitting on the edge of the bed and ignoring the debauched scene in front of her. Francisca promptly plunged my bruised throat back on her cock as the three discussed dinner plans.
She looked unphased. But what must this girl have been thinking, seeing one of her countrymen impaled at both ends by two sexually aggressive transsexuals? It was utterly humiliating. And I loved it.
“Have fun!” Sarah chuckled as she left the room. At this point, Francisca had seemingly grown tired of my mouth. Pulling out, she rubbed her palm over my face to coat it in a layer of spit and pre-cum.
Without saying a word, she moved next to Ana and spanked her asscheek as though they were a debauched tag team. Ana’s shemale dick slid out of my hole, releasing a humiliating gust of air from the intense fucking.
By now, I expected I could take Francisca’s larger cock with ease. But I was wrong. She was less merciful than Ana. Throwing me on my side, she lifted one of my legs for support as her one-eyed monster eyed up my hole.
Now tending to Ana’s latex-tasting cock, my eyes rolled wildly as her friend’s dick pushed its way into my ass and proceeded to ruin it further. She was considerably stronger than Ana, and her muscular thighs smashed into my tender cheeks like a tank.
Sarah’s orgasmic moans bring me respite
Francisca’s relentless pounding of my ass had been going on for what felt like well over ten minutes. At this point, I was on the verge of tapping out. My jaw ached, and my ass throbbed. Then, salvation from the Shemales from Hell came in the form of Sarah.
I hadn’t heard Sarah’s lover arrive in the intensity of the sex and loud music. But it seemed the two had made their sordid session in the adjacent room. Hearing a hint of the sex, the two shemales hushed, and Ana turned down the music to listen better.
“Fuck me cunt, Darnell! Make me cum like a whore! Oh fuck, I’m going to cum on the big black cock!” Sarah roared in the next room. Honestly, she looked like she didn’t have it in her. But English sluts can often be surprising.
We listened for about a minute until it sounded like her lover, Darnell, pulled out and blew his load somewhere over her body. This voyeuristic addition to the sex sent the shemales from Hell over the edge. It was time to finish this sordid affair off.
“You’re gonna taste our cum, you nasty boy!” Francesca shouted whilst unceremoniously pulling out of my ass, leaving it burning from the intense fucking. The snap of a latex condom being torn off initiated the finale.
I was now staring into the pumping transsexual cocks of the Brazillian shemales from Hell as they prepared to mark me as their anal slut. “Spit on them, bitch; our cocks have worked hard on you today!”
I did as I was asked and spat whatever I had left on these throbbing members. Ana came first. Ropes of hot shemale cum spattered my face and rolled down into my eyes and mouth. This triggered Francisca.
Her cumshot was more of a drooping trail of cum. But my god, there was a lot of it. It looked like a faucet of hot white water. To show my appreciation, I threw my head underneath and opened my mouth to swallow as much as I could.
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A blend of cum from the Shemales From Hell decorated my face and throat. It was one of the most sexually satisfying escapades I’ve ever undergone. After a post-not talk, we jumped into the large shower together.
As I walked to the shower with the girls, I saw the freshly-fucked Sarah sitting on the couch with a drink. She flashed me a mischievous look as I walked bow-legged, surrounded by the big black shemale cocks that had done the damage.
In the shower, I was rewarded for my dedication. The girls gave me a soapy double blowjob. Francisca couldn’t help herself and tried plunging as many fingers into my gaping hole as she could. Probably in the hope of triggering another anal session with me.
But it wasn’t on the cards. I said my goodbyes and shared a farewell kiss with the Shemales From Hell. Now content with the answer to how they earned their nickname, I boarded the tube back to my hotel with a wry smile on my face.
The next day, my bruised ass was branded with a pleasurable pain that graphically reminded me of the sordid affair whenever I sat down. It was a visit to London I’ll never forget.
Disclaimer: The following shemale sex story is true, but names, dates, and locations of the story may have been changed to protect the identity of those involved. Photos featured in the article may not necessarily be of the incident in question but may have been provided from the public domain to break up the piece and make it easier to read. Finally, this article may contain affiliate links. If a purchase is made through them, we receive a small commission that goes towards running the site.