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Shemales Porn Stories

Another from the GurlTown Files Softly #1

FetishShemalesTaboo

Softly Leanne Leanne and Eddie had been together for 6 months, still unknown to everyone but Charlie. Eddie had moved back to regular day shift, filling in for vacationers. He was still hearing comments about “the Ice Queen”. Often hearing that many still wanted to get in her panties or that she had to be gay. He just listened, smiled and let them pass. When he saw Leanne, he relayed the comments and often they became scenarios in their sexual play. He asked her if she had considered fucking any of them? She said, not really but if he wanted he… Read more

Posted by GurlTown 3 hours ago 191 100%

Mutual wanking upstairs at the party

Shemales

Was it the red tinted light in the bathroom, the loud music from the party downstairs, or the drink that was making his head spin a little he wondered as he pulled up his zip and flushed the toilet. He unlocked the door and stepped into the hallway shadows, quickly gaining his focus on her, standing with her back against the wall, running her finger back and forth across her lips as she eyed him up and down. He'd saw her earlier at the party downstairs, her tight leather skirt, the knee high boots that tightly wrapped her long sexy legs, catching his eye as she walked past. Her dark red lip… Read more

Posted by ass_pussy_fucker 5 hours ago 502 67%

Black Tranny Turned Out

Interracial SexShemalesHardcore

Purge, purge, purge, hotter, hotter, hotter, how it is, true story, more forthcoming. Over the years, I have gone out walking very early mornings, to prance and strut, usually wearing shorts or short-shorts, with tennis shoes or flip flops, sometimes bringing dresses and high heels along if the environment right. It was mostly for my own experiences to test how I truly felt and later became for my own pleasures, although simultaneously sorta expecting and/or looking for another hard dick to please, sure enough, inevitably. To my surprise, straight appearing men got at me almost immediately, u… Read more

Posted by btg00sf 10 hours ago 499 100%

Carla goes out

Group SexShemalesAnal

As a cross dresser who loves to dress as a dirty slutty girl I was sat at home thinking about what it would feel like to go out dreesed in public. I had often thought about it but never had the courage to do so. I was so fucking horny and wished I had a reason to go out and do something rather than sit at home alone. I thought about the times when I took my Dog for walks on summer evenings and we would walk in the woods and fields for hours at a time. I no longer had my dog sadly so didn’t get out much anymore. It got me thinking though, about what I came across whilst out walking with my Dog.… Read more

Posted by Carla_Kitten_3 just now 3 1,163 100%

Sex in the mind is the best kind (sissy)

AnalFetishShemales

Sex in the mind is the best kind My inner thighs rubbing together across my skin tight grey polyester jogging bottoms felt so nice as I strutted my stuff around my local woods. My work in progress hormone shaped arse bouncing and jiggling freely was giving me so much satisfaction that my body was becoming that of a women’s. light grey not the best colour to choose as my arse sweat patches were starting to show through… ops, I knew my tight pink gym shorts underneath would be revealing their outline too, cupping my bum. A pathetic loose cut short gym vest sat on me so well, waiting for my bo… Read more

Posted by dirtyjenna just now 536 100%

Wie ich von zwei Shemales gefickt werde....

AnalShemalesInterracial Sex

Zur Erklärung, stelle mir vor, dass ich Batman bin in einem geilen engen Latex Kostüm. Ich habe erfahren, dass sich Harley im Keller eines Geschäftshauses aufhält. Also schleiche ich mich in den Keller, komme in einen langen Gang mit einer Tür am Ende, welche angelehnt zu sein scheint und ein Lichtschein wird auf den Gang geworfen. Langsam schleiche ich mich an, an der Tür angelangt lunse ich hinein. Was ich sehe ist nicht viel, ein Tisch in der Raummitte und den Rest des Raumes kann man nur schemenhaft wahr nehmen, da dort nicht viel Licht hin fällt. Langsam öffne ich die Tür und schleiche mi… Read more

Posted by mgarni just now 259 100%

Quickie: Mortha's Heat

ShemalesFetish

This is a word for word copy paste of an ERP I had with my favourite subby slut. If people seem to enjoy/request this kind of content I'll add more as I have a literal archive. Tags: Futa (of course <3), breeding, transformation, stomach distension/bulging. Mortha strode through the establishment with her freshly purchased slave in tow, the girl already collared with her leash wrapped firmly around Mortha’s wrist. The orcess was a familiar sight in the station of Lust and the patrons parted like the red sea as the two and a half metre tall behemoth moved to the secluded room sh… Read more

Posted by Nashala just now 381 100%

Trained by a Shemale Mistress PART 3

Shemales

Ashleigh's words, whispered in my ear just as our last session was ending, have bounced around my psyche, dominated my inner fantasies, and been a recurring source of personal pleasure. "I should whore you out."....nothing more was said beyond the instruction to clean my cum off of her titties, dress and leave, never to be late again for your training with Mistress. I obeyed. Month's have passed. I have often looked on Backpage, and Eros at the photos of transsexual escorts, sometimes sorting by Tumblr to find those with more explicit photos and videos. Never called or arranged to meet… Read more

Posted by macaddict123 2 days ago 1 666 100%

Prisoner

ShemalesFetishBDSM

It’s very late at night when you answer a knock at your door. On opening, you see me standing in the little pool of light in the darkness; a young, above average height girl, with shoulder-length dark brown hair and hazel eyes. I’m wearing a pretty dress and in my hands I’m holding a pair of strappy heels and a clutch bag. I’m a bit mud-splattered and bedraggled. “I’m so sorry for disturbing you but I need some help. My car broke down a little way along the road. I saw your light and hoped I might use your phone. I have my mobile, but it’s dead”. Facing me I see a tall, well-built, older man.… Read more

Posted by cyclosiss 3 days ago 1 2,087 100%

Polish Police Officers Sucks :o

AnalShemalesHardcore

I was visiting two girlfriends in a city in poland. The booze over there is cheap and strong, so we were partying for the third day in a row. They were going to this hooker and pimp party. So I wanted to go shopping for some pimp outfit ... They didn't agree?!? Seemed they knew I was a crossdresser :o I tried to deny it, but then they showed me some pics I'd posted online. I blushed and stuttered. They laughed and told me not to worry. My heart dropped when they had layed down my outfit on the bed in their bedroom :o A black laced minidress, a black braw, a ton of bracelets, fake earloops,… Read more

Posted by saracuda 3 days ago 1,128 100%

Trained by Shemale PART 2

Shemales

My second "date" with Ashleigh, a top only shemale Mistress, was a few months later, in New Jersey, but down near Philly this time. Again, on business, our paths cross.A day hasn't gone by where I have not thought about Ashleigh, her control and authoritarian manner, not cruel....more seductive with just enough dominance to make me submissive. I ended up caught in traffic, and arrived at her hotel a bit late. Ashliegh was in a robe, as she had decided that I was not coming so she took a shower. I sat down beside her, and tried to explain why I was late, but she just asked me if I saw that… Read more

Posted by macaddict123 3 days ago 1 1,015 100%

Trained by a Shemale Mistress

First TimeHardcoreShemales

I had often fantasized over the years about having an experience with a transsexual. On a drive to NYC I had the opportunity to make this happen. I thought that a one time experience would be enough. Little did I know that Ashleigh had other plans, or soon would have. I drove to her hotel where she met me at the door. 5'10", shoulder length blonde hair, light make-up, very pretty. A semi see through blouse showed off her white bra. Black skirt below the knees, stockings and black open toe shoes. Elegant, and sexy. She invited me in and after a bit of small talk she took my hand and… Read more

Posted by macaddict123 5 days ago 2 2,576 82%

Transition to Vikki, part six

AnalShemalesFirst Time

Continuing the story of Steven Jennings and his becoming Vikki. Mk 2 version, too many typos, and just didn't feel right. I woke early the next morning, still tucked between the soft, currently sleeping bodies of my two girls. Gina had turned in the night to face me, her halo of long black hair thrown all around her face, the pillows and duvet. She lay there smiling to herself as she slept, lost in some dream. Her breasts pressed teasingly into my arm, the metal nipple bars adding to the sensations. Right now she lay with a leg d****d over mine, her free arm across my chest. She looked so lov… Read more

Posted by fluffy1 7 days ago 2 983 100%

First time Public sissy outing

AnalFirst TimeShemales

First time Public sissy outing I was actually doing it, my ear phones filling my brain with girl power motivation through my sissy playlist but still I’m nervous as fuck my little heart going a dime a dozen. I was certain the men in the pub could hear the sound of my high heels as I stopped to pull open the entrance door, no going back, I was about to ride this wave where ever it took me. The very second I opened the large class door a gust of wind swept my white dress up about to reveal my knickers and potentially my tucked little cock, quickly I pushed my dress down, one hand at my… Read more

Posted by dirtyjenna 7 days ago 3 2,119 89%

Another from the GurlTown Files Softly

FetishGay MaleShemales

Soft Lee After working the normal day shift in the warehouse, Eddie had moved to night shift restocking. For over a year he had heard talk of “Softly”, the district auditor. She was said to be a dark haired beauty with alluring eyes, shapely and sexy. Her schedule was always uncertain but everyone brought their A-Game when she was around. It was implied that she was an “ice queen”, totally untouchable. Training with Charlie on night shift he asked more about her. Charlie took him up to her mezzanine office. It was more like a glass cub… Read more

Posted by GurlTown 8 days ago 8 1,653 90%

Tranny Arschfick in der Jugendherberge

AnalShemalesFirst Time

Fabianes ersten Erfahrungen Fabiane, die ursprünglich einmal Fabian hieß, war eine Tranny und hatte gerade ihren 20. Geburtstag gefeiert. Sie war Berufsschülerin. Als solche übernachtete sie regelmäßig die Woche über in dem Hotel, in dem ich an der Rezeption arbeitete. Dieses Hotel war zwar an sich eine Jugendherberge, aber ganz im Stiele eines Hotels. Somit hatte ich mit vielen jungen, coolen Menschen zu tun. Mit einigen entwickelten sich manchmal Freundschaften, so auch mit Fabiane. Sie kannte niemanden in Dresden, daher hing sie oft bei mir an der Rezeption ab, wo wir stundenlang qu… Read more

Posted by jackmckanzy 8 days ago 497 100%

The Emancipation of RomaFox

ShemalesHardcoreTaboo

The Emancipation of RomaFox Through the haze of cigar smoke and aroma of incense mixed with bourbon in the air I slowly but nervously swung my ass and swayed to the music as they watched with anticipation, the tempo picked up, I danced in unison with the motions as I was temporarily lost in the moment of my triumph! Yes, I have crossed over into the world acceptance of my emancipation! free to love and be loved and be adored for who I am and what I've become. The music loud, hard and deafening created an environment of fantasy, and illusion oozing sex in the air as I danced like a she-de… Read more

Posted by CDRomaFox 9 days ago 5 738 91%

Plezier in Brazilië

ShemalesHardcore

Ik was in Brazilië voor het werk, een klus die twee maanden ging duren. Mijn werkgever had me een mooi appartement geregeld in Sao Paulo en elke avond zat ik in een gezellig restaurant op het terras wat te eten, kijkende naar het vrouwelijk schoon dat kwam langs lopen. Braziliaanse vrouwen zien er fantastisch uit, vind ik, veel rondere vormen dan onze westerse vrouwen, en enkele avonden kijken was ik zo geil dat ik moest neuken. In mijn appartement googlede ik escort services en ondanks dat de dames er enorm opwindend uitzagen, had ik meer zin in een tranny. De shemale escorts zagen er zo moge… Read more

Posted by NonkelBob 10 days ago 343 100%

C/D Teens Hitchhiking Adventure: PT 3

ShemalesHardcoreTaboo

C/D Teens Hitchhiking Adventure: PT 3 [More of my memories to share, hopefully represented in a proper format as much as possible I take heart to what I write as they are from my adventures that I cherish, altho I'm no wiz at this computer or an accomplished writer I do write my own, hope you all enjoy these stories as some have] The days leading to months fell off the calendar as my life took a turn for the unexpected, chance encounters turned into something real and crazy loving, having the opportunity to live life to my bidding was rare but it has turned into something I will never forget… Read more

Posted by CDRomaFox 11 days ago 4 3,531 93%

C/D Teens Hitchhiking Adventures PT 1 Revised

ShemalesTabooHardcore

C/D Teens Hitchhiking Adventure: PT 1 Revised [For the sake of clarity and a better representation my of my adventures as a C/D teen to you all, I've revised my first story published here as I was in haste with earlier said post, My apologies as I am not a computer wiz or distinguished writer, hope you enjoy,thanx] It was a 200 mile journey from the city to the outskirts of a small town by the countryside where I live, I have hitchhiked this road many a time but this day proves to be an exhilarating adventure into my first cross-dressing sexual encounter. I had a large backpack I carried wi… Read more

Posted by CDRomaFox 12 days ago 3 2,114 100%