Shemales Porn Stories

Prisoner

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. ... Continue»
Posted by cyclosiss 1 hour ago  |  Categories: Shemales, Fetish, BDSM  |  
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Polish Police Officers Sucks :o

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,
... Continue»
Posted by saracuda 3 hours ago  |  Categories: Anal, Shemales, Hardcore  |  
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Trained by Shemale PART 2

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 ... Continue»
Posted by macaddict123 9 hours ago  |  Categories: Shemales  |  
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Trained by a Shemale Mistress

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... Continue»
Posted by macaddict123 2 days ago  |  Categories: First Time, Hardcore, Shemales  |  
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Transition to Vikki, part six

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... Continue»
Posted by fluffy1 3 days ago  |  Categories: Anal, Shemales, First Time  |  
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First time Public sissy outing

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... Continue»
Posted by dirtyjenna 4 days ago  |  Categories: Anal, First Time, Shemales  |  
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Another from the GurlTown Files Softly

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... Continue»
Posted by GurlTown 5 days ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Tranny Arschfick in der Jugendherberge

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... Continue»
Posted by jackmckanzy 5 days ago  |  Categories: Anal, Shemales, First Time  |  
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The Emancipation of RomaFox

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... Continue»
Posted by CDRomaFox 6 days ago  |  Categories: Shemales, Hardcore, Taboo  |  
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Plezier in Brazilië

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... Continue»
Posted by NonkelBob 6 days ago  |  Categories: Shemales, Hardcore  |  
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C/D Teens Hitchhiking Adventure: PT 3

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... Continue»
Posted by CDRomaFox 8 days ago  |  Categories: Shemales, Hardcore, Taboo  |  
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C/D Teens Hitchhiking Adventures PT 1 Revised

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... Continue»
Posted by CDRomaFox 9 days ago  |  Categories: Shemales, Taboo, Hardcore  |  
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Going Sissy

After the party things where just normal, Toni and his boyfriend would still come into the store and they acted like nothing happened. I bough my girlfriend her birthday gift and she loved it. I bought her something special too, a similar maid out fit that I wore at the party.
She wore it for me the night before she went back to college as we were having sex I could feel the material up against my skin and my mind started to wander about me being in the maid uniform taking that hard cock. I came so much.
My girl left for school and I was just working and hanging out. Steve came into the stor... Continue»
Posted by lndsay 10 days ago  |  Categories: Gay Male, Shemales  |  
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Karen My School Teacher 6

The music started. But i frooze. How did i get here. I'm going to show myself to Mick, my teacher. His going to see me fully dressed as a girl. Mick have known me about 5 years now. The music stopped. “Hello Brian! Are you there?. You need to come out when the music starts” I wanted to do this. And on the other hand i won't. “Ok ok. I'm coming. But you can't record this ok?” “No no i wasn't going to. But i really wanna see you. You already talk like a real girl. Sounds so fucking sexy. So come out show yourself. I know you want to” I took a couple of deep breaths. “Ok start the music from the ... Continue»
Posted by HosieryQueen 11 days ago  |  Categories: Fetish, Group Sex, Shemales  |  
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Hitchhiking teen crossdresser: PT 2



Well a lot has happened to say the least since my first time cross-dressing encounter with Jim, suffice to say I've had no misgivings about our perverted encounter out on the countryside altho I never anticipated what was to follow afterward, nevertheless as promised Jim kept his word as did I of returning to the city together to shop for a considerable amount of expensive wardrobe enough to please any woman (or a faggot, sissy-boy girlfriend in my case). We've shopped lingerie, western, women's office apparel as we enjoyed role-play, and heels lotsa sexy heels stilettos etc. I was ... Continue»
Posted by CDRomaFox 11 days ago  |  Categories: Anal, Shemales, Taboo  |  
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Sissy brothel whore

Well it was time for another medical conference in Chicago. I love going there because they have the best cross dressing store there. They always get me resupplied and give me a whole makeover. Every time I leave there I look like the hottest street walking whore ever! After 3 days of lectures my free night was here. I went to my store had them make me up to be a complete sex kitten. Even though I am somewhat new to this I do know what I want. I got a nice 2 room suite at a local motel on the dodgy end. Opened my laptop and placed my ad. Before I got a single response I saw a post from a black... Continue»
Posted by dncn31 11 days ago  |  Categories: Group Sex, Hardcore, Shemales  |  
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Sissy brothel whore

Well it was time for another medical conference in Chicago. I love going there because they have the best cross dressing store there. They always get me resupplied and give me a whole makeover. Every time I leave there I look like the hottest street walking whore ever! After 3 days of lectures my free night was here. I went to my store had them make me up to be a complete sex kitten. Even though I am somewhat new to this I do know what I want. I got a nice 2 room suite at a local motel on the dodgy end. Opened my laptop and placed my ad. Before I got a single response I saw a post from a black... Continue»
Posted by dncn31 11 days ago  |  Categories: Group Sex, Hardcore, Shemales  |  
483

Sissy brothel whore

Well it was time for another medical conference in Chicago. I love going there because they have the best cross dressing store there. They always get me resupplied and give me a whole makeover. Every time I leave there I look like the hottest street walking whore ever! After 3 days of lectures my free night was here. I went to my store had them make me up to be a complete sex kitten. Even though I am somewhat new to this I do know what I want. I got a nice 2 room suite at a local motel on the dodgy end. Opened my laptop and placed my ad. Before I got a single response I saw a post from a black... Continue»
Posted by dncn31 11 days ago  |  Categories: Group Sex, Hardcore, Shemales  |  
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Crazy revenge on ladyboy part 2

So as she looked slightly shocked at the seriousness in my eyes I also noticed her guilty face trying to hide her arousal... I felt so in control and like this moment was mine , she was flushed and in awe just by me being in the room.. I thought to myself, that although my nature is more tender and caring, if she wanted me to be dominant and sissy'd then who am I to deny her...

She showed she wanted this In every way possible.. And to be honest, I just craved to see her gag on my unwashed cock still tarnished with my cutie filipina girlfriends naughty juice...

A young narcissist on a que... Continue»
Posted by upforanything121 12 days ago  |  Categories: Anal, Shemales, Taboo  |  
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Hitchhiking teen crossdresser

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 my large backpack I carried with me with my belongings including in secret my lingerie, heels makeup etc. about 60 or so miles out a 4 wheel drive hauling a horse trailer pulled up alongside me, rolled down the passenger window a man who seemed to be in his middle 40's asked if I needed a ride, hell yes I answered it's mighty hot out and I appreci... Continue»
Posted by CDRomaFox 12 days ago  |  Categories: Shemales, Hardcore, Anal  |  
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