Shemales Porn Stories
Page 82

Crossdresser getting TRAINed

I was home alone when i got a call from a friend that is train driver / railroad engineer. He is 40 years old and spend most time alone driving a train. He asked me if i could not come over, because he is feeling alone. I had nothing better so i visited his flat. So i put makeup wig and some tight dress with thong and heels. I wanted to put stockings but already had heels so i decided just to go with my smooth legs, it was hot that day anyway.

He already had prepared some beer and drinks. We talked about his boring job while watching television. After a while he started rubbing his p... Continue»
Posted by Nirien 1 month ago  |  Categories: Anal, Gay Male, Shemales  |  
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Friendship Bands

Chapter 1: At the Market

John and Craig were old friends, right back to when they were both k**s
causing trouble around the streets of South London. As they grew into
men they'd both had a keen eye for the girls and had no shortage of
success. They made a good team.

John was a natural leader with his broad shoulders, 6ft 2in height, dark
hair and handsome features. The girls would all swoon over him. Craig
was usually happy to provide back-up, chatting up the best friend of
John's preferred girl for the night and saying what a great guy John was.
"John's got hidden depths," he... Continue»
Posted by lana100 1 month ago  |  Categories: Shemales  |  
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Daniel Effeminate College Student

Chapter 1
The Beginning

Daniel, an Italian boy in his late teens is starting a fine arts program at a college in the US. He had been awarded a full scholarship as part of an exchange program with the international arts community. He arrives before classes begin and has to stay in a hotel at his expense as the residence on campus in not available for a week. He is happy to be there as this is freedom for the boy as he can now begin to express his true desires to be gay and effeminate. At home it was not possible with the closeness of his f****y, friends and values of his community. However ... Continue»
Posted by colourfast 1 month ago  |  Categories: Gay Male, Mature, Shemales  |  
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The Apartment Part 2

I had found myself a new flat but was just discovering that it came with strings attached. I am not sure, but they are into swapping partners at a party. I was at my first.

I was sucking George's little fat cock while his tranny wife fucked me from behind. While we are in full flow, the other couple come into the party. Roger and Diana. Diana was a plump thing with a sweet cock while Roger was tall and thin. His skin was very white and covered with dark hair. His cock was hard and he stood in front of me while Diana kissed me! She moved from me to George holding her cock out for him to suck... Continue»
Posted by dasilva1672 1 month ago  |  Categories: Fetish, Shemales  |  
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Мой первый мужчина

Привет. Я расскажу реальную историю о том как я стала женщиной. Сейчас мне уже почти сорок лет, но события того лета до сих пор свежи в моей памяти.

Мне было 18 лет и я был высоким и стройным юношей. Но широкие бёдра и узкая грудная клетка отличали меня от моих атлетически сложенных ровесников. Я был романтичным и нежным и в отличии от них не интересовался футболом и мотоциклами. Я любил читать и смотреть мелодрамы и любовные истории, а на красивых и сильных мужчин смотрел с замиранием сердца. Так как я с детства считала себя девочкой, то повествование буду вести именно так.

Один такой м... Continue»
Posted by miss_slonik 1 month ago  |  Categories: Anal, First Time, Shemales  |  
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Daniel Effeminate College Student Chapter 2

Chapter 2
The Party
At the end of their successful meeting Serge invited Adrian and of course Daniel to a party at the home of his employer for that evening. It was an event with a large number of people invited from the arts and business community artists, buyers and supporters of the arts and some musicians and a few from the theatre community. Adrian and Daniel arrived together and Daniel looked spectacular with his new hair style and wearing one of the new outfits which were purchased that afternoon. He felt wonderful and as he entered the large foyer. He looked in a huge mirror and admi... Continue»
Posted by colourfast 1 month ago  |  Categories: Gay Male, Mature, Shemales  |  
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abused shemale toy strikes back

These are excerpts from a horny chat i had with a guy. All I did now was taking out our sidetalk and try to correct any errors, since we are both non native english speakers. he knows it is used here and I am sure the story will continue. I'd love some feedback to see if i will upload the next parts.
The story includes rough sex, dominance, breath play, v******e, and generally hardcore stuff, so if you are offended by that, stop reading. Since they are from a chat, perspective will change between us two, so everything from his perspective will be bold.

I come home to you. You are stan... Continue»
Posted by hikahuk 1 month ago  |  Categories: BDSM, Fetish, Shemales  |  
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Mayberry, the Black Goddess

tranny – shemale - cocksucking – anal – spanking – domination – submissive

Another lonely night led me to walking down the dimly lit street and wandering into the sex shop. There wasn't too much adventure to be seen there, very comparable to my apartment.

I was looking at toys. Specifically, butt-plugs. Not that I didn't already have one; in fact, I was wearing one at the time. The little bell above the door rang.

I looked at the cashier, she stood there- blowing her bubble gum. I couldn't see who just came in. I was curious. I continued to look at the toys. I squatted to get o... Continue»
Posted by naughty_bi_interest 1 month ago  |  Categories: Anal, Fetish, Shemales  |  
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Room 209: First Sex as a Crossdresser

crossdresser – trans – interracial – lgbt – first time – virgin – black cock – crossdressing – natural tits – bra

I've been crossdressing for much of my life, as far back as I can remember. I would even go to sl**p as a k** and pray that I would wake up in a girl's body. In the last few years, now that I live by myself, I spent about $1,000 on a whole wardrobe of women's clothes for myself - bras, thongs, dresses, tops, stockings, lingerie, make-up, perfume, etc... I have also been overweight for some time so I have breasts. As a man, I have to minimize them all the time. As a women,... Continue»
Posted by naughty_bi_interest 1 month ago  |  Categories: First Time, Fetish, Shemales  |  
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Cockatoo Part 11

Cockatoo Part 11
Nikkie Silk

Areeya returned to the apartment sometime after we had gone to bed as the moorings needed more attention than Areeya had initially thought. After she and Shane had eventually got Cockatoo 3 safely secured on the pier, he had gone back to his hotel and Areeya headed back to get some sl**p in the apartment.
In the morning I had changed back into being James, albeit with a little reluctance. Alex had suggested I go on the boat as James and change into Scarlett for the evening. I thought it was one of Alex's better ideas as I didn't have anything suitable for the... Continue»
Posted by nikkiesilk 1 month ago  |  Categories: Shemales  |  
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My first shemale experience

so i've read plenty of stories on this website and thought I would share my own with you from 2011

For years I had fantasised about being with a ladyboy, but didn't know how to go about it as I didn't want to pay for an e****t.
I found a ladyboy dating website and created an account, it cost $30 for the month but was still cheaper than paying for an e****t and slightly more classy.
After about a week of sending messages to compatible matches, I finally got a response from an Asian TS who was visiting from Malaysia. She said she liked my photos and wanted to meet with me that weekend, so w... Continue»
Posted by mick_c1990 1 month ago  |  Categories: Anal, First Time, Shemales  |  
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Jamie's Descent Part 1

Jamie's Descent

Nikkie Silk


Chapter 1

What did we do before social media? How did we manage to get through
the day without that endless stream of dirty jokes, funny photographs,
gossip and links to dodgy websites that now fill our lives? Yeah,
yeah, I can hear you grumble. Get on with it, I can hear you say. Well,
dear reader, it was one of those links that started me down the road
to... oh, you'll find out soon enough. I was 18 and I had just come
down to London from my hometown in Norfolk after leaving school.

A friend of my father's had offered me a job in an off... Continue»
Posted by nikkiesilk 1 month ago  |  Categories: First Time, Shemales  |  
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Becoming a Slut

slut



Fuck I been getting down on my knees for a few years now, every since I was
caught given a guy a blow job by my father. Fuck lets start at the
beginning .

My name is Peter I live in the united kingdom in the north of England they
are quite a lot of chavs here and I used to get bullied a lot at
school. One day while I was skipping school I met a guy in the toilets in
the park.

I am quite effeminate long hair smooth pale skin and very skinny I am only
5'4 so small for my age and I am 14 my mother died when I was eight from
cancer and I have four older b*****rs I always w... Continue»
Posted by klammer 1 month ago  |  Categories: Fetish, Shemales  |  
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Jamie's Descent Part 2

Chapter 2


'That's it, baby,' Vanessa purred as she snaked her hips forwards and
back, gently sliding the strapon in and out of my mouth. I could no
longer think rationally, as any self control I still had slipped away and
trance like, my eyes closed, I sucked the rubber phallus in and out of my
lips.

'Baby, you love this don't you?' Vanessa's voice took on a hypnotic
tone, gently encouraging me to take more and more into my mouth.

I was too far gone with lust and desire to even register the question
let alone give her any answer.

'This is what you want, isn't it? You w... Continue»
Posted by nikkiesilk 1 month ago  |  Categories: Anal, First Time, Shemales  |  
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MY PORN SHOP CONFESSIONS

AZNSWAG

if you read my blog on my profile , you can see my background into how i got into the porn shop business..
i thought it might be fun to share some of my personal stories: things that i have seen & done while working at the many different porn stores across my city. this is one of my many experiences that i will never forget


ill just name it.. my porn shop confessionals =)

i worked at this particular porn store from 2006 - 2010. usually porn stores are very hidden. usually they are in some abstract location where privacy is held to its highest... Continue»
Posted by AZNSWAG 1 month ago  |  Categories: Shemales  |  
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Enslaved



As I stepped into the department store, I had to resist the
natural urge to turn left and head for the electronics section.
Instead, I turned right, penetrating deep into the mysterious
world of women's apparel. Feeling conspicuous, I tried to look as
if I belonged, relieved that there were no crowds so early in the
day. This was the third time I had attempted this, and I was
determined not to chicken out again.
I knew what I wanted, but not where to find it - and I was
far too nervous to ask for help. Of course, it ended up being in
the last place I looked. Wandering anxiou... Continue»
Posted by klammer 1 month ago  |  Categories: BDSM, Fetish, Shemales  |  
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Maybe


As I stepped into the department store, I had to resist the
natural urge to turn left and head for the electronics section.
Instead, I turned right, penetrating deep into the mysterious
world of women's apparel. Feeling conspicuous, I tried to look as
if I belonged, relieved that there were no crowds so early in the
day. This was the third time I had attempted this, and I was
determined not to chicken out again.
I knew what I wanted, but not where to find it - and I was
far too nervous to ask for help. Of course, it ended up being in
the last place I looked. Wandering anxiously... Continue»
Posted by klammer 1 month ago  |  Categories: BDSM, Gay Male, Shemales  |  
718
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The Wild Isabella

This is about the woman of my dreams. That I long for. That I crave. So let me tell you about a moment of madness I will never forget.

Her name was Isabella and she looked nothing like the posts on the forum. I'd heard reports that she was over 6ft, that she was fat, that she was not for the inexperienced.

It took an age to find her apartment and when I got there she poked her head coyly round the door. She was slim and Spanish, with blonde hair and big, blue, mischievous eyes. Perky tits and an hourglass shape - she sure was fuckable; although we I never got the chance, as she was the... Continue»
Posted by waraxe13 1 month ago  |  Categories: Fetish, Shemales  |  
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Jamie's Descent Part 3

Jami’s Descent Part 3


The limousine took me to Harley Street, home of the UK's private health
industry, for the medical Vanessa had mentioned. To me it had seemed
less of a medical and more of a preparation for something. There were a
lot of the usual bl**d pressure tests and urine samples, but there had
also been a lot of measurements taken, especially around my upper body.
The doctor and nurses were efficient though and seemed satisfied with my
overall condition.

I felt the doctor spent a little too long on what he had said was a
prostate check. The doctor's finger seemed to ... Continue»
Posted by nikkiesilk 1 month ago  |  Categories: Shemales  |  
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Drink or Dare

crossdressing – threeway – first time – oral – anal – strap on

Ever since I was a c***d I had always fantasized about being a girl. Every chance I got I would sneak into my moms closet and try on her panties, slips, nylons and dresses. The feel of the sheer silks and nylons against my skin would drive me crazy. When I hit puberty and discovered the joys of masturbation these two activities seemed to combine perfectly. So much so that while jacking off dressed as a girl I would fantasize about being sexually used by men. Eventually I felt I needed a real life person to place my desire... Continue»
Posted by naughty_bi_interest 1 month ago  |  Categories: Anal, First Time, Shemales  |  
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