Shemales Porn Stories
Page 3

Me and Molly

This is a work of fiction featuring Male on Shemale sex... enjoy!

I considered myself straight all my life. I say that because I recently had some experiences that changed my inner definition of myself.

I met a girl at a local coffee shop. Actually, I saw her there every morning when I stopped in for my morning cup. I'd always admired her figure and beauty from afar, she was a very pretty redhead with a killer body and great taste in clothes. She was always wearing some kind of form-fitting dress that usually ended mid thigh or higher and more often than not a pair of sexy high he... Continue»
Posted by kevinj631 29 days ago  |  Categories: First Time, Shemales  |  
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Making Up and Breaking Up

Breaking Up And Making Up

“Well, Nobody’s Perfect!”
Joe E. Brown ‘Some Like It Hot’

by Nikkie Silk

Chapter One

Danny stood at the bar and looked around the pub. It wasn't his usual,
but this one had looked bright and warm from the outside on a gray,
rainy day. The after work rush wouldn't start for a couple of hours or
so yet, so there were only a few old boys who looked like regulars,
nursing their pints and looking miserable, cursing the smoking ban. A
couple at a table in the corner seemed to be in the middle of an
argument. The girl looked upset, and the man s... Continue»
Posted by nikkiesilk 1 month ago  |  Categories: Shemales  |  
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My first time with a man

I had been dressing privately for a number of years and never
been with anyone while dressed up. That is, until I discovered
this support group for other CD/TV and TS girls. I joined
the group, which held meetings once a month about 40 miles
from where I lived. I quickly made some friends and after
the first meeting Emily asked if I wanted to go to the local
gay bar and hang out. I had never been to a gay bar before,
or even out dressed other than the meeting site. There were
about 12-15 of us "girls" at the bar and we had
taken over 2 or 3 tables and just talked and got acquainted.
... Continue»
Posted by LisaTn 1 month ago  |  Categories: Anal, Gay Male, Shemales  |  
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Doing what I love

This is a true story that happened years ago. I hope you enjoy it.

I have been cross-dressing for several years. Long before I met my first wife, we had been married for about four year. One day my wife came home early and caught me dressed up as a woman. We had a long talk and at first she liked it me dressed as a girl. We would walk around in panties and tee shirts in front of our two k**s, a daughter 3 and a son 2. They kind of liked it that they had two mothers. My wife and I would go out dressed together and pick up men. We would take them home when the k**s were at their grandparent... Continue»
Posted by pamalacd 1 month ago  |  Categories: Anal, Fetish, Shemales  |  
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The Leatheress 103 - "Closing Time"

"The Leatheress", Episode 103: "Clo
As far as I was concerned, that late autumn a few years ago, I was easily the luckiest closeted crossdressing and bisexual fetishist in the world. Ever since I was quite young, I'd had a secret desire for dressing up in sexy women's clothing, painting my lips up, and smoking long cigarettes while acting out intricate fantasies about spending passionate evenings with plenty of men; real, famous, or completely imagined. But when my first opportunity to step out and indulge in these passions for real first presented itself, it happened in an amazing way. You s... Continue»
Posted by SexyLeatheress 1 month ago  |  Categories: Anal, Gay Male, Shemales  |  

Not Just Another Gradual Change Story - PART ONE

As I write this I am sitting at the computer wearing a summer dress that's pretty damn short. I'm about to go out again because yesterday was so fun...

As we all know, certain unnamed stores in the not too distant past (stores that were already very LGBT friendly) decided to start allowing people to choose the bathroom they want to go to regardless of what their birth gender happens to be. As a closeted bi guy who loves to dress up on occasion, I realized that this must also mean that the store policy is not to harass people simply based on them wearing clothes that may not match their bi... Continue»
Posted by cumquarts 1 month ago  |  Categories: Fetish, Shemales, Taboo  |  

The Leatheress 102 - "The Full Monty"

"The Leatheress" - Episode 102
"The Full Monty"

Growing up, I had always been secretly in love with dressing up in women's clothes; the rule always was, the shinier and softer, the better. In my more formative years, this began with satin nighties and underwear that I'd "borrowed" from the female members of my household, but my lust was always most reserved for leather. Oh, how I used to search out and spend intimate hours with any pics of sexy women in leather that I could find. So naturally when I moved out of home, and had a little more privacy, I wanted to get myself a little collect... Continue»
Posted by SexyLeatheress 1 month ago  |  Categories: Anal, First Time, Shemales  |  
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Revenge is a dish best served cold. Part 1.

I’d like to introduce myself. I’m Julia, and I work with Fiona at I help out around the place, feed the cat and make sure our Admirers are happy.

So, before we go any further I would like to tell you a little about me. I grew up in a small mid west town and went to school there. I liked it, but there was one incident when I was thirteen that I won’t be forgetting in a hurry. Being quite slim, and small framed, I was bullied and teased a lot. Some of the boys co... Continue»
Posted by JulieRenner 1 month ago  |  Categories: Anal, Shemales  |  
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The Futanari Doctor

After having an intense threesome with my friends Miranda and Sara, I felt as if I was at the top of the world sexually. I consider myself quite the nymphomaniac, always craving the next sexual encounter. While I worried that it would be difficult to top this experience, I was confident I would. Until my girl cock started giving me problems.

For those who aren't familiar with my exploits, I'll fill in some gaps. I'm a futanari girl, or futa girl for short, which means I have the body of a woman entirely, with one major addition: I have a cock. Right above my pussy I have a long, bulging co... Continue»
Posted by BiancaBigTits 1 month ago  |  Categories: Fetish, Lesbian Sex, Shemales  |  
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Sissy Slut For mistress

"Wake up" she slaped my face with her satin glove.
opening my eyes its darrk theres a bright light shining at me i try to raise my hand to my eyes and relise im bound. sitting on a lether hump my wrist and ancles are bound together. thats when i felt something in my ass. it felt big it was deep and i could barely move with it in me.i tried to speak but my mouth was gaged with a ballgag.
" its time for your training" she ran her hands all over me. the satin felt so sensual against my skin.
I tried to remember how i got here. as i stared at the woman in front of me straining to see against th... Continue»
Posted by freakofleash 1 month ago  |  Categories: Anal, First Time, Shemales  |  
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Ukrainian girls rough gangbang

[/user analadmirer]

Katya aged 18 and her s****r Andrea aged 20 moved to London to find work. They have been waiting on tables at a local restaurant and the owner has given them both Friday night off. They decide to go out clubbing for the night and are hoping to score. They dress up to look like teen sluts wanting to get fucked, short dresses, stocking and hi heels with no panties or bras. As they go to the door Katya says to Andrea " We look like a right pair of horny cunts!" With that Andrea pushes her younger s****r against the wall and starts kissing her pushing her tongue deep into h... Continue»
Posted by analadmirer 1 month ago  |  Categories: Anal, Group Sex, Shemales  |  
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We carefully hobbled back up the stairs in our high heels and then back into Samantha's bedroom. We then set up some cameras and Samantha expertly connected up the lights and set up their tripods. She then went out of the bedroom and from another room returned with, what looked like, an Art Deco chrome barstool. She placed it near the dressing table and giggled mischievously. Samantha then said to Penny calmly how about sitting on the stool. The stool had four chrome legs with a bar at the front to place your fe... Continue»
Posted by SheerNylonPenny 1 month ago  |  Categories: Anal, Fetish, Shemales  |  

My first tranny girl experience got me hooked

I have always wanted to have sex with a tranny. I find these women sexy. In my daily life I dont know any, so I look online find a tranny to fuck. As I look online I find a sexy Cuban t-girl advertising sex. I instantly give her a call and arrange a time to go meet. One thing that turned me on is that she just moved from Cuba and had an spanish accent that turned my dick rock hard. Once I get to her home she leads me to the bedroom. She is 5'5 about 125 pounds. My girlfriend is 5'9 160. So my T-girl is smaller than my real girlfriend. When we get to her room we start to undress. She is la... Continue»
Posted by snickersbar 1 month ago  |  Categories: Shemales  |  
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Jamie's Descent Part 8

Chapter 8

I stared open mouthed at Lexi.

‘What do you mean we’re going to be auctioned?’ I hissed at him.

‘People bid for us and we get bought for the night. I can't believe your
Mistress didn't tell you.’

I shook my head and Lexi reached out his hand to hold mine.

The man on the stage began to speak again.

‘My Lords, Ladies and Gentlemen. We will now begin the auction. Please
remember our rules, if you make a successful bid, you will be entitled
to take your prize to one of our rooms for the night. The prize will
perform whatever services you require during this peri... Continue»
Posted by nikkiesilk 1 month ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Another Dream/Fantasy

It was early evening and I was sitting at home alone, and dressed. My phone beeped with a message, "Hey sissy. I see you're home alone. How about you meet your new daddy." I paused for a minute and responded with, "Who is this?". The response I got was, "It's your new daddy. If you don't meet me, I'll send these photos to people you know.", and attached with some photos of me dressed up. My response was, "Ok, well who are you?". I didn't pay attention to the next few texts, and went about my evening. About 20 minutes later I got a call from a coworker who had been sent the photos of me. I sudd... Continue»
Posted by LorissaLovescock 1 month ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Feeling rather delicious in my Maids attire I walked over the the wardrobe and looked through the lingerie debating in my mind what I would like to dress Samantha up in. I couldn't believe how many packets of nylons and tights she had. I decided first on a pair of natural tan Aristoc Wonderbum Tights. I thought these would look rather yummy on Samantha with their reinf***ed bottom lifting panels. Samantha sat on the bed expectantly as I help up the packet of tights and whispered, 'I think we'll slip these on you first Aunty.'
... Continue»
Posted by SheerNylonPenny 1 month ago  |  Categories: Anal, Fetish, Shemales  |  
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Bi MMF, FemDom, Cross Dressing, Cuck - Part 3 Oh M

All dressed up super sexy, I was setting out for my erotic date with my new lovers, former friends. I felt so desirable and sexy as I drove to my erotic destination. I couldn't help but have a boner the whole time I was driving. I kept feeling myself while I drove. Feeling my exposed thighs, my smooth legs, my silicone tits, my sexy cock.... I was insanely turned on. I also kept looking down at my fuck me pumps. I'm addicted to heels more than anything else so just the sight of my sexy nylon/fishnet clad legs was enough to drive me crazy!

It was still light out, late summertime about 7:15... Continue»
Posted by chrissylegs 1 month ago  |  Categories: Group Sex, Hardcore, Shemales  |  

Sissy whorehouse veronica

Chapter 1 - The Capture

Before I became a girl I was a lonely boy with no friends. I couldn't seem
to make friends with anyone. I hated myself and I hated my life. One day I
decided to take a walk and try to get away form my troubles. It was early
in the morning, the sky was a pretty pink, and no one else was out. But
then, out of the corner of my eye I spotted a black van with heavily tinted
windows coming down the street. It slowed down beside me and as it did I
got a little scared. I was alone on a deserted street after all. There was
an attractive yet manish blond woman in the pa... Continue»
Posted by keripinkpanty 1 month ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Bianca Fucks Miranda (A Futanari Story) Part 2

"Sara! Oh gosh! What are you doing here?!" I was balls deep inside of Miranda's pussy, and even in the embarrassment of getting caught in the act, I couldn't stop myself from thrusting upwards into her. Miranda, sitting on my lap, turned beet red, and looked at Sara, who still stood in the doorway in shock.

"I was just...I wanted to run some ideas for my meeting by you...but I can tell you're busy..." Sara started to back away, but through her work skirt, I could see her futa cock begin to grow and push against her clothes. She didn't take her eyes off of the fucking scene in front of her.... Continue»
Posted by BiancaBigTits 1 month ago  |  Categories: Fetish, Lesbian Sex, Shemales  |  
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Ninasissygurl opens up about her sexual urges. Par

Hi there all you horny perverts!

My name is Nina, and if you take a look at my profile, you will see that I'm a bit of a sissy faggot.

I used to go out with females, and have illicit encounters with anonymous gay men on the quiet, but slowly, I have become more and more attracted to men, and in particular, crossdressers/transvestites/transexuals.

I still find women attractive, but I don't think my penis would get hard properly for a normal, straight woman.

But I always get rock hard when I look at anything vaguely gay or shemale-like.

I think I know what this means, that I am j... Continue»
Posted by barclay2011 1 month ago  |  Categories: Fetish, Gay Male, Shemales  |  
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