Shemales Porn Stories
Page 15

What would it Take??

What would it take, to entice a nice handsome black man into my life?
Maybe if, the first time we met in person, meeting him at the door, dressed in my shortest mini skirt, highest "cum fuck me heels",toenails done in a bright pink to match my fingernails, advertising my sissy attitude, my tanned legs encased in a pair of thigh high fishnets, and a top that pushed my little A cups up and out. My nipples, hard as steel, straining against the material, wanting to be the center of his attention..
With my "sluttiest" make up on.. lips with the brightest red lipstick, outlined to perfection. The ... Continue»
Posted by bobbie_lee48 5 months ago  |  Categories: Shemales  |  

Satan and his sissyboi wannabe

Got inspiration to write this from a friends profile and content ( ). Satan is a strong figure for many of us whether its love or hate....worship or revulsion. This story is just a fictional story of a young sissyboi who worships Satan.

Billy had always been different from the other boys his age. At 16 he had never been into sports or chasing after girls, he had always been a shy and reclusive boy. This had been due to his timid nature many assumed but the truth was much more shocking as Billy was not only a chronic masturbator who spent almost all of h... Continue»
Posted by thebuttboi 5 months ago  |  Categories: Gay Male, Hardcore, Shemales  |  
  |  10

Scary!!!! my friend's mom has a dick!!!!

It happened last Sunday when I visited my new neighborhood Jack's house... They have arrived in the city a week ago from that day... Jack and his Mom(Aunt May). As we came to know aunty may was a single mother. She was a woman of 40-45 years with heavy tits and pale white skin. She looks like a perfect milf. Me and Jack has just completed our school so we were planning for some camping, hiking and mountain climbing. When I visited his house last Sunday then I came to know that Jack slipped from the stairs last night which cost him a fracture in his right leg. That was really surprising for us... Continue»
Posted by hunter043 5 months ago  |  Categories: Anal, First Time, Shemales  |  
  |  2

Jessica meets Master M and Mistress V (Part 1)

Jessica was lazing around in bed one weekday morning. She rolled to the side and reached for her tablet on the bedside table. Laying face down, naked under her duvet, her little clit pressed against the mattress.
She unlocked the tablet and opened the browser to log online and check her new messages on her favourite site. When she opened her inbox and saw new messages from the married couple she was chatting with her heart beat a little faster and a smile grew on her face.

She read the messages, re-reading to make sure she had read everything correct. They were going to be nearby that week... Continue»
Posted by Want2BeTrans 5 months ago  |  Categories: Group Sex, Shemales  |  
  |  9

Birth of a Sissy

I met Jeff one day at the nearby tennis courts. I could never have imagined
what the result of that meeting would be. I suppose I should tell you a bit
about me. I'm a happily married 34 year old. About average in most
respects. A little spare tire trying to form around the middle but in
decent shape. I wear my hair short with a mustache and goatee. I had been
married for about 6 years and had been physically faithful to my wife. I
say physically, as I did think about other partners on occasion, though
probably no more than most men. What was a little unique was my "dark"
sexual se... Continue»
Posted by klammer 5 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
  |  14

shazza my first bi experiance

Hi all you wonderful people this is the story of the start of my crossdressing adventure, this is chapter one of many It all started 35 odd years ago when I had my first bi experience my father passed away when I was quite young and my mum used to walk about at home in her undies, always stockings suspenders and bra and I loved the look of the undies, I had seen plenty of porn pics at work and most of the women were wearing stockings, I decided to try one of my mums suspender belts and a pair of stockings as I put the stockings on my cock got so hard it hurt, I stood looking in the mirror I pu... Continue»
Posted by cdshazza 5 months ago  |  Categories: First Time, Masturbation, Shemales  |  
  |  11

Halloween...a long time ago

Halloween...1991 I was still married and still very new to crossdressing
when this occurred, with very little bisexual experience

My wife and I were asked to attend a Halloween party with
some friends at the local VFW, the same one we attended the
year before and won first place for most original costume,
which I had chosen. I went as the Pope and she was the devil.
She asked me to pick this years theme since I was always more
creative than her and had such great success the previous
year, and since I had gotten more into my crossdressing, I wanted to go as a Continue»
Posted by LisaTn 5 months ago  |  Categories: Fetish, First Time, Shemales  |  
  |  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 5 months ago  |  Categories: First Time, Shemales  |  
  |  12

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 5 months ago  |  Categories: Shemales  |  
  |  12

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 6 months ago  |  Categories: Anal, Gay Male, Shemales  |  
  |  11

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 6 months ago  |  Categories: Anal, Fetish, Shemales  |  
  |  2

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 6 months 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 6 months 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 6 months ago  |  Categories: Anal, First Time, Shemales  |  
  |  1

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 6 months ago  |  Categories: Anal, Shemales  |  
  |  3

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 6 months ago  |  Categories: Fetish, Lesbian Sex, Shemales  |  
  |  6

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 6 months ago  |  Categories: Anal, First Time, Shemales  |  
  |  1

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 6 months ago  |  Categories: Anal, Group Sex, Shemales  |  
  |  2



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 6 months ago  |  Categories: Anal, Fetish, Shemales  |  
  |  1

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 6 months ago  |  Categories: Shemales  |  
  |  4