Shemales Porn Stories
Page 15

My 1st experience with a "Special Girl".

Let me tell you something about myself. I'm your average Hispanic male. I can honestly say I'm not gay or attracted to men. In contrary, I'll truly get turned off by that scene. Im also turned off by hair/hairy skin and bad hygiene (who isn't... LoL). It's just not for me. Yet something about a cute shemale with a booty is something i cant resist. I found myself enjoying shemale porn. A cutie with a booty takibg it up her booty hole. My favorite scenes involve a passable tranny (Ts Foxxy, Sianna Grace, Ts Celeste, etc.) Wrapping her ass cheeks around a dick. Skip the scenes were shes getting a... Continue»
Posted by socal805 5 months ago  |  Categories: First Time, Shemales, Taboo  |  
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My Mom The BBC Shemale and My Wife, The Virgin

After the wedding, we didn’t move out from my mother’s house as my salary is not enough to cover our expenses and since my wife is also not working.
Mom allowed us to stay with her since she will be living alone if we move out.
I had no issues with this as I save my expenses and on an off without my wife’s knowledge I can suck mommy’s dick and be fucked by her. Mom is also looking forward to this encounters I suppose.
Her age is pushing 60 but she still looks attractive most probably to her testosterone production that delays her menopausal syndromes. She still maintains her cock size which... Continue»
Posted by yarracuda 5 months ago  |  Categories: Mature, Shemales, Taboo  |  
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shazza my first bi experiance chapter 2

Hi everyone I hope you read chapter 1 because you will understand chapter 2 a lot better this is a true story which some of you might be able to relate to.
I was a little confused with my little episode with Fred I wasn’t sure what I wanted I had wanked another man’s cock and I had let him cum over me was I becoming gay even though I had a girlfriend, Just thinking about it was making me horny I would have to talk to Fred but I felt sort of embarrassed I needed to collect my undies he was washing for me, I often used to pop in to see him to ask when my next driving lesson was or when we were ... Continue»
Posted by cdshazza 5 months ago  |  Categories: First Time, Masturbation, Shemales  |  
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Moving in with Jim and Candy - Part 5

Not long after the scene with the pool guy and Janice occurred, Jim was called out of town on business for a few days. A couple of days after he left, Candy and I were eating dinner and just chit chatting about things. It was getting late into the summer and college would be starting soon. Candy took a sip of her wine, "So are you going to try to keep working at the store while you're going to school?"

I shrugged , "I'm thinking about it. I already talked to the owners and asked them if I could have a couple of weeks off while I was getting used to the school schedule. They said sure. I'm g... Continue»
Posted by Mrtommyboy 5 months ago  |  Categories: Anal, First Time, Shemales  |  
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Owned and Bred

'When we meet, that's it, you're mine. And then I'm going to fuck ya and breed ya.'

So said Conor at the end of the last phone message before I traveled to Dublin to meet him. For the first time. Though I had known him for years in Internet chat rooms and numerous phone calls. But no, we had never met.

I had tried to - on two occasions. I had booked an hotel room in the city centre and he couldn't wait to see me and again he had said the same thing.

'When we meet, that's it, you're mine. And then I'm going to fuck ya and breed ya.'

Except we hadn't met. He canceled - at the las... Continue»
Posted by sissypansyfairy 5 months ago  |  Categories: Shemales  |  
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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  |  
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Satan and his sissyboi wannabe

Got inspiration to write this from a friends profile and content ( http://xhamster.com/user/pornperve666 ). 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  |  
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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  |  
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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  |  
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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  |  
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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  |  
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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
also.


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 woman....natura... Continue»
Posted by LisaTn 6 months ago  |  Categories: Fetish, First Time, Shemales  |  
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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 6 months 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 6 months 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 6 months 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 6 months 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 6 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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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  |  
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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  |  
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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 http://FionaDobson.com. 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  |  
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