Shemales Porn Stories
Page 15

A night out with my s****r

Following in from Shopping with my s****r - Please read my other stories first to set the scene.

Jane and I lie embracing on her bed, our naked bodies merging into one as we hold each other closely.

"What do you want to do tonight?" I ask

"I was thinking we could have a night out together, maybe a meal and a few drinks, see where the night takes us!" Jane replied.

"That sounds good to me, I haven't been out for a few weeks because of my exams."

"Well, I'll treat you to a nice meal and a bottle of wine on one condition" Jane offered with a devious smile on her face.

"Go on,"... Continue»
Posted by ukdan78 3 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 3244  |  
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Airconditioner repairman laid some pipe

I was literally bored to death when my mom went on a vacation, i was hoping that i was gonna enjoy freedom when mom's away but things got worse as i found out the air-conditioner wasn't cooling the house, it was the dog days of summer and i really hate this muggy, hot weather. So i gave a call to the place where we bought it and asked them if they could send someone to fix it. Like i said, the weather was terribly hot, therefore i was wearing a micro-mini short which was showing of my curves in a very revealing way. It was almost 4.00 pm when the doorbell rang. I was expecting the same guy... Continue»
Posted by Slave4str8twinks 9 months ago  |  Categories: First Time, Hardcore, Shemales  |  Views: 3237  |  
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The Next Morning

I hadn't planned on getting d***k last night but what can I say? The mood was just right for it, me and Nicole are c***dhood friends and although we've branched out and built our own lives and become two very different people, we still find a way to make our friendship last throughout the years, you could say that she's my best friend, I've been there for her and she's been there for me and people like that seem rare to come-by these days so it's safe to say she means allot to me though clearly I meant much more to her because here was, waking up in her bed next to her the following morning.
... Continue»
Posted by RunandCummer 9 months ago  |  Categories: Fetish, First Time, Shemales  |  Views: 3235  |  
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Four Guys And A Shemale

My big br0ther enjoyed humiliating me when I was young.
There was this guy in school that picked on me all the
time, calling me "tits" and groping me in the hallways.
I couldn't complain because I was a known freak and
slut so I just tried to avoid him and his asshole
buddies. I was terrified of Donald and his three friends.
One Saturday morning when m0m was visiting grandma I
showered, blow dried and came down the stairs naked
because that was one of my b*****r Johnny's rules:
whenever m0m wasn't home I had to go naked or put on sheer
black stay-up nylons if he told me so that he
... Continue»
Posted by yutubeslut 2 months ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 3229  |  
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Weekend retreat

When I go to work, I am in 'boy' mode. I certainly am not the most masculine person, and I am pretty certain that everyone knows my sexual preference. I often get mistaken for a woman even when in 'boy' mode. Whatever. I am who I am... deal with it :)

A few years ago my former workplace had a nice mountain retreat weekend. I love these retreats, not because I become closer to those I work with, but because they are so peaceful.

I arrived at the lodge on a Friday night and spent the next day communing with nature. My fellow workers were doing other activities, and I spent most of my t... Continue»
Posted by zaria_ts 11 months ago  |  Categories: Anal, Shemales  |  Views: 3226  |  
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My shemale boss part 2

Friday 12pm was here, I nervously knocked at my bosses door part excitement part apprehension ran through my body.

A clear come in could be heard from within by my boss Miss Jones so I went in. Ahh Rob right on time, take a seat and I'll be with you in a minute, she said.

I sat down opposite her desk whilst she continued to study her paperwork. Her black rimmed glasses were on the tip of her nose and with her finger, she curled her long black shoulder length hair. Through her glass desk I could see her tight black leather trousers she had on and black 5" heals. She had walked through my... Continue»
Posted by big_rob49 1 year ago  |  Categories: Shemales  |  Views: 3215  |  
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A Trannie takes her first big black cock

Sitting on the lounge at my local sex club I was watching the guys go by. You get to notice certain guys going past trying not to look like they are checking you out on the sly (and vice versa) thinking how they can approach me.

Normally it’s just the usual crowd of guys but several weeks ago a big heavy set African guy in his mid 30’s kept going past me and looking at me out of the corner of his eye. After about his third walk past I gave him little smile. When I could see him coming down the hall the next time I got up and slowly walked around the corner into the next hallway so he could... Continue»
Posted by toniparr 3 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 3197  |  
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The Studio and the Shemale

When the company I worked decided to relocate to the north of England, it was made clear to me that there would not be a job for me there and so the decision whether to move woth or leave was decided for me. The redundancypayment was extremely generous, as it should be, I had been with them since I left school. So now I had to find a new job and the decision was whether to stay in the line I was in or change careers, but With the redundancy payment as it was there was no rush.
Quite by chance I discovered that a photographic studio, which was literally a 5 minute walk away was looking for an ... Continue»
Posted by dasilva1672 4 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 3194  |  
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Helping a friend

Anna has been working in my office for a year now. I have never heard her talk about a boy or girl firend. Anna is 5'7'', long legs, light brown hair almost to her waist, very pretty. I have always talked to her, had lunch, but she had never opened up until she needed some help.....

Anna had bought a house that needed work. A couple of months after she bought it, she was complaining that her sink leaked. I told her i had done odd jobs through out my life and i would be more than happy to check it before she called a plumbler. She told me to come over friday after work.

Friday came,... Continue»
Posted by edukateme 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 3193  |  
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Tentacle impregnation

I had just finished a session up at the gym and began walking back to my car. It was dark out and the large car park was empty, nobody could see me. I was wearing just a tight grey leotard.

My big bulging cock showing clearly up my stomach, small wet patch from a little pre cum, my tits free, no bra, nipples erect from the cold, wobbling as I walked, along with my ass and thighs.

As I got to my car I got in and got myself comfortable, suddenly I was locked in my own car, from under my seat crawled fleshy huge tentacles in the shape of huge cocks, all dripping pre cum. They tied me to m... Continue»
Posted by drew1207 16 days ago  |  Categories: Fetish, Sex Humor, Shemales  |  Views: 3196  |  
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Four in four hours - am I a whore? (Part 2)

So, I'd had my passing quick bj and the guy I blew has already sent me a message thanking me for what I did for him and asking me when I'm available again, perfect !!

From the quickie it took me a while to get to the hotel, called when I was in the car park, heels on and walked across the car park with more delicious feelings between my legs, I adore walking in heels and stockings, they're always so sexy. There was a couple going into another room and the guy did a double take and smiled, murmered a 'bonsoir' before he went into the room, I think I scrub up pretty well.

It was a budget ... Continue»
Posted by antoniaf 10 months ago  |  Categories: Group Sex, Mature, Shemales  |  Views: 3186  |  
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I Disco

By - Tex Lee

I Disco

I discovered crossdressing in my early teens when I was once
using the bathroom I noticed my mothers red lipstick on the
bathroom counter. I opened the tube out of curiosity and
twisted out the red phallic looking lipstick and felt
compelled to put it on. I felt a strange and exciting sexual
arousal that I never felt before and soon was wearing
lipstick and masturbating every chance I got. Eventually I
started wearing my mom's and s****r's panties and bra, then
dresses, skirts and high heels. By the time I was 16 I
accumulated a nice little wardrobe of sexy... Continue»
Posted by jayymie 3 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 3187  |  
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A little fantasy...

This is a work of fiction. It's a small window into a huge world of fantasy for me. Enjoy!

It was a wonderful day. Kristy had just moved into a new town and settled into a new job as an accountant for a local practice specializing in debt recovery and settlement. Kristy had spent the last 2 years in school and had finished to start life a new and on her own. She grew up under the yoke of her mother and older s****r. Kristy wasn't like other girls as Kristy was really born a male. At an early age Kristy displayed signs of being very feminine and showing interest in very feminine things. She ... Continue»
Posted by russianrabies 5 months ago  |  Categories: BDSM, Gay Male, Shemales  |  Views: 3183  |  
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My First Day as a Hooker or a Busted Date Part 3

"So what did you have in mind?" I said in my best sultry voice while turning part way around. My back was arched slightly to make my ass stick out just right. It must have made the two young men a little nervous. One, for being so forward and assuming in my nature and what would you expect. My body was well worked over finishing less than a hour ago by four delicious cocks and the opportunity to make a couple more quite happy was, well, when on a roll, to be taken advantage of. And two, that's simple. I loved being the instrument to give someone else pleasure and here I was answering that call... Continue»
Posted by LeslieStone 28 days ago  |  Categories: Fetish, Group Sex, Shemales  |  Views: 3189  |  
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Caught!

Let me start out by saying that I was very much in the closet about my dressing and the fun I have when I'm dressed when this happened. But more and more I kept fantasizing about one of my male friends. He's very good looking and keeps in shape by jogging every day. Several of the times we've gone out boating him and I ended up skinny dipping, so I've got to see his cock several times and have secretly wished I could get him to screw Kristy. He's been divorced for about 5 years and doesn't go out much, and several times he's told me he hasn't been with a... Continue»
Posted by kristygurl 3 years ago  |  Categories: Shemales  |  Views: 3166  |  
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Dad trains me to be his wife


After a long and unstable marrage of 20 years, the divorce papers finally came. My wife and I only had one c***d, William, and he is very gay. My wife was too much of a homophobic bitch to support him. Even when he was younger we knew he would turn out gay. Always wanting to wear girl's clothing, dress differently, speak differently, even walk differently. I always supported him as a dad and as his friend. I never understood and I still don't understand my wife and how she could just leave her only c***d and I. I remember it was his 18th birthday, about five months ago. She came home from wo... Continue»
Posted by nicoleinberlin 1 year ago  |  Categories: Gay Male, Shemales  |  Views: 3162  |  
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A night out with Tamanna

We had been chatting online for a few weeks , when Tamanna said she would love to come it with me.
The doorbell rang at my flat and I wobbled on my stripper shoes to the door. The butt plug Imwas wearing made me squeeze my ass cheeks together and gave me a wiggle in my black latex dress to die for.
I opened the door and there she was for real.
She looked gorgeous, a red headscarf framed her cheeky smile and her pink lippy set off against her rammed skin, made her sooooo kissable.
We kissed on the cheek and she came in. Her red shoes went beautifully with her outfit and I just wanted to ... Continue»
Posted by diesel41 1 month ago  |  Categories: Group Sex, Hardcore, Shemales  |  Views: 3162  |  
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How I became a sissy

So it all started from answering a random craigslist posting that didn't even have a picture. I was off work and horny so I was cruising the ads and I came across a Cross dressing married dom and his wife looking for a sub. I was no stranger to the lifestyle and it intrigued me so I began to write an email. We exchanged back and forth for several weeks and then began talking on the phone. The day had come and they invited me over. I was nervous. I am a married guy. My wife knows all about my past experiences but had no knowledge of this relationship. I got my things together and put them in a ... Continue»
Posted by tg2027 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 3162  |  
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Black Master gets a white sissy Part one

Black Master gets a white sissy

Part One

by
sissy4blackmaster


Every one who saw me at work used to think I was Mr. Clean, Mr. Respectable. I work in advertising and I used to model my appearance on the sort of guys you find between the pages of GQ. Very American, very preppy. I was a nice middle-class boy with a nice expensive haircut and a nice expensive suit. I went to an up market health club to keep my body in peak condition. I'd even dated a nice girl from time to time. So you'd be right in thinking that I was a bit of a closet case. I used to pass a gay bar on my way home fro... Continue»
Posted by sissy4blackmaster 2 months ago  |  Categories: BDSM, Interracial Sex, Shemales  |  Views: 3157  |  
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Allison the pool slut part 1

Allison had now had her fair share of whore experience. The teen boyslut had fallen in love with big cocks, anal creampies, facials, swallowing, and the rest of the nasty fun she had while becoming a sissy whore for her black neighbor and his dark dicked friends. Little did she know she was going to get the fucking of her life soon…


One day Allison arrived home to find a package on her door. It was addressed to Mark(her boy name) and did not have a return address just a note. The note read “Allison, I took the liberty of buying you some nasty whore clothes for when I return home in a coup... Continue»
Posted by AllisonCumms 1 year ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 3153  |  
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