Shemales Porn Stories
Page 15

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 3 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 3189  |  
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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 9 months ago  |  Categories: Group Sex, Mature, Shemales  |  Views: 3186  |  
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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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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: 3164  |  
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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: 3161  |  
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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: 3160  |  
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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: 3152  |  
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Got Caught

2 weeks ago i found myself alone as the wife had taken the k**s away for the weekend i felt the need to play. I went to work and finished early and raced home feeling very naughty indeed. I got in and ran a bath and had a nice long soak indeed and thought about what i would do and where i might get some fun at such short notice?

I got out my gear and put on a black basque with fake 40c inserts, lacy see thru black panties, black lacy top stockings, black strappy heels, skirt, top. I put on my wig and did the make up as best i could being a novice and looked into the mirror and got extremly... Continue»
Posted by abicd 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 3146  |  
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How i became a sissy/my first blowjob

I'm a 17 year old sissy now but i started crossdressing 4 years ago when i was 13 :).This is the story. One day my parents went to our lake house for the weekend with my s****r but i was feeling sick so they left me with my grandparents. They were taking care of me for a day or two and i got better so they left and i was home alone.I had 5 more days until my parents were back.One day i was feeling very bored so i opened my s****rs closet and looked at her stuff. I noticed thongs,i never knew she wore them (she was 17 back then). I wondered how they would feel so i put them on. I never felt sex... Continue»
Posted by sissygirl1988 1 year ago  |  Categories: Fetish, Shemales  |  Views: 3148  |  
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hotel steam room

Once I got to high school my thoughts of wearing panties and sucking cock subsided as I became a normal teen with a girlfriend,It wasn't till I was 22 that I would realise my true passion.I traveled to Toronto with my b*****r and his girlfriend so she could right an exam.We were on a budget so we all shared a room downtown.The first evening I was tired so they went for dinner while I stayed in.While getting a beer from the fridge I noticed her suitcase open and a bra laying on top.I immediately got hard as I looked at it and had memories of my younger days wearing Lingerie.I locked the door so... Continue»
Posted by sluttysherri 12 months ago  |  Categories: Gay Male, Shemales  |  Views: 3146  |  
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A Little Twist at My Last Massage ...... By BigSof

I have a really bad back from an auto injury several years ago and have been getting massages to relieve some of the discomfort I have. The problem with that is I, like so many people with injuries, have an addiction. I’m not talking about pain killers… I am now addicted to massages! Now I know some of you are laughing thinking I am trying to 'be cute', but I am telling you, I could get a massage right now and 1 hour later if given the chance I’d do it again, and again, etc. The overall feeling of serenity and calmness you feel is my addiction. Of course any time you get a ... Continue»
Posted by bigsoftee 2 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 3132  |  
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mom made me her sissy

"Mom! I called out as I got home from baseball practice, "I'm home!"

"Hello Danny, we have to talk," she responded, while exiting my room.

When I saw what was in her hands, I became nervous. Some of the guys I pal around with talked me into shoplifting a few things from a department store.

"Please explain where these items came from."

I should have told her I was sorry, and that it was just the one time,

But instead I said, "Tommy made me do it. He said it was a dare. I didn't want him to think I was a sissy."

The next thing I knew, I was in big, big trouble with Mom. I got ... Continue»
Posted by momandboys 1 year ago  |  Categories: Fetish, Mature, Shemales  |  Views: 3134  |  
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Double Stuffed oreo

Met these two dark rich ebony beauties in this roof top bar, sweet and petite they were. Brown Sugar is what they called themselves. Brown has these baseball size titties with hard nipples. She stands at 5'9 with 3" heels, some of the fullest softest lips I have seen. Six pack, bun of steel WOW she can put a hurt-in on me. Sugar has long wavy hair mid of her back, eyes any man can get lost in. No tits just very large nipples,the kind to chew on. Thighs and cafes I would love to sink my teeth into. And some of the most sexiest feet and toes. These girls had something special going on.

We tal... Continue»
Posted by Gehld 1 month ago  |  Categories: First Time, Interracial Sex, Shemales  |  Views: 3129  |  
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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: 3130  |  
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my first gay fuck

I've slways crossdressed, from when I was 12 years old. I started by wearing my Mum's knickers and bra, tights, knee high boots and a dress or skirt and top. it felt fantastic wlaking around on high heels, in the back garden, knowing that all the neighbours had to do was look over the fence and see me all dressed up! My cock got so hard and I'd wank myself dry!
I carried on all through my teenage years, using girlfriends underwear. At the swimming pool, where I used to work, I'd have a shower wearing the girls high cut swimming cossies! The feel of the wet lucra around my ass and cock was rea... Continue»
Posted by Nikki_xd 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 3127  |  
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3 weeks in Thailand

6 weeks ago I went to Thailand – Koh Samui for a 3-week holiday just to get out of the system.

I was on my own, in my 50s, divorced and mainly hetro but enjoyed a passing gay experience with “Jon” from a now closed down massage parlor in Manchester UK (told that story a few months ago). So went to Thailand - thank god for Viagra – to fuck a few hookers, get d***k and have a nice break. The bars at Chewang Beach were crowded and “factory like” , full of tit and sweat and I didn't like them. The girls were “well worn” and “routine” if you get my meaning – “me make you fucky fucky long time” ... Continue»
Posted by jimtheman699 8 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 3127  |  
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Valerie on an Island


I’ve been here at the house for about a week. It sits on the side a hill overlooking a valley of trees and shrubs, some farmland, the nearest house is a half a mile away. The room that I’m kept in has a little window and it’s been breezy and cool with a bright sun almost every day.

It’s an old house and the walls seem to be two feet think in most places. That along with the metal bars on the windows gives it the feel of a cell, although a very nice cell. A large metal four poster bed, covered in silky sheets and pillows and a dresser and a large mirrored closet loaded with women’s shoes a... Continue»
Posted by subval79 12 days ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 3131  |  
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My first BBC fuck!

I went clubbing last week with my girlfriends that I work with and they recommended a hip hop club in a seedy part of town. I was alittle scared but we went anyway and well, and we were really having some fun there!!! I decided to dress like a real lil slut this night, a black minidress, lacey thigh highs and garters and black fuck-me pumps.

My girlfriends hooked up with some cute black guys and took off leaving me there kinda by myself. I was being hit on constantly by these hot black guys but I wanted a white guy, or at leas... Continue»
Posted by sataori_fukame 1 year ago  |  Categories: First Time, Interracial Sex, Shemales  |  Views: 3113  |  
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I final found him and his friends

For the last 7 years or so I have been from one guy or girl to another looking for someone that I could serve sexually and not interfere with the rest of my life.

Last month I finally found him. I was at the local porn shop on Friday night cruising the theater and the peeps as usual. I was in the Theater by myself in the back row when a guy walked in he looked to be about 35-40 average build dressed in blue jeans and black shirt. He sat down across the aisle from me on the back row out of site from everyone coming in and out of the 2 doors. I sat there for awhile then decided to move ba... Continue»
Posted by tim_likes 8 months ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 3111  |  
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long saturday at the arcade

what you are about to read is a true and accurate accounting of a day I spent in a video arcade booth

its early Saturday afternoon, and i'm sitting here in an arcade video booth dressed only in sexy little bikini panties, training bra (for my little a cup puberecent like titties) and a white silky like full slip, I have left the door slightly ajar while I rub my little sissy clitty, which is confined in a tight fitting chasity devise, and tucked back between my legs, while watching a really hot gang bang video, hoping for some action. when I happen to glance up at the door, I see your eye p... Continue»
Posted by robinlikesitrough 2 months ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 3104  |  
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