Shemales Porn Stories
Page 60

Trip to LA

I was out in Los Angeles on business and as I would dress up every nite and see if there was anyone who wanted to play a bit. On Friday around 5 pm I decided to go all out and I dressed in a corset with garters, panties, bra, stockings, red heels and a black lace cocktail dress. I finished it off with a blond curly wig and some rhinestone earrings. I had taken my time with my makeup so I looked pretty hot.
I had some conversations with Tom during the week but they always ended up with just talk so I figured Friday’s conversation would be the same. I was chatting with a few guys as well and... Continue»
Posted by MichelleSEmass 1 year ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1295  |  
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Preparing For a Special Date

Preparing For a Special Date



I have a date to night with a girl called Lucy just like myself another Transvestite who I met on the net over a month ago. She is a little smaller than me with nice little breasts, nice little clitty and brown hair like mine but shorter, she is a little younger and good looking and we get on so well. We have met five times now dressed, mainly in the back of her car and have tasted each other on every occasion, I have put my fingers inside of her and she has done the same to me but ... Continue»
Posted by alanyagirl 1 year ago  |  Categories: Anal, Mature, Shemales  |  Views: 1493  |  
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my wife make me her sissy slut

I married Jen when I was a successful high earning bachelor at the age of 30. She
was 25 at that time. 5'4" same height as me, 120lbs, petite blonde with
blue eyes, a set of DD tits and an ass to die for. I was short, skinny yet she was
attracted to me when we first met in a bar down town. Later on I found out that it
was Laura her friend who had told her that the porsche parked outside was mine.
Now, after 5 years of marriage, things were quite different. Things had actually
started going down hill after the first few months when subsequently Jen had clearly
stated that my 3 inches coc... Continue»
Posted by nicoleinberlin 1 year ago  |  Categories: Gay Male, Shemales  |  Views: 6665  |  
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first time web hook up crossdressing dominatrix

crossdressing has always been my secret pleasure I even had a cache of out fits make up wigs and heels. it started when I was younger but evolved as I got older, now as I got older ive refined my skills and abilities and can pass as a girl when dressed. I had fooled around with guys before but I had never dressed for one only indulging in self pleasure with toys and my fingers. when I got off work on friday I was excited for the up coming three day weekend going home to get dressed up maybe go shopping and get some new outfits. I love going out in public dressed like a slutty girl im very pass... Continue»
Posted by lillolly 1 year ago  |  Categories: Shemales  |  Views: 721  |  
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Dad uses me for 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 work... Continue»
Posted by nicoleinberlin 1 year ago  |  Categories: Gay Male, Shemales  |  Views: 3940  |  
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Tammy's Fantasy Field Trip

Tammy's Fantasy----a short story
A pretty cross dresser goes camping alone in the high country. Thinking he/she is all alone, she dons her favorite outfit which happens to be a lot like the one worn by Julie Andrews in the Sound of Music, only very much shorter and frillier. It is a perfect day as the sun is shining and there are some fat clouds drifting by to provide a short relief from the suns rays. She decides to walk out in the green meadow away from the trees where she is camped. As she nears a bubbling brook, she thinks she sees something move over by the bend in the creek that h... Continue»
Posted by cdtamara 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 1363  |  
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Crossdresser drinks cum

Nikki looked up at me with her big, brown eyes as her head bobbed on my cock. Nothing was quite so sweet as one of her blow jobs. She had this way of dragging her tongue along the underside of my cock that made me want to cum in seconds. I always tried to hold it, but Nikki wouldn't let me. When she wanted me to pop, she'd plunge her head all the way down my pole.

Less than three minutes into the BJ, my cock disappeared into her face. I shot my load. Nikki froze while I unloaded. She couldn't say a word, but the bemused look in her eyes told me she was loving every second of it. I must've d... Continue»
Posted by MasterDavidsslut 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 2012  |  
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Daddy and Sir: I want to be Daddy's girl

"Next time I want to film it." I said, wiping my face and licking the cum from my fingers.
"You want me and Daddy to record us fucking that sissy ass? This just for you, or you gonna post it on the internet?" Sir asked.
"I have a profile on this site where you can post pictures and videos. I've only got nude pictures of myself on there, so far. But I've always wanted to put a video up of me getting fucked." I said as I licked the last bit of cum off my fingers, savoring the taste of Daddy and Sir's collective load.
I stretched out on the bed. I was on my back, facing upward, staring at D... Continue»
Posted by bttmblw 1 year ago  |  Categories: Gay Male, Group Sex, Shemales  |  Views: 1767  |  
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Sissy Slut Amanda Part 1: The Beginning

The Story of Sissy Slut Amanda

This is a story of fiction

Part 1: The Beginning


When I was twenty-three I meet my Sissy Slut Amanda for the first time. Now he was only eleven at the time and it would be many years before I would know him as Sissy Slut Amanda, but still funny to look back at now. The first time I met my future sissy slut, he was Mark, son of the woman I was dating. He seemed like a nice k**, very shy and timid but sweet nonetheless. It’s wasn’t too long after our first meeting that I would be asking his mother to marry me. We had a good marriage and although I nev... Continue»
Posted by TheSissyFucker 1 year ago  |  Categories: First Time, Shemales, Taboo  |  Views: 2491  |  
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Moving to a Retirement Community

Chapter 13
(This chapter, as well as the next one, is dedicated to a reader who has become a big fan of this story. I've chatted with him several times and in one of those conversations he mentioned something that stuck in my mind. He knows who I'm talking about and I do hope he enjoys these next two chapters. I will also give credit to those who inspire me with ideas to use in my stories, whether intentional or inadvertent. Thank you very much, T.)
That afternoon I was out doing my daily walk around the neighborhood I met a very interesting woman for the first time. Her name is Barba... Continue»
Posted by eprise01 1 year ago  |  Categories: Mature, Shemales  |  Views: 662  |  
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Moving to a Retirement Community

Chapter 14
All I could do was stare.
I thought I was imagining it, but there it was, a cock!
Barbara has a cock between those beautiful legs.
"I guess you hate me now, don't you?" she asked.
While I'd been staring at her crotch, she'd raised up on her elbows and was looking at me. I could see sadness on her face.
I found that I wasn't mad at her though. I could feel the pain she was in and I reached out to touch her cock for the first time.
"Don't!" she said.
"Buy why?" I asked.
"Because I'm a freak!"
"No you're not. You're lovely," I tried to assure her.
"No, I'm no... Continue»
Posted by eprise01 1 year ago  |  Categories: Mature, Shemales  |  Views: 638  |  
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Moms Trannie

It was Saturday night and my friends had told me about a new club. It was about an hour out of here and had an older crowd. This sparked my interest some what having a fondness for older women.

I walked into the place and looked around, not much going on so I wandered over to the bar and ordered up a beer. A little while later the crowd picked up and things started to get moving.

The women were defineatly older here, I asked a few to dance and had a few takers but couldn't seem to lock in with them.

While I was dancing I must have missed the two that came in, a blonde and brunette wit... Continue»
Posted by frswriter 1 year ago  |  Categories: Shemales  |  Views: 4540  |  
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Aimee and Me

My name is Shaye and I’m a 27 year old pre-op transsexual. This is the story of my only sexual encounter with another shemale, which turned out to be one of the most intense sexual experiences of my life.

I first started speaking to Aimee about two years ago on an adult chat site. We had some cyber fun for a few months, jerking off on cam and generally having a good time. Eventually, Aimee asked me if I wanted to go around to her place for some real fun. I didn’t need to think about it and I arranged to go to her house a week later.

It took me two hours or so to drive to her house. More ... Continue»
Posted by gellid12 1 year ago  |  Categories: Shemales  |  Views: 711  |  
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The morning after my night out with my s****r

Continued from my other stories...feel free to read those first to set the scene.

I woke, feeling a slender arm d****d over me, gently stroking my cock which is getting harder in the knickers I'm still in from the night before.

I relax and enjoy the feeling of nails through the black lace. Before long Jane's hand slides inside my knickers and takes her cock in her hand, she whispers 'I want this inside me Danni'.

My heart races, my cock twitches at the thought of sliding deep into my s****rs wet pussy. I role to face her and we kiss slowly and passionately. Our rongues entwined as ... Continue»
Posted by ukdan78 1 year ago  |  Categories: Shemales, Taboo  |  Views: 1929  |  
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my first cross dressing play time

i sucked my first cock the other day. i posted a ad on craigs saying i like to cross dress and would like to find somebody to dress up with and take turns being sluts to each other and then i posted a few pics of me from my xhamster profile and actually got alot of replies. it took a few weeks but i finaly found somebody that like to dress up and he came over during the day and we started watching porn and i pulled out all my slut clothes and we picked out things that we wanted the other person to wear. he wanted me to dress up just like the pics i sent him so i did, after we got dressed up we... Continue»
Posted by floyd1985 1 year ago  |  Categories: Fetish, First Time, Shemales  |  Views: 1412  |  
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Daddy's Caddy

From the moment my Daddy first took my young, naked body in his strong, masculine arms, I knew that he was not like other men. At least not like any of the men that I had gotten naked with! Daddy knew something was different about me when he began catching me, his 12 year old son, playing dress up with my Mommy's make up and wigs, outfits, jewelery, hose and heels! It was shortly after my 14th birthday when we became lovers.

Every morning, I would wake up at 430 am so that I could jump in the shower, shave myself smooth, and put on something sexy for Daddy. Around 5 am, as quietly as he ... Continue»
Posted by cdsexslut 1 year ago  |  Categories: Group Sex, Shemales, Taboo  |  Views: 1074  |  
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monday night football

HELLO EVERYONE
I hope everyone enjoy my last story happen on black Friday please leave comments so I know how much u love the story thank you

Well we getting close to football playoff and every other Sunday some one throw football party at their place sometime I get invited sometime I don’t depend what kind of party and what kind people their as you know im a pretty shemale and im proud of it.
My story always a real experience happen to me or my friends I love to share after all us shemale also have feeling too

On Monday night football Texans vs patriot one of black gay friend throw
... Continue»
Posted by shawn777 1 year ago  |  Categories: Hardcore, Interracial Sex, Shemales  |  Views: 1776  |  
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its monday night football

HELLO EVERYONE
I hope everyone enjoy my last story happen on black Friday please leave comments so I know how much u love the story thank you

Well we getting close to football playoff and every other Sunday some one throw football party at their place sometime I get invited sometime I don’t depend what kind of party and what kind people their as you know im a pretty shemale and im proud of it.
My story always a real experience happen to me or my friends I love to share after all us shemale also have feeling too

On Monday night football Texans vs patriot one of black gay friend throw th... Continue»
Posted by shawn777 1 year ago  |  Categories: Hardcore, Interracial Sex, Shemales  |  Views: 2092  |  
50%
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I meet Bam [dildo/poppers/training]

So I had the place to myself again, and if anyone has read any of my other stories, you probably know what I like to do when I'm alone...

My wife wasn't gone more than ten minute for a weekend get away with a girlfriend, when I was out the door too. I was heading to my local sex shop to pick up some fresh poppers,and maybe cruise the video booths and look for some dick. When I pulled up to the store, I was a little disappointed because there were no cars in the lot. I made the trip, so I decided I'd go in anyway. When I walked in,the first thing I noticed was empty shelves-"not good" I t... Continue»
Posted by pbg732 1 year ago  |  Categories: Anal, Masturbation, Shemales  |  Views: 2302  |  
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My first time with a tranny

I had been looking at shemale porn for a while and dreaming of being with one. A few years ago I got away from work early and decided to have a few drinks. I was horny and soon looking at adverts in the paper when I stumbled across one for a ts hooker in the area. I called then number and the husky voice told me the address and to come in 30 minutes.

The next 30 minutes I was very nervous and took a minute or so before I worked up the courage to ring her doorbell. She let me in to her flat dressed in very little. Slightly taller than me, amazing breasts, big slutty shoes and an already erec... Continue»
Posted by ross80 1 year ago  |  Categories: Shemales  |  Views: 3306  |  
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