Shemales Porn Stories

Hotel Encounter.

The man had met her at the hotel bar, away from home on another work trip, a little tipsy, a little lonely. She had smiled at him so sweetly and when she touched his hand it seemed inevitable that there was more to follow. After a couple more drinks he had followed her up to her room, away from the noise and the crowd.
She takes his hand and leads him into the room. They stand, holding each other tightly as they kiss, long and deep. She is wearing a knee length, black dress, belted at the waist with buttons running down the front. He pulls away slightly and then nuzzles her neck, kissing... Continue»
Posted by furrygurl 1 day ago  |  Categories: First Time, Shemales  |  Views: 1695  |  
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My day with Maggie

I kissed my wife jumped in the car. As I turned out of the driveway I dialed in work and called in sick for the day. As I drove to Maggie's I could feel my rock hard cock beg for relief. I tried not to think about it but my cock stayed hard the entire drive. As I pulled into the hotel and walked to the room number she had text me I felt nervous, excited and so horny all at the same time. No matter how many times we have sneak off together I always feel the same. Maggie opened the door and I quickly slid into the room put my arms around her as our lips touched. The kissing turned to passion as ... Continue»
Posted by iheartm2f 1 day ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 1724  |  
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mom teaches son to be a slut

I loved women. A lot. My obsession with women later became a desire to wear women clothing. One day, three months after my 18th birthday, I could not hold back any longer, and I put on the the most accessible lingerie I could find - that of my mother.

Since then, I frequently visited my mom's wardrobe whenever she was out. I would wear her clothes, and it would make me feel sexy. I would pretend I am a woman, and take sexy pictures of myself. I realized how much I liked this, and this led to me realizing my bisexuality. I wanted a man to make me his woman.

Because I wanted a man so badl... Continue»
Posted by momandboys 2 days ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 2480  |  
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Mommies little sissy slut


I have been crossdressing for years now not known to my mother (or so I thought). she is the only person I live with at the moment. when she was going to be out for a few hours I went to her underwear drawer and inside was the most sexy, silky, feminine underwear set I had ever seen complete with calf length stockings and a garter belt. I wasted no time stripping off and sliding on the sexy underwear, next I found her makeup bag and applied some red lipstick and black mascara. that was when I heard the front door open, my mum was home early!! I tried to hide but before I could she strode int... Continue»
Posted by momandboys 2 days ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 1785  |  
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The Booty Inspector (Part 4) –


The Booty Inspector Part 4 –
“Dick Jone’s Circus PORNO”

by markfayer

Picking up with our protagonist, Dick Jones, the Booty Inspector where we last left off,
He and his Intrepid companion, Junior ,and their two lesbian Love slaves – Tall, dark-Skinned Nubian Sex Goddesses – have gone to the Circus which came into town, and convinced the 4 hermaphrodite Circus Freaks to film a Sex-Orgy with them – the TWIN “PENISED” LADIES: 2 Shemales – little petite, 5 ft tall, ladies with 8 ½ in Long Schlongs, and also the 2 BOXLER b*o’S – 2 Tall, 6’4” Men, Hulky, and Manly, ex... Continue»
Posted by markfayer 2 days ago  |  Categories: Interracial Sex, Lesbian Sex, Shemales  |  Views: 271  |  
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Happy Birthday to Me :-)

So last month, I was lucky enough to experience one of my favoritest annual events ever: my birthday party!!! Now, for those that don't know, I take my birthday VERY seriously. You see, I was only 12 years old the first time I played with a pecker...and I've been lickin' 'em and suckin' 'em and bouncin' up and down on 'em ever since :-) I suppose my love of being gangbanged and making guys cum on my birthday all began on the eve of my 14th...

It was a hot night in June and I had invited about 20 friends to a backyard birthday party sl**pover. 14 of my best buddies showed up. I had blown... Continue»
Posted by cdsexslut 3 days ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1967  |  
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My Date with a Crossdresser

A couple of months ago, I was contacted by a crossdresser here at Xhamster. She has asked me not to reveal her identity.

We arranged to meet one night at a motel near the Pittsburgh International Airport. I arrived at the agreed time, but when I knocked on her door she told me she wasn't ready yet and asked me to wait half an hour. I agreed.

Half an hour later, I returned to her room, but she still wasn't ready. She was apologetic, and asked me if I would rather come back in another half hour, or would prefer to wait in the room while she finished dressing. I told her I would like to wai... Continue»
Posted by johnny_antares 3 days ago  |  Categories: Shemales  |  Views: 1264  |  
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My meeting with Trannymilf Sandy part 3

After that she stood up and after that she sat down on my hard trannycock.I'm gonna ride you she said with my tight trannyhole.It felt awesome mm fuck me fuck me I groaned fuck me with your beatiful trannyass. Just as I was about to cum she got off. Now it's my turn she said! On all four now slut she said! Of course I did as she said she stood on her knees in front of my face I'm gonna fuck your mouth you cheap bitch she said after that I'm gonna fuck your trannyass.It felt so good to feel and taste her big juicy trannycock slidin' in and out of my mouth. She suddenly stopped fuckin' my mouth!... Continue»
Posted by NellieTranny 3 days ago  |  Categories: Shemales  |  Views: 418  |  
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becoming a slut

It all started when I was 13 and discovered the joys of wearing women's clothing. It started with my older s****rs panties then my highschool girlfriends things by the time I was 18 I had a pretty good collection of womens clothing even with never having the nerve to purchase any of them myself. Then came the urge for more when dressing up and masturbating wasnt enough I wanted more. I always considered myself straight despite my crossdressing but when dress would get the urge to please a man. So one day I got my s****rs 7 inc dildo. I got dressed up in some sexy thong panties some nylons and ... Continue»
Posted by RenoBoi 3 days ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 2693  |  
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The Booty Inspector of the Old West (pt. 3)

The Booty Inspector pt. 3 by markfayer

“Freaky Felatio Foursome”


Dick and his intrepid Lieutenant, junior, had no sooner arrived at the Barnaby’s Circus Fairgrounds when they spied the performers’ ring of campers set about in a cozy circle, creating a small common open space for the freaks and Acrobats and other members of the Freak Parade.
“Alright, Dick, what’s our plan of Attack?” quipped Junior.
“Well…I figgur we just waltz into the Boxler b*o’s trailer, give them an offer they caint refuse—by which I mean they get to fornicate with our Nubian Amazons-in-tow in a no... Continue»
Posted by markfayer 3 days ago  |  Categories: Interracial Sex, Sex Humor, Shemales  |  Views: 352  |  
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best friend

my buddy and i had been friend from day one. we grew up together. played sports together. we partied all the time and both had women come and go. i had finally found a steady girl friend, but for some reason he could never keep a girl friend. "i perfer being single, play the feild." he would always say.

after being in a steady relationship we naturally started hang out less and less. and eventually months went by. one day i decied to pop in and say whats up. see how things were going. figured id suprise him with a six pack of beer and some pizza just to hang out like the old days. little d... Continue»
Posted by souljah89 3 days ago  |  Categories: First Time, Shemales  |  Views: 2013  |  
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Young Black Motel Stud

I placed a personal ad, something along the lines of “Sexy, slutty, white CD looking for horny black man”. Much to my chagrin, I got little in the way of a decent response (I placed the ad kind of late in the day on a Saturday). Anyway, I spent the afternoon doing a full body shave, bubble bath, etc. so I could be ready for an evening of fun, if it were to happen. Around 10:00 PM, figuring I was out of luck (You should have seen the lame responses I got), I decided to head out to a local sports bar for a few drinks. Hoping I would get a late response. I made sure I had my clothes, makeup bag, ... Continue»
Posted by cdncleggs 3 days ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 1412  |  
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First time dressing up: Part 2

Dressing in my s****rs clothes became a regular thing after about 2 months of doing it, I would use her vibrator on my ass at least once a week. My f****y was gone more often so it gave me plenty of time to prefect doing my make up, hair and shaving my legs. One night when my f****y WAS home i was looking for a pen to write a card. I went too my parents room to look for one and on my step mom's dresser was a small blue key, i had no clue what it would go to and for some reason it seamed important. I put it back and continued on looking for a pen

Two days later my f****y was i out so imminen... Continue»
Posted by Badassgirl123 4 days ago  |  Categories: Masturbation, Shemales, Taboo  |  Views: 1533  |  
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Marie's playtime: An evening with Susan

Marie woke for work like it was any other day, all hard and swollen, first thing she did was rub her smooth legs together. The silky feeling alone was enough to send a tremor of pleasure through her. Desperate to cum but conscious of the impending lateness to start her day she quickly dressed and assumed the guise of her male alter ego. This meant a grey man's suit, but before that went on so did a pair of 10 denier stockings and garter belt with a lacy mesh fronted pantie through which her cock was clearly visible, under her jacket she wore a tie and shirt, nothing to exciting.

Time passed... Continue»
Posted by Marie_metal 4 days ago  |  Categories: Anal, Fetish, Shemales  |  Views: 804  |  
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First time dressing up

I was always interested in women's clothing. I don't know what it was but it just made me wonder what it was like to be a girl. When i was 15 i finally gave into my curiosity and wanted to browse my s****rs clothes. I went into my s****rs room when the house was empty and opened up her closet. I saw all of her nice shirts, blouses and dresses, i looked around pulling some stuff out and eventually made my way to her dresser and saw all the panties and bras. I wanted so badly to try on a whole outfit but i was terrified of getting caught.

Then i got an idea. I picked out the clothes i wanted... Continue»
Posted by Badassgirl123 4 days ago  |  Categories: First Time, Masturbation, Shemales  |  Views: 1451  |  
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My friend's new roommate and her surprise

So my friend Rebecca and I were planning on going to this bar for the evening but she called me and said she was running a bit late and that I should wait at her place and that her new roommate Shawna should be there to open the door for me. Rather, than wait in my car I went upstairs to her apartment like she suggested. The door was slightly open so I walked in saying hello; to see if anyone was home. I heard some noise in the kitchen so I walked over to check it out. It was Shawna cooking. She was actually a pretty cute girl. She was wearing a white tee shirt that just about covered her ass ... Continue»
Posted by lovingitman 6 days ago  |  Categories: Anal, First Time, Shemales  |  Views: 7193  |  
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Tgirl Hooker pt5

All my stories and based on my own experiences.

All other parts are on here and would recommend you have a read.

The next time I saw Emma my ass was still sore and I was quite bruised inside from how are she had fucked me, so we went for a curry and a few beers.

After Emma had been perved at all night by the staff and some older business men in the restaurant but I know she loved it, the cute little giggle she done, the way she would look at them and bit her lip, for all I know they could be clients of her's. The thing I learned was although I was her fuck buddy, I was still paying he... Continue»
Posted by dirtydisco99 6 days ago  |  Categories: Anal, Fetish, Shemales  |  Views: 1018  |  
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If You Go Down To The Woods Today

If You Go Down To The Woods Today.
(You could be in for a big surprise)

Simone was a very beautiful, sexy figured, totally convincing, submissive, twenty one year old red headed male to female transvestite living in Prague in the Czech Republic. She stood 178cm, or five foot nine inches tall in her bare feet. She wasn’t vain, she didn’t consider herself to be sexy or beautiful at all but anyone who met her became captivated by her sheer feminism. Very few passed her in the street, men and women alike, without taking a second glance and thinking, “Oh I wish”.

It was a Thursday ev... Continue»
Posted by susan-page 6 days ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1367  |  
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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 7 days ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 2934  |  
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Tgirl Hooker pt4

All my stories are based on my experiences.

For those who may not have read pt 1 to 3, Emma is a Eastern European Tgirl hooker who I found online, Pt 1 & 2 are about my first experiences with Emma and pt 3 she told me I was no longer a client but a fuck buddy....

So after that night when Emma told me I was now her new fuck buddy, we spoke all the time and had been out a few times to eat and it always ended with us boozing and me picking up the bill. I was beginning to feel a little used by this as nothing sexual was happening and the money I had spent could of paid for a good few hours ... Continue»
Posted by dirtydisco99 7 days ago  |  Categories: Anal, Fetish, Shemales  |  Views: 969  |  
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