Shemales Porn Stories
Page 66

Office Fun - Part 2

Marcia was sitting in the car park of the office, about to leave having just finished work, when she saw Lee walk out of the building and head towards his car. It had been four days since they had fucked in the office, and she was eager for a second round. She checked herself in the rear view mirror before beeping the horn. Lee looked towards her and she beckoned him over, winding down the window as she did.

“Hey,” she said with a smile.

“Hi,” he replied, ducking his head in through the window. She caught him taking a quick glance at her cleavage.

“You wanna come to my place for some ... Continue»
Posted by gellid 2 years ago  |  Categories: Shemales  |  Views: 1101  |  
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My favorite time with a man as a Tgirl

I was in the dance clubs with my friends and we were very sexy dressed in heels and low tops and I was in high heels and a mini dress that was flowers all around it. My ass looked so big and round in that dress. It was low on my big boobs and very tight so my boobs looked like they have coming out. I was told by my friends I looked hot and like a real girl.

I felltd like a real girl. Very girly and my hair was long wavy and reach just above my butt. I was sitting down drinking with my girl friends. A man ask me to dance and we dance close and all night. He really like me alot. I was drinkin... Continue»
Posted by JackieRosa 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1100  |  
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Losing my crossdressing virginity

This is the true story of my first time with a man while fully crossdressed.
I answered an ad in the local paper for a guy looking to meet a crossdresser and exchanged some text messages before agreeing to meet.
I took the bus to where we had arranged to meet, it was a flat in a not great area of town. Nervously I rang the buzzer and entered the block, getting the lift to the fourth floor I went to the door and rang the bell.
The door was answered by a man in his early fifties of middle eastern appearance who showed me into the flat and told me he was married and this was a friends flat he ... Continue»
Posted by lucytv75 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1099  |  
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vicky`s fun


you get a video in the post, when your alone with the house to yourself you put on your favorite panties and play the video

it starts with me lieing on a big double bed I`m wearing a all in one red fisnet body stocking I`ve got thick red lipstick on.

two naked men appear from behind the camera and join me on the bed. one starts to play with my cock while the other offers his into my mouth, my full red lips wrapping around his cock taking deep into my mouth. the other one is slowly fucking my arse with his lubed up fingers two at first but soon he`s got four up me I`m writhing around on... Continue»
Posted by vic74 6 months ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 1097  |  
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I posted a craigslist ad.

8 years ago I began crossdressing again and playing with toys. After playing one day while watching videos online I decided I wanted to take the next step and be with a man again. My holes craved it but the butterflies in my stomach had stopped me before. Afraid they would do it again this time I got dressed as slutty as possible and put up an ad on craigslist with a photo of me dressed and spitroasting myself with toys. Pic required I put in the posting. I was amazed at the responses and how many people couldn't read or just saw the photo and replied without reading. I didn't think it w... Continue»
Posted by bibottomboi 2 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 1096  |  
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My First Tranny

I met Charkara (her real name) through an adult dating site. You can find her pictures on my xhamster page titled,

"My First Tranny". We corresponded through the dating site quite regularly before we decided to take it to next

level and exchange phone numbers and email addresses. We talked on the phone getting to know each other, what we

liked to do sexually, etc. She came off as a total freak willing to do most anything which was an extreme turn-on

for me. We then begun having phone sex with her telling me how she wanted to suck my dick and drink my cum and how

she wa... Continue»
Posted by ghostdawgg62 2 years ago  |  Categories: First Time, Shemales  |  Views: 1091  |  
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me and connor at the movies

me and Connor loved to fuck around in public clearly from our first time.. but this time we were bold and wanted to be noticed... we walked into the theater and as soon as the lights went down we snuck up to he front just in front of the screen... and we layed down and started to 69 while the movie was starting... nobody could see us and Connor was especially excited and i had something special for him.. i grabbed his cock and said "shove it in me sweety i want to feel your cum deep in me"... he his cock deep in me and i felt his balls slapping my ass... i was trying to hold in my moans and sc... Continue»
Posted by drewcd 2 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 1091  |  
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angel encounter

We both work in Angel Islington, most days we catch the same tube. Most days we stand close on the endless escalator. Most days we leave the station separate ways We never talk, some times I can smell her shampoo and sometimes and I can barely see her. I know she watches me, but she never catches my eye.

Three days ago she did. Momentarily, if it hadn't been for the raised eyebrow I might not have noticed the look.

She walked off quite quickly, leaving me mouth open like a guppy. I regained my composure and followed her, keeping her in view. She glanced back at me, catching me leeri... Continue»
Posted by j0shr0gan 6 days ago  |  Categories: Hardcore, Shemales, Voyeur  |  Views: 1092  |  
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car fun!

Some years ago, I had overnight business travel and I cross-dressed in my motel rooms after hours. I had some married men that I met online that would come see me when I was in their towns, and get some sweet head from me on their way home from work or whatever. One of my regular hookups, named Frank, pulled into the motel parking lot late one afternoon and looked up and saw me on the balcony. I was in a mini dress; heels and all dolled up, waiting for him, but was just getting a little "exposure" time in, as I waited. When Frank came in he said that he could tell that I was into being seen an... Continue»
Posted by dana213 2 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  Views: 1089  |  
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The Waitress

Janet sits in a corner cafe, her emotions all over the place. As she surveys her surroundings the tables were in need of a wipe, the gloomy ochre, smoke stained paintwork peeling away from the Victorian brickwork beneath. The gloomy surroundings fitted her mood, the girl she was supposed to meet hadn’t turned up, Janet felt alone, lonely, unwanted and depressed.

A new girl appeared at the far side of the counter, it was easy to see by the waitresses wide shoulders and slim hips that she wasn’t a real girl, her black dress and white pinny rather shorter than would normally be expected for a ... Continue»
Posted by susan_page 9 months ago  |  Categories: Anal, Shemales  |  Views: 1087  |  
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The alleyway

She pressed close against his body, so close that he could smell the leather from her jacket. As they walked along, her arm around his waist, he could feel her nails through his shirt gently stroking above his pubic region; with each stroke he felt the bl**d rush towards his cock.

They turned the corner and walked further into the alleyway, him guiding her into the shadows. He looked down at her face, her eyes staring back up at him and what little light there was reflecting off of her lipstick. He slid his hand down her back and slid it under her coat where her could feel her bare back bel... Continue»
Posted by ass_pussy_fucker 1 year ago  |  Categories: Shemales  |  Views: 1086  |  
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My fantasy, soon my reality

Mistress summons me to her quarters and places me in shackles, collars me, and calls me slave. I feel the cold steel restraints on my skin and my body quivers as she leads me to her dungeon. The dungeon is dark and dimly lit by candles burning around the room. She orders me to prepare for inspection. As I stand there naked I stare at my beautiful owner. She is dressed in a shiny black body suit with a collar that snaps around her neck with an opening that exposes much of her breasts but not all. She is wearing black stiletto heel boots that go up to her thighs and is holding a crop. Her beauty... Continue»
Posted by janine69aa 8 months ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1085  |  
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THE DARK BACKWARDS !

Let me begin by saying that I am fascinated with shemales! I AM IN LOVE WITH SHEMALES! How did this love affair begin? For me it started back in 1984 when I saw a shemale magazine lying on my high school campus. Someone left it behind or it fell out of a bookbag. That image of a redheaded shemale left an impression on me that I will never forget. Initially, I was slightly shocked because I had never seen a magazine like that before. Then my shock turned into curiosity.

Fast forward to 1987 and I'm in my local video store. I muster up the courage to browse the ADULT SECTION. I see t... Continue»
Posted by bryanferryfan 1 year ago  |  Categories: Shemales  |  Views: 1084  |  
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Chrissie's New Client

I run a small investment consulting firm. Very small, actually it's just me. It's really just a cover business for what I really do which is to service my male clients clandestinely.
There are an average 20-25 active clients. They are all successful proper business man, many of them you would classify as professionals.
They are all referrals and have been carefully screened. Most of the men are straight but just like a girl with "something extra"occasionally. There are also some who I suspect are Bi-sexual. I don't really cater to the overtly gay community.
That's for no particular reason ... Continue»
Posted by chrissieCD 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 1083  |  
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My ts fuck

Patong beach thailand a few years ago, a few drinhs at a bar with some friends on going to toilet at public loo which was next door to ladyboy bar. Standing and relieving myself in runs two lovely ladyboys from next door. Who proceed to do there make up and have a good look at my cock for good measure! Now at this point I hadn't any feelings one way or another, but now I was very curious indeed!
So I made my way back to my friends at the bar finished my drink and with a lame excuse left in the direction of the ladyboy bar, feeling nervous as hell I entered. It was dark with loud music a... Continue»
Posted by kawa696969 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 1081  |  
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A NIght Out - A work of fiction

After the fun I had had with Jane, I decided it was time for me to get out and about and meet other transvestites. I had a taste for sucking tranny cock, and I wanted more. I couldn’t believe myself, after one evening of hot tranny sex I was a cock hungry slut, who couldn’t wait to get her red lips round another hard and sweet cock.

I decided that the best way to meet girls was to go on one of their nights out. I chatted To Jane online as usual, and she told me of a night out in Glasgow in a couple of weeks. Unfortunately she couldn’t go, which disappointed me as I wanted to play with h... Continue»
Posted by misssuzywhyte 1 year ago  |  Categories: Shemales  |  Views: 1081  |  
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Interview with Tara Strong

When I was younger, one of my favourite shows growing up was Fairly OddParents. A few years later, I was in college and one day I was researching something which linked me to Tara Strong, the voice actress who had performed the voice of Timmy Turner, the main character of the show.

I found out that she lived near to where I went to college, so I e-mailed her and asked her if she would like to do an interview with me as part of a project I was working on. She e-mailed me back and told me that she was all for it.

Two weeks later, I arrived at Tara Strong's front door. I ran my fingers thr... Continue»
Posted by IFuckedYourGF 1 year ago  |  Categories: Celebrities, Hardcore, Shemales  |  Views: 1080  |  
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SUBMISSIVE PANTYHOSE FEMME...LTRS2DAD

AD I AM WRITING YOU ABOUT...

Sucking my straight friends dick

It was a typical Friday evening; I had just got done hanging out with a group of friends, and one of my friends decided to come over to my house and hangout for a while. My friends name is Dave, I met him in high school when I was on the football team my sophomore year, he was a big time jock and became a co-captain on varsity as a middle linebacker. I quit all sports basically, but we remained to be kind of good friends over the years, and through our main group of friends we developed a nice relationship. Dave is about 6’2 ... Continue»
Posted by blkice2u 6 months ago  |  Categories: First Time, Interracial Sex, Shemales  |  Views: 1080  |  
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Never Wanted To Be Your Girlfriend Ch. 03

Derrick really took advantage of having me captive that first weekend. He spent the entire time making me watch porn videos, and then had me recreate the scenes with him. He said, that he needed his girlfriend to be fully versed in all the ways he liked to be pleased. His appetite for sex was unreal. The only time we ever really took a break was to eat. And I have to admit, he made the most amazing strawberry milkshakes to go with the food. It was almost worth the humiliation of being fucked sideways by my best friend's b*****r just to get those shakes.

By Sunday night we were both exhauste... Continue»
Posted by sparkyking 15 days ago  |  Categories: Shemales, Taboo  |  Views: 1085  |  
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The fuck of his life.

This story was inspired by a message from cigardad4dad. I hope all who read this enjoy. And as always keep the comments and suggestions cumming.

Eddie is a small but well toned man in his mid-thirties. He never had any luck with the ladys however. So one nite he decided to go around town looking for a good time, when he came accross Veronica, a lady of the evening. Her long lushious legs, heart shaped ass, and breast that poured out of her shirt appealed to him.

She leaned over into the car window and in a sultry smooth voice says "So you ready for the fuck of your life?" "Got a place we... Continue»
Posted by sexforall 2 years ago  |  Categories: BDSM, Shemales  |  Views: 1077  |  
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