Shemales Porn Stories
Page 71

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 2 years 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: 1100  |  
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The unusual girl...and boy: Part 6

Part 6: "A new beginning."

Sam was now 8 months pregnant and she had just turned 16 in july. The last time we went to her doctor for her sonogram was two month's ago and the doctor said it was gonna be a boy. Sam had to go get another one but this time the doctor also gave her some bad news, saying that since she was going to be having a baby, she would have to consider losing her under developed testicles. Without thinking it over twice Sam said, "Thank you for letting us know doctor... But I'm more than willing to cut my balls off myself for this baby, so that won't be an issue for me." I... Continue»
Posted by adblman 2 months ago  |  Categories: Anal, Masturbation, Shemales  |  Views: 1100  |  
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Teen pussy rendevous!

Yes, she said she would meet me at the same bathroom stall and would not you know it, she did exactly that! I was already in the ladies room, wahing my hands, and in she walks, absolutely stunning, heels on , short summer dress, beautiful face and hair and what a body, my cock got so hard right then! She went into the furthest stall, good choice baby, and i followed her in immediately. We embraced and kissed and just carressssed out bodies, clothes still on ,yet thet quickly came off and her tits were big and lovely, with large brown nipples, and her pink pussy had but a little pussy hair, i c... Continue»
Posted by cumsquirter 3 years ago  |  Categories: Shemales  |  Views: 1101  |  
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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 2 months ago  |  Categories: Anal, Fetish, Shemales  |  Views: 1100  |  
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Halloween Pt1

Another damn Halloween story. Pure fiction.

We were probably stoned when we came up with the idea. Todd and I had been roommates for our first two years on college, and got on well enough that we moved off campus for our junior year.

Anyway, in late September we were talking about Halloween, and trying to come up with ideas. One of us, I forget whom, suggested we go on the usual pub crawl in drag. We laughed and laughed and laughed, before laughing about some doofus who fell into a swimming pool on some blooper show on TV. And then we laughed some more.

A couple of days la... Continue»
Posted by TransContinental 2 months ago  |  Categories: 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 3 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 3 years ago  |  Categories: First Time, Shemales  |  Views: 1093  |  
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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: 1093  |  
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THE RECREATION OF BILLY ZERO

Life was okay before I lost my Mom I was a teenager and in my final year of high school I liked to play soccer and was on the team and it was when Mom was coming to pick me up from practice that it happened a d***k driver ran a stop sign and smashed into the drivers side of her car she was killed instantly I found out all this later when after a long time Jerry who was Mom's second husband showed up he looked bad and had been crying I could tell he said something bad happened to your Mom she was killed on her way to pick you up a d***k driver ran a stop sign and now shes gone! I was in shoc... Continue»
Posted by laceysgirl 26 days ago  |  Categories: Anal, First Time, Shemales  |  Views: 1098  |  
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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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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 11 months ago  |  Categories: Anal, Shemales  |  Views: 1086  |  
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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: 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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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 10 months ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1083  |  
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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: 1082  |  
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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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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 9 months ago  |  Categories: First Time, Interracial Sex, Shemales  |  Views: 1080  |  
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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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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 2 years ago  |  Categories: Celebrities, Hardcore, Shemales  |  Views: 1077  |  
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