Shemales Porn Stories
Page 8

How I got started dressing

I was a sophomore in high school and like any teenage boy I was extremely horny. I masturbated atleast once a day usually 2 or even 3 times because I had so much time on my hands. I started off watching plain straight porn but I watched so much of it daily that I started to get bored of it. I just used sites like google or yahoo to find videos by typing in whatever I was into that day. It started out with just words like "blonde getting fucked" or "girlfriend giving blowjob." Once I started to get bored my words started to get more descriptive "Slut takes huge cock in ass."I was skimming throu... Continue»
Posted by pantyyboy 3 years ago  |  Categories: First Time, Masturbation, Shemales  |  Views: 4275  |  
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Uncles Lessons

I posted this story on another site years ago. I had some nice feedback, but not many views.

In '91' during my senior year of high school my folks split up. The whole thing was a mess, with me being sent off to relatives while my mom took my younger siblings to the gulf coast to stay with her parents. They sold the house and Dad moved to be with his new future 'ex-wife' outside of Dallas.

Since I am older by about 7 years, and was in high school I did not want to leave town in my last year. No way did I want to be sent off to someplace I did not know, and be the 'new k**' loser.

Wit... Continue»
Posted by Cuckarama 9 months ago  |  Categories: Gay Male, Shemales, Taboo  |  Views: 4269  |  
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Night With A HOT Sissy!

June 28th, 2009. End of senior year of high school. I, Angus Corleon, actualy graduated. I wasn't a model student. I've been a leather jacket wearing, rebel rousin, beer drinkin, hell raisin son of a bitch since middle school. My parents didnt care about me, after all my b*****r is a cop and my s****r is a lawyer, and im the law breaker. Anyways, enough about who i am. My buddies johnny, brandon, timmy, and danny have a hell of a party planned for tonight. Big bon fire out in the back woods of where we live. Must be 200 people were expecting. We set everything up, fire pit, band equipment, cha... Continue»
Posted by CDboy9097 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 4260  |  
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A Slut is born


There I was, one week before the end of high school. Going to college in the fall. Nice car, good f****y, friends.
I had it all. So, what was I doing on my hands and knees in a video booth on the wrong side of town,
dressed as a cheerleader with a cock in each hand, one in my ass and one buried in my throat?
It had all started a few months ago. I was locked out of my house in the pouring rain,
and I went over to our neighbor’s to see if I could hang out with him until my parents got home.
He was a cool guy... Continue»
Posted by vosmou_vrot 6 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 4241  |  
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Sissy Emma is turned

I had been a crossdresser all my life but completely in the closet and hidden from all my friends and f****y. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.
I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean I talked of having implants, of being tattooed, hair permanently removed etc but did I really want that? I also talked ... Continue»
Posted by emmahighheels 1 year ago  |  Categories: Shemales  |  Views: 4238  |  
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Black Mamba -

Most of the following is true. I'll leave it to the reader to judge what is
fact and what is fantasy. Until six months ago I was known as John Evers.
Blonde, five foot seven, slightly built and heterosexual, I had just gone
through divorce after a stormy six year marriage. Not into the bar scene and
at loose ends for things to do in my spare time, I decided to redecorate the
house the way I wanted it. The first order of business was to completely
repaint the interior which I proceeded to do. After prepping and painting
every night for two weeks, I was ready for a break from the tedium ... Continue»
Posted by germanboi4bbc 9 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 4236  |  
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Daddys little helper

Maybe if I'd minded my own business and stayed off my dad's computer, my life would have been a whole lot different. As it is I wouldn't change it for the world.

My name is George Mason Jr. I was twenty years old when I moved back in with my father (George Snr, obviously) after my mum left him and took up with some arse-wipe she met at her gym. He had been devastated by the betrayal and I had moved back in to keep him company and make sure he didn't do something stupid. I was quite a good cook and a bit of a neat freak, so it worked out okay for both of us. I got out of my shitty one bedroo... Continue»
Posted by sparkyking 23 days ago  |  Categories: Shemales, Taboo  |  Views: 4227  |  
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Am I A Bad Aunt - Part 4

Am I a Bad Aunt - Part Four

By billy69boy

(Part Three ended with Aunt Eve and her niece Ariel getting ready to pleasure each other with Ariel's favorite black strap-on.)


Ariel pleaded with me to fuck her first, such was her heightened state of arousal, as she regaled me with the details of her first sexual episode with Malcolm. After she helped me adjust the straps, she handed me the baby oil, and bent over the end of her bed, reaching back to spread her ass as best as she could with one hand. She was silent as I first lubed the thick black dildo, and then I dripped some down her... Continue»
Posted by billy69boy 5 months ago  |  Categories: Lesbian Sex, Shemales  |  Views: 4211  |  
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Finding a Great Roomate

I had just moved to the Great NorthWest and was lucky enough to land a job as a convenience store clerk working a shift from 8pm to 4am. Money was tight so I went to the classified to look for an apartment to share. I found one that was fairly cheap and close to my job. It was a two bedroom apt. and I would share the kitchen and common area with my roommate. I gave the guy a call and set up an appointment to see the apartment and be interviewed by him. I went to the address and rang the bell. The door was opened and there stood huge guy, well over 6' tall and I would say around 260lbs. H... Continue»
Posted by rikki50 1 year ago  |  Categories: Gay Male, Shemales  |  Views: 4144  |  
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My First Cock

I always knew I really was meant to be a girl. For a while I thought I was simply gay, but I loved wearing thongs and bras. I loved masturbating while pretending my asshole was a vagina. I never made it a secret. I'm very flamboyant and girly. I still managed to have lots of friends in high school. Several of them knew I wished I was a girl.

One night I was very upset about God knows what. I was crying with a good friend of mine at his house. He was straight and had a girlfriend (another good friend of mine). I began venting to him about wanting to dress like a girl and be treate... Continue»
Posted by hotchickinchitown 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 4137  |  
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Fist visit to my sexy new female doctor

Yesterday I went to the doctor because i felt like i was peeing too much, i'm sitting in the waiting room and the doctor calls me, and she is the hottest woman i have ever seen. Late 20s/early 30s, gorgeous middle-eastern face, nice curvy lips, big dark eyes. She's very friendly with a thick Persian accent which i find very sexy. i explained to her my situation, and then she asked if i was sexually active, and i said no a bit too quickly, and she looked surprised for a second. She got me to pee in a jar, dipped the testing strip, and came over to show me the results. She got me to hold one end... Continue»
Posted by wet20 5 months ago  |  Categories: Sex Humor, Shemales  |  Views: 4137  |  
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2nd Shemale experience

All my stories are based on my own experiences

After my first experience with a shemale (also pasted on here, She was a He) I wanted to have a second, but this time for me to knowingly know what I was about to do.

I trolled chat rooms and dating sites for a few months, getting to know a few girls and then approached the subject. I soon was going to go on my first date with a shemale.

We meet at a local station and she was as stunning as her pictures and so convincing, she was even turning heads as we walked down the road. The evening was lovely and the food was great. We connected an... Continue»
Posted by dirtydisco99 1 month ago  |  Categories: Gay Male, Shemales  |  Views: 4131  |  
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Getting caught on purpose ( true )

I had gotting tired of my mother showing up at my house everyday with out notice.She always came in and whated to move stuff around and say something about a dish in sink or what I had cooked for dinner last nite.I love her but since her boyfriend past away she was driven me crazy.
So I woke this morning early and asked her if she wanted to go shopping with me.She said yes I bought some heels bras painties and we went got our nails done.She asked do you own any male clothes I told here no.Well I dropped her off at her house and left and 20 minutes later she showed up I tried to tell her cal... Continue»
Posted by cdpaula 2 years ago  |  Categories: Anal, Shemales, Taboo  |  Views: 4126  |  
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The Surprise Vacation



The Surprise Vacation


by an unknown author and Tristmegistus

1. Chapter - Innocent Beginnings

"Did you take your vitamin, dear?" Ellen called from the bathroom.

I rubbed sl**p from my eyes and picked up the pill bottle, rolling a big
tablet into my palm. "My horse pill? I'm doing it now."

"Have you noticed any difference yet?"

"Nah. Vitamins are pretty much all alike." She'd gone on a minor health
kick a month before, insisting that I needed to lose a little weight and
take better care of myself. I hadn't actually made it to the gym to wor... Continue»
Posted by klammer 6 months ago  |  Categories: Anal, BDSM, Shemales  |  Views: 4122  |  
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MY GIRLFRIEND HAS A PENIS???

I met Gina at a club she was by herself at the bar and when I looked at her I was smitten I knows that sounds cliche but it was like that for me! I sat down a few seats down and ordered a drink a whiskey sour I believe it was took a few pulls to get up my courage then I offered to buy her a drink and she looked over at me with these incredible sea green eyes and actually smiled at me "Ok " she said and ordered white wine which she sipped so sexily I asked her if I could sit beside her and she patted the seat next to her I couldn't believe my good luck to find such a babe here and she likes ... Continue»
Posted by laceysgirl 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 4102  |  
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The Tgirl Hooker

All my stories are based on real life experiences.

I spent a few weeks looking at e****t sites, reading reviews, services, likes & dislikes, pictures... until Emma caught my eye.

Emma was Eastern European, had a tight slim body, blond hair, very fem and a nice cock. I wasted no time and contacted her to set up a visit and within a few hours she replied and we discussed what I wanted.

The day soon arrived and I was quite nervous through excitement. I had visited e****ts before but never a Tgirl. I pulled up to this house in a normal road and knocked on the door, and there stood Emma i... Continue»
Posted by dirtydisco99 1 month ago  |  Categories: Anal, BDSM, Shemales  |  Views: 4069  |  
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My first time with another crossdresser.

In this story, I'll go in depth on how I became the "girl" that i am today. It all started when i was about 5 years old. I obviously wasnt sexualy active way back then, but thats the age i remember i fell in love with pantyhose. One night after my parents came back from a wedding, i was home with my b*****r and s****r. They came home, changed and what not and went to bed. well my mother who changed in the bathroom left everything that she wore in there. i happened to pick up her pair of sheer to waist with reinf***ed toe suntan wolford pantyhose. They were incredibly silky and soft. i rubbed t... Continue»
Posted by sissypantyhoseboy90 3 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 4064  |  
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Frank's Friend

Frank is a buddy of mine. We grew up and went to college together. While we were in college Frank and I went on a road trip from Lubbock to Dallas. We got to Dallas went to a few strip clubs and then finally found ourselves on Harry Hines Blvd. It was about 1 in the morning we were both horny and a little d***k. Frank pulls up to this leggy blonde in a short skirt and fishnet hose and asks how much. She told us she would do us for free for a ride home. We said fuck yes. Frank had me drive to her house while he had her in his lap, kissing and groping her. We got to her house and went i... Continue»
Posted by biguy52x 1 year ago  |  Categories: Gay Male, Group Sex, Shemales  |  Views: 4019  |  
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Sex with teacher(sissy)

I was the 2 year of high school back then. My grades werent going realy well moastly becuse i spent most of my freetime blowing guys,and sticking thing in my ass,then studying.My parents one day decided that i need some extra classes,so they hired a tutor. I wasn't realy up for that idea,but they somehow talked me into it. After a while it was the time for me to have my first class. My parents left for work,and i was home alone waiting my teacher.Then the dorbell rang , i felt so nervous as i opened the door. In walked a handsome 25-6 year old man,fresh out from college,in a very nice suit. We... Continue»
Posted by sissygirl1988 10 months ago  |  Categories: Anal, Shemales  |  Views: 4016  |  
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she trained me

I was sent to Aunt Fergie when my parents were killed. She is about 5'7"
and 200 lbs she was your stereotypical aunt with some fat and wide hips and
big breast. She picked me up at the bus station in her car.

She said," My household is different and special I have girls who you
will find are very unique. I too am unique and I will show you what I mean
when we go home."

We rode for a half-hour and we arrived to her big old which I would find
was an old Victorian with a widow's roost on top of the roof.

She e****ted me to the bedroom that would be mine and told me," Put your
... Continue»
Posted by pcarter 2 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 4009  |  
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