Shemales Porn Stories
Page 64

My first sex

I left home when I started college and had to take a part-time job delivering advertising leaflets in order to pay my way.

I had been doing the job for a couple of weeks when one houseowner, mowing his front lawn, asked me if I would like to do some Saturday gardening. He named the wage and I readily agreed.

I started that Saturday and after a couple of hours Tom called me into the house where cakes and soft drinks were waiting. He said he had an appointment and he left his wife Terri to keep me company.
Terri was a tall, graceful brunette with 48-inch doubleD breats that looked as if... Continue»
Posted by Dav10 4 years ago  |  Categories: First Time, Group Sex, Shemales  |  
1998
  |  
92%
  |  3

PF's Black Romp and JoyceLynn's Awakenin

PF's Black Romp and JoyceLynn's Awakening

To start with you can see my profile at http://profiles.yahoo.com/joycelynntv1 which also has some phoito albums and my primary email address. I have a 360 page at http://360.yahoo.com.JoyceLynnTV1.

When my wife and I first met, our sex life was fantastic! She was a very sexual lady and always made herself available. She usually wore stockings and garter belt or thigh highs, high heel sandals, and something that was sexy and suggestive. We made love and had sex in every room of the house, including the kitchen while she was making dinner. Once I ... Continue»
Posted by JoyceLynnTV 4 years ago  |  Categories: Interracial Sex, Mature, Shemales  |  
1995
  |  
95%
  |  26

Party Favor(s)

My getting into Blue Mountain State U., in the early 1970's was a blessing in so many ways. For one thing it got me out of a bad living environment in my little "Hick Town". I got accepted on a Music scholarship, not Football or Basketball, like most Black students there at the time, so I had to make the most of it. Back then no one asked bout sexual orientation, but since I managed to become the Drum Major for our high school band it was assumed, that I was "lite in the loafers", for some reason. It just happened to be true, but like so many back then I buried it deep and tried to no... Continue»
Posted by Keith_Walters 2 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
1995
  |  
100%
  |  5

My first time with a TS woman, the next morning

After sucking my new ts girlfriend and holding her close on the couch, we spent the night sl**ping together.

I woke with her in my arms. We were sl**ping on our sides and face to face. Her body felt so nice and warm against mine. Then I noticed that she was hard. Her cock was hard and hot and pressed against my cock.

I reached down between our legs and started to stroke her hard cock. Soon she woke in my arms and kissed me while I stroked her. She enjoyed my attention for a while then suddenly she jumped out of the bed and grabbed my hand. She pulled me to the bathroom and into the showe... Continue»
Posted by tsLove888 3 years ago  |  Categories: Anal, First Time, Shemales  |  
1992
  |  
21%
  |  8

Tranny Gas Station Attendant

This happened about ten years ago and I thought I'd share it with you all for your enjoyment and mine! Like I've said before, although I'm bi-sexual, I don't walk around checking out other guys, nor do I like to be intimate with one. Sure, some might consider taking a cock in the mouth or ass intimate, but I consider it just sex. When I say I'm not intimate with other guys, I mean I don't kiss or cuddle or anything like that. It's always just sex, with no strings attached.......usually! There are exceptions to any rule, and this experience is one of them!

... Continue»
Posted by panteeluvr 6 years ago  |  Categories: Shemales  |  
1991
  |  
97%
  |  16

Confessions of a first time dogger

I’d been dressing for some years at home before one day, I dared step outside climb into my car and go for a drive. I was dressed in my school girl outfit which was quite daring considering this was my first public appearance. I headed straight for a local dogging spot I knew. An old stretch of road that is now only used as a cut through for the odd bit of thru traffic. I drove slowly up and down passing a few parked cars and vans whilst cautiously looking at the drivers to see if they were looking. After a short while a guy who was parked up smiled at me. I drove back passed him once again to... Continue»
Posted by mirandacarlton 2 years ago  |  Categories: Anal, First Time, Shemales  |  
1990
  |  
100%
  |  6

Old Black Carl (part 1)

Old Black Carl (part 1)

This is a true story that took place just as I graduated from High School.
I grew up in a small town, and there wasn't a lot of diversity. I had a very thin, smooth body, and long flowing hair that went halfway to my ass. In those days, I thought I looked like a rock star, and so did the girls. I did pretty well. I met a lot of girls from a town about 20 miles away, and I didn't have a car. But back then you could count on getting a ride if you hitchhiked, and I did so to hang out with the girls, often. And that’s how it all started.
I was dressed in a pair of jea... Continue»
Posted by cocksucker4bbc 2 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
1988
  |  
100%
  |  8

I Could Really Use Some Extra Money (Part 1)

Boy, I could really use some extra money, I was thinking as I walked over to George’s for a Saturday visit. Maybe George would have some ideas.

I arrived at George’s house. He greeted me once I was in the house with a kiss while he squeezed my ass cheeks. I loved the way he touched me.

I’d known George for two years, since I’d started mowing his lawn.

I lived with my Mom. She was a d***k and paid me no mind; I might as well have been living alone.

But George had taken a keen interest in me from the beginning.

We got some coffee and sat down to chat. After awhile, I brought up ... Continue»
Posted by ssup28 1 year ago  |  Categories: Shemales  |  
1988
  |  
100%
  |  6

sold into sissyhood

They were standing in a small group, drinking beer, smoking, and laughing. I could hear the rap music thumping aggressively from their boom-box. I could see them watching our car.

It was late, well after midnight, and this particular park was no place for a white sissy to be at this hour. I've never been a physically or mentally strong person. Im very easily intimidated. And there I was in a tiny plaid mini and white pump sandals about to mince my way passed a group of young black street-toughs. Even in broad daylight, even in guy-clothes, I'd have been terrified…

Lise sat behind the whe... Continue»
Posted by momandboys 3 years ago  |  Categories: Fetish, Interracial Sex, Shemales  |  
1984
  |  
100%
  |  5

Finally




Finally



I had decided it was time, finally, to try the experiences I had dreamed
of my whole life. I had been a secret crossdresser since I was a c***d,
and had hidden this side of me from my wife and c***dren. The last few
years of my marriage had been empty, staying together mainly for the
k**s and a kind of inertia. But now, they had grown up, married and
left the area. I knew I would only see them infrequently. With their
departure, my wife and I quickly came to the realization that we were
better suited to live apart, and the divorce had been quick and
am... Continue»
Posted by klammer 11 months ago  |  Categories: BDSM, Fetish, Shemales  |  
1984
  |  
100%
  |  1

How I developed a crush for transvestites

How I developed a crush for transvestites


I am a 33 years old woman who loves sex very much. My name is Desirè. With my boyfriend Errol we have a very happy and open relationship. Since I am also a bisexual from time to time we make love with another woman. We also had group sex a few times.

Last week I left home to go to my girl friend Natalie's summer place to have a threesome with her husband. Just when I was approaching the suburbs I noticed that I forgot my cellular phone. Since it was early enough I returned home.Errol had told me that he would go fishing. When I ent... Continue»
Posted by CDDilekGul 6 years ago  |  Categories: Shemales  |  
1983
  |  
17%
  |  8

Presurgery fun

So. I had back surgery the 2nd of May, was supposed to be there that day but my dr called me and had me come in the night before.

I forgot i was wearing my black baby doll under my clothes, what follows is my last sexual encounter in over a month now.

i got to the hospital and they took me into the surgery prep area to start with, and it was then and there i remembered i had my black baby doll on, and nowhere to hide it so i just went with it. and by that i mean i stripped down to it right in front of the sexy little nurse who looked at me kinda funny then said that's cute. She said here... Continue»
Posted by Caryli 1 year ago  |  Categories: Anal, Shemales  |  
1982
  |  
100%

A TV in the Shoe Store



I work at a ladies shoe store at a large metropolitan mall.
My name is Jillian, though my friends all call me Jilly.
Those same friends also say that I am blessed with a
beautiful face, and an athletic body! Pretty heady for a 30
year old woman whose ideas of athletics never got beyond
sports illustrated and Cosmo! But friends tend to flatter,
that is why we are still friends! I tend to dress with a
flare towards teasing. You see I always wear my skirts and
dresses a bit shorter than fashion demands, and I always
wear sheer reinf***ed heel and toe stockings. A habit
started by a ... Continue»
Posted by jillynylons 5 years ago  |  Categories: First Time, Shemales  |  
1981
  |  
99%
  |  36

Submissive desires



Submissive desires


Sometimes fantasy becomes reality. That can be something very satisfying,
or even terrifying.

I love erotic stories and am a voracious reader of stories on the
internet. My favorites are ones about trannies or cross dressers being
dominated and used to please men. That's what I love, both in my fiction
and in my own sex life, to tell the truth. I've been cross dressing for
years, having finally given in to my urges to dress up and be the best
sissy slut I can be, and let me tell you honey, I am good! Somehow I
became fascinated with b**st stories,... Continue»
Posted by klammer 2 years ago  |  Categories: Anal, BDSM, Shemales  |  
1979
  |  
100%
  |  2

Hotel Surprise

Working in the big city has it's perks and drawbacks. The other night some of my coworkers and I went out for a small celebration at a local restaurant. Everyone ordered drinks and we enjoyed our latest professional success. Finally the crowd thinned out and I was leaving with some others. One of the guys suggested a place near the art center for the city to listen to some soft jazz and blues. A few of us met there and were nursing drinks not really wanting to get d***k just feel good. I noticed an attractive woman sitting by herself at a small table. Our eyes met several times and fina... Continue»
Posted by biguy52x 4 years ago  |  Categories: First Time, Mature, Shemales  |  
1974
  |  
94%
  |  3

an akward encounter

once I made a guy cum like 8 times in one evening/night. he was the dad of my best friend. he was married with 2 k**s, both were in my school it was middle and highschool they were 14 and 18 at the time i was 18 too. i didnt know it was him untill the most akward time possible. he opened the door to the room I was in, there was music going I was about 8 feet from the door, face down with makeup and whiskers and cat nose painted on, furry paws(gloves boots), ass up in the air oiled up, hands spreading it, lights pointed at it, banana barely sticking out all while wearing my skirt and stockings ... Continue»
Posted by carefreeguy 4 months ago  |  Categories: Gay Male, Hardcore, Shemales  |  
1974
  |  
93%
  |  3

My Semale Girlfriend part 2

Andrea finished her smoke and too me by the hand and led me downsatirs to her "Fuck room" mirrors everywhere, big T.V. couch, chair, bed and a closet full of toys, everything a sexy shemale or bisexual guy could ever want. We stood in the middle of the room kissing and exploring each others bodies "sit on the couch, put your legs up....." She told me in a very commanding voice. I layed back sprad and lifted my legs, Andrea knelt down and stroked my cock licked sucked my balls. her tounge run up the lenght of my cock to the tip then bac down....I moaned and reached for her head, but she backe... Continue»
Posted by rockerroller 3 years ago  |  Categories: Fetish, Hardcore, Shemales  |  
1973
  |  
90%

My first stranger.

I practiced dressing hundreds of times before I went out in public. I went out in public dozens of times before I tried to pick up someone. I wasn't attracted to gay men - I liked men who appreciated me for my feminine side, so because of that I only wanted to be with a straight guy. Obviously this proves difficult, since straight guys don't want their girl to have a cock. I have found that usually they are so turned on by the time they find you have a cock that they don't care.

This is the first time that happened to me.

I finally decided I was ready to try to pick up on a guy.
... Continue»
Posted by hotchickinchitown 4 years ago  |  Categories: First Time, Gay Male, Shemales  |  
1971
  |  
94%
  |  6

My beautiful tranny !

This guy picks up a girl and takes her to his place. Can you imagine his surprise when he finds out that this girl has a dong?

Hi! My name is Andrew! I’m a 5.4 feet tall, with some cute beer belly, crew cut light brown haired guy, blue eyes. My friends say I have a big noseJ but it’s not that I should worry about! Men of my f****y have always been stocky, and thickset. So a big nose and stocky figure are not a trouble! I’m working in a Western City College as a tutor of English Literature. I teach student best masterpieces of Shakespeare and Charles Dickens, and so I am in my whole b... Continue»
Posted by cute_girls_with_dick 3 years ago  |  Categories: Anal, First Time, Shemales  |  
1972
  |  
75%
  |  2

my transformation... 101

I was at a very tender age of 10 years when my story begins. I was born male. With all physical parts in tact. But there was something deeper which was unfathomable. I was a very lovable sweet k** just entering fourth grade. I studied in an all boys school. On the out set I knew I was a bit different from the others. I had to much love and care than what a similar aged young boy would do. People thought I was to mature for my s****r age. Least did they know how I felt within. Let alone others I too didn't know how I felt until I grew up.

An incident changed my life at this tender age. I sh... Continue»
Posted by tran4mate 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
1968
  |  
44%
  |  2