Shemales Porn Stories
Page 65

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

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  |  
1990
  |  
99%
  |  36

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  |  
1986
  |  
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

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

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  |  
1985
  |  
100%
  |  2

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  |  
1981
  |  
100%

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  |  
1978
  |  
100%
  |  1

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 5 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  |  
1971
  |  
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 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  
1968
  |  
44%
  |  2

A New Dawn Arises






A New Dawn Arises


-


Chapter 1

The Arising

To celebrate my transformation and to increase the effect of my
feminization, Mistress Lynn decided a name change was in order.

"What's a good name for a useless, slut French Maid," she asked herself
aloud. "I shall call you Dawn. I think it's appropriate because you are
at the dawn of a new way of life."

Another belt was strapped around my waist. It had a number of loops. My
mistress attached my wrist restraints to the strap.

This allowed me lim... Continue»
Posted by klammer 2 years ago  |  Categories: Fetish, Shemales  |  
1972
  |  
83%
  |  1

blew him away

recently i met a frustrated 32 year old married man who was not getting sex from his older wife,he told me he was straight. I met him in holiday inn in town,i arrived in reception and met him.My hair was very long,i had lots of make up on,was wearing 8 inch black heels,black stockings,suspenders,g string,black bra,body jewellry,belly button stud,on top i was wearing a red tight dress,my nails were painted,had thick red lipstick.

He gave me a kiss and said i looked beautiful and i followed him too his room, i look embarassed as everyone looked at me,i felt like a prostitute becasue of the wa... Continue»
Posted by ladyboyslut 4 years ago  |  Categories: Anal, Shemales  |  
1967
  |  
91%
  |  1

My beginning

I have been a closet cross dresser since my early teens seeking my mother's panty hose and underwear I thought I had kept it well hidden when I turned twenty I got a place of my own I found it very hard to get my women's clothing since I didn't have the courage to go out in public which brings me to my story . a friend of moms named Sherri was bag ng problems with her old man and they had spot up she came to me and asked if she could move in and help with the rent I was all for it Sherri wes a tall red head very pretty and we'll built a couple of weeks went by she was gone one evening a pair o... Continue»
Posted by mike63bear 8 months ago  |  Categories: Fetish, First Time, Shemales  |  
1966
  |  
93%
  |  2

Purchasing Panties and Finding Playmates

I've found a very easy (and fun) way to obtain the used panties of strange women. 

All of the thrift store chains around town carry used women's underwear.

I'll put on some synthetic fabric sweat shorts with no underwear and go shopping. A lil caffeine pill is probably bad for my k**neys and heart, but it sure gets me in the perv mood.

The first thing I do when I enter the store is look to see what cashiers are working, and I begin to scope out the youngest and cutest one they have available. Sometimes I don't manage to get a chick, and it's a dude. Still kinda fun, but I prefer to ha... Continue»
Posted by cumquarts 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  
1963
  |  
80%
  |  2

A Date


Dad sat across from me at the table and shoveled oatmeal into his mouth more out of habit than for nourishment. Dark circles under his blue eyes confessed a lack of sl**p. His constant sad expression made him look older than his forty-seven years. It didn't help that his hair had rescinded back to his ears. Worry had thinned his once bulky frame. He had been in a declining emotional state since my mother had left us last spring.

The day after I graduated high school my mother packed her suitcases and ... Continue»
Posted by Batman_112 2 months ago  |  Categories: Taboo, Shemales  |  
1964
  |  
91%
  |  1

A Warm Cum Bath, on Sara's Hen Night

Part 1. The Meeting with Alise

No one can say that Swedish girls can't attract attention, especially on their last night of freedom, on the eve of their betrothal, some will be found d***k, and some found stripped nude, and even some having a last minute sex with old boyfriends and so on, but one, only one had the experience, most girls cream their knickers thinking about, and this is her and her e****ts account, of her wildest fantasy come alive, the night 200 men ejaculated onto her, boys and men alike, all strangers, doing what men like to do to a beautiful blond 18 year o... Continue»
Posted by MarieL 2 years ago  |  Categories: Fetish, First Time, Shemales  |  
1960
  |  
100%
  |  4