Shemales Porn Stories
Page 2

My Transgender BFF

One of my best friends Sarah is a transgender. When we first met I had no idea, no one did. She has always looked very feminine, I sometimes think that she looks better than me. She had some classes with me so we started to talk and we became friends quickly and started hanging almost every afternoon. Eventually she stayed the night at my place.
Things were normal until it got late and we were both in my room laying down. She was going to sl**p on the ground but instead she was laying in bed with me because we were chatting. We were both facing each other and my bed was small so we were v... Continue»
Posted by sweetiepi99 4 months ago  |  Categories: First Time, Shemales, Taboo  |  
13942
  |  
98%
  |  27

The pretty girl with her thumb out

It had been a couple of years since my wife left and I was finally starting to enjoy trips by myself. So that fall I through some stuff in the car and headed out to see things and clear out my mind some.

As I turned at the freeway ramp there was a young woman standing at the side with her thumb out. So I quickly pulled over and, with a smile, she hopped in. As we chatted I learned Chris had recently turned 18 and was using her new status as an adult to head north to see a friend. That worked out great since it was the direction I was already going for my trip.

Chris had long blonde hair ... Continue»
Posted by need2try 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
13639
  |  
98%
  |  20

Gloryholes and hot cum

I was young when I first started to think about what it would feel like to have another mans hot cock in my mouth. I used to fuck around with this guy all the time at his parents house. They would be sl**ping upstairs meanwhile we were 69ing on the queen cot down stairs. I would sl**p on the floor and I laid in wait for a quick tug of my shirt, just to raise up and stuff this thick monster in my throat......soon it turned into me fucking him up his ass. Which felt amazing sinking my hot thick cock deep into his waiting ass was pure bliss for me and even though i never not had luck with th... Continue»
Posted by chuckdawg802 11 months ago  |  Categories: First Time, Gay Male, Shemales  |  
13598
  |  
98%
  |  13

Mom Loves Not Her Daughters

IT SEEMED LIKE the ideal time. Amy was at school and mom had gone to shop
about an hour before. I had waited purposely to make sure she hadn't
forgotten something so she would return right away.
I'd been thinking about it for a long time. I mean, I'd looked at mom
and s*s's stuff before. But that was only in the bathroom where they
sometimes hung things around or in the dirty clothes or even in the washing
machine if I had to load and unload it.
I went to s*s's room first. It was really pretty disappointing. I
mean, she had panties and one spare little training bra but that ... Continue»
Posted by BeeJay69 1 year ago  |  Categories: Shemales, Taboo  |  
13480
  |  
97%
  |  1

Neighbour fucked my s****r - but it was me

When I was 16 I stayed home alone for a week when my parents were on holiday. My s****r Jenny had just left home - she was 18. I'd been crossdressing for several years already, and I loved nothing better than to turn myself into a pretty teen girl in private. Fortunately for me, Jenny had left some of her clothes behind.

One night that week, I decided to play some dress up. I went into Jenny's bedroom and opened her drawers and closet door. I knew her clothes so well. What would I put on?

First I chose one of her bras. It was pink and heavily padded as Jenny had small tits. I put it on m... Continue»
Posted by pollyperverse 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
13441
  |  
100%
  |  11

The Magic of my first Black Cock.


Wow ! This was my first real experience with Black Cock. it was right after my divorce. I was in my late twenties. I ran my ads as a crossdresser on a few dating sites and on Craigslist. I recieved a message on my AFF site from a member whos profile mame was BBCRicky. My interest was immediately peaked. His profile discribed him as a dominant black male 6'4" with a 10 inch thick cock. He was older in his late 40s, Interested in meeting petite submissive white sissys which fit me perfectly. I replied back and almost immediately he responded. He loved my pics and profile and said he had ... Continue»
Posted by tvtrinity 5 months ago  |  Categories: First Time, Interracial Sex, Shemales  |  
13303
  |  
93%
  |  4

The morning I needed a hand job, part one

I had just woken from a deep restful sl**p to the sound of my s****r Lori giggling in the open door way of my room . My eyes slowly opened and focused on her standing there in her pink nightie. She never wore panties or a bra to bed and I could see right though.
As I realized what was happening I felt a soft tug on my hard cock I saw a feminine hand softly stroking my morning hard on. It was
my mom's best friend Sandy. She lived with us and often came up stairs to wake me on school days when I overslept . That's when I realized what happening. The night before I had spent the evening dres... Continue»
Posted by michellesilk 11 months ago  |  Categories: Gay Male, Shemales, Taboo  |  
13239
  |  
87%
  |  10

Shemale Surprise

A married man is seduced and taken by a friend of his wife's.

"You can stay with Robert if you wish," Mary said on the phone.

I looked up from my laptop where I was pretending to be working when, in reality, I was reading, for the hundredth time, the brilliant novella 'Shemale School: a Teacher Seduced'. The story had created a new obsessive fantasy I had never even considered before: to be with a Shemale.

I even contacted the authoress to tell her how much I enjoyed it, and have since became one of her editors. I had just finished editing a gay cocksucking story that, althoug... Continue»
Posted by magas911 9 months ago  |  Categories: First Time, Shemales, Voyeur  |  
13171
  |  
100%
  |  20

Caught cumming

When we moved into our new house I got first pic of bedrooms, instantly I chose the bedroom in the loft with a nice big skylight, I love having the sun in my room and when it's raining I like watching it drop all on the window.

One day I decided to have the blind open while I went to bed, waking up the next morning I had discovered my favorite place ever. I stripped naked and lay on my bed again, my huge tits flat on my chest as I lay there I began to wank. Where we had moved to was across the road from an all girls school, what I noticed was at the right angle I could see up under the bri... Continue»
Posted by shemalecharlotte 2 years ago  |  Categories: Shemales, Taboo, Voyeur  |  
13116
  |  
98%
  |  10

Daddy's Girl





Daddy's Girl

The Hitchhiker

It had been snowing all day. A wet, heavy incessant snow that was covering everything including the highway. Combined with a wind-chill factor in the teens, Christopher was almost frozen stiff. He was elated when the huge semi pulled over to pick him up. He climbed up into the cab and smiled thankfully at the driver.

"Thanks a lot mister. I was just about frozen out there."

"No problem, son." The driver smiled at him. "Name's Zeke," the driver said and extended his hand.

Christopher took the offered hand and shook it. His hand seemed to disapp... Continue»
Posted by klammer 1 year ago  |  Categories: Fetish, Gay Male, Shemales  |  
13095
  |  
94%
  |  10

Crossdressing - Teen fantasy with Panties to Cock

Confessions of a Crossdresser

I am a crossdresser. It is an addiction. I’ve tried, but I really can’t stop myself: fantasies, endless looking at pornography, shopping, dressing, masturbation, and inevitably, seeking men to please. I started out as a young teen as a panty fantasizer and have progressed to where I am today. I think that I am pretty “normal”: dating girls, and now a responsible man, married with a f****y. But, I have evolved to a cock sucking crossdresser. I’m writing to try to understand how I have evolved.

If I was a woman, I would be a cum dumpster: intelligent, attracti... Continue»
Posted by ericalace 1 year ago  |  Categories: Fetish, Masturbation, Shemales  |  
12985
  |  
100%
  |  10

Thailand Part 2

I woke up after the wank session hearing somebody in the apartment making coffee, I got up in my underpants and found my friends wife in her Brazilian type bikini behind the counter making coffee. This bikini did not cover up much and her heavy tits were just covered while her arse and cunt was split by a string. I could see her pussy lips spread by the string and I had the starting of a boner.

After coffee we went down to the pool and managed to get a couple of sun beds by the pool, she asked if I would rub lotion on her back and I worked my way from her shoulders, down her back to her bum... Continue»
Posted by daveaverage 1 year ago  |  Categories: Group Sex, Hardcore, Shemales  |  
12890
  |  
93%
  |  6

Bobbie and Me

First my backstory.
I am Micheal or rather Michelle. Let me explain that , you see this story starts when I was six or seven. In school I learned the name of a classmate was Michelle and that was the feminine version of my own name. After learning this I really wanted to have that name, explaining to my mother that I should really be a girl and I do not feel like a boy at all. My mom already had taken note of my girlish tendencies and agreed. So since then I had been allow to dress and basically be a girl as much as I wanted. Of course I always wanted to be in dresses and act like a little gi... Continue»
Posted by ponyup22 22 days ago  |  Categories: First Time, Shemales, Taboo  |  
12820
  |  
94%
  |  12

Apartment to rent

When my wife suggested that we rent out the guest rooms above the garage to a college student it sounded like a good idea. It was very much like a small apartment, with a bedroom, bathroom, and small living room. No kitchen of course, but we could share ours and it seemed like a good way to make a little extra every month. We'd only recently gotten married and had just bought the house, so we could use the money.

Being my wife's 'project' as it were, I left the details up to her. I was working hard at my new job anyway. We were both just twenty-six then and recently graduated from the unive... Continue»
Posted by Alic91lovesporn 2 years ago  |  Categories: Anal, Hardcore, Shemales  |  
12755
  |  
87%
  |  4

Caught by Neighbor

Caught by Neighbor


- 1 -

It was a beautiful warm day, and I had it to myself. My wife Sam was interstate on business for the week, and not due back for another five days. For me that meant housework to be done, but plenty of time to enjoy my own space, and entertain one particular hobby. I smiled to myself, and not for the first time, I stopped in front of a mirror and pulled my tracksuit pants down, admiring the bright pink, silky panties that I'd been walking around in all day.

I'd been cross-dressing for many years before I met Sam, but it really wasn't her thing. So I tended to ... Continue»
Posted by Femluver 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  
12543
  |  
98%
  |  28

First time getting caught wearing Pantyhose

When I was 16 years old, I babysat for my moms best friend. I had know Joanne (my moms bff) all my life, she was my second mother. and a single mother at that. And Joanne was smokin hot! Had thee biggest crush on her since i can remember. Joanne always wore pantyhose or stockings, and i mean always, one night i slept over at her house, i peeked in her bedroom and she was wearing a teddy and pantyhose, and ofcourse i had to masturbate, because like i said, she's a woman who gives an instant boner at first sight. Anyways, she had asked me to babysit her 2 boys on a friday night. Not a big deal e... Continue»
Posted by sissypantyhoseboy90 5 years ago  |  Categories: Fetish, First Time, Shemales  |  
12081
  |  
90%
  |  28

Mom the shemale bitch

Hi I have always had this fantasy

The fantasy starts out in high school a number of years ago, when I started having dreams of the kinkier kind, but not really understanding why. The dreams were about women that had big breasts and large hips as well as being tall and big boned.

The dreams always started out the usual way with a date, dinner, kissing, and petting, but as soon as I got the breasts out and satisfied that part, the girls were pulling down their pants for me, but not complaining I went straight for my goal.

The problem was that as the pants came down, the package would a... Continue»
Posted by frswriter 3 years ago  |  Categories: Anal, Mature, Shemales  |  
12023
  |  
66%
  |  9

How it all began

My mother had 4 c***dren, 3 girls and a boy. I was the youngest. My s****rs were 5, 4 and 2 years older than me. Being the youngest I had to do as my older s****rs told me, including being dressed up as a dolly to play with when I was 4. When the oldest started wearing make up at 11, I was used for practice by all three of them, so I learned how to apply it myself.

When the oldest graduated from high school and went into the Army I was the same size as my youngest s****r and took to trying on her clothes. The feel of her bra’s & panties was awesome compared to my cotton tee shirts & briefs... Continue»
Posted by Andii18 1 year ago  |  Categories: First Time, Group Sex, Shemales  |  
11735
  |  
96%
  |  22

My sister, my first, the tranny

A little something different to spice up your lives

*******************************************************************************************************************************************************************************************

It was the first week of June and school was out for the summer, I was 18 and had just finished my senior year. One night while we were eating dinner, My Mom and step dad informed me that they were going away for two weeks. When they got married they did not go on a honeymoon, so they wanted to take one now. Jack, my stepdad, told me they were going to... Continue»
Posted by 6270daniel 2 years ago  |  Categories: First Time, Shemales, Taboo  |  
11670
  |  
98%
  |  16

The Making of a Sissy (Part 2: The Metamorphosis)

As the morning rays of sunlight pierced through my bedroom window I was awakened from the most intense dream, reenacting what had happened the night before. My throbbing hard little cock was gently humping against the sheets of my bed while I couldn't stop thinking about the amazing big black cock I had in my mouth just hours ago. I could still taste him on my tongue, and I could smell him on my lips. What had happened to me? Why was I so turned on by all of this? I thought to myself, "Maybe it was just a one time thing, like a one night stand." My mom had been dating a lot lately, so I ... Continue»
Posted by briantid8 6 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
11663
  |  
100%
  |  13