Shemales Porn Stories
Page 6

Going to the Gym

“I’m headed to the gym, baby,” the six-foot-three-inch two-hundred-sixty-pound Black man said to his wife of seven years.
“Ok,” she replied barely looking up at her beefy, brown-skinned husband. “I’ll be at the hairdresser by the time you get back.”
“Alright. See you later,” Darius Woodham smiled.

The former Division One linebacker started his black metallic 2012 Ford Expedition and backed out of the driveway. At the end of the street, he stopped at the intersection and pulled out his phone. He sent a message to the person he was heading to see.

Three months prior, Darius was watching ... Continue»
Posted by faggyboi 9 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
7461
  |  
100%
  |  3

Shemale Surprise

anal – shemale – transgender – transsexual – oral – pantyhose – first time – stockings – wedding – lesbian

"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 e... Continue»
Posted by naughty_bi_interest 1 month ago  |  Categories: Anal, First Time, Shemales  |  
7464
  |  
97%
  |  17

Caught by the Neighbor Crossdressing While Home Al

Do you know a crossdresser who got caught in the act?

This is a real life story of a crossdresser caught in the act!

This happened around when I was 15 yrs. old.

As my s****rs were off at college and it was just my mom and I at our apt. I was home from school as we didn’t have any school that day. But my mom was still at work. So I got myself all dressed up looking pretty. As I thought I will make it a girl’s day in. I decided to wear a pair of my mom’s dark navy pantyhose with one of my s****r’s jean skirts and a blue and white sweater with some black 3 1/2 heels.

I put my ma... Continue»
Posted by sparkyking 1 year ago  |  Categories: First Time, Shemales, Taboo  |  
7423
  |  
97%
  |  12

Brittany The Cheerleader

It was my second year as an assistant counselor at River High School. I was young, in my mid twenties. Everything was typical in the small town school. I would help students with scheduling issues, direct them towards colleges, and help them with different scholarships and programs that would benefit them. It was entirely unremarkable and nothing out of the ordinary happened until I met Brittany.

One day a woman walked into my office. She was tall for a woman of her age, yet very slender and petite, with an almost non-existent chest, gorgeous round bottom, tanned skin, and long deep brown... Continue»
Posted by wedgietime 10 months ago  |  Categories: Fetish, Hardcore, Shemales  |  
7295
  |  
100%
  |  1

Becoming the neighbourhood slut

The following is a fictional story but mixed up with some real experiences and a few of my actual desires :)



The first real days of spring were finally upon us. This was extra cool since I would be alone for a week or so. I took a few days off of work too, so I can spend the time dressing up at home and possibly try to find some real fun too.

When I got a few free days I always did the needed grocery shopping in the morning so I have the rest of the day completely free to dress up and stay dressed up. I usually went to a shop nearby, grab the needed stuff quickly and go home.

I di... Continue»
Posted by analhottie 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
7250
  |  
94%
  |  20

Bikini Boy

boy in panties – bisexual threesomes - bisexual lust – s****rs' panties – boy on boy sexfest – crossdressing pleasure – luscious girl on girl sex – secret lingerie stash

I was the boy my father had hoped for after 3 daughters before me. Life in our suburban middle class two-story house was as normal as anyone else's. My dad was a loving father bringing me up and doing the things a father likes to do with his son – baseball, fishing, camping, working the garage. Then came the divorce. The fights, the yelling & screaming about the "other woman" resounded through the house & the k**s tr... Continue»
Posted by naughty_bi_interest 1 month ago  |  Categories: Fetish, Gay Male, Shemales  |  
7214
  |  
97%
  |  4

Fun with the Mechanic

Last weekend, I had a date to go out to a bar with some other CDs in another state and a 2 hour drive. I would get dressed when I got to the motel. On the way I had car trouble, but kept driving to the motel. Told the girls who were already dressed that I couldn’t go to the bar or play because I could not relax knowing my car was having problems. I was so horny because we had set this date up a few weeks ago and I had spent the day trying on my new sexy short black dress and getting ready.

I left the girls at the motel and headed home with the car having transmission problems. On the ... Continue»
Posted by hotcdsub 1 year ago  |  Categories: Fetish, Hardcore, Shemales  |  
7216
  |  
100%
  |  4

True story of an old man in the woods

I was just a young lad the first time i did any thing with another guy, i was still living with mom in the house she inherited from her father after he died in a small village that mainly had elderly people living in it.
There certainly wasn't any one my age about so contact with other youth's was limited to school.
Most of my time was spent playing alone or helping mom about the house, then some thing happened that was to change me for ever.
It was a Sunday morning and mom was home doing some house work, i was watching cartoons on the TV when she called to me to help her get the washing in... Continue»
Posted by fun_boy_fan 1 year ago  |  Categories: Gay Male, Mature, Shemales  |  
7189
  |  
98%
  |  10

mommy's new girl

It's true that I had become accustomed to drama in my f****y. My father was loud and mean, especially when he was d***k, which was most evenings and every weekend. He would back my poor mother into a corner of the kitchen and berate her, towering over her in that threatening way that I knew so well, telling her she was fat and ugly and stupid and spending too much money on me. He would get louder and louder until she finally began to tremble and sob – then he would storm out of the house in disgust, as if her crying gave him the right to leave his "silly emotional wife" and visit his drinking ... Continue»
Posted by momandboys 2 years ago  |  Categories: Fetish, Mature, Shemales  |  
7183
  |  
98%
  |  4

Kitty got caught - in college!

I love risky sex. I like to humiliation. I like to be treated as a useless piece of fucktoy for real men’s pleasure! I love the thrill in sex when there are chances of getting caught or something else that pushes me. So how did I figure that out?


Dressed in lingerie and wearing pink lipstick in my college, kneeling on the floor beside the toilet, waiting for the door to open, my mind kept going around in circles to what led me here, wondering if I could have done anything different to prevent it.

I remembered sitting on the toilet earlier today looking at my bright pink nylon and whit... Continue»
Posted by CumLovingKitty 5 months ago  |  Categories: Gay Male, Hardcore, Shemales  |  
7151
  |  
96%
  |  10

Fitting Room Fun

It’s about 8:45 at night and I am at this department store looking for some new clothes for the weekend partying. There weren’t too many people in the store, just an older married couple, a few employees, some teenagers, and a mother with her k**s. As I am headed towards the jeans/bottoms rack I notice a girl in some skinny jeans bending over. She had a cute little ass and a thin, slender body. She was pretty short about 5’4” with hair just down to her neck. I was about to walk up to her when suddenly she starts heading in my direction. That was when I noticed that she wasn’t a girl at all, bu... Continue»
Posted by pleasurenfun 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  
7150
  |  
100%
  |  10

Aunt Jenny's Perverted Futa-Cock


Sex has always been a taboo topic in my f****y. My Mom, Judy, was strict about enforcing a 'No Pornography' ban in the house, and on the rare (but still far too often) occasions that she caught me masturbating...She never told me not to, but the tone was clear: she disapproved.

My Aunt Jenny, on the other hand, was (and is) the opposite of my Mom. She loved sex and didn't care who knew it. My friends even found a few old pornos that featured her on the internet and made copies for me. (My Mom had inst... Continue»
Posted by Batman_112 20 days ago  |  Categories: Taboo, Shemales  |  
7138
  |  
95%
  |  2

A Nurses Fantasy

This is a fantasy. Very, very Loosely based off of my experience at a hospital over my 18th birthday. Enjoy!




When I was s*******n I found myself in the hospital for a few weeks. It just so happened that I was going to spend my 18th birthday in the hospital and was really bummed out at first, but I soon realized that being in the hospital wasn’t all that bad. Though the doctors set strict rules, I found out that the nurses pretty much ran the show because doctors never stuck around, and were pretty much never even in the hospital after noon. I am a pretty charismatic guy and my person... Continue»
Posted by wedgietime 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
7127
  |  
96%
  |  3

school girl and her daddy

Its Saturday night and I'm getting ready for some fun. I just finished my bath, which included some nice scented oils and a shave making my body totally smooth. Well except a cute little landing strip. I step from the tub and towel off, as I let it drop to the floor I take in the sight from the mirror. There I stand smooth as can be, erect nipples sticking out with the rings running through them. A dangling belly ring hangs below. I am very excited and that is evident in my little girl cock getting hard.

I begin with my hair doing it into two long pigtails, guys love pigtails and I want my ... Continue»
Posted by tanyacd65 18 days ago  |  Categories: Fetish, Gay Male, Shemales  |  
7121
  |  
86%
  |  3

Boy gets Fucked by Shemale

This is the story of my first she male. I had always been curious about dicks. I had always been attracted to women and I loved to watch a woman get pounded by a big cock. But after awhile I realized that when I tried to imagine the porno, I always imagined myself in place of the girl. One day, when I was sixteen, I decided to see what it felt like to be a girl. I had never tried anal before (I could never bring it up to my girlfriend) but I knew I had to try something. So I gathered all the necessary tools and went into my room. I locked my door so my mom wouldn't accidentally walk in on me a... Continue»
Posted by ClassicCockx 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  
7099
  |  
98%
  |  23

Turned into Jasmine by BBC :)

It was just another warm Sunny weekday morning like any other in summer. My wife kissed me goodbye as she left for work, I took my usual pervy glance at her as she wiggled her hot behind out the door, I was setting up in my home office, ready for another day of working from home.

I listened to the car roll out the driveway then the gate closed, I started working through the usual emails and meeting requests.. I got bored of work after a couple of hours I decided to go into our bedroom and rifle through my wife's huge array of skimpy clothes and sexy Lingerie as we had just had a very steam... Continue»
Posted by JasmineSissyCD 1 year ago  |  Categories: Anal, Interracial Sex, Shemales  |  
7086
  |  
95%
  |  9

FUCKED BY MAN'S WORKMATES

I live with a very handsome guy who works the night shift from 10pm to 6am at a local factory, he leaves for work at 9pm so i am on my own from the time he leaves. He left to go to work one night last week as usual so before he left i was dressed in a sexy g string panty lace bra and i was looking real hot so he could think about me all night at work. About ten minutes after he left i heard a knock on the door so i thought he had forgot something so i opened it without thinking that it was his two workmates that wanted a lift to work as there car had broken down. I stood there in my lace bra ... Continue»
Posted by hotbitch5 2 months ago  |  Categories: Shemales  |  
7083
  |  
95%
  |  2

Call me megan.

I was in high school, and i was about to go on the school trip to germany.
I was really excited to go and enjoy my week off, until i found out one previously unmentioned fact in the trip meeting, that we would be sharing rooms with two other boys.
I had recently started masturbating about guys, and was desperate to feel the thrill of giving another guy head, so desperate i had spent the last two weeks in my room every evening, sucking on the rounded back handle of a hairbrush whilst my dick grew harder and harder in my boxers, then sliding it into my tight teen ass and cumming over my toned ... Continue»
Posted by hardcoresissy 11 months ago  |  Categories: First Time, Gay Male, Shemales  |  
7060
  |  
97%
  |  13

black man's sissy boy

I started jerking off to ejaculation when I was around 18. Once I started doing it, it was all I thought about, 27/7 it seemed like. I collected fuck mags and porno tapes wherever I could find them, to use as visual aids. Just looking at those sexy nude women being loved up by their hot men made my dick so fuckin' HARD! Because of that I was able to convince myself that I was normal, of course, in retrospect it is obvious that I was identifying with the women.

One day when my mom was at work, I was laying in her bed, masturbating. I got up and rummaged through her underwear drawer. The draw... Continue»
Posted by nicoleinberlin 3 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
7023
  |  
100%
  |  14

My First Time Pt. 1 - The Boss makes his move

I was stocking boxes in the warehouse at plastics company. This was my after school job, at 18, not bad at $10 and hour.
My boss, Bob walked in behind me. I could hear him fumbling around, moving boxes. He was always in and out, so I didn't really care.
I didn't look back b/c i just wanted to get my work done and go home.
I knocked down a couple boxes which spilled some of the box filler, I was so fucking embarrassed. But hey shit happens even when it's bad timing.
I instantly dropped to my knees trying to scoop them into the boxes before Bob said anything.
I was wearing tight jeans and a... Continue»
Posted by adampanties 1 year ago  |  Categories: Gay Male, Mature, Shemales  |  
7018
  |  
100%
  |  1