Shemales Porn Stories
Page 10

Mom Transforms Son into a Transsexual.

I'm a very sensitive white teenage boy who's always been close to my Mother,but my Dad looked upon me with disgust calling me fairy,sissy,faggot, and other choice words, Father was a Marine he is six feet seven inches tall, black hair, Blue eyes, and a Alcoholic. My Mommy is six feet three inches tall, 42DD 28 44 inch frame, long red tresses that flowed over her Boobies and she like to show them off. My parents divorced two years ago he drifted off into alcoholism some place, I was watching porn on Moms computer checking out Shemale and Cross dressing web sites when all of a sudden I heard... Continue»
Posted by sissytimmy 1 year ago  |  Categories: Interracial Sex, Shemales, Taboo  |  
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Doing Time

Keno Reese finished his lunch of a chicken patty, one slice of white bread, baked beans, apple sauce, and two-percent milk surrounded by the other three hundred plus inmates at the prison. He walked his tray up to the front and hurried to his cell to sneak a quick call on his contraband cell phone. The former d**g dealer asked his mom to put a few dollars on his books via Green Dot. She agreed to send him fifty right then. He waited on the phone as she completed the purchase online. Then, the five-foot-ten-inch, slim light-skinned biracial brotha walked out of his cell and onto the yard.

Ke... Continue»
Posted by faggyboi 1 month ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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My son got seriously hot

Well, life sucked after divorcing my little sheboy, he was everything to me, but I had to let him go see the world, he went to college, after leaving his job as a freelance babysitter to find himself, he was very good at his job, he worked as a babysitter for a filthy rich f****y, he used to make over £400 in 6 hours spread over a whole week, sometimes he takes overtime, however this overtime was more like parentsitting than else.

He would stay for a further hour to take care of the parents by getting into naughty games together, the couple were rather young, the man was just midway through... Continue»
Posted by starlight8998 1 year ago  |  Categories: Fetish, Masturbation, Shemales  |  
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Chapter 1

Aas is usually the case, three years of marriage our love making had grown
a little stale. I decided that we needed something to spice it up and I
broached the subject of adult videos to my wife to see if she would like to
try something different. She was initially hesitant about anything
"pornographic" but I told her it was just "soft porn" and thought we ought
to try it just once. My wife is very strong minded and was raised very
strict so I knew it would be a big job to sell her on it but I kept after
her. She finally agreed and I stopped ... Continue»
Posted by aimen72 2 years ago  |  Categories: Fetish, Gay Male, Shemales  |  
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My first time with a shemale

Let me tell you a little bit about myself I'm five feet 10 inches tall around
220 pounds, brown hair and eyes very muscular, I'm an ex-professional boxer.
Around 10 years ago I I was working as a bouncer erotic a nightclub in Fort
Lauderdale, when one night I heard a commotion in the parking lot. There were
several men beating up a beautiful woman, when I tried to break it up I ended up
getting very banged up myself.
Her name was misty, she thanked me for helping her and a... Continue»
Posted by palitro1 2 years ago  |  Categories: Anal, BDSM, Shemales  |  
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The Room Mate

The Room Mate
My wife and I have been happily married for about nine years now. We had never slept with anyone else during our relationship. I have greatly enjoyed my time with her. However a few weeks ago a coworker of my wife’s moved in with us. Her name was Denise and she had just lost her job, car, and about everything she owned in about three days. We were glad to help her out in any way we could. We set up a second bedroom in our modest apartment.
At first things were normal, at least for having another person living with us. Then something happened, something I did not expect. I need... Continue»
Posted by raastible 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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Camping and a Spit Roast

I went on a camping holiday with a small group of friends and it was awful, it was raining, muddy, and there was nothing to do but go to a pub that was nearby. So one night everyone's passed out d***k, and I'm wide awake so I go back out to the pub, and I stay there with my thoughts for a little while, everyone's leaving and it's all feeling very glum, then two girls walk into the pub. The one girl is fairly tall with a very curvaceous body and a noticeably large behind, while the other was relatively short with a much skinnier physique.

I don't really pay much attention, but then they stan... Continue»
Posted by wherethewhitewomenat 9 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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How I became gay pt 1

When I was in my teens I was only interested in girls and thought that being involved in a gay experience was completely disgusting. I never would have even thought of it if it wasn't for what happened when I turned 17.

On my birthday me and a few friends got fake I.D.'s and went to a bar in town. We all started drinking and getting as shitfaced as we possibly could. There was 4 of us and my three friends had all spoted the girls they wanted to fuck that night so I was left alone at the bar.

Within a few minutes this girl sits next to me and I immediately started checking her out. Sh... Continue»
Posted by Gayluva67 4 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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Fantasy cums true

I was on a business trip staying in a nice Hotel. After a business meeting in my room I called down for room service. The maid came up a few minutes later and I let her in. She was stunning, 5' tall with black hair and the bluest eyes I have ever seen. Under her uniform you could tell she was very well endowed at least a 34 DD. She came in and took care of the room. Thru small talk I found out her name was Terri, she was 28 and single. I thanked her and gave her a tip when she was done. As she left I had to watch her walk down the hallway, her little heart shaped ass swaying back and forth.

... Continue»
Posted by tittie-baby 2 years ago  |  Categories: Shemales  |  
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Completely Fooled

I could not have expected the encounter I had the other night. Having recently separated from my wife a buddy and I went out to a local pub for a few beers. While we were sitting at the bar deciding what beer to try next a very hot redhead comes over and sits next to me. We exchange hellos introduce ourselves. Soon begin to talk about the different complexities of the beers we are tasting. She is so sexy with small b cups and a perfect mouth. After a few beers my buddy decides to take off leaving Veronica and I to get ourselves. She is just a darling; her smile, her laugh, her sensual demeanor... Continue»
Posted by IndieMe 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  
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my first black cock

One day when my mum was at work, I was laying in her bed, masturbating. I got up and rummaged through her underwear drawer. The drawer smelled like perfume and the odor made my dick stiffen. Some of her panties had stains - I think they were cum stains - on the crotch. Anyway, I don't know why, but something prompted me to try on a pair of her silky nylon hose. The material felt so good on my legs! Next I stepped into a pair of her red french cut panties. Then I caught a glimpse of myself in the full-length mirror - and was electrified.

I was about 5', 2" then, and the only body hair I had ... Continue»
Posted by allisontranny 6 months ago  |  Categories: First Time, Interracial Sex, Shemales  |  
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Spit roasted in an Adult Theater

One day I was feeling particularly horny from not having any satisfactory hookups in quite some time. So I showered and shaved my legs smooth and slipped on a pair of bright pink bikini thong panties. I put on a pair of sweat pants that I could easily slip off and just put on an old sweat shirt as a top. I then headed off to a popular adult theater a few towns north of where I live, about a 45 min. drive away. I paid the $10 admission, got my ticket and walked inside the theater. I immediately headed for the back row and sat down in the last seat next to the wall. Next to me on my left w... Continue»
Posted by rikki50 2 years ago  |  Categories: Gay Male, Shemales  |  
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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 1 year ago  |  Categories: Anal, BDSM, Shemales  |  
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Chloe's Slutty Night at the Truckstop

If you have read any of my previous stories, you know that the freedom of college took my secret life as a slutty cross dresser to a whole new level of naughty. I became a great cocksucker and I started to constantly crave a hard cock in my boypussy. I started dressing more often, going from 1 or 2 times a month to at least once a week. I was building up my collection of clothes and toys and getting more and more daring every time I went to meet a guy. I started to just go to my destination in full slut attire instead of getting dressed when I got there. Anyway, this constant escalation of my ... Continue»
Posted by cumslutchloe 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  
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Me, Mom and the Hair Dresser

Growing up as a only c***d I was smothered by my Mother, I don't know if it was normal ,but at 14 she was still breast feeding me,bathing me, and sharing one bed . I was a very shy boy, we moved every year so I was always getting beat up at the new school. I had no thoughts until my 14th birthday. It's funny how these things change so fast,I had received my first computer, I was looking up and typed in the words "Mother and Son" I was directed to a porn site one of the pictures was of a mature woman pegging a teenage boy wearing lingerie I got my first erection. So when Mom called me for break... Continue»
Posted by sissytimmy 1 year ago  |  Categories: Gay Male, Shemales, Taboo  |  

Happy Birthday to Me

So last month, I was lucky enough to experience one of my favoritest annual events ever: my birthday party!!! Now, for those that don't know, I take my birthday VERY seriously. You see, I was only 12 years old the first time I played with a pecker...and I've been lickin' 'em and suckin' 'em and bouncin' up and down on 'em ever since :-) I suppose my love of being gangbanged and making guys cum on my birthday all began on the eve of my 14th...

It was a hot night in June and I had invited about 20 friends to a backyard birthday party sl**pover. 14 of my best buddies showed up. I had blown... Continue»
Posted by cdsexslut 1 year ago  |  Categories: Group Sex, Shemales, Taboo  |  
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Sucking my straight friends dick

It was a typical Friday evening; I had just got done hanging out with a group of friends, and one of my friends decided to come over to my house and hangout for a while. My friends name is Dave, I met him in highschool when I was on the football team my sophomore year, he was a big time jock and became a co-captain on varsity as a middle linebacker. I quit all sports basically, but we remained to be kind of good friends over the years, and through our main group of friends we developed a nice relationship. Dave is about 6’2 and like 220 pounds, so he’s way bigger than myself, he’s basically yo... Continue»
Posted by pantycum666 2 years ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Fucked by daddy's friend

This story was a fantasy of mine from when I was about 11yrs and still think of it happening now even tho the guy in question, is in his mid 60's

I'd be at home from school alone as my parents were at work. This is when I would go through my mums sexy underwear draw. I picked out a black suspender belt, matching bra and see through panties and some black seamed stockings. Luckily I was young enough to have a hair free body and was the same dress and shoe size as my mum. So I picked out a dress theat finished half way up my thighs but covering my stocking tops and a gorgeous pair of black 4"... Continue»
Posted by danny241976 11 months ago  |  Categories: Anal, Shemales, Taboo  |  
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Mommy and sissy

I really had been expecting to be shopping most of the
morning, but I got to the mall and miracle of miracles,
not only did I find a place to park close in, the mall
wasn't at all as crowded as I had expected. I got in
and picked up the few things I needed, and headed home.
One of the things I had to get was a couple of new
bras. It just seemed that the elastic in the ones I had
were wearing out. I sort of calked it up to their being
more cheaply made, every thing was any more it seemed,
being made in China or wherever.

I pulled into the drive and I didn't open the gara... Continue»
Posted by 6270daniel 4 months ago  |  Categories: First Time, Shemales, Taboo  |  
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My Shemale Stepmother

My parents split up when I was eighteen, I was a little distressed by it but we had never been as close as some. Still, I didn't really see what had driven them apart so quickly and so thoroughly that they never even spoke any more. I guessed maybe one of them must have had an affair and that was really all that I thought about it. I went off to college and life went on. That following summer, when I was nineteen, I moved in to live with my dad for the summer. He had bounced back quickly following the divorce and had already found someone new and I had to say, he had done pretty well for himse... Continue»
Posted by bi_hengst 1 year ago  |  Categories: Shemales  |  
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