Shemales Porn Stories
Page 6

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  |  
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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  |  
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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  |  
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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 4 months ago  |  Categories: Gay Male, Hardcore, Shemales  |  
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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  |  
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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  |  
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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  |  
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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 1 month ago  |  Categories: Shemales  |  
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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  |  
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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  |  
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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  |  
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Loved it in my ass

Hi all
It all started very innocently but turned into an obsession.
Me and my girlfriend (Karen) at the time had a perfectly normal if slightly boring sex life, wow was that about to change. One night we were at it and in the heat of passion she wanted me to fuck her arse which is something i had never done previously, at the time it would not have mattered what she asked i said of course and dutifully filled her lovely arse with my hard cock, it felt so tight and good that within minutes i was spraying her arse with my hot cum. She smiled a looked at me and commented on how good that was an... Continue»
Posted by blueone71 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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MY GAY PRISON SISSY ****


I'm sure many of you have seen a number of movies or television programs based on prison life behind bars. Having recently spent some 29 months in an undisclosed New England State Pen, I'll now share with you first hand, some of the wildest and most unbelievable sexual experiences one could ever imagine.

While still on parole now, I will change my name here and not mention the state facility involved. Other than to substitute a few names for some of the real ones involved, all of what I'm disclosing here actually happened between late July of 2007 and Dec. of 2009. My work... Continue»
Posted by cddixie 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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Cum hungry paper boy sissy

Cum hungry paper boy sissy



When I was thirteen our next door neighbor Pat offered me a summer job
helping him deliver papers and magazines. I quickly said yes and my
foster parents agreed. I liked Pat a lot as he always patted my ass when
Vance and Liz were doing something when he came over for dinner as he
smiled and winked. I loved the way it felt and smiled back as my cock got
hard.

I was light build and kept my long blonde hair in a pony tail and always
wore cut off jean shorts. I had also been jerking off and eating my
creamy delicious cum loads for over a year as I loved... Continue»
Posted by jayymie 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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Morning with the Sissy

Dwight dropped his twins off at their elementary school. He drove the royal blue 2011 Chevy Avalanche as he made a quick call to his wife. He got her voicemail as he figured since she was at work. He was tired after pulling an all-nighter at the plant. But he had one more stop to make. He turned into the neighborhood and pulled to a halt in front of the white ranch-style house where his wife’s mother and stepfather lived.

He knocked on the door was greeted by stepb*****r-in-law. Dwight studied the five-foot-five-inch, one-hundred-twenty-pound, nineteen year-old that was wearing a purple ca... Continue»
Posted by faggyboi 5 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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my wife make me her sissy slut

I married Jen when I was a successful high earning bachelor at the age of 30. She
was 25 at that time. 5'4" same height as me, 120lbs, petite blonde with
blue eyes, a set of DD tits and an ass to die for. I was short, skinny yet she was
attracted to me when we first met in a bar down town. Later on I found out that it
was Laura her friend who had told her that the porsche parked outside was mine.
Now, after 5 years of marriage, things were quite different. Things had actually
started going down hill after the first few months when subsequently Jen had clearly
stated that my 3 inches coc... Continue»
Posted by nicoleinberlin 3 years ago  |  Categories: Gay Male, Shemales  |  
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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 10 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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My Transformed Wife

"Sometimes I wish I just had a dick," my wife said, wincing and squeezing her heating pad into her abdomen. She said this at least once a month, when her period would bring on two or three days worth of cramps and bloating.

I grinned and rubbed her stomach, "If you had one, you would just spend all your time playing with it and peeing standing up."

She giggled and squeezed my cock through my pants, "That doesn't sound so bad."

We never said anything beyond this, but from the first time she had mentioned it, it sparked a desire within me that I had never known I wanted. I had always ... Continue»
Posted by drew1207 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
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Cum Eating made easy (CEI guide with no acrobatics

This post is dedicated to all of those, like me, that have fantasized about eating their own cum. This kind of fetish is something really, really hot and kinky, and I know that most of you are already excited and in... mmmh tension, I guess. And I also know that most men who indulge in such a fantasy have often chickened out as soon as they experienced their orgasm. All lust gone, all desire of a thick load in their mouth gone. Of course there are already an awful lot of CEI videos out there that have methods to ease the balance between desire and the act itself.

[image]http://ep0.xhcdn.com... Continue»
Posted by sissyAlyna 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  
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Trapped and Trained Sissy Ch. 01

Trapped and Trained Ch. 01
I responded to an ad on Craigslist from some guy asking for help to move some furniture. He was paying pretty well and, after I practically laughed at him for asking if I could lift the furniture, he agreed to have me over to get it done. We moved everything around for what felt like hours, often moving the same piece of furniture to what seemed like the same place it was originally. Finally he decided he liked the new arrangement, which wasn't that drastically different than how it looked when we started. Obviously exhausted, I sat down on the couch. He asked me if... Continue»
Posted by hpm12 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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