Shemales Porn Stories
Page 119

Chrissie's High School Reunion

Chrissie’s High School Reunion

When the announcement arrived in the mail notifying Kelly and I that our High School graduating class was organizing a ten year reunion we spent that entire evening discussing the pros and cons of attending. I was fairly certain that I wasn’t interesting in attending but Kelly insisting on listing all the reasons why she felt we should attend.
She was interested in going because she wanted to make passes at all the “stuck-up bitches” that pissed her off in high school. She said it would be fun to hit on these girls in front of their husbands or boyfriends. S... Continue»
Posted by chrissieCD 3 years ago  |  Categories: Anal, Shemales  |  
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Male to Female Transformation

Male to Female Transformation

Genre : TG SOS or Surgery/Transformation Male to Female
Story : Cristine Carter
CH - 1

The last thing I could remember was walking out of the Bank
and crossing the road to my car. I had just been to see my
bank manager to discuss transferring some money from one of
my accounts into a high interest savings account.

I had won quite a bit of money on the Lottery, enough to
change my life. I was unaware just how much my life was
going to change.

I had just reached my car door when I felt someone bump
into me. Then everything went blank...
... Continue»
Posted by cristinestone7575 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  
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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 20 days ago  |  Categories: Gay Male, Shemales, Taboo  |  
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on my way to work

there I was driving along on my way to work in harlow listning to the stereo and watching for the occasional trafic cop and thier little trafic calming measure that they point at your car. There was a car with a puncture (itwas leaning to one side) at the side of the road just ahead of me, as i stopped to enquire and perhaps offer some assistance the lady stayed in the car with the window up high enough but just down enough to speak out of, she mentioned that she had a puncture and her jack was not where it should be and can only assume that her pertner had taken it from her car and not re... Continue»
Posted by natasha1975 3 years ago  |  Categories: Shemales  |  
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What I Did Last Night!

What I Did Last Night.

I dressed up for hours last night! Black nylons, heels, a red and black baske/corset. Wig (cheap halloween type).

I got my dummy (lover) down from it's hiding spot in my garage rafters. Attached my homemade dildo. Made that a few years ago with a large condom inserted into a 1.5 in plastic pipe, then filled with pure silicone caulk. Took Months to Dry. Dummy body is some stiff foam attached around a wood frame that hold the dildo. Even has foam legs and but covered with black nylons of course.
I lubed my ass and propped the dummy like he was sitting. I got on his... Continue»
Posted by nylonsblack 3 years ago  |  Categories: Gay Male, Shemales  |  
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My life as Daddy's sissy

Hello Daddy,

I would so love this life…

I wake up thinking of you, dreaming of kissing you, of sucking your cock, of feeling it fill my boicunt.

I spend all day preparing for you, so impatient to be with you. You are at work and I’m home, enjoying my role as your slut and maid.

I clean the house wearing pink sissy sweat shorts and a tank top, pink sneakers and pink socks. I want our home to be perfect for you, and I take pride in taking care of the house you work so hard to provide.

I then go to the gym in sexy little workout outfit. No one there cares that I’m a sissy anymore. ... Continue»
Posted by NancyRoseTV 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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House Hunting Chrissie


When I casually mentioned to one of clients during a session that I was toying with the idea of perhaps buying a house
and renting out my condo he needlessly took the time to remind that he owned one of the largest realty offices in
town. It must a salesman thing, not being able to leave business behind for an hour or two. You're no doubt
thinking to yourself "Hold on there Chrissie, don't forget you're a bit of salesperson yourself. After all your selling
your body to your clients every day." Let me clear something up for you. I've never had to sell my body... Continue»
Posted by chrissieCD 3 years ago  |  Categories: Anal, Sex Humor, Shemales  |  
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Rene and Me (a Chrissie Conway story)

Rene and Me

I recently wrote of my introduction and first encounter with Rene. At this time I would like to expand upon my relationship
with Rene and reveal certain details related to how the relationship evolved.
When I first met Rene that night at the museum benefit I must admit I was instantly attracted to him. At the time I was finding it
a little difficult to make enough money to support my somewhat lavish lifestyle which seems to grow more costly every minute.
Up to this point I had yet to amass anything faintly resembling the "client list" that I ... Continue»
Posted by chrissieCD 3 years ago  |  Categories: Anal, BDSM, Shemales  |  
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Devina in trouble

Devina's in trouble.

I woke up with a start and leaped out of bed.

"Oh god I thought, my Wife is due back tomorrow, and I better clear up
this mess before I go to work today."

The mess was actually quite a lot of womens clothes spread across the
bedroom floor. You see I am a cross dresser, in private I loved to dress
in Womens clothes, slutty tarty clothes, I loved to be dressed as a
slutty whore. But my biggest fetish was to wear Macs and raincoats, all
sorts, any kind, but especially PVC Macs.

Before I was married I used to dress and occasionally go out dressed as
Devin... Continue»
Posted by Devinatv 2 years ago  |  Categories: Anal, BDSM, Shemales  |  
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Ladyboy in a Whore House

I was born a “hermaphrodite” and I had B cup
tits when I was very young.
I was skinny so they looked BIG.

This story is from Pms I sent to SuperSatin
I was a prostitute when I was very1 3young for
a rich perverts' club.
So here's a collection of Pms that add up to
a story.

There was a client who liked me to suck him off
again and again.
he could cum 5 or 6 times. sometimes more.
I know he limped the next day!!

He fucked me too, rested then cummed
again and again.
Another client liked to cum on my face.
he'd feel up my naked body then play with himself
i'd kneel o
... Continue»
Posted by Utubeslut 2 years ago  |  Categories: Fetish, Lesbian Sex, Shemales  |  
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car fun!

Some years ago, I had overnight business travel and I cross-dressed in my motel rooms after hours. I had some married men that I met online that would come see me when I was in their towns, and get some sweet head from me on their way home from work or whatever. One of my regular hookups, named Frank, pulled into the motel parking lot late one afternoon and looked up and saw me on the balcony. I was in a mini dress; heels and all dolled up, waiting for him, but was just getting a little "exposure" time in, as I waited. When Frank came in he said that he could tell that I was into being seen an... Continue»
Posted by dana213 3 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  
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I remember the first time I found myself in bed with a shemale. I had just broken up with my girlfriend. I was lonely, I was horny, and
I had zero intention of finding myself in another relationship with a woman. When I told my buddy, Bob, he told me he knew just where to take me to solve this. So he took me to this club over in West Hollywood. The place was FULL of gorgeous women. My head was swimming - they were almost all slender and dressed in very sexy attire. Short skirts and sheer nylons everywhere.
"Wow!" I told Bob. "These chicks are all drop-dead gorgeous. What's the catch? Are the... Continue»
Posted by madnessx 3 years ago  |  Categories: Anal, Masturbation, Shemales  |  
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Car Bonnet Cockriding Whore

Hi Guys,

This true story dates back about 4 1/2 months now, and takes place outdoors, well over a car bonnet to be exact.

I had been chatting to this lovely guy called Dave, we had been chatting on a different site and arranged for him to come over from where he lived to where I live in Droitwich. Well I had been getting my self ready most of the evening showering, shaving my self totally smooth including my pussy, made a real effort to look hot with my makup and clothes. The usual things, stockings suspenders, 1/4 cup bra with matching thong, and high heels, a loose fitting top ... Continue»
Posted by donnamarie09 11 months ago  |  Categories: Anal, Shemales  |  
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Watching too much porn

It’s another night at home alone.  You get that aching again so you go to put on your favorite video.  You just love big asses and big titties.  The video starts and you see the gorgeous blond strutting in wearing her 5 inch heels, incredibly short skirt that is flashing her skinny red thong, a thin, white, button up shirt that she has forgotten to button all the way.  The few buttons that are buttoned are barely holding her large breast inside.  Her nipples already erect and showing through the pockets just screaming “lick me!”  As she passes the camera just can’t help but stare as her sweet ... Continue»
Posted by urgonnaputthatwhere 2 years ago  |  Categories: Interracial Sex, Masturbation, Shemales  |  
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Cumming of Age

When I was younger I can remember summer vacations with the guys. We were a small group of six or seven close friends. I can't remember who made the suggestion but we would set or stand in circle facing each other and masturbate. I'm sure that is when I first sensed a curiosity of having sex with another guy. I know I've always enjoyed watching another guy get off ever since those early days. Glory holes would cum later.

When I got older my sexual thoughts pointed me in the direction peep shows. It was pretty much an age of sexual freedom when the only worry was how fast could I get a... Continue»
Posted by milkmanj 3 years ago  |  Categories: Anal, Fetish, Shemales  |  
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The Road to Submission

by Onyx (this is a story started by my friend and completed by me)

I was tired of sitting in board meetings and phone conferences all day.
My name is Brandon Morgan. I'm a 41 year old white accountant for a very
prestigious firm in town. I'm 5-11, 160 lbs, politely built w/short
blondish (slightly receding) hair, blue eyes, thin lips, and a long
straight narrow nose. I'm very average looking and hairy all over. My
cock is fat, and I have huge hairy balls. I'm straight (except for that
those times I fooled around... Continue»
Posted by saud31 1 year ago  |  Categories: Lesbian Sex, Shemales  |  
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BIG changes happen on Fridays ;) continued

Friday 11/4/07 Continued

After doing my duties around the house I moved upstairs and lying on my bed was something that took my breath away it was a dress my first proper dress (Mistress Isabella had given me many dresses before but they were never very ladylike they always carried a message with them that I was her plaything a doll to be played with and fucked at the drop of a hat) a real dress I picked it up and held it against me it was a soft red satin Square Neckline mini Cocktail Dress with long sleeves it was perfect I knew what to wear with it instantly I grabbed my favourite pair ... Continue»
Posted by Sissy_Kara 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
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The alleyway

She pressed close against his body, so close that he could smell the leather from her jacket. As they walked along, her arm around his waist, he could feel her nails through his shirt gently stroking above his pubic region; with each stroke he felt the bl**d rush towards his cock.

They turned the corner and walked further into the alleyway, him guiding her into the shadows. He looked down at her face, her eyes staring back up at him and what little light there was reflecting off of her lipstick. He slid his hand down her back and slid it under her coat where her could feel her bare back bel... Continue»
Posted by ass_pussy_fucker 1 year ago  |  Categories: Shemales  |  
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Fantasy of a Fantasy

It wasn't that I was opposed to man-on-man sex. It's that I wasn't for it. I mean, it didn't get me hard, but it didn't turn me off either. I know this not because I sought it out, but a gal I dated for a while confessed she loved gay porn, and had a fantasy of a threesome, where she'd back off and watch the two guys go at it. This was years ago, of course, and being the open minded guy I was, I said I'd consider it, if, big if, the other dude was okay.

But, as I said, this was years ago, and we never got around to trying. She went her way, I went mine, and eventually found myself in a... Continue»
Posted by TransContinental 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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Magic Panties Ch.06 (sissy story) by noflon - Fina

This story is a work of fiction, all characters are fictional and obviously the events are fake. You may reprint this as needed, just give credit to the author. If any differences occur between continuity, accept the one you like better as truth, and enjoy!

Here's the last recap for you loyal readers out there (I apologize for the delay, life got hard, unfortunately, not the fun kind), Got your cocks out? Good, because let me tell you, this one's gonna be a ride! Two weeks ago, I went on vacation from work, got stood up on a date, and the following day a package arrived at my apartment ... Continue»
Posted by sissyAlyna 9 months ago  |  Categories: Fetish, Shemales, Taboo  |  
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