Shemales Porn Stories
Page 122

First fuck for Freda

I'm such a slut. It's not easy to know where to start. I suppose my routine - that's what got me into this, I guess.

Each morning, after my mother went to work, I had three or four hours before my shift at the factory started. I would get the box from under my bed and dress myself. The stockings, the suspender belt, the bra, the patent heels.

I would brush down my long hair and apply my make up, slip into a short mini-dress and admire myself in the mirror. I loved turning from Fred to Freda in the mornings. I'd always put my panties on last, for some reason; I just liked it that way. My ... Continue»
Posted by laceonlegs 4 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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It doesn't get any better than this!

15 years ago, I went into my older b*****r's room to grab a porno mag. He had stacks of them all over the place. I wasn't too choosy. I picked the magazine off of the top of the pile that was closest to his bed and went into the bathroom. My usual routine was to open the mag, find a babe, pull out my cock, and have at it. When I opened the mag, my jaw dropped and my dick got so hard, so fast it practically popped out of my pants! I could not believe what I was seeing! It was a gorgeous babe alright, but she had a BIG hard-on where her snatch was supposed to be! My cock was pulsing in my pants,... Continue»
Posted by bugaboobed 3 years ago  |  Categories: First Time, Shemales, Taboo  |  
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The Coach's Chance Encounter

Eddy McCants rolled the rack of basketballs back into the athletic storage room at Liddell County High School. After coaching the varsity boys to the final four in the state tournament last season, he had a good feeling that his team would make it at least as far this time around because he had three returning starters. The six-foot-one-inch light-skinned man walked into his office and waited for his assistant coach. He propped his size twelve feet up on his desk. He and Coach Jones discussed this afternoon’s practice and their strategy to push the guys even harder tomorrow.

Eddy checked hi... Continue»
Posted by faggyboi 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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My dream encounter with a tranny

There is nothing more hot than to have a slim, pretty body on my hands to fondle. To feel their erections starting to grow and to taste their cocks in my mouth. I lose control when I'm around a shemale.

I have fantasized a lot about getting fucked for long periods of time and in a lot of different positions. Unfortunately, all my shemale hookups have been with e****ts that do the deeds rather quickly and then leave. I still have to find a shemale friend to spend long long hours either fucking, fondling or sucking.

I dream about a hot, slim, tender shemale arriving at my doorstep. She beg... Continue»
Posted by feinor11 4 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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Alex One: House Sitting For A Friend

Sorry, this is a little rough. I've tried expanding the original
version but ... i dunno. Anyways this should be a continuing series
of some sort. (I might post the original old version too...)



Alex One: House Sitting for a Friend.
By Alex Shouse.

My friend Karen had worked her way through a somewhat bitter
separation and had decided to cash in some vacation time from work
to take a little trip to 'get it all out of my head' as she said.
so she had asked me to House Sit while she was away for 2 weeks.
obviously not having anything else to do, and not particula... Continue»
Posted by AlexShouse 3 years ago  |  Categories: Shemales  |  
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The Origin of Sgt. Steel Part 2: Iraq, Internet Po

For a long time I skated around the periphery with my attraction to shemales and fembois. After my initial exposure watching Jaye Davidson in "The Crying Game," I went back to living with my soon to be future ex-wife and my two stepdaughters.
I didn't really start considering shemales and fembois until my second deployment. In August 2007 I arrived in Iraq. Although I have been in the military for over thirty years, I’ve never been one of those gung ho types. To be honest I’m more of a cynic. Kind of like a character named the Comedian in a movie called Watchmen. He looked at all the serious... Continue»
Posted by sgtsteel 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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I Can't Control It

woke up, laying on my left side, to the sound of Marissa making quiet whimpering noises. I
knew it was her because she had an unmistakable “little girl” voice that she moaned with while we had
sex. Or while she masturbated. Just whenever she had pleasure.. down there... My back was to the edge of the bed, and normally Marissa slept in my arms more towards the wall. I opened my eyes and saw
her over on my small blue couch in the corner of my room. She had her legs pulled up and head down,
curled in a ball with both hands in between her small thighs. Her back was to me, I only saw her back.... Continue»
Posted by bigdick2012h 3 years ago  |  Categories: Shemales  |  
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BECOMING THE SECRET FISHING CAMP PRINCESS


BECOMING THE SISSIFIED FISHING CAMP PRINCESS!!!!!!!!
Between being raised by a strict single parent mother, and living far out the boondocks of a small remote New Hampshire country town, my life was different than that of the other town boys.. Yes homework and then houseword were all I ever seemed to be doing.
By fully LEGAL age 18,
I was a good three to four years younger in mental developement as my mom was super protective of me, I was also still the physical size of most jr.high school boys but I could cook just about anything and even sew and do every single bit of household chore... Continue»
Posted by cddixie 1 year ago  |  Categories: Gay Male, Shemales, Taboo  |  
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Mistress sissy slut


Waking up, sometimes, can be rather difficult to do, especially when you know that you were d**gged the night before. Or, at least you HOPE it was only the night before. And this time, it was far worse than the first times. So many things have changed about me from the first time I was d**gged, unwittingly and unwillingly, though as I look back, I can’t really say that I am upset about the outcome of each of these times. Well, I have to admit that I was, kind of, pissed off the first time, as I never really expected something like that. But that was quite some time ago and now, well, I gues... Continue»
Posted by Latexslav3 10 months ago  |  Categories: Shemales  |  
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Transformation

Transformation

Fran Avatar



Damn, that hurts! And it stinks too! No escaping either of it. The pain
and the smell don't seem to be affecting my cock though, my meat is
rock hard. So's my master's, buried deep within me. He's enjoying this.
Probably more than I am - and I'm about on cloud nine! With every touch
of that electrolysis wand I keep going further onto that cloud. My
reaction and the fact that it's him who's holding that damn thing is
what's keeping him hard inside me even with his moving around for any
friction. Just the thought of it all. The thought o... Continue»
Posted by klammer 7 months ago  |  Categories: BDSM, First Time, Shemales  |  
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Late Night Visitor

First I stayed a Motel 6 for day, he met me at the room the first night and after sucking him off he jumped in his car, took a room key and said he would be back at 10 tonight. He instructed me to be in a nightie, heels and to be shaven all over. Also I had to be in the bed, pacifier in mouth, on my stomach with the sheets uncovering my bottom. I did as I was told, laid in bed, pulled the covers up leaving my bottom half exposed and actually almost fell asl**p. Around 1am I heard the door un-lock and Steve say “Daddy’s home” I put the pacifier back in my mouth as pretended to be sl**ping.

“... Continue»
Posted by MatureBrownMan 1 day ago  |  Categories: Gay Male, Mature, Shemales  |  
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The Bondage Whore, Chapter 7

The Bondage Whore, by Rachel St. Clair, All Rights Reserved.



Chapter 7 - Payday Surprise

On Monday, Rachel woke up in a perky mood. The start of three days off, and also her first payday! As she swung out of bed, for once she barely even noticed the chastity belt. Rachel had spent much of her time these past two weeks daydreaming, and planning what to do with her new-found wealth. As she showered, all she could think of is what $4,000 would feel like in her hands. She'd never had that much money at one time before. One thing she knew she wanted to do, was get out of the "fleabag", in... Continue»
Posted by thongcutoffs 4 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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Inmate Succumbs After Seven Years

In the seven years that Damon Winslow had been locked up for home invasion, he had never once had sex with a guy. He was not gay was not about to start just cause he was in the slammer for 10 years. The twenty-eight year-old light brown prisoner swiped the screen of his contraband phone. He was looking at ass pictures of his ex. After getting a hard on, he decided to jack off his fat meatiness. After shooting a decent sized load, he drifted off to sl**p.

The five-foot-eleven brotha was up just before the C.O.s came around to announce it was time for breakfast. He brushed his teeth and went ... Continue»
Posted by faggyboi 3 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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Origins of a Whore

The Origins of a Whore


I really became a prostitute by accident. Okay, well, not really, but sort of by accident. I had been going to a chat room online and found there were quite a number of admirers of t-girls, she males, cross dressers, chicks with dicks, sluts with nuts, whatever you want to call us. I hate the term drag queen because it is so demeaning and inaccurate. I much prefer to refer to it as dressing “en femme”, and call myself a “girl with something extra”. But I digress. There were a number of guys who wrote that they were interested in meeting and some were serious ... Continue»
Posted by Chrissycdslut00 3 months ago  |  Categories: Shemales  |  
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turned into a slut by my dad

I opened my eyes, blinked, yawned, closed them again.

I felt confused, disoriented in a way that was... strange. It wasn't like waking up was supposed to be, I wasn't half asl**p. I can't remember getting in the bed, in fact I can't remember the last thing I remember. Where did consciousness end last? I was clueless.

I tired to move my body and I found it difficult. I could move though, I rolled over onto my stomach and opened my eyes, I was on the guest bed in the basement. Blinking didn't clear the fuzz from the world, so I went ahead and tried to get out of bed. As I stood I felt an i... Continue»
Posted by crossD93 3 years ago  |  Categories: Anal, Shemales, Taboo  |  
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How i became a girl

Hi my name is Mandy and this is my story..in parts. I started dressing when i was in my early teens. At first it was just panties, maybe pantyhose and masturbating with my friend B, but it soon became wearing skirts and heels, little tube tops and sexy dresses, then it was makeup and wigs, and soon we were both dressing up fully, doing our makeup and hair, and accesorizing with pocketbooks and jewelery.

We had suuuuccchh hot sex, kissing and fondling each others sexily clad bodies, our hands and lips and tounges roaming, licking, stroking and nibbling each other erogenous zones, before a ... Continue»
Posted by miniskirtmandy69 4 years ago  |  Categories: Shemales  |  
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Caught

This is how I got caught masturbating and lost my virginity to my stepmom.
I was still in High School but had just turned eighteen, and was still living with my dad and stepmom, Beverly. I was ashy kind in school and did not get many dates, this lead to lots of jacking off. I did not realize it at the time but not only had my dad married a transsexual, but Beverly liked to sl**p around. I later found out my dad, liked it and enjoy hearing her tell about a how she seduced strait guys.
So I was watching some porn on the internet when Beverly walked in on me. I quickly changed windows and made ... Continue»
Posted by raastible 3 years ago  |  Categories: Mature, 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 9 months ago  |  Categories: First Time, Shemales, Taboo  |  
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The Bondage Whore, Chapter 10

The Bondage Whore, by Rachel St. Clair, All Rights Reserved.


Chapter 10 - An Unwanted History Lesson


"Well, well, well... I do believe this just might be my worst student ever, little trouble-maker Rachel Wells."

"Oh no, Mr. Linebrink!" Rachel couldn't believe her horrible luck. Her old 6th grade US History teacher!

Mr. Linebrink stood there, with an ear to ear grin, looking straight down at Rachel's imprisoned face. "Yep, was I right! Wasn't I Rachel? You do remember that day in class, don't you? That day when I told you that you'd wind up a prostitute, or a stripper, or may... Continue»
Posted by thongcutoffs 4 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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Whore Street

bylittle Sebastian

It was just too many nights, that I had not been fucked, so I decided for the best way of hunting for cocks, another night as a hooker.

First the outfit. Tight pink half shirt that zipped in the front, padded leather bra with "B" cups, black leather mini skirt and thigh high black fishnet stockings. I packaged my manhood in the tightest jock strap that I could squeeze into. Then came the bright red lipstick and make up.

I must say I think that I looked like the hottest whore I had ever seen. Looking at myself that way made me incredibly horny.

It was now time t... Continue»
Posted by aspiringtsxxx 6 days ago  |  Categories: Shemales  |  
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