Shemales Porn Stories
Page 75

Alice 2

Alice part two

I checked out and drove home in deep thought, I knew I was in love with Carol, I could only hope that she felt the same about me. How am I going to explain to my dad about dressing up and most importantly about my job. I decided that I would be dressed when he got home from work, then tell him what has happened, he obviously would have found me out anyway. I arrived home about lunchtime, I stripped off, had a shower and douche, I picked out a nice black above the knee cocktail dress, nice silky black underwear, near black ... Continue»
Posted by ratty9uk 5 years ago  |  Categories: Anal, Shemales, Taboo  |  
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Interstate Reas Area Whore

Driving down the interstate the sign said Rest Area one mile. My heart skipped a beat and there was slight stiffing of my male meat in anticipation of events to unfold. This interstate rest area was always packed full of eighteen wheelers as many as forty. Surely one or two of these truck drivers would be horny enough to over look the fact that this slut had a little something extra a top her nylon covered legs.
I had a black merry widow corset on that pulled my waist in a nice four inches. Eight garters held up my coffee colored FF nylons. I had on five inch red stiletto pumps. My bla... Continue»
Posted by littleoralvee 4 years ago  |  Categories: Shemales  |  
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CD And Trucker

CD Adventures Truckers Ch. 02a
Part 2A: Portland to Bakersfield
I turned....
At least four things went through my mind the moment I heard Hank ask me to go along with him.
- One my wife was gone for at least 2 weeks so that was no problem.
- Two, with wireless connection and my laptop I could take my job on the road.
- Three, I had hardly any clothes in my bag that I was carrying. All the clothes in the bag were girl
clothes; my boy clothes were in the back seat of my car.
- Four, my ass (oops, my pussy) was on fire and now stinging a bit from Hank's big cock taking my
virginity just ... Continue»
Posted by pr1456a 2 years ago  |  Categories: Shemales  |  
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caught masturbating & crossdressed living at a

This is the first story of a few that I was so lucky to be a part of and I would love to share them with you!

I had hired this woman as a delivery driver because the store I had just taken over had ruined the reputation of the business with terrible service. Her bubbly demeanor, bordering on ditzy was cute and she was herself a beautiful 40 year old woman and a milf for sure! She would be my best tool in the road to rebuilding the business. The customers will love her. She was tall with long slender legs and a real nice round ass, small titties with huge pinky size nipples. Her hair wa... Continue»
Posted by happytayls 2 years ago  |  Categories: Hardcore, Shemales, Taboo  |  
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THE BUSINEES TRIP - PART I

HI

This is another one of my real life experiences. All my cross dressing and sex experiences are on my work trips as that is the only time I am alone and I can indulge in my pleasures ( as I live in a joint f****y n India so cross dressing at home or in my home town is not possible).

So here I was getting ready to go on another work trip to Lucknow ( a big town in the state of UP in India). I reached there by train around noon and since the office was about 60 kilometers out of town I hired a cab as I would be staying there overnight. I contacted the travel agent at the rail station and... Continue»
Posted by hornyboyind 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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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 7 months ago  |  Categories: Shemales  |  
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Daddys whore


I had always been fascinated by the feel of womens clothes against my skin, and today was no different. Mom was away on a business trip to Canada, and dad was away at work for the next couple of hours.

I had always had an effeminate look to me, with me being 6’1” and thin as a twig at 19, I was scrawny. I had bought a black wig to go with the outfit that I had picked out. It was black 6” heels, black pantyhose, a black garter belt and panties, with a short black skirt and a little black tube top. I was hard just thinking about what I would look like.

I took a shower and completely shav... Continue»
Posted by nicoleinberlin 2 years ago  |  Categories: Gay Male, Shemales  |  
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Summer affair with a latina ts mmmm

So, we all are busy and have our jobs n all and not much time for fun...So i'd thought ill try craig's list for the hell of it-which was something I would never have tried in a millions years lol. Jokingly I was repulsed by what i saw under the casual encounters but decided, "what the hell." I put up an ad with a toss away email saying something along the lines of 'big black juicy cock for horny latinas and white.' Mind you in the small town of Chico California i doubt any one would even check it, even left my cell number on there as well lol. So far, tons of spam, a few responses but they wer... Continue»
Posted by iluvtgurl 1 year ago  |  Categories: First Time, Shemales, Taboo  |  
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Gender bent – Ch 9 – Lack of free will

Gender bent – Ch 9 – Lack of free will

“Nikki, he Nikki?, Wake up” I heard a voice as I opened my eyes. “What happened?” I muttered as all I could remember was being dolled up like a bimbo slut encased in pink latex looking like a flat chested girl with a bubble butt with a ton of fake tats on me. “The process finished” J said as Kandi stood right next to him. “Wow did It work?” Kandi said. “Did what work?” I replied. J looked at Kandi and then pressed a button on the watch and said “Looks like it, but let’s test, Nikki standup” I stood in a instant is if my legs had moved on their own. “Wh... Continue»
Posted by youngprboi 2 months ago  |  Categories: Group Sex, Hardcore, Shemales  |  
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My Date with a Crossdresser

A couple of months ago, I was contacted by a crossdresser here at Xhamster. She has asked me not to reveal her identity.

We arranged to meet one night at a motel near the Pittsburgh International Airport. I arrived at the agreed time, but when I knocked on her door she told me she wasn't ready yet and asked me to wait half an hour. I agreed.

Half an hour later, I returned to her room, but she still wasn't ready. She was apologetic, and asked me if I would rather come back in another half hour, or would prefer to wait in the room while she finished dressing. I told her I would like to wai... Continue»
Posted by johnny_antares 1 year ago  |  Categories: Shemales  |  
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One night I

The last time I got fucked was in may or june 2011,. in spokane, wa. I was horny and d***k in my mums apartment with no privacy,. so I got on craigslist,. and sent out a few emails to people who have posted looking for a bottom boi, or something to that extent. I got a few replies back but chose the one closest to me (just north of the fred mayer on freya) cause I didn't have a car,. and would have to hike over to meet him. luckily it was only a few blocks away.

I got to his place and waited around the back for him to come to door,. I didn't knock ,. but texted him and let him come outside ... Continue»
Posted by villelohne 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
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Whore For Two Mexicans

One night I came home from work and saw a old beat up truck from Texas parked in in spot next to my room. As I walk to my room I looked in truck and the back was full of tools and junk, then looking in the cab I could sdee it was a mess with trash everywhere. I thought who ever it belonged to must be slobs. As I got to my room I saw my guess was right as two mexican guys came out of room next to mine and they were a dirty mess. I looked at them and said hi and sort of smiled, they both had sort of nasty grins on there face as they looked at me.

That night I was standing outside having a bee... Continue»
Posted by sissy_gurl 3 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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super cock 14 inches meets angel buxom (written by

This how I see the biggest cock in the world violating the biggest tits in the world ,was looking at the news one day when they had announced the opening of a very unique new building that was just built in NY NY and clamed to be the tallest in the world at 4500 stories tall it was the biggest building on the planet ,it is uniquely shaped like a massive erect cock shaped after Mr Supercock the longest most powerful cock in the entire world the next biggest would only be about half his length the building is owned by Mr Supercock ,multie zillinare porn king ,king of the cock.
They showed some... Continue»
Posted by huge_cock_rules 10 months ago  |  Categories: Fetish, Shemales, Taboo  |  
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My shemale boss part 3

I was woken by the vibrating noise of my mobile and looked over at the time, the bedside clock said 1am. The caller I'D on the phone simply showed Bitch, naimly my boss Miss Jones, would she never leave me alone.

I answered the phone and still being half asl**p simply said 'yes'.
'Don't answer me with that tone Rob' she said. 'Sorry, but its one in the morning' I replied.
'Be a darling Rob and pick me up from the club, text me when your outside'. Before I could say anything she hung up.

I pulled my arse out of bed, slipped on some tracky bottoms and a t-shirt, jumped in the car and dr... Continue»
Posted by big_rob49 2 years ago  |  Categories: Shemales  |  
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Peaches And Cream #1

Prositutes – lingerie – hookers – transsexual first time – butt plugs

I have a little problem.

Well, to be honest, it's more than just a little problem. Some might consider it to be a huge problem.

I am addicted to prostitutes.

I have been pretty much all of my adult life, since I first walked out of the front gate at Lackland Air f***e Base in Texas and saw a pretty young girl sitting on the hood of a car in front of a massage parlor. When I glanced over at her she had slipped her shorts aside and exposed her hairy vagina, and I had followed her into the massage parlor and ... Continue»
Posted by naughty_bi_interest 1 month ago  |  Categories: First Time, Fetish, Shemales  |  
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A night to remember with G/F and a sweet little tr

At 52 years old i have had a extensive sex life. I have always been impressed by and i will use several words to describe Shemales, trans, Gurl, Traps, cross-dressers. I guess I like the fact that they take some time to look and or change into a better person and going from male to female can take some time and tricks.

Boston MA 1997: My G/F and I decided to add some spice to out very adventurous sex life. We went out one night to a alternative club that had a fashion show. Most will call it a drag show, this was a little slice of heaven for her. She played with my cock through my pants as ... Continue»
Posted by wankingamerica 2 years ago  |  Categories: Anal, First Time, Shemales  |  
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LADYBOY DOMINATRIX

YOUNG LADYBOY DOMINATRIX
by utubeslut


If you read my other stories you know I'm intersexed
and I was a ladyboy prostitute when I was um, very young.
I don't condone such activities.
They were sick perverts who used me.
True I got a lot of money and expensive gifts but
that doesn't make it right.
They should all be castrated.

This is a story about one of my clients.


Let's call him Mr. submissive.
My sex club supervisor gave me a sheet of paper with all
of Mr Sub's needs and desires.


How do I begin this? It's almost unbelievable.

An expensive hotel room, laminated h... Continue»
Posted by Utubeslut 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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Halloween Pt3

My enthusiasm waivered a little once his crotch was in my face. I could see his cock straining against his sweat pants. But, I considered the alternatives: He was horny, and he was expecting relief. We were in his frat house. And he was much bigger than I was. And, I was dressed like a young woman hot for the D. If I told him no, he could easily beat the shit out of me. And then tell everyone he was fooled. God knows what his frat b*****rs would do.

Besides, he'd sucked my cock. How bad could it be? Women liked giving blow jobs, and obviously some guys did too. It's not like anyo... Continue»
Posted by TransContinental 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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My life at home.

This is a purely fictional story, and in no way reflects real events.


My name is Greg, I am 47, 5'11", 225lbs, and a widower. My wife died shortly after c***d birth. She was on her way to the store, when a stolen truck, driven by a man wanted by the police. She left me to raise our son, terry. for the last 16 years, I have been mother, and father to him, watching him grow from a little boy, to a young man.

Terry was never into sports, just accademics, and these he excelled at. He was never muscular, kind of thin, graceful. I work as a product designer for a multi-national com... Continue»
Posted by chefjohn2112 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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Boston Surprise

Boston Surprise by FRSWRITER
It had been weeks since I saw the gurls, their memory burned deep in my brain.

Hanging around the house with not much to do didn't help either. I had been trying to call Jill for a few days, but she would not answer. About now I was thinking it was a dream and never happened.

It was getting late and I was contemplating going out and trying to score, headed for the shower to get cleaned up and go. The water felt good and I was getting hard just thinking about what tonight may bring. When I was all soaped up the fucking doorbell rang, I yelled but I guess they... Continue»
Posted by frswriter 3 years ago  |  Categories: Shemales  |  
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