Shemales Porn Stories
Page 64

Chrissie and the Professor

Possibly the after hours engagement with an English Literature professor at college may have been the thing that convinced me that older
men might be more to my liking.
It was during my Junior year at the university when we were discussing the poetry of Arthur Rimbaud, the French poet, that I became infatuated with my professor. He was a typical scholarly gentleman one would expect to encounter at a major university. He was in his mid fifties, and still in remarkable condition for his age. He was about just under 6 feet tall, blue eyes with salt and pepper hair. In class he was charming, w... Continue»
Posted by chrissieCD 2 years ago  |  Categories: Anal, Shemales  |  Views: 918  |  
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Daddys little helper

Maybe if I'd minded my own business and stayed off my dad's computer, my life would have been a whole lot different. As it is I wouldn't change it for the world.

My name is George Mason Jr. I was twenty years old when I moved back in with my father (George Snr, obviously) after my mum left him and took up with some arse-wipe she met at her gym. He had been devastated by the betrayal and I had moved back in to keep him company and make sure he didn't do something stupid. I was quite a good cook and a bit of a neat freak, so it worked out okay for both of us. I got out of my shitty one bedroo... Continue»
Posted by sparkyking 2 months ago  |  Categories: Shemales, Taboo  |  Views: 4257  |  
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Atrip to the dentist

My wife thought I was at the dentist but I was really with my special friend Sandy. It had been over a month since I could sneak away to see Sandy. My cock was wet and hard just from the ride thinking about what she would be wearing and how we would please each other. When She met me at the door I almost exploded just looking at her. She had blonde hair today in a long braid d****d over the front of her shoulder. Her eyebrows were dark thin lines followed by different shades blue all the way to her eyelashes. Her cheeks were painted a blush color and her lips a dark crimson. She wore a black ... Continue»
Posted by Zeffer1 2 years ago  |  Categories: Shemales  |  Views: 1201  |  
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Chrissie's New Client

I run a small investment consulting firm. Very small, actually it's just me. It's really just a cover business for what I really do which is to service my male clients clandestinely.
There are an average 20-25 active clients. They are all successful proper business man, many of them you would classify as professionals.
They are all referrals and have been carefully screened. Most of the men are straight but just like a girl with "something extra"occasionally. There are also some who I suspect are Bi-sexual. I don't really cater to the overtly gay community.
That's for no particular reason ... Continue»
Posted by chrissieCD 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 1081  |  
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My night of first times!!!

I was sitting in the bar with my friends when she walked in. Black short dress, low cut neckline. I can see the garter straps holding her stockings. I think that is what caught my attention first. I had seen garters and stockings in movies but never in real life and her legs looked great. I couldn't keep my eye off her all night. I had to seem like a stalker with my eye's, I wasn't paying much attention to the conversation at the table with my friends she was lust at first sight. I had to make a restroom trip and when I walked out she was standing there. My heart skipped a beat and my stomach ... Continue»
Posted by Trudru 3 years ago  |  Categories: Shemales  |  Views: 1964  |  
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caught spying

i would love to re act this with someone ;) any offers?


A young man, 18, is caught spying on his girlfriends mother in her bedroom, and is taught a hard lesson. Characters: Tim, 18, Student; Susan, Tim's Girlfriend; and Julie, 44, Susan's Mother ;-).

Julie sat at her dressing table, preparing for bed; she brushed her long dark, which was one of the pride and joys. Normally, this would help her relax and unwind, but tonight, and on several other nights, she found that remained tense. She couldn't get over the feeling that somebody was watching her, for several days, perhaps a week; when... Continue»
Posted by leadpencil21 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 2490  |  
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Transformation

This is a cross between real life and fantasy. A deep, dark desire which may never be fulfilled but I can't help a part of me wanting it anyway. I hope you enjoy.

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I was a usual guy. Or I had thought so anyway. I mean, I had worn some of the female members of my house' panties and swimsuits on occasion as a young boy but I always thought that was normal. I mean, apart from the silky smoothness of lace and satin massaging and teasing the penis, y-fronts are exactly the same really... just with less frills. It didn't last long though, I mean, how can a boy in a strict and straigh... Continue»
Posted by shyadam89 2 years ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 1601  |  
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The fun part of stephons run in with sora

Ok, its going to be ok stephon. I think to myself as I reveal her cock. It turns out shemale cock isn't that different from regular cock. Or at least mine, I have never sucked off a guy so......

Anyway

Mouth, neck, upper chest, natural breast, chest, belly button, below belly button, shorts, panties. I stop, im still second guessing myself and then just nut up, expose her cock and lick it.

Umm.... This feeling is different than I expected. I think that I'm actually enjoying it. Like three minutes go by and im sucking on the head. sora is moaning so I guess I'm doing good. I was fuc... Continue»
Posted by cooler34 2 years ago  |  Categories: First Time, Interracial Sex, Shemales  |  Views: 419  |  
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Clara Bow's Academy for W-B Ladies Part 4

Greville Hambleton tried hard not to think of the ginger sissy; he was married to a fiercely independent woman who was very much in charge in the bedroom, and who knew all too well of Greville’s weakness for effeminate transgendered she-males. As he was often cuckolded, Tara his wife being partial to sampling cock, she turned a blind eye to his discretions. Like a lot of otherwise heterosexual males who enjoy the assertive control by the superior sex, he had a keen dominant streak which revealed itself with a preference for younger ladies, and even more so for sweet effeminate sissies. His ... Continue»
Posted by midsummerman 1 year ago  |  Categories: Anal, BDSM, Shemales  |  Views: 312  |  
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Hedonistic Crossdressing, Part 3

The best way to describe Vince, probaly is that he was a socially functioning pervert. I had no idea just how varied, and intense, his sense of erotica was, but I was going to find out as time went on. Perhaps the worst thing is (or best perhaps, depending on your point of view), is that I became quite the little "apprentice", you might say.

I'd been his "guest" for only a few hours, and I'd experienced more than I'd ever dreamed. I've dressed, I've sucked my first ever cock, been fucked hard up the ass, taken cum, been made to cum like a girl, been made to take ass to mouth, w... Continue»
Posted by elainetgrl 3 years ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 1408  |  
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Massage parlor surprise

I have to admit one of my biggest turn ons are shemales/ladyboys. In all my little ventures to asian massage parlors for some relaxing relief only once did I get a total surprise. About a year ago I visited one of my favorit little places and Mama said I should try her new girl....I might like her. So I agreed to meet with her. Waiting in my little room in walks a very hot sexy little asian girl and we started our massage session. While getting my rub down I started letting my hands wander to her thighs and lower butt to rub and feel then and to let her know i was cool for some extra if on the... Continue»
Posted by longrod4u 2 years ago  |  Categories: Shemales  |  Views: 1708  |  
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Xdresser Roxxi's black cock obsession Part 1

This is only a fantasy of mine at the moment however I hope one day it comes true .For a long time now I have been going to hotels and dressing up spending the night wearing various sexy outfits .Taking pictures of myself fantasizing about being a girl and what type of guys I would like and what I want them to do to me .After years of doing this I have worked out what really turns me on and off, this story is my fav fantasy .I'm very submissive when I dress up as a girl ,i want to be man handled ,to feel a mans smooth muscles ,the strength of a large black man .He would be over six foot tall v... Continue»
Posted by foxxiroxxi 2 years ago  |  Categories: Fetish, Interracial Sex, Shemales  |  Views: 370  |  
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the train ride




The Train Ride

Has anyone taken a night train following a major event in an
Asian country? I have. If you think trains are crowded during
peak hours in New York, you must experience riding trains in
Asian countries. Then you may ask what is common between a
crowded train in Asia and a can of sardine.

The idea to see the festival was planted in our minds by George,
who was our bartender at the hotel. He stated that the Kandy
parade was a once in lifetime experience, two days before we were
to head back to Oslo. After hearing what we were about to miss,
we made plans to hit... Continue»
Posted by pcarter 2 years ago  |  Categories: First Time, Interracial Sex, Shemales  |  Views: 1689  |  
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My First Tgirl Deepthroat.

Before I, start, I will tell something of myself.

My name is John, I am 48 Yrs old, I never thought I would attracted to Tgirls,

I am average built, 5ft 10in tall, 190 lbs, I am Hawaiian, Phillinino, Chinese
Nationality.

Well 2yrs ago I was cruising in town (Honolulu) and went to a bar to chill for awhile a had two beers just cruising, when this beautiful Asian girl sat down next to me, She was hot smoking hot, damn.

We started talked, simple confersation. I kept staring at her full lips and I was getting a hard on. I was hope she would not notice my fidgeting around on my chai... Continue»
Posted by jkain 1 year ago  |  Categories: First Time, Shemales  |  Views: 2303  |  
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POP GOES THE CHERRY

POP GOES THE CHERRY

I recently read a delightful account of a young gurl loosing her virginity to a f****y friend. Got me thinking about loosing my own virginity.

First, you should know, my mother made me a sissy. She took great delight in dressing me as a little girl, thinking back I can not remember when she did not. We lived in the country and most of the time growing up I played outside with my dolls in dresses. The only time I wore little boy’s clothing was when f****y visited or I went to school.

Everyone in town knew I was a very sissy acting little boy. I was bullied a ... Continue»
Posted by littleoralvee 2 years ago  |  Categories: Shemales  |  Views: 1216  |  
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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 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 5166  |  
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Glory...

I walked into the bookstore paid my way and went into the peeps; I
usually avoid the theatres since there is not any privacy for
playing. I guided my way in the dark letting my eyes adjust in the
dark. I walked to the back where the stalls with the gloryholes are
and found an open booth.

I sat down and pushed to find one of three channels I liked and there
it was the shemale channel, with a sexy shoulder length blonde and
redhead with deep dark red lying on her shoulders. They were kissing
and touching and boy was I getting aroused, so much, so that I did
not notice the booth next t... Continue»
Posted by NaughtyNshy 3 years ago  |  Categories: Gay Male, Shemales  |  Views: 1049  |  
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My Sissy Fantsy pt 001

Chapter 1

I reach the campsite just as the sun is going down and the clear sky is bright orange as if in memory to the beautifully warm day it has been. The campsite is popular yet set on secluded farmland and as the season is just over it is practically deserted. The whole camp is surrounded by woodland and a stream lined with more trees cuts through the campsite, dividing it into unequal sections. Walking through the larger first section I can see only ten other pitches occupied by either tents or caravans and I hurry past them. Crossing the rickety bridge I enter the second smaller secti... Continue»
Posted by monalottanow 2 years ago  |  Categories: Gay Male, Hardcore, Shemales  |  Views: 449  |  
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Bar Hopping with my s****rs

My two older s****rs asked me to go to the bar with them which is always cool considering i am Transexual and they are not, course i always felt the reason they always asked me to go with them is because i had a way of drawing men to our table like bears to honey ha ha ha.(not that i think i'm all that and a bag of Salsa Doritos, but i'm alright looking i don't scare c***dren and dogs so i must be doing something right XD

It was Friday night and i decided to wear a purple mini dress with 3/4 sleeves with my 3 inch thigh high black suede boots and my black lace bra & ... Continue»
Posted by Shalimar 4 years ago  |  Categories: Anal, Shemales, Voyeur  |  Views: 2795  |  
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Moms Trannie

It was Saturday night and my friends had told me about a new club. It was about an hour out of here and had an older crowd. This sparked my interest some what having a fondness for older women.

I walked into the place and looked around, not much going on so I wandered over to the bar and ordered up a beer. A little while later the crowd picked up and things started to get moving.

The women were defineatly older here, I asked a few to dance and had a few takers but couldn't seem to lock in with them.

While I was dancing I must have missed the two that came in, a blonde and brunette wit... Continue»
Posted by frswriter 1 year ago  |  Categories: Shemales  |  Views: 4564  |  
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