Shemales Porn Stories
Page 80

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: 2584  |  
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Sometimes, mistakes do happen but they can be real

A few weeks ago I was wandering round some of the nice tv/gay sites for this area of France when I got a message from a guy asking me if I would like to meet. Well, I was very horny at the time, so nothing new there, was aching to do something to somebody or have them do something to me, you know the feeling, when you ache to feel something nice and long in your mouth or being slipped in your pussy.

I thought to myself why ever not, he seemed like a nice guy, he wanted to meet on his way home from work so we arranged to meet in a quite well known gay rest area between his destination and t... Continue»
Posted by antoniaf 2 years ago  |  Categories: Masturbation, Mature, Shemales  |  Views: 1441  |  
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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: 930  |  
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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 3 years ago  |  Categories: Shemales  |  Views: 1211  |  
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my first tranny (pt. 1)

you always remember your first time.


I remember my first blow job from an ex. (believe me, thats another story.) the first time I touched a pair of tits. the first time I ever ate pussy. the first time I fucked a woman in the ass. & I'll always remember the first time I was with a tranny.

her name was brooke. I always wanted to be with a tranny because I was always curious. I mean, shes a chick right. but then she has a dick. you all know some trannies are drop dead beautiful. this one was. I was looking in the e****t section of one of those paper you get at a porn shop. I always want... Continue»
Posted by radec_24 3 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 2706  |  
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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: 2804  |  
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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 3 years ago  |  Categories: First Time, Interracial Sex, Shemales  |  Views: 421  |  
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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: 1603  |  
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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 2 years ago  |  Categories: Anal, BDSM, Shemales  |  Views: 331  |  
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Going swimming with sibling

I am 18, I have a younger sibling who is 2 years younger than me called Emily. Even though she is younger than me and we both come from the same parents, she has a better body than me. She is curvy, taller than me, wider hips, small waist, amazing big round ass and huge tits. I'm a D but she is an E, almost F. She turns me on a lot, I know it's wrong but I get horny thinking of her naked.

We both love our swimming. Even though this is an awkward sport for me as I am tiny and it is hard for me to hide a big 8 inch cock. I usually tuck it between my legs pushing up against my ass, on top I wi... Continue»
Posted by shemalecharlotte 1 year ago  |  Categories: Masturbation, Shemales, Taboo  |  Views: 10451  |  
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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 2 years ago  |  Categories: Shemales  |  Views: 4570  |  
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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 3 years ago  |  Categories: Shemales  |  Views: 1713  |  
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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 2 years ago  |  Categories: First Time, Shemales  |  Views: 2322  |  
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I've dumped my boyfriend. Now he wants cock..

Me and Marc had been going out for 7 months. He's nothing that special to the eyes but he has a way with words. He could put a simple sentenced together and get any girl, any age, with any genitals?
I thought it was only a rumor going around that he was Bi-sexual so i ignored it completely because he was great in bed.

Tall strapping lad about 6'3", toned body, tanned skin and semi long hair about ear length. Long enough to twirl in your fingers while he's pushing himself into you.


After 7 months, he kinda gets boring. Like he lost interest in me and i lost interest in him. I actually ... Continue»
Posted by sophie101 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1994  |  
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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 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 5198  |  
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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: 1055  |  
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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: 373  |  
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How I Became Vanessa Chapter 1

PART I:

I was a man before becoming Vanessa, and my name was Mike. I was heterosexual and I was going out with my first "serious" girl friend for two years when all this started. I was still living with my mother who had been divorced for a decade before getting remarried. Her new husband moved to our place with a beautiful daughter named Elena who was only 18. I was a handsome 22 year old blond boy, quite feminine in my features and certainly very shy with girls because of this very reason. My girlfriend, July, was actually my first one, and she did the first step towards me. I was not rea... Continue»
Posted by slutyvanessa 2 years ago  |  Categories: Shemales  |  Views: 603  |  
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BIRTHDAY

I had just got home from work , and what to my wondering surprise my gf is naked and waiting for me on my lazy boy , with her legs spread , playing with her pussy.

ON the couch are 3 shemales also naked and playing with there cocks , how she did this i have no idea , but its been my fantasy to have a shemale and my gf in a sexual frenzy ,now i had this and plus two more , wow what a girl.

IM licking my lips as i watch all 4 of them playing , my gf tells me she has run a bath for me and has nikki one of the shemales lead me upstairs to get washed and relaxed , and says we will be waiting... Continue»
Posted by cocklover47 3 years ago  |  Categories: Shemales  |  Views: 1277  |  
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From manager to sub sissy

Cindy was a co-worker; well actually I was Her manager. Even though I was Her manger, W/we were very close friends. As a matter of fact I still consider Her my best friend. Everyone in the office was sure that we were having an affair, but we were just friends. I must admit that I would have loved to have an ongoing affair with Her. I know that I am not near man enough for Her and I have always know that from the first time I saw Her. Eventually after being friends for many years, I confessed to Her my desire to serve a Dominant Woman. She attempted being my Dominatrix, but could never g... Continue»
Posted by wannabesubformt 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1848  |  
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