Shemales Porn Stories
Page 69

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 2 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 2674  |  
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How i became a sissy fuckslave pt1

How i became a sissy fuckslave.

It all started after a series of failed relationships led me alone.Having always been a closet crossdresser, i started dressing more and more often and posting pics and vids of me on a website called xhamster.In time, i started posting vids of me toying my sissy ass, and also gradually building up my fem wardrobe.

After several months and many pics and vids, i met a man who offered to train me online.This was mustually pleasurable to both of us and as time went by he started having me cam for him.Toying my ass while he watched always turned me on, and he ... Continue»
Posted by analsubbieinmissouri 3 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 3206  |  
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My Great Adventure

One morning after dressing in s*s’s clothes and she is a hot one.....black fish net stockings and 5” patenet leather pumps and corsets to die for and a pair of padded inserts to enhance her already endowed breasts, I needed some excitement besides the usual pulling of the wang and using my soft foamy dildo,
So I saw that she left the keys to her car and with mum and dad off on holiday...and s*s gone with her boyfriend, I stayed dressed in her clothes and added a yellow slicker and a bonnet to hide the hot cum fcuk me clothes and started up the Audi and off I went to the next town and though i... Continue»
Posted by mia1 3 years ago  |  Categories: Shemales  |  Views: 2280  |  
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My First Time with a Shemale

I had watched porn for a long time, graduating from straight porn to videos of shemales, falling in love with TS stars such as Leilani, Julie Bond, and the gorgeous hermaphrodite Dane Harlowe. However, as much as I fantasized about being with a shemale or cross-dresser, I never thought it would happen.

Then one night when I was living in Indianapolis, after being out drinking and dancing, I stopped at the local adult video store. I had parked near a white van and, as I was drinking some more of the six-pack that I had in my car, I saw that there was a woman in the driver’s seat of the white... Continue»
Posted by TSfanxxx 1 year ago  |  Categories: First Time, Shemales  |  Views: 2416  |  
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My frist time wearing sexy lingerie. Part 2

I could not wait to get home from school the next day after wearing my moms sexy panties the night before.

No one was home so i could have fun.

As soon as i got into my room i took off all my clothes and went into my moms bed room to see what I could put on.

With my mom working at Macy's in the lingerie department she had bought some sexy lingerie there.

I was looking thru her sexy panties and than I found a pink baby doll.

I rember see the girls wearing sexy lingerie like this in the pictures that my uncle had so I put it on.

As I put the baby doll top it made me feel so sex... Continue»
Posted by suecd58 2 years ago  |  Categories: Shemales  |  Views: 1690  |  
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Flirting at the mall.......are you sure about that

Before I begin my story let me say that the next time you're at the mall be very observant because there are more of us t-gurls out there than you might think. Since I am one I know what to look for and can pick them out.......so, ask yourself sometime........is that hottie I'm watching for the next few moments a female or a t-gurl??? Wink wink.

OK, so, at the mall. Shopping for shoes......everybody does it including us "gurls". The real trick to "doing the mall thing" for t-gurls is to totally blend in and be just like the women that are there. They dress down and go totally casual for ... Continue»
Posted by tgurlusa 3 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 2527  |  
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The Developing of Emma part Three

She awoke to the sickly smell of a woman’s perfume; the silky stockings were still there, but Emma was now naked apart from a chiffon negligee, her hands bound behind her back. The voice of the woman broke the silence.

“Hello again ‘Emma’; that’s a very pretty name you’ve chosen for yourself, we shall soon have you worthy of being Emma, and you’ll soon know your place amongst men, and women.” The woman was sat with her legs crossed in a throne-like chair, no store clothes now, she wore a one-piece black leather bodice which accentuated her mature curves exquisitely, and black seamed panti... Continue»
Posted by midsummerman 2 years ago  |  Categories: Anal, BDSM, Shemales  |  Views: 530  |  
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When I Still Dressed Chaper II

We layed on her carpet fro a few more menutes than i started to suck her cock again going down here shaft to her balls back to her very beautiful ass hole. I was so hot from just cumming in mouth the was very horny and her cock started to get hard all over again she starts to moan over my ass hole side do you want to fuck my ass i said hell yes. So i raise up her ankles to her head which really opesn up her ass and slip right in she very hot and she looks so sexy. I get a rythm going in and out in and out she goes you feel just right now fuck me harder and harder i didn't ne any more erging i... Continue»
Posted by rafael0058 3 years ago  |  Categories: Anal, Shemales  |  Views: 421  |  
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A Soul touching story from my Beautiful Master, De

I come home, I'm wearing the suit you like me in, you always get so aroused seeing me in this suit, it's power, the lines, the way it d****s my masculine physique, it just speaks to the man I am and the man you love.

I'm tired, but you've been home all day, waiting for me, dressing up sexy, trying on different lingerie, you can't wait to see me. I perk up, my lovely sissy needs some attention. So I relax on the sofa, instructing you to crawl to me, your soft smooth ass cheeks rising and falling as you approach me like a lioness. I unzip, unfold my cock, and let you go to work on me, you nee... Continue»
Posted by Hotassboi 2 years ago  |  Categories: Fetish, Hardcore, Shemales  |  Views: 449  |  
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Xdresser Housewife Roxys daily chores while wife i

Well i must be the luckiest guy in the world ,my wife earns all the money so I stay at home to do all the house work and cooking .Now I've always wondered what it would be like to be a girl because women to me are so powerful when they are hot and sexy ,a women can get what she wants when she wants without even speaking as long as she has a sexy pair of platform heels on with a tight micro mini and a great set of tits that's enough to get anything from anyone ,if that isn't power what is ?
So this brings me to what I've been doing at home while my wife is at work .It all started one day when ... Continue»
Posted by foxxiroxxi 2 years ago  |  Categories: Fetish, Interracial Sex, Shemales  |  Views: 687  |  
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A Different Kind of Woman

As I was leaving work, a car stopped at the corner in the drivers seat was the most sexiest woman that I have ever seen. She had a pair of breast that was to die for, and legs that seemed to stretch for ever, and a smile that would bend steel. She saw me looking at her, probably with my mouth hanging open, she smiled and sorta of waved than drove off. I could not get her out of my mind, when I got home I jerked off thinking about her.
Two nights later I was at the corner waiting for the light to change, the same car pulled up, as I stepped into the streets, she moved forward just a little... Continue»
Posted by d4david 3 years ago  |  Categories: Anal, BDSM, Shemales  |  Views: 915  |  
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A Slut Is Born

There I was, one week before the end of high school. Going to college in the fall. Nice car, good f****y, friends. I had it all. So, what was I doing on my hands and knees in a video booth on the wrong side of town, dressed as a cheerleader with a cock in each hand, one in my ass and one buried in my throat?

It had all started a few months ago. I was locked out of my house in the pouring rain, and I went over to our neighbor’s to see if I could hang out with him until my parents got home. He was a cool guy, single, mid 30’s, worked for a software company, and drove a nice car. Had bought me... Continue»
Posted by MacDaddy714 1 year ago  |  Categories: Anal, Shemales  |  Views: 4546  |  
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Crossdressed bondage

She was proud of her position. Headmistress of the Finishing School for TGirls.

So many beautiful shemale girls had left her careful administration and gone on to happy lives, or sometimes porn careers. Sometimes they had been bought outright to be used as sex slaves, but always they had gone in the best possible way.

She smiled as she looked down at the latest batch. The youngest were 18 and they were often brought in by rich families that didn't know what to do with their very effeminate boys who had painted nails and lips.

The school was there to bring the best out in transgender... Continue»
Posted by davinna_lush 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 875  |  
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My First Bukkake

It was shortly after my 14th birthday and I had already discovered (at the tender age of 12) how much fun it was to have sex! Me and my BFF, Ashley, were always finding people to get naked and have fun with and we were ALWAYS together ;-) We quickly learned that we enjoyed wearing stockings and heels, wigs, makeup and sexy outfits, dressing up like whores for men. We quickly learned that we loved sucking cocks and licking balls. We learned that we liked having our blossoming, young bodies provide pleasure for men. But most of all...we learned that we enjoyed making men cum...older men...well-h... Continue»
Posted by cdsexslut 2 years ago  |  Categories: Group Sex, Shemales, Taboo  |  Views: 3343  |  
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The Making of a Sissy - Part Twelve

Bella tried not to look too downhearted as Sandy dropped the pretty sissy back at her Aunt Jane’s. She told her to keep her chin up, keep the phone well hidden and use it to call her whenever she liked, regardless of what time it was. Her aunt smiled wickedly at the now primly dressed sissy as she pulled her indoors.

“Well, you’ve certainly impressed Mr Roberts, and it’s nice to see you with your clothes on again. We are quite the little harlot now aren’t we? We’ll soon have you back down to earth; I’ve lots of chores for you!” Now it was sandy who was downhearted as she drove away fro... Continue»
Posted by midsummerman 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 771  |  
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Shemales- The Martini affair - Part 3 - finale

I could not stop thrusting back with my ass on her face as her tongue went crazy over my anal clit and tight bud. But I could not take it for long as I fell to the floor turning around to face her on my back. As if knowing what I had in my mind, she looked into my eyes and slowly took my cock throat deep in her mouth. Just as she did that I pulled her ankles and she knew what I wanted.

So very gently she moved her hips towards me and came over me with her glistening throbbing precum weeping cock right above my eyes. I took a moment to take in and enjoy that beautiful view. Then grabbing bot... Continue»
Posted by socuri 3 years ago  |  Categories: Shemales  |  Views: 447  |  
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Gloryhole

I have had a fantasy since college. I was in the adult viewing booth when I heard a tap. I loooked down at the hole and heard a womans voice asking if I wanted my dick sucked. Obviously I did, so I pulled it out and stuck it through the hole. At first it was just licked with some tugging on my balls. Once I was fully erect she took into her mouth. She sucked it with just her mouth at first. She then started working it with one hand while gently rubbing my balls with the other. I counldn't hold back any longer. I came with such intensity I thought I would pass out. It was the best blowjob I eve... Continue»
Posted by swordlvr69 2 years ago  |  Categories: First Time, Shemales  |  Views: 1720  |  
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My first time with a shemale



Let me tell you a little bit about myself I'm five feet 10 inches tall around
220 pounds, brown hair and eyes very muscular, I'm an ex-professional boxer.
Around 10 years ago I I was working as a bouncer erotic a nightclub in Fort
Lauderdale, when one night I heard a commotion in the parking lot. There were
several men beating up a beautiful woman, when I tried to break it up I ended up
getting very banged up myself.
Her name was misty, she thanked me for helping her and a... Continue»
Posted by palitro1 12 months ago  |  Categories: Anal, BDSM, Shemales  |  Views: 5182  |  
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Carl's Day Off

Carl hung up the phone with his eleven year-old daughter that currently live half-way across the country. He opened the refrigerator in the kitchenette of his 350-square feet efficiency apartment and quickly realized that he had absolutely nothing to eat save for a box of Arm & Hammer and three bottles Bud Light Platinum. He headed over to closet and pulled out his worn leather jacket. Thankfully, he had shaved earlier that Friday morning. He put on his black Converse Rapid Response CT SZ work boots that he generally wore during his long days.

The 39 year old, caramel-skinned man rushed to ... Continue»
Posted by faggyboi 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 3065  |  
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Sissy Emma is Turned Chapter 5

After that they let me go home.

Everything had been removed other than the cage which they said should remain on throughout the week to ensure my mind was attuned to being a sissy. Once home I showered myself completely and fell into a deep exhausted sl**p.

The following day I went to work and tried to act as normal as I could despite the fact that I was wearing stockings and panties underneath as instructed, not to mention having a butt plug stuffed up me and my 'sissy clitty' in a cage. All day the sensations reminded me they were there, the silkiness of the stockings against my hairle... Continue»
Posted by emmahighheels 1 year ago  |  Categories: Shemales  |  Views: 1367  |  
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