Shemales Porn Stories
Page 71

The Adventures of Georgina part 1 - First Time


These are the real life stories of a straight guy who becomes a sissy slut. Names and places have been changed to protect the not-so innocent! Enjoy!

Ok, who am I?

My name's George and I am a man in his early forties, living in a large town in rural England. I'm pretty normal really.

Physically I am slim and naturally thin-boned, 5'8" tall and 140 Lbs. My cock is what you would call a "grower" rather than a "shower". When cold it almost disappears due to shrinkage and when fully aroused, might make five and a half inches. I'm told that's average, but I think I'm on the small side! I... Continue»
Posted by 5155y 8 months ago  |  Categories: Fetish, First Time, Shemales  |  
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Being a Wife: Part 1 The Wedding Night, Planning t

My name is Lexi. I am a 6 foot tall leggy blonde, with a natural round phat ass, a regular sized dick, natural b-cups. My skin is milky smooth, my hair is shoulder length, and I am a total sub.
My partner is Jenna. She's six one, brunette with green eyes, long hair, big double D breasts. She's white, and has an 8 inch long cock that I adore.


I was stroking my wedding ring with my freshly french manicured fingers, sitting on the side of the bed when Jenna walked towards me and said "Hey Wifey?!". She was stunning, tall, sexy, in charge. she had stripped down to a black satin night gown t... Continue»
Posted by alexismorel 8 months ago  |  Categories: Lesbian Sex, Shemales  |  
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A Close Encounter Of The...

Two guys hook up with shemale.

Bisexual male - anal – threesome male – transsexual – shemale – shemale oral – shemale anal – blowjob – tits

Another great tape and another great yank of the crank. Yea, she-males were pretty hot, Tom thought as he hit the eject bottom on the tape deck, but where on earth would he really find one? He had little doubt that if he did find a place where they hung out that there would be more than a few with a serious case of ugly. The chances of finding one like the ones in the video taped he had just been watching was pretty slim. But, he knew if he n... Continue»
Posted by naughty_bi_interest 8 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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Busted Wearing Panties Ch. 01

panties – bisexual – strapon – submissive – stepdaughter – bi sex – caught – dom – crossdressing – nylons

I went through forty-five years of my life as a single man, no one to answer to but myself. I watched my friends marry, have c***dren, and get divorced. I kept hearing the same old stories, 'money problems', 'she wasn't the same in bed after the k**s came', 'we are too tired because of the k**s', and the best of all 'we fight too much over money and the k**s'. I would just listen and laugh in my head at them. Then I met Emily. Emily was just your average sized woman on the outsid... Continue»
Posted by naughty_bi_interest 8 months ago  |  Categories: Anal, Fetish, Shemales  |  
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Exploring My Husbands Sweet Tight Little Ass

Several months back my husband & I were having some intimacy issues & we just weren't connecting sexually like we used to......but that all changed over night a couple weeks ago. We had decided that this rut we were in was going to end one way or another & so we made plans for the upcoming weekend & booked an expensive 5star suite at a hotel for the entire weekend. Well we still had to make it through the week before our little get away. So we went about our normal routine getting up in the morning & going to work & then coming home & eating dinner together......you know all that normal every... Continue»
Posted by AryanGoddess_1488 8 months ago  |  Categories: Anal, First Time, Shemales  |  
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Red Handed by a Nanny Cam (Lilia) PART 2

(as the fantasy continues with Lilia...)

We were out of tequila, and there were only couple of blocks away a small 7/11 store. I pulled my pants up, put my shoes and decided to go.

Lilia decided to come with me, she was making sure I was not going to escape from her.

She is panty less and that was driving me very locaaaaaaa.... I was comando too.

We held hands, not a word was said, we were buzzing but still in control. Got the store and bought 2 bottles and some chips for the munchies...

She told me, "why dont we go to your house? We are closer."

I agreed.

Reache... Continue»
Posted by ilialenyc 8 months ago  |  Categories: Fetish, First Time, Shemales  |  
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My Feminine Side


gay – lesbian – feminization - cross dressing - panties - oral sex – blow job

I just want to get this out of the way first, before anything else. I am a dude - 100% male. I just like dressing up in girl's clothes.

I'm actually a much better looking girl than I am a boy. Dressed in sexy clothes, with makeup on and my hair done, I make a very pretty, very sexy girl. I'm thin and I have long legs that look great when I shave them and I have heels on. Guys hit on me all the time when I'm dressed like a girl, and I love the attention. As a boy, I'm simply ordinary. Average looks, ver... Continue»
Posted by naughty_bi_interest 8 months ago  |  Categories: Lesbian Sex, Gay Male, Shemales  |  
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The Adventures of Georgina part 2 - Missing &

I hope you enjoyed part 1 of my story, in which my female alter ego, Georgina sucked her first cock.

If you read through to the end, you will remember that Jeff had left me, used on the floor of my house, having well and truly fucked my sissy face.

In bed that night, wearing my satin nightie, my hand rubbed my little sissy clit as I recalled the events of the last few hours. Wearing a nightie is so much more feminine than pyjamas. I love the way it rides up your thighs and gets twisted about as you move in your sl**p. It's far more sensual than being naked. It reminds you how feminine yo... Continue»
Posted by 5155y 8 months ago  |  Categories: Fetish, Hardcore, Shemales  |  
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Busted Wearing Panties Ch. 03

tranny – bisexual – anal – strapon – busting cherry – lingerie – mmf – seduction – first time – threesome

I was in a deep sl**p dreaming about Jessica and Chris, our naked bodies intertwined. I wanted to play more but the ringing in my ears kept getting louder and louder. My eyes flew open as it registered that the phone was ringing. I sat upright in bed and fumbled for the phone on the nightstand.

"Hello?" I managed as I put the receiver to my ear.

"James did I wake you again? My timing is perfect isn't it?" A smile crossed my face as I heard Emily's voice.

"You did, but it... Continue»
Posted by naughty_bi_interest 8 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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Frannie's Femboy

Gay - cross dressing – femboy - feminization – blow jobs – anal sex – hand job – lingerie

When I was finishing high school, I did a lot of different jobs to raise money. I mowed grass, worked part-time on a construction crew, and pumped gas, all to raise funds for college. I had been accepted to the college of my dreams on a partial wrestling scholarship, but my parents weren't going to be able to help with the other expenses. While I hoped to eventually turn the partial scholarship into a full one, I was doing everything I could to raise enough money to avoid missing a year.

In a... Continue»
Posted by naughty_bi_interest 8 months ago  |  Categories: Anal, Gay Male, 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 8 months ago  |  Categories: First Time, Fetish, Shemales  |  
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PANTYHOSE SANTA and LYCRA POLLY


They didn’t need to advertise the job for Santa’s helper. I already offered my services. Since I was fairly popular and I could provide my own costume, a skintight green catsuit, my copper wig and boots, my supervisor went for it. I must admit that my main motivation was that I would be paid to wear a skintight costume, and hopefully get a few curious glances at my ass and body in the shimmery material!
The Santa for the job was some retired security guard called Alfred who used to work at our store, who a few times I served pantyhose to in the pretext that they were for his wife. In fact ... Continue»
Posted by leotardlust 8 months ago  |  Categories: Fetish, Shemales  |  
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sl**ping With The Enemy

sl**ping With The Enemy
The present day…

The wedding party was in full swing now and I anxiously scanned the guests to see if everybody was enjoying themselves. The noise levels had risen in line with the amount of drink being consumed, so I guess that was a good enough proxy for enjoyment. I was holding a glass of champagne in my perfectly manicured fingers and as I took a sip I caught the eye of my new husband who had been buttonholed by two of my aged relatives. His eyes pleaded at me to rescue him but I simply grinned and raised my glass to him; I would leave him there for a while to t... Continue»
Posted by nikkiesilk 8 months ago  |  Categories: Gay Male, Shemales  |  
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The secret exchange (Sarah)

"Your wife told me you were a crossdresser 12 years ago, still doing it?" Sarah asked me.

Very calm, I sip my coffee and answer, "Yes."

This is how this story got to this point. Sarah has been friend with my wife for about 14 years, out of college they met in the bank they both used to work. They became very good friends. Thirteen years ago I met my wife, she did not know about Iliana, back then I was just trying to be myself with my then girlfriend and one day I decided to let her know about my closet life style.

To my surprised she reacted very well, she asked tons of questions ... Continue»
Posted by ilialenyc 8 months ago  |  Categories: Fetish, Masturbation, Shemales  |  
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The Biograph Cinema

I visited the Biograph Cinema in Victoria London in the 70’s as a fairly naïve teenager, who ended up m*****ed. Shame the place closed, I was enjoying being fiddled with by dirty old men.


The Biograph was clearly the haunt of the Dirty Mac Brigade, and all of those sorts of men my Mother had told me to watch out for. Aged 18 I’d never even kissed a girl let alone had someone else make me cum. So, I was drawn back to the place. Like any teenager I wanked at least daily, but the previous episodes had become my favourite wanking material and I just had to go back for more.

A week after m... Continue»
Posted by Vikkinylons 8 months ago  |  Categories: First Time, Mature, Shemales  |  
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DADDY AT THE TRUCKSTOP - 4

Daddy at the Truckstop - 4

The van didn't have many windows, but there wasn't a lot to see anyway where I was. Tucked neatly in a cage, my wrists and ankles were chained to the bars, and a ring gag kept my mouth open, at first drooling a bit, but over time my mouth started to become dry. The vibrating plug in my asspussy didn't slow at all. I could feel the bumps of the concrete as Daddy sped down the freeway, and I had no way of knowing how far he was taking me from the truckstop. Was it 30 minutes? 45? It was hard to say. At first I was filled with shame and fear after Daddy made m... Continue»
Posted by StaceyDeprave 8 months ago  |  Categories: BDSM, Gay Male, Shemales  |  
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A Reluctant Gang Bang

byTonyaTV69©

This story was stolen and posted here by a LIAR claiming it was theirs but I am the real author and they were just a cheap barely literate FAKE!!!

Hi all! I have been cross dressing and playing with men for many years now. One of My first experiences was being gang fucked by about 9 guys at an adult arcade. I was 18 at the time and it kind of traumatized me as it was pretty much a gang **** at an adult arcade. I was dressed up in a white flowered sundress panty hose and white strap on high heeled sandals all borrowed from my older s****r. I had my make up done up just ri... Continue»
Posted by Tonyatv69 8 months ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  
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Tranny Motel

Tyrone and Kimberly Woods kissed as all of the guests at their house party cheered them on. It was their first anniversary and they were celebrating this night with f****y and friends. There were close to forty people in attendance – most of whom had brought some form of alcohol and all of whom had brought a gift. There was great music and excellent barbecue as Kimberly’s dad and Tyrone’s uncle manned the grill. Folks were laughing, dancing, and having a great time. In one corner of the yard, there was a game of dominoes transpiring. Next to it, a foursome was playing Spades.

Several minute... Continue»
Posted by faggyboi 8 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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A Very New Year

Sometimes things happen unexpectedly. Those words describe my entire New Year's Eve. My night started with me downtown. Now ordinarily I wouldn't step foot downtown on New Year's Eve if I could at all avoid it. The place becomes a zoo of d***ken bafoons and desperate revelers. But through an unfortunate series of events I found myself behind virtual enemies lines too late into the day this New Year's Eve. Many of the roads had already been blocked off and those that weren't were highly congested with the other like minded people that would give anything to be out of here before things got too ... Continue»
Posted by rhyze 8 months ago  |  Categories: First Time, Shemales  |  
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Cockatoo Part 1

Cockatoo


Nikkie Silk


It’s a cliché, isn’t it? Man comes home early and finds his wife in bed
with someone else. Only slightly less of a cliché in my case, as the
‘someone else’ was my wife’s closest girlfriend - closest in every sense
of the word.


It was a quick divorce; no k**s, only a rented flat, so the only
squabbles were about books and cds. In the end I told her to keep the
lot. I wanted to make it a clean break. I managed to fit all I owned
into the boot of my small car. I was 28 years old, fit, healthy and with
a good but frankly boring job in a software company j... Continue»
Posted by nikkiesilk 8 months ago  |  Categories: First Time, Lesbian Sex, Shemales  |  
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