Shemales Porn Stories
Page 13

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 4 months ago  |  Categories: Anal, 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 4 months ago  |  Categories: Fetish, Hardcore, 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 4 months ago  |  Categories: Lesbian Sex, Gay Male, Shemales  |  
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Busted Wearing Panties Ch. 02

Tranny – boyfriend – bisexual – anal – strapon – step daughter – transexual – panties – crossdressing

I can't believe I am walking down the hall, wearing a black leather corset with matching panties, after my step daughter just fucked me in the ass with a dildo. I entered my bathroom, turned on the hot water in the shower, and slowly stripped out of my sexy clothes.

I stepped into the shower and soaped my body down. I poured liquid soap in my hand and rubbed it all over the cheeks of my freshly fucked ass. I ran my soapy hand down the crack of my ass and felt it still a little ope... Continue»
Posted by naughty_bi_interest 4 months ago  |  Categories: Anal, Gay Male, 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 4 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 4 months ago  |  Categories: Fetish, First Time, 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 4 months ago  |  Categories: Anal, Fetish, 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 4 months ago  |  Categories: Anal, Gay Male, 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 4 months ago  |  Categories: Lesbian Sex, Shemales  |  
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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 4 months ago  |  Categories: Fetish, First Time, Shemales  |  
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Experiences Of A Crossdresser

This is an introduction to my crossdressing experiences – touching upon highlights along my journey. I will write more about these, and other encounters in detail, in time. These really are all true stories, no embellishments whatsoever.

I had always been fascinated with women's clothing, specifically tights (pantyhose) and anything silky and sheer, like slips and sheer blouses. I would typically be drawn to anything black, but did have a fondness for nude tights and white slips, also.

I usually liked the 'mysterious and seductive' look. I wore mostly black – tight dresses or skirts, of... Continue»
Posted by naughty_bi_interest 4 months ago  |  Categories: Anal, Fetish, Shemales  |  
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A night with Louise....a very special "girl&q

Before telling about an evening of 'earthly delights' with a crew member on my boat, I want to say this story is dedicated to a new online friend, Zoe.

As I have mentioned in some of my stories, I owned and operated a 100' charter yacht in Alaska for over 20 years. My target audience could be any race, age, size, or sexual orientation. What they all had in common was they had to have the financial assets to pay top price for a 10-15 day trip with only 12-15 passengers.

One year I needed a crew member immediately and one was hired in Seattle one morning, and that afternoon he was landin... Continue»
Posted by 1kaaboom2 4 months ago  |  Categories: Hardcore, Shemales, Voyeur  |  
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The guy on the bus

I was not having a good day, my car was in the shop and would not be ready for three days.It was a fouteen mile ride home in the bus. I hadnt been on a bus in twenty years and was not looking forward to the journey. As I made my way to the bus station, I was aware of , a younger woman walking in the same direction. She had a nice ass and wore a shot skirt which showed off her long legs.
There were only a few passengers on the bus so I picked out a seat right at the back so I could stretch out and be comfortable. The same girl got on the bus and sat a couple of rows in f... Continue»
Posted by gjstott 4 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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Gideon

An old story of mine but you might enjoy it

Gideon

I couldn't believe my eyes when I saw the message and telephone number
written on the inside front cover of the book. I smiled as I recalled
the number of times I had idly opened these books in anonymous hotel
rooms on my business trips. It had started three years earlier when I
had joined the sales division for the company I worked for. I was
twenty-three and had never worked in sales before, but I was keen to
succeed in my new role.

I was going to have to adjust to quite a few new lifestyle changes, not
the least of which wou... Continue»
Posted by nikkiesilk 4 months ago  |  Categories: First Time, Shemales  |  
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Public Panty Change

Bisexual male - mmm threesome – crossdress - panties – bra

It had been a couple of months since I'd met and dressed up for my sugar daddy. He'd had a lot of money and was willing to buy me any outfit I wanted, along with panties and makeup for the complete girly look. In exchange, of course, I dressed up and provided him with an afternoon of hot sex that had left my little girly hole stretched and aching. So, when he contacted me once more and suggested another day of shopping, I jumped at the opportunity. I made the usual preparations: shaved my girly hole smooth and rinsed myself o... Continue»
Posted by naughty_bi_interest 4 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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Panty Fantasies - Coleen's Magic

Feminization - body change – gender swap - sissy - panties – satin – lingerie – cocksucking

He swallowed hard, his body tense with anticipation and admittedly a small amount of fear. He didn't _really_ know this woman and her beauty was no guarantee of her honesty. He was exposing himself as he had never done before, all in a desperate attempt to capture his dreams, to experience the most intense pleasures.

Looking around the bathroom he saw that it was finely appointed with grey and pink marble and fine Italian tile. The towels were Egyptian and felt wonderful. The whole penth... Continue»
Posted by naughty_bi_interest 4 months ago  |  Categories: First Time, Fetish, Shemales  |  
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meeting the girlfriend's f****y part 3

Ok guys and gals, in this part of the story Sarah finally gets completely naked around DJ. But there's a surprise waiting for him

I went to the kitchen to get something to get something to drink, I looked outside and saw Sarah laying down on a lounge chair topless but still sweatpants. I poured two glasses of lemonade an went out to join her. "Hey what are you doing?" I asked handing
her the glass of lemonade. she took the lemonade and placed on the table next to her. "Nothing just chilling" she said standing up. She grabbed my cock and rubbed it with lube until it was hard, she then turn... Continue»
Posted by kingdick97 4 months ago  |  Categories: Anal, Shemales, Taboo  |  
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Lesbian Date.

She walked through my door looking nervous, like a first timer. I didn't ask if that was the case. All I tried to do was be myself. I've always been a very welcoming person and this situation was no different.
I offered her a drink as she sat on my sofa knowing full well it normally cuts through the tension and uncertainty from my experience as an e****t.

I poured a drink for both of us and sat next to her offering a comforting smile. I knew she felt uncomfortable as she was in male mode and perhaps felt threatened as I wasn't. "I don't have a male mode" I said jokingly and assured her "I'... Continue»
Posted by Bombshell_TS 4 months ago  |  Categories: First Time, Lesbian Sex, Shemales  |  
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Back to School

Back To School
Nikkie Silk

I was so excited. This was going to be the first day at my new job. I had recently been appointed as the receptionist and administrative assistant at the local Elementary School. I set the alarm to wake me up early, so that I could get ready and make sure I would be on time. I was excited but also nervous. I had yet to meet my new boss, Mr Michaels, the Principal of the school. I had been hired by his deputy, so I would be meeting him for the first time today.

The State had just enacted an affirmative LGBT action hiring program. This meant that as a pre-op tr... Continue»
Posted by nikkiesilk 4 months ago  |  Categories: Anal, Shemales  |  
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Crossdresser Dominated For The First Time

Chapter 1: A Couple of Painters

One very long boring day in the middle of summer, i was home all alone, my parents were at work and my siblings out somewhere. I decided it would be a good day to dress up and have fun while i was home alone. I went to my secret stash of clothes i keep in my closet and picked out my purple lingerie. It consisted of a purple and black lace bra with matching thong and garter belt with black stockings. I put it on then went to get my cute blonde shoulder length wig, it fitted nicely as i applied my make up.

Once i looked like a sexy girly slut i... Continue»
Posted by Badassgirl123 4 months ago  |  Categories: First Time, Group Sex, Shemales  |  
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