Shemales Porn Stories
Page 72


It Started With Tattooed Eyeliner

"We settled on black, right?"

"I'll leave it up to you," I said. Lynn began organizing her bottles and
tubes, preparing the ink for the tattoo machine she used for applying
permanent makeup. In this case, she would applying permanent eyeliner to
my upper and lower eyelids.

"Good. Black is basic. Now, we never really settled on what style. There
are a lot of things you can do with eyeliner, and you've specifically
asked that I not take into account your being a male. Is that still what
you want? This is the last chance to change your mind."

"Y... Continue»
Posted by klammer 5 months ago  |  Categories: Fetish, Shemales  |  
  |  1

Yesterday we went shopping...

Yesterday we went shopping.

Master Silk had decided that my undies were dowdy, and my heels not high enough, so we went shopping. Naturally, we shopped in a town not too local to us - we didn't want our cover completely blown! (OK, it was Bath! Lovely tea shops in Bath!)

I wasn't wearing my sissy outfit - I'd not convince anyone! But I was wearing tight jeans to show off my bum, and a girly blouse. A dog collar around my neck was disguised by a pink silk scarf. Our first shop was good old Marks and Spencers, a stalwart of the British high street. M&S may have an old fashioned imag... Continue»
Posted by sissy_jenny 5 months ago  |  Categories: Anal, BDSM, Shemales  |  
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Gracie and her best friends son...

Gracie was attending a birthday party at her friend Rachel's house, who's son was turning 18...

"I've known Rachel for more ten years now and she is one of the few type of friends who actually stick around. It felt as if not too long ago I was turning 18, but I was now in my early thirties and Rachel probably felt old too now that she was was nearing forty!... But anyways let's continue with the story...

There was plenty of alcohol available, for those in the appropriate age range of course, and Rachel loved her drinks whenever the occasion called for it. I was the only other f... Continue»
Posted by adblman 5 months ago  |  Categories: First Time, Shemales, Taboo  |  
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Wet dream PART 2

Driving to my place it was a conflict, I was totally wet and my companion I bet she was too.

Olga was my co-pilot and could not help to notice that she was day dreaming, I looked at her and under her glasses I saw in her dark sparkling eyes that she wanted something. Her imagination was running wild.

We came to a traffic sign and she in a sudden move got into my crotch, unzipped my pants and let herself into my manhood, moved again my thong and .... I had to go, the light was green, this little brat got me again!!!! We took the highway and she was kissing and pumping me at 90kh.
... Continue»
Posted by ilialenyc 5 months ago  |  Categories: Fetish, First Time, Shemales  |  

My Ex-Girlfriend's Mom #3

The three of us were laying in Lana's bed, recuperating from an awesome sexual experience. Or at least awesome for me. I could only imagine what kind of sexual experience these two beautiful, busty, extremely hung ladies have had. Lana, the "mother", very sexy for an older woman, with a ten inch cock. And Jill, the "daughter", a knockout in her prime, with a twelve inch cock!

We talked about what we had just done. They told me I was a natural at sucking cock and couldn't believe I had never done it before. But it was true. I told them I had only had sex with real girls before tonight. But f... Continue»
Posted by naughty_bi_interest 5 months ago  |  Categories: Anal, Gay Male, Shemales  |  
  |  8

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 5 months ago  |  Categories: First Time, 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 5 months ago  |  Categories: First Time, Fetish, Shemales  |  
  |  6

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 5 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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An old story of mine but you might enjoy it


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 5 months ago  |  Categories: First Time, Shemales  |  

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 5 months ago  |  Categories: Hardcore, Shemales, Voyeur  |  
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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 5 months ago  |  Categories: Anal, Fetish, Shemales  |  

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 5 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 5 months ago  |  Categories: Lesbian Sex, Shemales  |  

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 5 months ago  |  Categories: Anal, Gay Male, Shemales  |  

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 5 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 know all that normal every... Continue»
Posted by AryanGoddess_1488 5 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 5 months ago  |  Categories: Fetish, First Time, Shemales  |  
  |  2

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 5 months ago  |  Categories: Anal, Gay Male, Shemales  |  
  |  10

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 5 months ago  |  Categories: Lesbian Sex, Gay Male, Shemales  |  
  |  5

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 5 months ago  |  Categories: Fetish, Hardcore, Shemales  |