Shemales Porn Stories
Page 7

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 1 month 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 1 month 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 1 month 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 1 month 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 1 month 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 1 month 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 1 month 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 1 month 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 1 month 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 1 month 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 1 month 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 1 month 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 1 month ago  |  Categories: First Time, Group Sex, Shemales  |  
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Submissive Crossdresser Dominated For The First Ti

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 1 month ago  |  Categories: First Time, Group Sex, Shemales  |  
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Daddy at the Truckstop - 1

--This was an encounter that almost happened with a Daddy a while back. We talked about doing this for a first meet to make up for other times that didn't work out, and while talking about it with him was undeniably hot, it ended up not happening for a few reasons, chief among them safety. I think about how hot it would have been to smash a lot of my boundaries this way, though. Enjoy, and comments welcum :) ----

I couldn't believe I agreed to this, but here I was. The truckstop is maybe an hour from my house, and I was pulling into it from the highway now, dressed in stockings, panties... Continue»
Posted by StaceyDeprave 1 month ago  |  Categories: BDSM, Gay Male, Shemales  |  
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DADDY AT THE TRUCKSTOP -2

Daddy guided my head with the leash as I sucked him. It had been a while since I had a cock in my mouth, so he only gagged me occasionally to get me used to it. 'Good, Stacey, mmm. You need more practice, but that's why you came today, right?' I could only nod and moan into his cock as he thrust it in again, gagging me. With my hands cuffed and locked behind me, I was helpless to his whims, just as we talked about. It was scary to be tied and exposed like this - dressed like a schoolgirl slut- in the woods next to the truckstop, but it was turning me on so much, too.

I closed my eyes, los... Continue»
Posted by StaceyDeprave 1 month ago  |  Categories: BDSM, Gay Male, Shemales  |  
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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 1 month ago  |  Categories: Anal, Gay Male, Shemales  |  
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My Ex-Girlfriend's Mom #2

I still couldn't believe all this was happening! I had just met up with my ex girlfriends mom randomly in a bar, found out she had a dick, (a big one at that), came home with her, given my first blowjob, received my first load of cum in my mouth, got caught doing so by my ex girlfriend, and found out she had a dick too! This had been one crazy night, to say the least! And it looked like it was about to get even crazier!

Jill looked amazing. Even better than I remembered. She must have had a boob job, because I remember her only having about a B cup. Now she had to be at least a D cup, proba... Continue»
Posted by naughty_bi_interest 2 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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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 2 months ago  |  Categories: Fetish, First Time, 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...

Gracie:
"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 2 months ago  |  Categories: First Time, Shemales, Taboo  |  
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