Free Shemale Stories

Masturbation fantasies: Amanda, queen of the peep show

A guy visits a peep show with unexpected results. As he gets to watch a girl with something special, he discovers his hidden desires. This story contains: peep show – voyeur – gloryhole - fake tits – group masturbation – male masturbation – shemale – frottage - titfucking When William finall... read more

ThatEroticWriter July 24, 2019 91%

Masturbation fantasies 2: Looking for Amanda

Previously: William, a young lawyer who has no luck with women, decide he needs some relief from a live girl. Scared of going with a prostitute, he decides to try out a peep show first. Without knowing that the stripper he chose is kind of special, he ends up in a show with a shemale called Amanda w... read more

ThatEroticWriter July 24, 2019 100%

Masturbation Quiz

Basics: Are you male or female? male Age? 35 At what age did you start masturbating? I think around 11 years old How many times a week do you masturbate? nearly every day How many times do you orgasm each time you play with yourself? one Where do you masturbate: In bed? rarely In the showe... read more

Betas84 January 27, 2020 100%

BANGING AROUND BANGKOK

BANGING AROUND BANGKOK: THE AMOROUS ADVENTURES OF CAITLIN "MEOW" MORRISON after living and working in Thailand/SE Asia for many years i decided to write an erotic story based on some of the people i have known, venues and places i have been, and the P4P night-scene where i spent way too much... read more

bkkldby June 17, 2019 85%

Camming Down the Rabbit Hole Ch. 12

We woke up many hours later, still intertwined, my morning wood throbbing as Ellie slid inside my panties and wrapped her hand around it. This was a much better way to wake up than usual, and we proceeded to have a really relaxed slow fuck. She reached a much more low key orgasm but I knew I wouldn’... read more

Dani_does_Dallas May 9, 2022 100%

Transsexual Savage

John had walked for eleven days. He was headed towards Fort Winston at the Hiat River, and he still had about three days ahead of him. The Hiat River was the natural border that separated the civilized world, where he came from, and the savage and brutal wilderness, where the natives lived and pract... read more

Anal Orgasm July 10, 2020 80%

HOW ONE PEEPING TOM MORNING TURNED ME INTO A SHEMALE SISSY BITCH

It was while cutting across his back trailer park lawn around 7pm on misty July Saturday evening, when I first discovered that Mr. Parker was really a fag. How else could you describe a man wearing a long blonde wig on his head while below he wore only a large somehow stuffed pink lacey woman's bra ... read more

CDDIXIE4U January 8, 2019 100%

I got anal creampied at the beach!

As soon as we got onto shore, I knew it was the perfect place. The hot sun was beating down on us and my body was tense with anticipation. Finally, we were going to be alone out in the wilderness with nobody around and could enjoy each other thoroughly. My hunky date and his monster cock were going ... read more

Madison Heights December 1, 2022 100%

The best of two Worlds Part 4

After our adventure on the beach Jacqui had a moral and physical hangover for a few days. She would do things to me that went beyond my expectation. She was absolutely fascinated with my cock, giving me head jobs the moment I walked in to the door. Upon my arrival home I would find her half naked, h... read more

shemale lover April 26, 2012 100%

How I sucked my first shemale cock

It was the beginning of the year 2023, in January, three days after New Year's Eve. I was driving home in the morning from a party 100 miles away from my hometown. On the highway, after going half the distance, I received a notification from my dating app, and I was like, "Oh, a new match", I'll che... read more

cock&heels69 May 25, 2023 100%

An Evening's Pleasure in Plastic Panties

Dear RubberPanties I have enjoyed wearing plastic panties for many years now. Although I don't have any at all the moment, I'll be ordering three pairs next week as a little Christmas present to myself. After the ones I'd had for a several years began to fall apart, the replacements I bought were... read more

shemale lover December 22, 2011 66%

Devastating and dominating

Tracy drove the black SUV with her friend Miss K in the passenger side, both of them struggling not to be bored to sleep with the monotonous countryside I-64, the scenery broken up only by the occasional road sign or truck stop. The Madonna CD thumping in the stereo helped matters though, the t... read more

shemale lover January 29, 2012 50%

Be My Bitch

After a long day at work, I get in my car, and look forward to the long drive home. It gives me time to unwind and relax. I try to forget about the hectic office and concentrate on my beautiful girlfriend waiting at home with that warm smile that she greets me with when I get there. However, tod... read more

Go Balls Deep or Go Home August 6, 2018 66%

My Awkward Phase

My Awkward Phase ©Alexandra Rios 2019 The greatest lie is that what happens in high school doesn't matter, because life begins in college. I pretended to agree, although I never believed it, for I was the world's greatest liar. Wannabees I was hanging out with my friends Quinn, Barb and Anne ... read more

the greatest liar June 14, 2019 85%

Camming down the rabbit hole Ch1

Back in January 2020 I guess I was lucky, I did have a regular job although the pay was miserable and I did have my own place. On my wage all I could afford was a miserable bedsit in a neglected part of town, but on the upside I didn’t have to flat share and it worked well enough for me. The west... read more

Dani_does_Dallas August 11, 2021 100%

Lady Regina

I know that many say that I I’m a coward because I am comfortable living in the closet as a part time female and not expressing my special female side completely. My friends all tell me to go out and have fun and not worry about what people say or think. In spite of that, and because of the prudish... read more

Regina10 July 1, 2022 50%

The Making of Erica - Sperm Loving Crossdresser

Confessions of a Crossdresser I am a crossdresser. It is an addiction. I’ve tried, but I really can’t stop myself: fantasies, endless looking at pornography, shopping, dressing, masturbation, and inevitably, seeking men to please. I have only sucked cocks, but over a hundred at my las... read more

shemale lover September 3, 2015 84%

Dead Ends

* * * My job is simple: I'm a masseuse (code word for prostitute). It used to be fun, too, but, after a while--well, let's just say the thrill is gone. I mean, how many cocks can a girl suck or fuck until the novelty's worn off? (In my case, I reckon the number at about 3,000.) So, I don... read more

shemale lover January 27, 2012 50%

David to Dee

"Dave," she purred, "you know you can tell me anything. Surely you know you can trust me not to judge you by your fantasies." He was squirming under her touch, his eyes tightly shut, trying to avoid telling her his deepest secrets on the one hand, and on the other, hoping beyo... read more

shemale lover July 29, 2012 100%

Wild after-hours for a working... effeminate crossdresser

Left work after-hours, cross-dressed underneath w light lingerie & lots of colored little tattoos I draw myself over my hairless body. After drinking lots of spirits on my way home, arrived at my neighborhood park late at night & felt like wishing to be ..... badly abused! I got rid of the... read more

Alexia Pikara September 7, 2011 100%