Free Shemale Stories

My cross dressing journey

I am a man who likes to cross dress, currently single and living alone in Beijing. I like to dress up as a woman and go out, passing through every street, entering nearby shopping malls and supermarkets, as well as the women's restroom inside, and live streaming on a live streaming platform. I also ... read more

boysgirls February 15, 2024 100%

Next time fucking her cross dressing husband and bred his wife

Wachenheim dressed up in a pretty skirt and loose blouse with his wife watching walked up to and knelt between my legs. He sucked my thick long black cock. His wife watched and masturbated as he worked my cock deep in his mouth. She knew as soon as I did him that she ws next. It was her wishes for t... read more

Rocky Wachenheim September 23, 2014 68%

A Downtown Moment

I had reason to head downtown for a meeting with some industry colleagues and after my meeting I dropped in to see a friend of mine who I used to work with. Loretta and I worked together for about a year on similar project as contract workers, I moved on to other things and she stayed with the compa... read more

shemale lover February 28, 2012 100%

First Time Buying Lingerie

As a youngster, I couldn't help but notice the carousels of hosiery on display in various shops that my mother would visit. Displays of stockings and tights (pantyhose) for the discerning housewife. Brands like Pretty Polly, images of nylon clad legs on the glossy cardboard and a see through window... read more

Daddybear71 September 13, 2023 100%

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%

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%

Janine awaits

My story is not typical. Sure, it mirrors many of the others you’ve read except for one aspect, that is my age. I recently celebrated my sixtieth birthday. Yep, the big 60. And not that I am trying to brag but I am one of the sexiest bitches around. As recently as five years ago I looked like any ot... read more

bunny cat February 4, 2019 83%

Shemale Porn

Nowadays, I masturbate exclusively to shemale porn. Like most guys, I started out reading, then watching, straight pornography. Sure, there was the titillation of happening across a cross-dressing tale in the glossy flesh mags, but they were for a ‘straight’ readership, and didn’t quite scratch that... read more

Daddybear71 May 24, 2023 100%

Steve to Stephanie Chapter 1

This is my first attempt at a longer story with deeper characters and a more evolved story line. Stay tuned for the next chapter. As always comments are welcome. * Steve was mild mannered guy with a big secret. Steve was an avid cross dresser, very bi actually leaning towards being gay. Steve... read more

shemale lover January 29, 2013 100%

HOW MY AUNT AND SISSY NEPHEW CHANGED MY LIFE FOREVER! (fictional

It was the very first night of my month long North Carolina July summer vacation stay when my Aunt Meg suddenly entered the bedroom that I was temporarily sharing with my younger cousin Rudy. Being so openly effeminine in his body language,voice and looks, I had already planted such dirty thoughts ... read more

CDDIXIE4U January 8, 2019 91%

It had been a while...

The first time I dabbled with cross-dressing was as a horny teenager. I discovered my grandmother’s vintage collection of lingerie, and I had to know how it felt to be encased in girdles, basques and corsets, to feel the taboo delight of having my legs encased in sensuous nylon, to figure out how to... read more

Daddybear71 October 12, 2023 75%

Planting Trees

Jacky peeled her sweatshirt over her head, looking toward the sun, squinting. "Hot day." Kevin treated himself to a quick up-down. "You're looking sweet in your husband-beater." "Thanks," she answered flatly. "I live to have my eye candy status affirmed.&qu... read more

shemale lover September 2, 2012 0%

A Win-Win

A Win-Win By Sabrina G. Langton *** Author's Note: Hi, just a quick, crazy story about a wife actively participating in her CrossDresser husbands sex life. Just a bit of fluff, hope YOU like it.) *** We were laying in bed, sex was done, my wife could now relax for the rest of the month ... read more

Brina Giselle March 31, 2024 100%

Crossdresser Caught in Act

I do not consider myself gay, nor do I think I am bisexual, but I do enjoy a nice big cock. I am not attracted to men at all and under normal circumstances find any and all homosexual activities quite disgusting, until I get really horny that is. When I get all hot and hard, I can't help but want a ... read more

shemale lover March 31, 2012 100%

SUMMER VACATION by Spanky de Bautumn

In our house, it was a well-known secret that my mother kept her change in the top drawer of her dresser. The same drawer she kept her slips, chemises, panties, and all other satin, nylon, or lacy ladies undergarments. During the summer, my brother and I would run to that wondrous drawer when... read more

SpankydeBautumn January 22, 2021 84%

Biker Boys Replacement

Last week I met my old friend Mike for a farewell drink at our favourite bar. Mike's decided to jump on his trusty hog and head to Europe for a year long tour. After quite a few beers Mike told me about a hot cross-dressing mistress he'd met through an advertisement he'd placed in a contact mag. He ... read more

shemale lover June 12, 2012 66%

On School Grounds

It’s amazing how good the cloth feels against your bare skin. I had never thought of myself as anything but a straight and regular Joe. I didn’t think that I’d get a stiffy wearing woman’s clothing like this. I looked at myself in the mirror, just to see if my padding was ... read more

shemale lover September 5, 2012 75%

Becoming a Drag Queen

I was thrilled when my boss told me he was sending me to San Francisco for a conference. It was a location on my "Top 10 places I wanted to go". I went online and Googled the major attractions and tourist "must sees in San Francisco. The conference was Wednesday to Friday and I figure... read more

shemale lover March 1, 2012 90%

Karen, My School Teacher Part 4

Meeting my other teacher By FoxyHosed Next morning as I woke up, I jumped in my clothes and got myself a coffee, and went to school. I got in 15 minutes early because I didn't want to run into Karen. As I entered the door to the school, I saw some of my classmates. I thought the coast was clea... read more

FoxyHosed February 17, 2021 100%

I Give Up

The following story is the first of four parts of a tale that explores the theme of transformation. It is thematically similar others that I have submitted but has a larger narrative arc. I hope you enjoy reading the first portion, Act One & Two. I continue to work on better editing and someone h... read more

ASSEaster5678 September 14, 2018 100%