Free Shemale Stories

A Perfect Pandemic: A Transsexual Transition in a Troubled Time

A Perfect Pandemic A Transsexual Transition in a Troubled Time A Novelette by Alexandra Rios Text Copyright Reserved © August, 2021 Dedication Transgender Day of Remembrance is a solemn occasion. I am offering “A Perfect Pandemic” for free as an antidote to the fear, phobia, discrimination, d... read more

the greatest liar November 16, 2021 100%

Group Sex

Jan and I have been together now about 4 years but known each other since High School. We are both in our early fifties. We had met a transgendered girl (Gabby) about a year ago and we get together about once a month and enjoy each other’s company, going out playing and having intimacy together. Gab... read more

Jon Paul April 19, 2021 80%

My TV Sex Adventures Hot time in the Gurl&#

After sucking off the custodian of the offices next door I went back to the club. I was seriously disappointed. I loved how big and hard his dick was and I really wanted a serious cock like his to fuck. I got back into the club with only a knowing grin and a chuckle from the guy at the door. He was... read more

shemale lover July 5, 2012 100%

Florida TG Experience

I had known Jan from High School, we always had an attraction for each other but were dating someone else or married at the time. Jan had actually married a friend of mine and I was envious of course. She at that time had sandy blonde hair, and a body to die for. One evening we had them over for dr... read more

Jon Paul August 13, 2018 100%

Vanessa gets more than she bargained for!

Vanessa had it all planned out meticulously. She had taken the day off and planned on doing a bit of last minute shopping before checking into the hotel in the early afternoon. She eventually decided on buying a massive dildo to get her ready for the party. This would give her plenty of time to take... read more

Vanessa Luv May 15, 2020 100%

Steve

So on AFF, I used to be gold but guys will just hit you up, sooo I got hit up by an 8in boy. Wasn't sure I'd want to prep up an 8 so I didn't get all ripped up, but nice profile and a fucks a fuck sometimes. What to wear to get cum in tonight? Still pretty warm, I'll go mini with tighter leotard (mo... read more

smtmsbrianne September 16, 2020 100%

MY Party Favor Fantasy

My Party Favor Fantasy A fictional story built around an old fantasy of mine I ran a notice on one of those sex sites that said” Help me fulfill my fantasy and I bet we take care of some of yours also. Hi there, I am Penny and I am a total bottom trans w... read more

pennypenny January 8, 2019 92%

Totally dominated

I was out walking one night, a walk i used to make with my girlfriend. We had just broken up a few days ago. I don't know why I was walking here again, the memories weren't good ones. She had cheated on me with my best friend. Anyways, I was walking this familiar path through the city streets when I... read more

shemale lover October 27, 2012 100%

The four of us

Jan and I have been together now about 4 years but known each other since High School. We are both in our early fifties. We had met a transgendered girl (Gabby) about a year ago and we get together about once a month and enjoy each other’s company, going out playing and having intimacy together. Gab... read more

Jon Paul August 2, 2021 100%

Making my CD slut fantasies become real

Having an open mind and saying yes to a TS friends' idea has lead me to discover things I never even knew about myself. I’ve always been into kink, but my adventures as a CD have shown Me that I have filthy perverse cravings to satisfy with people I’ve yet to meet. I enjoy transsexual escorts and th... read more

pinkybrown666 May 20, 2021 100%

Towel Boi: Heading to Work

“Goddamn, white boi! You got the best fuckin’ ass,” declared the father of two. His steel manly form perspired as he moved hard into the bottom. “Look at all that butt shake! Twerk it for me, baby boi!” “Yes, sir,” cooed Kasey, gyrating rhythmically. “Hell yeah! It’s like fucking two big ol’ ma... read more

Faggyboi and Puzziboi November 17, 2023 50%

Freak House Superstar Come Fest

Kiki and Ty Blaze were doing their thing. They were living on their love and passion, literally. The couple had taken their love, passion and desire to please one another and turned it into their livelihood. They had become stars in the world of underground porn. Their production studio, Nasty Nigga... read more

shemale lover February 1, 2012 50%

badbadboi's walk in the park

...My boi hole was freshly washed, shaved and lubed with a lovely hot shower, my wand is perfect for cleaning my pussy, flushing it clean very time, I luv to let the water spray my hole driving deep enough to tickle the bottom of my prostate. My cock cage locked in place, my white crotchless panties... read more

badbadboi667 April 6, 2021 100%

Fucked By BBC pt 2

It has been 3 weeks since I became a bbc cocksucker, since then I have learned to enjoy the taste and the feeling of a cock in my mouth. I have also learned the guys name on the 2nd day of being used by the guy, his name is Darren. One day while I was at Darren's giving him a blowjob he tells me ... read more

kinkyguy18 November 3, 2023 100%

Interracial Sissy Story

(Some prior notes about me, this story and my writings: If MALE bisexuality, crossdressing or interracial sex bother you, don't even bother reading this further, much less commenting. Many have had secret fantasies about what it would be like to be the opposite sex, during sex. Some of my influences... read more

shemale lover May 1, 2015 93%

PF's Black Romp and JoyceLynn's Awakenin

When my wife and I first met, our sex life was fantastic! She was a very sexual lady and always made herself available. She usually wore stockings and garter belt or thigh highs, high heel sandals, and something that was sexy and suggestive. We made love and had sex in every room of the house, inclu... read more

shemale lover May 17, 2012 83%

CD and BBC Gangbang 1

My name is Mike, as a "Gurl" I go by Fiona. I am a gay man, mid thrities, white, 5' 9' 165, reasonably handsome, both in and out of women's clothes. One of the ways I express my sexuality is to dress as a woman and get fucked by other men. Preferably in a humiliati... read more

FionaFucked October 27, 2014 94%

vince

been gang banget by a group of bikers on my way to vegas..it was like 2.15 am when i pulled of the 15fwy to take a piss because it was hot and i was driving naked got out it was a dirt road and i walked to the bushes and started pissing when all of a sudden a bunch of bikers were rite at my truck i... read more

ima satisfer June 3, 2020 40%

Gangbanged at the beach

My BBC friend took me to the beach, where people make sex. We arrived in his van. I was in the back of the van, chained blind folded, with my mouth wide open and a huge horse dildo in my sissy pussy. Suddenly I hear the van door opening. I hear many voices of other men. My BBC friend was telling oth... read more

brunasissyslavedolrj May 9, 2022 100%

Tight Spot

XtinaSmith2017 Cody bit his lip as he looked over towards the shop, a little anxious about their planned endeavor but not wanting to come off as uncool to his friends, "Are you sure this is a good idea?" he asked. His friends grinned and laughed, playfully nudging him as they made their way ... read more

Gwapo67 July 22, 2022 100%