Free Shemale Stories

A Fetish Doll For Mommy

There is a very old saying," Be careful what you wish for because you might just get it." My fathers name had been James Bradley. He had been a CEO of a top Wall Street investment firm. My father didn't climb to the top by being a good guy. He was a total prick who would stab anyone he had... read more

shemale lover November 13, 2011 100%

A Secret Fetish Chapter 1

When teaching a section of my favorite class, "Modern Erotic Literature", I noticed a guy in the back of the room acting strangely. He was in obvious discomfort, and I wondered why. It was during the lecture where I discuss fetish stories. Students find it a revelation. The first thi... read more

shemale lover June 11, 2012 100%

My Asian fetish

I have a ongoing fetish and desire to dominate and have as my wife a petite asian sub t girl. I meet her online and fly her here and in the car she reaches over and pulls out my stiff cock. She coooes as she strokes my shaft and tells me how it is just the right size and thickness. She sucks me slow... read more

shemale lover August 25, 2012 71%

Banana Fetish

I was 27 and single and enjoying being free sort of the ‘sworn to fun loyal to non’ stage in young adulthood. I lived alone in a 1-bedroom apartment and loved working on my motorcycle which I kept in my living room. Most Friday nights for me were jamming out to music, enjoying a few beers and tinker... read more

AllenB February 16, 2023 91%

Brotherly Love, Sisterly Love Chapter 2

"RACHEL" My twin sister, and sometime brother, and I had been experimenting sexually with each other and crossdressing together for around a month, growing to love and to perfect our new feminine personas until they became the ones we thought of as our true selves. Whenever our parents ... read more

shemale lover September 28, 2012 60%

My transformation

is fiction It is strange where one’s desires can lead one. Take me as an example. Always entirely enamored of, infatuated with and completely submissive to all things feminine, a true devotee of Female Supremacy, my lifelong fantasy has always, since before I can remember, been to find a ... read more

shemale lover October 9, 2014 77%

An Invitation

"Oh come on,Sarah. There has to be a way." An innocuous enough statement, but that's how it all started. I'd just received an invite to Cressida's annual Christmas party which, maybe not on the Hollywood A list, was within the cognoscenti an occasion not to be missed. The soirees of ... read more

shemale lover November 16, 2012 100%

What Just Happened? Chapter 4

Chapter 04 -- I am no longer in control I looked at Beth and so did the pizza guy. The delivery guy started a discussion by saying, I do not want to offend you girls, but you are both very attractive and I see one of you has panties on because I can see them. So the other panties on the floor mus... read more

shemale lover December 16, 2012 90%

FEM FIRM 4-POP SECRET

Fem Firm 4: Pop Secret by: B-Man View Story Details Rating: XXXAdd Review Added: 11/20/2016 Complete:no Synopsis: Ruby learns a family secret which will change her life forever. Categories:Bimbo Workplace Situations Keywords:Long Finger Na... read more

bennyx709 November 22, 2016 97%

My latest Project

Hi there, I'm a slim, smooth boy from Germany who's totally obsessed with Fembois, Sissies, Traps, Shemales (small tits), dicks & CUM I'm also very style-obsessed: I love (androgynous) topmodels, catwalk fashion-shows and stylistic hair & make-up design! When it comes to sex, I'm pretty unexpe... read more

Boy001 March 22, 2021 100%

A Picture Perfect Sissy

"Holly, hold your breasts up. That's it honey. Squeeze the nipples between your fingers. Make them hard for me, sweetie." Jason lifted and pushed his soft breasts together, squeezed the small dark nipples, and hurriedly looked up to see if what he was doing was okay. He really wanted wh... read more

shemale lover May 27, 2012 87%

Cross-dresser Drinks Cum

Nikki looked up at me with her big, brown eyes as her head bobbed on my cock. Nothing was quite so sweet as one of her blow jobs. She had this way of dragging her tongue along the underside of my cock that made me want to cum in seconds. I always tried to hold it, but Nikki wouldn't let me. When she... read more

shemale lover March 29, 2012 100%

Sex with Jan

Jan reached for her packet of Rothmans Royals 120s, and extracting two cigarettes, offered me one. I took it in my long black PVC gloved hand. The fingertipless gauntlets revealed 4" long black false nails, that guided the sexy cigarette to my bright 'diva' red, heavily glossed, shiny, cock hun... read more

shemale lover August 10, 2011 50%

Birth of a New Sissy Part 2 Refinement

My life had changed so suddenly. One encounter with Jeff and everything was different. A week ago I was just an average married guy, with an average life. Sure I had the occasional Bi fantasy, but outside an college encounter all it was was a fantasy. Suddenly I found myself falling into one of ... read more

shemale lover November 17, 2011 91%

Caught cross dressed Part 3

The next few days felt like a lifetime for me. I couldn't sleep at night - every time I closed my eyes, all I could see were replays of myself, dressed like a whore, being strapped to a padded sawhorse while it fucked me from both sides. Everything I ate and drank had a horrid aftertaste of that bas... read more

shemale lover November 21, 2011 50%

Black Master, white sissy Part 2

I was a romantic despite the cynicism I projected in my job. This tough black skinhead yob had abused me - he had shaved me, humiliated me and yet for the next week what I remembered most was the kiss. Sure, the abuse had touched something in me but until I had met him it was unacknowledged - someth... read more

shemale lover November 23, 2011 85%

Bar trap Part 2

I was supposed to put on heavy makeup. Starting with the foundation, I applied a generous layer of a brand especially designed for the use on stage, that did a very good job covering up any dark shadows. After I was satisfied with the effect, I used a brush to put on powder and make it all smoot... read more

shemale lover February 26, 2012 100%

Becoming a Cock Worshipper

I first realized I was bi the summer after high school. Up until then I had only been really interested in girls. Like any high school guy I watched a lot of porn and soon realized that I really liked really nasty deep throat blow job scenes. I especially enjoyed watching a girl choke and gag and... read more

shemale lover February 29, 2012 100%

Daddies New Girlfriend

Doug suspected his 19 year-old son Jerry was stealing money. Doug worked far too much trying to provide for his son to supervise him properly but drew the line at theft. So he decided to set up a web-cam behind the mirror in his bedroom, he'd used the very same 2 way mirror to film his dead wife Cyn... read more

shemale lover March 9, 2012 100%

A Husband Changes

It was my wife Anne who helped me get started. And she was only my girlfriend at the time. I had spent the night with her and in the morning had no clean underwear. She offered me hers. Said it would do great things for my masculinity to wear her silky panties all day. Actually it did great things f... read more

shemale lover March 11, 2012 100%