Ladyboy Stories

221 results
Orientation
Length
Source
Infinite Scroll

Heidi’s Submission

by TimT1972 on Sep 19, 2017
Transsexuals & Crossdressers

Eighteen year olds are the same the world over. The handsome, tough and sporty are nearly always the most popular. Adam was none of these, he was rather effeminate, of slight build and definitely no sportsman. As such, he never had that many friends. His home life wasn't much better; his father was dead, he had no siblings and his mother worked every hour Go...

Twisted

by StiffClit on Sep 14, 2017
Transsexuals & Crossdressers

"Baby, are you sure this is the place?" Eve squealed a bit too loudly, her voice both high-pitched and thick from the third Cosmopolitan. "This looks so, I don't know; fancy-shmancy for a full on mix-it-up ladyboy bar. I know, I know, this is South Beach and everything here is la-de-da, but still, I thought it'd be more of a dive." She leaned deep into the f...

Biker Bitch Ch. 09

by MicheleNylons on Jan 6, 2018
Transsexuals & Crossdressers

Chapter Nine: Fuck the Trans Cooze! Cassie sat behind a desk in a stark interview room at the Los Angeles County Jail. ATF do not have their own detention facilities; they use Federal penitentiaries and often borrow local law enforcement facilities to temporally incarcerate suspects and interrogate them. She had been freed of her cuffs and her clutch purs...

Letter from Augusta

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom Deuce, my second son is finally beating me at Ping-Pong. The ball flies over my head! When I was a kid the balls were just white, but now they come in neon orange! Deuce looks relieved, I wonder why. Is it because I have always punished him, taking his pants down and spanking him hard with my paddle when I beat him at table tennis...what a...

Mistress Styles and the Humbler

by justincbenedict on Feb 26, 2019
BDSM

Styles. who'd gone by surname only since her Army days, smiled as she looked at her unfortunate husband, the ex-playboy Busby Letourneau. Busby moved uncomfortably on the hard kitchen stool. The seat was so small and of course his hands were tied behind his back, and it was a delicate balance. Styles stroked her husband's engorged cock and grinned, her ton...

Groomed to Depravity Ch. 04

by ssamlee2000 on Jun 1, 2020
Transgender & Crossdressers

"Wake up you lazy slut." I opened my eyes to find Mohamed's naked figure looking over me. His morning wood, erect in all its glory. Did he want me to suck him off? My tiny cock flinched as I recalled the adrenaline rush from being raped in the throat. "We need to be out at 9 if we want to make your first appointment. Put your make up on and get dressed, I'...

Okaikei

by bleepblorper on Apr 3, 2019
Anal

Note: This is the last chapter in the trilogy starting with Worth Every Yen and continued in A Few Yen More. It will not make sense without having read those first. ***** The alarm on my phone wakes me far too early to a room that's still dark. I turn my head to the left, then the right, hearing the bones in my neck pop. The noise seems loud to me, but it...

Miss Chianti's Troy-Boy

by justincbenedict on Feb 26, 2019
BDSM

Chianti finished brushing her hair and gave it a cursory look, and the doorbell rang. Chianti put her brush down, and pulled the scoop neck of her pretty pink sundress down a little, just so the jugs poked out a bit more. The bell rang again. "I'm coming!" What a beautiful dress, sleeveless and so short. Purchased by Ingersoll, a sad little man who needed...

Letter from Gander Cove

by justincbenedict on Nov 20, 2018
BDSM

Dear Shoeblossom, My teachers always said to me, "Norbert, you'll never amount to much, smoking weed and playing video games..." but I found I had hidden talents... Recently I joined a sadomasochistic group. It's a local thing. Amazingly, I met the hottest girl who wanted me to punish her! Victorine is a very attractive woman who's got about twelve or thi...

My First Ladyboy

by 69plus1 on Sep 19, 2017
Transsexuals & Crossdressers

I was in my forties and was bored with life. My job sucked, my night life was the same over and over. Bar hopping hoping to get lucky and pick up some woman who would fuck me and not be crazy in the morning. Or maybe a hot guy just for the change of pace. Guys were just about the sex and usually didn't bring any baggage. So I was surfing the internet and ge...