Ladyboy Stories

221 results
Orientation
Length
Source
Infinite Scroll

The Rose Diaries Ch. 21

by RoseB on Jul 16, 2019
Transgender & Crossdressers

Disclaimer and Notes: The Rose Diaries is an incredibly dark story focusing on forced (heavy emphasis on "forced") feminization of a completely non-compliant individual. There are elements of non-consent, violence, and dark subject matters. In addition, this story depicts dysphoria, dissociation, and general depression. I hope you do enjoy this chapter if...

28-year-old Bisexual Stepfather Ch. 11

by walterio on Mar 13, 2018
Transsexuals & Crossdressers

AUTHOR'S NOTE: This story contains straight sex, bisexual sex, gay sex and incest. *** RONNIE'S STORY When Ronnie was born the parent Geoffery and Hilda were disappointed because they were hoping for a daughter. Ronnie was a beautiful child but to complicate things, Hilda had trouble with childbirth and she could not bear any more children. Ronnie always...

Auntie Mabel Ch. 28

by drsnip on Sep 15, 2017
Novels and Novellas

Bill thought he was going insane, his sexual life had changed dramatically in the last weeks. He wasn't complaining, far from it. His wife Sue had turned into a sexual woman, after years of being a dull boring wife. She now wanted sex anytime he did, she loved to be fucked and would allow him to fuck her anywhere he desired. Even more amazing, she no...

Young Master Ch. 01

by smittysimon on Sep 11, 2017
Transsexuals & Crossdressers

It was supposed to be the best day of my life...and maybe it was, but definitely not in the way I planned. My 21st birthday...my first day as a man, as a true lord of the Manor...my first day as a Master. I was so nervous I threw up my lunch. Not very manly, I know, but just the thought of having my very own sissy to play with had me teetering between the...

Be Still Little-one

by highshine808 on Oct 3, 2018
NonHuman

All sentient creatures in this story are over 18 years old. ***** Priesterly drained the dregs of the Rat.Pac protein pod. Stakeout, on the edge of the Western Protectorate. Westerly had just dropped into his sleep shift, following the end of morning-twilight joint-observation hours. He had sent the morning report to Command before turning in for his 4 hou...

Made to Obey Ch. 04

by madetoobey on Jun 24, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to a shemale porn site by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). Ruth, as a part of my punishment, was setting me tasks until Esther (who'd taken my laptop and mobile phone) could verify I'd never visited such sites before. I'd been forced into a chastity cag...

The Screamer Ch. 12

by Liquor69 on Sep 16, 2017
Group Sex

"Is everyone packed," Gary said as Holly handed him a Rum Runner. "We are heading into the sex capital of the world and I want our people turning heads every place we go. I can't wait to hear the comments on Walking Street." Phil did a double take, "Are we going to go to Walking Street? I've heard about that place. I am told it is wild." "We are taking ove...

Secluded Bliss Ch. 01

by Liquor69 on Sep 13, 2017
Group Sex

Connie leaned back in her office chair and smiled. It was a gorgeous day on the island. She had a wonderful view of the main tourist area out one side of her office and the blue Pacific Ocean from the other side of her desk. Gary, Mark, Jeremy, Arne, Holly, Jill, and Michelle also had offices in this building. With their collective global organizations, they...

The Bet reLoaded Ch. 04

by jomar on Sep 26, 2017
Fetish

Sorry for the long delay in getting this one out! I hope you enjoy the kink. ********** We bet big. To the winner, anything goes for the weekend and the loser must comply. I thought I had it in the bag, but she won. And now I was fucked. Literally. Thursday night she waxed me stem to stern leaving me with no body hair at all save the fetching shoulder len...

Misstaken Identity

by thrillerauthor on Sep 11, 2017
Transsexuals & Crossdressers

As I write these memoirs, my deeply tanned legs are stretched out before me on a lounge chair on my lanai. My pink toenails provide a nice contrast to the aquamarine sea visible in the distance, framed by swaying palm trees on golden sands. I brush a strand of hair from my forehead, and tug my sundress a few inches towards my knees. Looking back, it's hard...