Femboy Fantasy Stories

82,714 results
Orientation
Length
Source
Infinite Scroll

Glory-Filled Hole

by femboyslut on Sep 12, 2017
Transsexuals & Crossdressers

Ever since I was little, I always enjoyed dressing up in my sisters' clothes despite being a boy. This may have been because my dad left before I was born and so I had a big female influence due to my 3 elder sisters and my mum. When I was about 11, my sister Alice, 14, and my other sister Izzy, 16, decided to dress me up as a girl using all sorts of make-up...

Caught In the Act

by secretanon on Sep 12, 2017
Fetish

Please read the previous 2 stories before you read this if you want to know a bit about the characters! They follow similar adventures if you enjoyed this and the story flows better. Thank you! ***** Once I had developed a friendship with a fellow panty boy, things started to get fun. I don't have anyone else I can talk to about wearing panties. It felt ex...

Through Heaven and Hell Ch. 01

by ScumDumpster69 on Jun 25, 2019
Transgender & Crossdressers

Author's note: Contains dickgirl on femboy. Fairly vanilla, other than said femboy receiving a rimjob. Second chapter will be a lot more extreme. ***** Scarlet sighed heavily as she looked through the surveillance footage. With a tired finger scrolling past several pages of nothingness, just students going about their day, she was about to call it quits an...

A Match Made in Heaven

by Jade298 on Oct 16, 2018
Transgender & Crossdressers

Hey guys, WARNING this story contains big butt femboys and dickgirls having sex... If you are not into that I would advise that you do not read, if you are enjoy! All characters are over 18. This is my second attempt at writing a story, apologies for any grammatical errors, I edited it myself. There really isn't much story, tried to keep it pure smut. I al...

Mikey’s Decision

by VeraCBlake on May 12, 2020
Transgender & Crossdressers

Mikey's Decision: A Feminization Story By Vera Blake Part I The Meeting During the third week of quarantine, I took a jog out into the deserted Carolina night and felt inconceivably light on my feet. For just a moment then, as shameful as it was liberating, I forgot I was a man; I forgot I was anything but a pair of eyes hovering just above the mist. Of c...

Izzy and Emily Ch. 01: Two Redheads

by inkstand on Oct 31, 2018
Transgender & Crossdressers

The thump and boom of music filled the darkly lit club. I could feel its pulse thunder in my chest. The sea of dancing bodies writhed and bobbed to the tempo. The crowd, stocked with painted femboys such as myself, crossdressers and those who straddled sexuality as neither boy nor girl but an amalgamation of both, moved as a single mass. I had joined the de...

The Birthday Party

by today_i_am26 on Jul 27, 2020
BDSM

Chapter 1 - The Negotiation We sat, the four of us, in a coffee shop on the high street. To the causal onlooker, we probably looked like university students meeting their parents for a catch up. The reality was something quite different. My Wife, Goddess, Dominant, Keyholder, had answered an online advert on my behalf; a couple looking for a Sissy to att...

The Farm Ch. 03

by ashmadison on Sep 13, 2017
Transsexuals & Crossdressers

CHAPTER 3: REFECTORY Georgie Suxcock has a name to live up to -- and a personal trainer all her own to help her practice! Dirk Shattler is one of the Fun Farm's assessors, working hard (quite literally) to ensure that the Farm's guests and patrons are fully satisfied. The door slid back, and I walked out -- a little unsteady in my high heels. Dirk wolf...

Born to Be Ch. 07

by DamienDeath20 on Jun 8, 2020
Transgender & Crossdressers

A.N. Return to the strap on! If this isn't my favorite chapter so far, it's definitely one of my favorites x))) Buuuut chapter 8 is preeeetty awesome too ;D I know I'm a whore. The Following Contains: Interracial between a tall black lady and a crossdressing femboy. Which in conclusion creates a formula of strap on penis being inserted into femboy bott...

High and Low Ch. 08

by bisexualsmoker on Sep 12, 2017
Transsexuals & Crossdressers

Simon was definitely getting addicted to cock. This femboy needed it more and more! As usual, dressed as a total slut in painted on low rise jeans, skimpy light blue halter top, wearing gypsy bangles and barefoot with toe rings, his wind swept now brunette hair just wild, this barefoot boy was looking to play. He looked club slut cool. A sexy sluttish fem...