Gay Femboy Stories

22,646 results
Orientation
Length
Source
Infinite Scroll

Somewhere else.

by latexdoll on May 23, 2010
Fantasy

Waking up this morning I bet you didn’t know it would be the last day you spent here on earth. Climbing out of bed you hit the alarm clock for the third time, you can’t quite place what is wrong, you just can’t seem to get out of bed. Getting ready for work is more of a chore than usual. For whatever reason nothing seems to want to cooperate. Your shower hea...

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Your inner femboy

by SkirtSkirt on Feb 10, 2021
Transsexual

The first thing you have to ask yourself is, who are you Are you an ignorant boy about to be turned into a little cum slut?But then who was there to show you who you really are?Or did you do it to yourself? Or are you already a cum dumpster about to reveal themselves? Or maybe you want to be a slutty crossdresser that's secret gets exposed,one throat fuck at...

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Suddenly Daddy

by grimbous on Apr 10, 2018
Bisexual

(Three things before I start this twisted tale. First, I started this over on my Patreon page and I wanted to thank my awesome patrons for supporting my stories. Second, I want to give credit to the one and only Incase for the cover art which I swiped from his comic Spicing Things Up. Finally, if the cover art isn't warning enough, take note of the category...

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The School Ch. 06

by NeighbourhoodSuccubus on Nov 20, 2018
Sci-Fi & Fantasy

Zam had never been in a dorm before but seen them plenty on TV, these long hallways with individual rooms, a small communal kitchen for each respective floor, common room and study areas. This wasn't it, though. The building was tall and fairly open with glass panes covering the outsides between tall and graceful-looking pillars of polished steel. It only h...

Growth-XX

by FlatCap90210 on May 20, 2019
Science Fiction

James felt as if he was going insane. It was summer, the sun was shining and he was at the beach ogling girls. Tits of all shapes and sizes surrounded him, wrapped in bikini tops, one pieces and other pieces of fabric of varying coverage. James' heartbeat pounded in his ears and throbbed in his crotch, digging a furrow in the sand beneath him. He was lying o...

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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...

Slut

by Burrows4 on Feb 3, 2021
BDSM

*Author's Note: I got tired of reading trash on CHYOA after lurking for years, so tonight I scooped up my own heap of trashy porn fantasies and set it loose to the internet. All characters are over 18 and this is trash. It is meant to be played with one hand. * You are Doe Johnson, and after a long search for the perfect private school, you landed on Gilden...

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The Imperial Infantryman's Uplifting Primer

by Naruyashan on Dec 6, 2018
Fan Fiction

(This is my first story on the site, and one of my first forays into the field of NSFW writing. Suggestions, requests, and feedback are welcomed.) I wouldn't recommend you go in looking for a very serious tone, though. As the synopsis suggests, this is intended to be a mix of lewd and humorous, and I can definitely see how that could put off some people. Als...

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iPad Roommate

by Oddballs on Dec 31, 2020
Science Fiction

“Pffff, another sweater.” Aaron says as he holds up the red, green, and white Christmas garment is aunt sent him. “At least this one as an actual cool design on it.” Ian says as he smiles at his roommate. In a small house in a secluded neighborhood covered in snow, two men in their mid-20’s enjoy a simple holiday together. With the pandemic still at large, b...

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Master's Femboy Maid

by KittyAshleyy on Apr 14, 2020
Transgender & Crossdressers

Ocean blue eyes looked back at me as I looked myself over in the mirror. My Master was hosting a get together of his like minded friends and had told me to dress in my best maid uniform. That was a black maid dress with a skirt that barely covered my ass, white gloves which reached past my elbows, a small white apron and fishnet stockings with a black garter...