Crossdressing Brother Stories

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Cindy's Panties

by secretanon on Sep 13, 2017
Fetish

I am around 24 years old and I have always enjoyed wearing panties. I think the feminine feeling of it all really turns me on. At a young age, I discovered masturbation from cumming on my mothers panties after deciding to be bold and try one out from curiosity. I was never able to fufil my love for panties, being in a house full of males, so I never had a si...

Happy 21st Birthday

by lpacphantom on Sep 1, 2017
Group Sex

This is my first submission, the first time anyone but me has read my work. I would like constructive feedback. I hope you enjoy. The events are fictional, but the desires and characters are based in real life. This story contains male on male action and hint of crossdressing. If that offends you, don't read it. It all started before I even had my first...

Slave Ch. 08

by slaveheathen on Sep 25, 2017
Fetish

Note: Story following the adventures of a bisexual submissive man. Some elements are based on my own personal experiences, some are purely fantasy. Yes, I love cock in my ass. Yes, I am slave to a Mistress who fucks my ass beautifully. Yes, a great many things that I write about we've either done or intend to do. There is bisexual sex, group sex, crossdressi...

Messy Melinda Ch. 03

by BossySon21a on Sep 13, 2017
Fetish

Folks, this is a pure fantasy story, intended purely and solely for entertainment. Nothing that happens in it is real, none of it is meant to be in any way realistic, real life is never, ever, ever like this. This is just some good dirty messy family crossdressing kinky fun! * As the chilly, golden egg-goo ran down her bare buns, Melinda was able to stop h...

Mando & Lek

by Purple_Raihne on Sep 16, 2017
Romance

(I was writing this story when I was involved with two people. The three of us were the character basis. But they ended up committing to each other and forgetting I even exist, so I have no desire to bother trying to finish this story in the slightest. No names need to be changed as I already changed their names and Marie is my own middle name. To whomever d...

My Life as Isaac Newton

by Prizmatic on Sep 16, 2017
Romance

This character has nothing to do with the Isaac in Midnight Plush (q.v.). The idea for this story came in a dream, and that was his name in the dream, so I didn't change it. This is the closest thing to a traditional short story I've submitted, and I would really like solid critique on it. Especially, did I do a good job of writing from a man's point of view...

Slave to She-Orc Cock Ch. 01

by SissyForFatFutaCock on Jun 9, 2020
Sci-Fi & Fantasy

Hey there Literotica! This is my first ever attempt and submission of erotica. It's a plot that has been done a few times, but I plan to take it about 5 steps further. On that note, there is femdom and male sub in this one. Future stories will get progressively nasty, including but not limited to, futa on male/female, piss and scat, non-con, incest, femini...

Hiding in the Shadows

by Kisara-ST on Aug 5, 2023
Fetish

Hiding in the Shadows Skinwalker Fanfic Synopsis Inspired by Mmmm101's story, Skinwalker, with their blessing. Edward was the disowned son of a rich family, surviving as a bartender far away from his parents, and living with his runaway sister. One fateful day, as he was on his way home after a late shift, he ended up......

The Bio of a Masturbator

by Chatomana on Sep 18, 2017
Toys & Masturbation

Disclaimer: Although this is a work of fiction, some parts contain actual facts and events. The author can not and will not be held responsible for any injuries that may occur if the reader tries to reproduce of these events. The author holds all copyrights to this story, printed and/or digital. Prologue This story is not about love, nor about romance, or...

Jamie's Story Ch. 02

by Michael142 on Sep 16, 2017
Fetish

Author's note: This next chapter is the story of Jamie's attempts to explore his sexuality on his own, after Anna. He will also explore Jill's new persona dating Tom and maybe others. There is a lot of sexual activity in this chapter, which may seem excessive or gratuitous to some. It's my belief that there is just as much sex as is necessary to tell the sto...