Fisting Crossdresser Stories

4,986 results
Orientation
Length
Source
Infinite Scroll

Transvixen Tranny Rock Band Ch. 01

by MicheleNylons on Sep 13, 2017
Transsexuals & Crossdressers

Chapter One: Panti and Cherri Pops Panti's red nailpolished finger lazily circled the glans of Cherri's erect penis through Cherri's gauzy nylon pantyhose gusset. Preseminal fluid seeped from Cherri's palpitating member and darkened the sheer nylon. Cherri's white satin panties were bunched around her thighs and she bucked and heaved as Panti gripped Cherri...

Life and Time of Lady Vargos Ch. 08

by rik581 on Mar 26, 2019
Transgender & Crossdressers

"Lies, Truth, and Innuendo" Martin was pressed into attending to his duties that week as Lady Vargos. With little or no manly pride left to swallow or cling to, he performed his daily routines dressed as a woman, both publicly and privately. Each day seemed to bring more heart felt shame and humiliation into his life as he stepped out and displayed his ema...

In from the Rain Pt. 02

by dreadknots on May 21, 2018
Transsexuals & Crossdressers

Well shucks! I got some positive feedback from the first entry, and a couple people were even nice enough to comment asking for another one! Let it be said that I'm not above placating the masses. By which I mean cute crossdressing smut. A little bit shorter than the first one, but I don't really have to introduce the characters too much this time. Don't wor...

Forced to Dress

by married40scouple on May 11, 2020
Transgender & Crossdressers

"Can I have two rum and cokes, please?" The sexily dressed, long-legged, thin brunette asked the bartender, speaking in a deep tone. "Lose a bet?" I asked the crossdresser who sidled up to the bar and order the drinks. "I don't want to talk about it." He replied in a husky voice. "At least you look real good." I smiled at him. "She dressed me up. I have...

Finally a Princess Pt. 02

by fireandlace0533 on Sep 14, 2020
Transgender & Crossdressers

Part two of a crossdresser who loves Disney who has come out to his wife while on a Disney Cruise. New experiences and adventures are ahead. Finally a Princess (Part Two) I woke the next morning around six thirty which was a little late for me. I laid in bed and thought about what had happened yesterday. I had actually spent time in front of my wife Sarah...

Tales From the Netherworlds

by JackOLantern on Jul 20, 2018
Fan Fiction

The Netherworlds. There are a countless number of them in the universe, all with their own societies and customs. Why, nearly anything you could think of could be represented in the form of one of these demonic worlds. A world that has been converted into a gigantic spa resort run by slimes that poison their customers instead of detoxifying them? Why not? A...

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Literotica Monthly Awards 2020: May

by Literotica on Jul 15, 2020
Romance

Manu and I would like to thank all the authors who submitted during the month, and all the other months for that matter! We've tallied the reader's votes, and are happy to announce the winners of May's Reader's Choice Awards. First Place ($150 Cash Prize Winner):'Twas The Night Before... Ch. 02 by BrokenSpokesSecond Place ($100 Cash Prize Winner):Succubus A...

A Sissy in the 22nd Century

by JerkGently on Jul 1, 2020
Transsexual

In a future not too far flung, humanity has progressed to a stage where almost all production and provision of society’s needs is automated. With no need to work, all citizens are instead driven to find lifestyles that fulfil their own and each other’s fundamental desires. This is achieved by the medium of an overruling system of artificial intelligences and...

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A New Start

by Stoked Flow on Jun 20, 2020
Transsexual

You spent most of your time at home playing video games and browsing the internet. You decided to take it easy after high school before deciding college was right for you. That was a couple years ago and now you sense a growing frustration within your mother. One afternoon after dinner, you found yourself suddenly sleepy and crashed onto the sofa. Your next...

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Literotica Monthly Awards 2020: June

by Literotica on Oct 5, 2020
Celebrities & Fan Fiction

Manu and I would like to thank all the authors who submitted during the month, and all the other months for that matter! We've tallied the reader's votes, and are happy to announce the winners of June's Reader's Choice Awards. First Place ($150 Cash Prize Winner):All That Glitters Ch. 17 by bigtddybrSecond Place ($100 Cash Prize Winner):Martha's Second Chan...