Fisting Crossdresser Stories

4,986 results
Orientation
Length
Source
Infinite Scroll

The Deviants' Room

by sissyrikki17 on Oct 14, 2017
Transsexuals & Crossdressers

Upstate New York, 2007 - Day 1 They all kept talking—bitching—about "sloppy seconds" but if you're drunk enough, and these guys were drunk most all the time, you don't really care about dipping your wick into a hole filled to overflowing with other guys' junk. You just stick it in, numbly hump for a few minutes, then make your own delirious contribution to...

Literotica Monthly Awards 2020: February

by Literotica on Jul 14, 2020
Erotic Couplings

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 February's Reader's Choice Awards. First Place ($150 Cash Prize Winner):The Beast by Averagejoe1992Second Place ($100 Cash Prize Winner):Watershed by onehitwandaT...

Literotica Monthly Awards 2020: April

by Literotica on Jul 14, 2020
Erotic Couplings

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 April Reader's Choice Awards. First Place ($150 Cash Prize Winner):The Rask Rebellion by SnekguySecond Place ($100 Cash Prize Winner):Matchmaker 03: March by Sanit...

Literotica Monthly Awards 2020: July

by Literotica on Oct 5, 2020
Loving Wives

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 July's Reader's Choice Awards. First Place ($150 Cash Prize Winner):S'mores Ch. 04 - Forever Please by BookwormmomSecond Place ($100 Cash Prize Winner):Home for Ho...

Literotica Monthly Awards 2020: March

by Literotica on Jul 14, 2020
Exhibitionist & Voyeur

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 March Reader's Choice Awards. First Place ($150 Cash Prize Winner):When Angels Cum Ch. 19 by CapDragon121Second Place ($100 Cash Prize Winner):Chasing The Last Roa...

Her Bully's College Roommate

by samwalser on Sep 26, 2017
BDSM

Amy was giddy with excitement when her parents dropped her off at the Central University of North Texas. Everything was about to change for her. She'd been teased and bullied all through high-school for her appearance (she's barely five feet tall, skinny, flat-chested (but with big, sensitive nipples, and freckled) and for her general nerdiness—she read a lo...

Open in Reader

A Sissy Story

by PinkRebecca on Feb 21, 2020
Fetish

You always were a normal boy growing up, weren't you? Played some sports, although not to an extent where you stood out anywhere or made any teams. You had a normal friend group, as far as you knew atleast. You liked girls, like most of the boys around you, although you lacked the curage to talk to them. Well not to talk to girls in general but in a romantic...

Open in Reader

Literotica Monthly Awards 2020: January

by Literotica on Jul 14, 2020
Mature

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 January's Reader's Choice Awards. First Place ($150 Cash Prize Winner):Home for Horny Monsters Ch. 49 by writerannabelleSecond Place ($100 Cash Prize Winner):Sound...

Crossdressing, Piss and Sex

by Lovinhose on Apr 14, 2020
Transgender & Crossdressers

This is a work of fiction, a fantasy that I would love to come true. It also contains 'pissing' (aka 'watersports'), crossdressing, and a crossdressers sex with men, so if you are not into these subjects, this story might not be for you, you have been warned. Also, comments are welcome, but please note, I'm NOT a professional writer, if I was, I wouldn't be...

Perfection

by ValoryG on Apr 23, 2019
Transgender & Crossdressers

It all starts, innocently enough, when Joanna's looking for a dresser. On one hand, she can just go to a big box furniture retailer and get an inexpensive, functional one that looks decent (and build it, of course). Or, she can browse around online and find a new or used one with a more elegant pedigree. Joanna, by the way, is a very practical, elementary s...