Crossdressing Stories

1,097 results
Orientation
Length
Source
Infinite Scroll

Ellie's Weekend

by RomeoDelta on Apr 10, 2018
Transsexuals & Crossdressers

This story is a work of fiction. Any similarities to persons living or dead is coincidental. The story has been inspired by things I have seen, read or conversations I've had. - - - o 0 o - - - I'd finished reading Carly's latest email. She had just invited me to spend the weekend with her in Brighton. We had never yet met in person, although we had been c...

April Fool Office Sissy

by lululuvsblack on Apr 10, 2018
Transsexuals & Crossdressers

"Dear Colleagues This week, in order to help with our efforts to raise money for charitable causes, we have decided to mix up our usual policy of dress down Fridays. This Friday we are instead instigating a "dress up Friday" in which staff are strongly encouraged to come to the office dressed in the office attire of the opposite gender (that's suits and tie...

Sissy at the Sorority

by secondsamuel on Oct 24, 2018
Transgender & Crossdressers

Author's note: I am recovering from repeated surgeries on both arms to correct a degenerative nerve condition. To write this, I am using a voice to text software which isn't always as accurate as I would like it to be. As my recovery time will take more than a year, I have decided to continue writing and give my best effort at doing the thing I love. Please,...

The Trespasser Ch. 03

by Midday_Crisis on Nov 6, 2018
Erotic Couplings

Cecilia woke up in a strange place. She inhaled the now familiar fabric softener scent from the pillow her face was buried in. 'That's right,' she thought to herself as she stretched like a cat enjoying the silky feel of the sheets against her bare body. 'I successfully invaded.' Looking around, she found herself in bed alone. The sun was bright outside a...

The Transvestite Stalker

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

The man sat at a corner table in the coffee shop surreptitiously eyeing off the woman sitting on a stool at bar. She was dressed in a navy blue suit; her jacket was open, revealing well-formed breasts swelling her white satin blouse, which opened to the second button so that a hint of lace bra was displayed. Her legs were crossed and her skirt had ridden up...

Basketball Crossdresser

by Cute Little Thing on Sep 14, 2017
Fetish

This story is about an athletic but small man who has fantasized about cross dressing from an early age. When his wife finds a strange number on the phone bill, she calls the number and has a conversation with his phone mistress. What follows contains blackmail, humiliation and of course - sex. If sex and crossdressing offend you, or if you are underage, ple...

The Diary of Jewel Delacroix Ch. 28

by BJGoodhead on Feb 3, 2020
Transgender & Crossdressers

The following contains themes of forced feminization, reluctance, non-consent, and other adult topics, so before we begin here are the usual disclaimers. This is porn, you must be over 18 to read this. If not, go away and come back when you are old enough. If you are old enough and this style of erotica isn't to your liking, then go find some erotica that is...

Julia, Ben and Lisa Ch. 17

by chloejacobs83 on Mar 30, 2020
Transgender & Crossdressers

Ch. 17: Thursday A few quick notes: 1. this is the seventeenth chapter of a longish story, a novel in many chapters 2. everyone is 18+ 3. there is no safe sex here - cause it's a fantasy, not an instruction manual 4. crossdressing and gender bending, not everyone's cuppa tea - be forewarned * We got up and wandered around in boxers (me) and pjs (her)...

Nathalie's New World Ch. 02

by Cagivagurl on Mar 17, 2020
Transgender & Crossdressers

The night was a restless one for me. Mia on the other hand seemed completely at ease and slept the sleep of a totally sated contented kitten, her little snores breathlessly echoing in my ear. As the grey light of dawn filtered in I felt more agitated than when we went to bed. I lay there petrified, what to do, how to approach this unbelievable turn of even...

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...