Cross Dress Stories

150,200 results
Orientation
Length
Source
Infinite Scroll

A Mage's Tale Ch. 11

by NeoShade on Nov 13, 2017
Sci-Fi & Fantasy

Chapter Eleven "Now what?" Clue asks looking up at me. "It's raining and all I want is a good fuck." "Tsk tsk, It's your first time and you have waited so long, I want it to be special." I say. "Your tall, hung, and magic. How is this not already special?" "You'll see. Come on." I say flipping my cloak up and dashing into the rain. She follows her bare...

Learning Cross

by Lisolette Gilcrest on Sep 13, 2017
BDSM

Cross couldn't help but chuckle as he realized that for the second time in a row the young Tala had become knowledgeable in a pleasurable experience beyond anything that she could have felt possible... then immediately passed out into a lovely slumber. He sat there on the bank of the hot springs for quite some time, smiling down at her and occasionally cares...

Abigail and Mrs. Cross Ch. 01

by cloacas on Sep 14, 2017
Erotic Couplings

It was a not unwelcome surprise to hear Abigail call my name on a Paris street. The last time had been almost eight years earlier, when she'd given my cock a last squeeze in my doorway before she drove back to her parents' house and then had returned to college. I remembered that scene well. She brushed her hair, bending slightly to the right to pull the co...

The New Girl Ch. 03

by BigMeanie on Sep 17, 2017
BDSM

With Lily still blindfolded and sitting alone in the back seat with her legs spread wide and the hem of her dress pulled up to her waist, I talked to Fiona about my plans for the three of us. "My initial thought was to turn her into a fuck toy as soon as we got to the house, but after seeing how easily she cums, I'm not so sure I want to do that. Instead, I...

Big Book of Wrestling Babes Ch. 07

by daxg2001 on Sep 14, 2020
Celebrities & Fan Fiction

WARNING: The following is a work of erotic fan fiction. The events of which are completely made up and did not happen, and is no true reflection of the characters, promotions, wrestlers, events etc depicted or referenced within. Fantasy is legal. This material is unsuitable to be viewed by those under the legal age limit of viewing pornographic material in y...

Cindy's Makeover

by CindyUSA on Sep 16, 2017
Transsexuals & Crossdressers

I would like to share my latest cross-dressing experience. Like many cross-dressers, I dress up part-time. I am married and my wife does not know of my fetish of warning woman clothing. My dressing need stems from my enjoyment to the attention I received from admires. I am new at this cross-dressing having only started dressing five years ago. Many cross-dre...

Freddie Becomes a Cross-Dresser Ch. 05

by BOSTONFICTIONWRITER on Sep 16, 2017
Reviews & Essays

Already, my feet hurt wearing these narrow flats. The pantyhose bunched up in my crotch and wrinkled every time I moved. I bought the queen size and it is a little too big in the hips. I had to roll it up to make it tight enough around my legs. I guess my thighs are smaller than women who wear these size pantyhose. The bra felt as though I was wearing a kna...

Summertime Cross Dresser Confession

by andtheend on Sep 14, 2017
Transsexuals & Crossdressers

After a long time coming, a lifetime of suffering, the first day of summer is when an aging cross dresser finally gives into the life he's always wanted to live. As if a new beginning, as if being born again, Donald looked to his transformation from man to woman, as his emergence from moth to butterfly. He couldn't wait to fly away to start his life anew. P...

A Bit of a Kiss and Cuddle

by Svejk on Sep 13, 2017
Transsexuals & Crossdressers

This is a story about my first time with another man, so if that makes you uncomfortable, well, frankly, I don't care. Don't get me wrong, I wasn't under age or anything at the time, I was 20, but some people, for some reason, don't like that kind of thing. Personally, I find it hot as hell (N.B this is entirely fictional, but hopefully it'll happen before t...

Destiny Fulfilled

by cannyjess on Aug 27, 2019
Transgender & Crossdressers

I had secretly cross-dressed since I was 6 or 7 years old. The compulsion never goes away and had stayed with me throughout my life. My marriage eventually broke up 5 years ago. Not because of sexual issues but because we wanted different things from life. It was not long before I started a new relationship with another beautiful woman. The sex was great how...