Crossdressed Stories

155 results
Orientation
Length
Source
Infinite Scroll

My Fantasy Pt. 01

by sexyctcd on Nov 6, 2018
Transgender & Crossdressers

This is a continuation of the story of Eric and Jessica. This is Part 1 of the next part of my story. We have been getting together for about 3 years in an NSA type thing. We are a true FWB both married and discrete. Eric is 47 6'2" 230lbs a bit of a hairy bear with an 8" cut cock nice and thick. I am Jessica 38 6' 200lbs non pass CD, because of my situation...

Morning Glory

by dreadknots on Apr 25, 2018
Transsexuals & Crossdressers

Reviews for my last crossdress-y story were pretty good! Hurray! This one is a little more teasing in nature, but is ultimately pretty fuzzy. I am a sap. *** Hardcore Fitness was the classiest gloryhole in town. All the right people knew what went on behind the illusory front of a 24/7 gym, and the syndicate behind its operation paid off the right guys in...

Magic Dress - Faye

by SlightlyRude on Jan 27, 2020
Transgender & Crossdressers

CHAPTER 1 It was a perfect summer day, warm with just a gentle breeze, and it was good to be alive in my new green dress. I walked along the side of the river, enjoying the green leaves of the trees and the colour of the bricks on the old houses. The feel of the breeze on my bare legs and the gentle movement of the cloth of my skirt was just right. I greete...

Ugly Duckling to Sissy Princess Ch. 02

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

(Continued from Part 1) My girlfriend, Carol, and I made love to each other about 2 times per week. She was also getting fucked on a regular basis by her jock fuck buddies. I never asked how many guys she was hooking up with on the side, but, I guessed it was at least five, because there were five jocks that she tutored on a daily basis. She put on skimpy c...

With Her Blessing

by komrad1156 on Sep 12, 2017
Transsexuals & Crossdressers

"Hello again, Kyleigh!" he said as he looked at himself in the mirror after carefully pulling on his very expensive human-hair wig. Ky Finley was now Kyleigh Finlay and she felt this wonderful rush of endorphins flood over her as she looked at the beautiful creature she'd become over the last ninety minutes. Ky had sandy blond hair so Kyleigh could easily b...

Robin and Jimmy Olsen - Sissies Ch. 05

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

Jamie Olsen hated Mondays, because on Monday morning she had to go back to being boring Jimmy Olsen after having spent all of the weekend as Jamie! Sunday evening had been disappointing. As usual she had been out on her street corner on the stroll. Last night she had chosen to look extra trampy, wearing torn stockings, her five inch heels, and her black lea...

Dolled Up To Rock 'n' Roll

by shawnavinyltv on Oct 12, 2017
Transsexuals & Crossdressers

I've always been a rocker, not that I don't love other types of music, too, but there was always something about going to a rock concert that had a special air. A kind of vibe that was hard to describe. Almost like an energy in the crowd connecting them to the band. Of course, I'd been to a number of shows over the years, saw some big bands, some unknowns an...

The Marriage of Martin Hastings Ch. 17

by rik581 on Sep 14, 2017
Transsexuals & Crossdressers

Martin sat alone in a small interrogation room. The large wood table with the two empty chairs on the opposite side of the table were all the furnishings in the room. The humiliation Martin had suffered as he was brought through the police station, the giggles, sneers and staring were still fresh in his mind. Though he was told he was not under arrest, he fe...

From a Husband to a Dutiful Sissy Ch. 12

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Twelve: New Days, New Times, New Possibilities. As in life the Sun still rises and sets, days will pass by, tears will dry, life will go on...Over the last few days, I have kept myself busy as I can to keep my mind off of Jack. It is hard not to think of him to sense him and to want to be held by him. He was my first love now that I live as a trans...

Isabella's Reversion Pt. 04

by silverbackteddy on Sep 11, 2017
Fetish

Note from the Author: This is a story about ABDL. The first word being Adult. All sexual encounters center around Adults, above the age of 18. This story also contains BDSM, plushophilia, watersports, and various other fetishes. For those that are grammar freaks, please don't comment on my improper grammar use. I could care less. At least it doesn't have L...