Shemales Stories

429 results
Orientation
Length
Source
Infinite Scroll

Joey Says Ch. 05

by MDesign on Sep 15, 2017
Transsexuals & Crossdressers

I watched as my sister Beth arrived and parked her car. I walked over to her as she got out. 'Hi Beth,' I said giving her a hug. 'Hi Mat. So this is the place.' We were way out in the countryside, at what appeared to be an exclusive country club. It was owned by Jack, the father of my wife Kate, from whom I was separated. He owned a group of companies and...

A Shemale Shock: A MILF Falls

by silkstockingslover on Sep 25, 2017
Illustrated

Summary: Mom catches her daughter with a teenage shemale and.... Note 1: This is a Nude Day 2017 Contest Story so please vote. Note 2: Thanks to Tex Beethoven, Robert, and David for editing this story. I was having a bad day. I'd spilt coffee on myself on the drive to work. I'd gotten a rip in my nylons. And I'd forgotten my notes for tonight's intervi...

Code Name Tequila Ch. 07

by Travel_by_day on Sep 14, 2017
Transsexuals & Crossdressers

The Brazilian immigration agent looked at the passport. American. April Cho. He looked at the picture, and then up at the woman standing in front of him. Thin, tall Asian woman. The woman smiled. The agent looked back down at the and flipped through it until he found the Brazilian Visa. It was a ninety day work visa. "Purpose of visit?" the guard asked in m...

Becoming the New Me Ch. 01

by Chris7sw on Sep 19, 2017
Transsexuals & Crossdressers

This is Chapter 1 of a two or three part story. The second Chapter will be forwarded in a day or two - Chapter 3 is still in the pipeline. ***** Talk about being pissed off. My wife of some five years had decided that she'd have more fun with a guy from work and had come home one day; packed her bags and left - just like that. Oh sure - we'd had some row...

The Billy becomes Billie Story

by Grey Eagle 286 on Sep 13, 2017
Transsexuals & Crossdressers

William Johnston read the notice again very carefully. It was posted on a Cross-Dressing Internet site he visited regularly. When he noticed the message on several more sites, he read it. Bill was not an active cross dresser or a transvestite but the idea fascinated him and had for several years. The ad read: Attention Young Men: We are offering a wonderfu...

Chemical Flavor

by Miles63 on Sep 13, 2017
Transsexuals & Crossdressers

Introduction: Sorry that it's taken so long to upload a new story. I've been sitting on this one for nearly a year as I loved the beginning but hated the ending. So after a big deletion and a big re-write I now like the ending. I've been just mentally drained for awhile and no story was coming to me, but now finally something to upload. Any errors please be...

The 1950s Housewife

by Travel_by_day on Sep 18, 2017
Transsexuals & Crossdressers

Drew and Paul were roommates, friends from college who had only graduated less than a year ago. They both got jobs in downtown, and wanted to live close to the action. Rents were high, though, so sharing a place seemed a good idea. Drew and Paul were sitting at home on Superbowl Sunday, watching the pre-game show. The New England Patriots hadn't lost a game...

The Ballad of Jaimie and Vera Ch. 03

by AwkwardMD on Sep 14, 2017
Transsexuals & Crossdressers

After the 'Establishing Shot', Vera and I hit the road. We rented an RV and set out cross country. Vera called it "Jaimie Bradley's Sexual Awakening Tour 2013: Coming to a city near you!" The plan was to go around and find people I could have sex with, have them sign a release, film it, and put out a DVD. Or start a website. That part of the plan was fuzzy,...

Made to Obey Ch. 01

by madetoobey on Jun 18, 2019
Transgender & Crossdressers

Let's get this straight. I'm not gay, not a sissy or faggot, I'm a normal 30ish heterosexual guy okay! So why you might ask am I writing this dressed in a dark blue dress, black stockings with suspender belt, light blue panties with a white polka-dot pattern and bow, matching bra, 3-inch-high-heels, with my cock in a chastity-cage and with my hair, make-up,...

Sissy/Cock Sucker Dictionary

by silkstockingslover on Jun 12, 2019
Reviews & Essays

Summary: A list of terms to aid in understanding the activities and nature of sissies and cock suckers. Note 1: The author's source material isn't Webster's Dictionary or anything similar, but is drawn from many years of interest in matters sexual and countless conversations, both spoken and online, with other perverts. Note 2: Thanks to Tex Beethoven and...