Transgender & Crossdressers Stories

12,569 results
Orientation
Length
Source
Infinite Scroll

A Police Matter

by ECHoney on Dec 24, 2019
Transgender & Crossdressers

This story was written for a friend of mine. This is a story about 2 Transgender females. ***** After a night out partying Amber and Casey began to drive home. As they are driving along Casey reached over and slipped her hand under Amber's skirt and begins to stroke her cock. Amber said. "If you keep that up I'm not going to be able to drive." Casey gig...

We Finally Meet

by fyredreams on Sep 16, 2017
Transsexuals & Crossdressers

My daydream . . . I'm at home, anxiously waiting, and I get her call on the phone. We've been talking over email, hoping to meet each other someday, and it's finally going to happen. My voice is quivering when I pick up the phone and say hello. I hear her soft, throaty, feminine voice, and I'm immediately enraptured. Her voice soothes and calms me, reass...

In Praise of Haitian Women Ch. 04

by Samuelx on Aug 27, 2019
Transgender & Crossdressers

Meet Giselle Lucien, a French Canadian Transgender woman living in the City of Ottawa, Ontario. Giselle is fairly active in LGBT circles and believes in fighting for justice and diversity. Born in the environs of Amos, Quebec, and raised in the Capital region of Canada, Giselle studied Women's and Gender Studies at the University of Ottawa, prior to working...

Alex, The Closet Sissy

by Areallysissyboy on Feb 11, 2019
Transgender & Crossdressers

My name is Alex, a closet crossdresser. 18 years old, never had a date. Too skinny, too weird, too feminine. I wore my hair long but not a hair on my body tho, not very athletic. Just a 5'3" skinny 125lb pale white boy with long black hair. Who loves dressing like a girl every since my older sister, Sam, moved out 1 years ago which left her old room unsuperv...

She's Got Balls

by Dar_Jisbo on Sep 16, 2017
Transsexuals & Crossdressers

I stared morosely into my drink. At the age of 38, divorced, depressed, slightly overweight from drinking too much lately, I knew I wasn't the best catch. At least I still had a steady job. My now ex-wife had left, with the kids (college-age now - twins, we had them when I was 20 and she was 18) a year ago. I was caught completely by surprise. She had thro...

Letter from East Hesburgh

by justincbenedict on Sep 24, 2019
Transgender & Crossdressers

Dear Shoeblossom Flash loves to tease my butt-hole, she runs her long nails in and out, and then, of course makes me lick off the crud. She will use her other hand to twist my cock head about, what do they call it, the glans? like she's trying to open a bottle of baby aspirin. I'm standing in front of Flash, who is resplendent in her little leather miniski...

Katsumi Nakasone of Japan

by Samuelx on Mar 7, 2018
Transsexuals & Crossdressers

"My name is Katsumi Nakasone-Hollander, but everyone calls me Kat," the tall, curvy, raven-haired, thirty-something Asian American businesswoman said with a smile. Jacques Moulin and his wife Renata Urbano-Moulin looked at her and nodded. They were in the City of Randolph, Massachusetts, at the headquarters of Nakasone-Hollander Realty. Interesting pair, Kat...

Magic Dress - Serena

by SlightlyRude on Dec 3, 2019
Transgender & Crossdressers

Note: The early part of this story can be found in Cream and Lace. ***** CHAPTER 1 It was the biggest surprise I had ever had on a birthday, and it turned out to be the best birthday present of my life. My darling wife Samantha bought a dress for me. To some extent it should not have been such a surprise. My brother Frank was staying with us, and he like...

The Hermaphrodite's Curse Ch. 08

by Cleophila on Sep 15, 2017
Novels and Novellas

PART TWO - CAMBRIDGE - 1 - "So..." Gabe said, unable to sit there in awkward silence any longer, "A transgender symbol, eh? What does that mean?" After almost an hour and a half of feeling uncomfortable in the back of the cab with the fearsome stare of the purple haired punk eyeing him up from across the seat, Gabe was feeling pretty nervous. He had accep...

The Parking Lot Ch. 01

by LatexSolarBeef on Jul 13, 2020
Transgender & Crossdressers

My buddy Robbie, an old family friend, is much younger than I am by nearly 20 years. But we've always been close and enjoy hanging out. He was working as a landscaper one summer while in college. He invited me to hang out at a bar in Lavallette where he and his pals shot pool and drank beer on weeknights. It sounded relaxing, so I went. Only one other guy w...