Crossdressed Stories

155 results
Orientation
Length
Source
Infinite Scroll

Frolicking on the Fifth Ch. 02

by Entrammeleur on Jan 22, 2020
Transgender & Crossdressers

This story follows the events of "Unleashed By Nair" and "Boned on the Fourth of July." *** After dancing on my driveway in my wife's off-shoulder mini peasant dress, I needed a drink. I sipped Gatorade through a straw to avoid messing up my lipstick, and leafed through the local paper while pondering my next outfit. An item near the automotive ads caugh...

The Bitch Bites Back

by MicheleNylons on Sep 13, 2017
Transsexuals & Crossdressers

Pamela stood huddled in the dark doorway, halfway down the back alley. It was cold and a light drizzle had settled in, the sheets of fine rain just discernible in the dull light of the single working lamp halfway down the alley. Pamela was in her mid forties and fighting a losing battle against the rising tide of age, her thighs and bottom were spreading, h...

Outdoor Liberation and Cuckolding

by Leighharding on Oct 15, 2017
Transsexuals & Crossdressers

After very nearly getting caught indulging my secret little hobby when my next door neighbour's daughter decided to step over the fence into my garden to look for her lost rabbit, I decided to renew the fence. I remember the feeling of horror realising what she'd have seen if she'd have turned around. A new fence has given me almost complete privacy and ye...

The Adventures of Joe the Pirate

by Noira on Sep 14, 2017
Humor & Satire

Author's note: warning, sarcasm ahead. Do not read if you are easily offended by stories that do not take themselves, or anything else, seriously. Written with the intent of getting as many Lit categories in one story as possible. — It was a brilliant day in Brilliantville, and Joe the Pirate sprawled out on his quilt, which happened to be made of various...

Michael Ch. 01

by discreetboy2004 on Sep 16, 2017
Transsexuals & Crossdressers

This is a true story about one of my experiences. As usual I changed people's names for their own privacy. I know it starts out a big slow, but just wait and see. XXXOOO Alissa. It was the late 90's and I was living in the East Bay area of Northern California in a medium sized city called San Leandro. I was in probably the best shape of my life, which iro...

Friday Night

by submissiveanne on Jul 3, 2019
Transgender & Crossdressers

I was in a chatroom when I met Cassandra, or Sandy as she preferred to be called. She was in her late 40s and was married. We lived in the same city and had many of the same interests. Now at the time I was in my early 20s and I lived alone. I had also experimented with straight and gay sex as well as crossdressing. Cassandra and her husband were poly amorou...

The Marriage of Martin Hastings Ch. 12

by rik581 on Sep 14, 2017
Transsexuals & Crossdressers

Martin was hurried down the hall to meet his husband. It wasn't that he was eager to get to him, but the pace he was being forced to take made him have to run to him. If nothing else the morning treadmill walks were schooling Martin in how to move quickly in high heels. "MMPPPFFF!!" Martin snorted as they reached the Baron. Martin pulled away from the man t...

Stranger Fuck

by hfernandez1983 on Sep 13, 2017
Transsexuals & Crossdressers

It's been a while since I have written something. It's mostly because I have felt so uninspired and didn't know what to write. My main fantasies these days revolve around a man crossdressed while he is pegged by a woman who likes to dress as a man. My last story series Jenny & Mike got a decent reception and I wanted to write more. But like I said, I've...

Making a Sissy Jock Pt. 02

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

I stared at Robin's card for an hour sitting in my truck completely freaked out and every time I touched my lips I felt that friction of Robin's cock. I tasted him. I got slammed with the realization I drank his cum and it was inside of me. I sucked cock and drank cum and just like the sissy porn stuff said I liked it. I was beyond freaked in going to th...

Life and Time of Lady Vargos Ch. 05

by rik581 on Mar 26, 2019
Transgender & Crossdressers

Chapter 5 "A Spa Education" Martin had been through a very traumatic week at the so called spa he had been taken away to. He cried himself to sleep most night wearing only ultra feminine nighties with loads of ruffles and lace in various colors of lavender and sapphire blues, black and even a rather childish looking very short nightie in hot pink. He had b...