Cross Dresser Stories

60,464 results
Orientation
Length
Source
Infinite Scroll

Remembering Louise

by Classygloves on Sep 16, 2017
Transsexuals & Crossdressers

The only times in my life that I can say that I have ever felt free and happy were those few years between marriages when I was living single and had my own apartment. Those were the days when I felt like a complete person. Although I could not live 24/7 as a woman because of my job requirements, I still managed to live most of my social life and most of my...

Hot Sex Instead of Dancing Ch. 12

by SusanJillParker on Sep 12, 2017
Transsexuals & Crossdressers

Please give me the support of your vote. * Wanting to look pretty, Walter has the uncontrollable urge to dress as a woman again. Sunday, the day of rest, Walter reflected over all that happened during the weekend. Linda had hot sex with his three friends, Jim, Henry, and Tom. Tiffany abandoned wearing her sexy nightgown to clean her kitchen in her even mo...

Cross Dressing for Valentine's Day

by SuperHeroRalph on Sep 14, 2017
Transsexuals & Crossdressers

This is a Valentine's Day contest story. Please vote. * First time in public, Frank attends his first cross dressing Valentine's Day party. Frank was online surfing the web, when he stumbled upon a site pertinent to him. He couldn't believe what he was reading. He had no idea such a thing existed. He pushed the button on his computer to print it and to po...

The Parable of Brian Brown Ch. 01

by RickNixon on Sep 14, 2017
Novels and Novellas

"The word of God to the people of God. And all of God's people said?" "Amen," Brian muttered to himself with 30 other congregation members of the Highlands Methodist Church. Pastor Jeff had just finished his lead-on devotional reading for this week's sermon. It was some gibberish from the Old Testament – Brian never understood why he frequently went back to...

Using Halloween to Dress as a Queen

by andtheend on Sep 19, 2017
Transsexuals & Crossdressers

A time to wear a costume, Jerry uses Halloween as his excuse to dress as a woman. Jerry loved October, his favorite month of the year, by far. The Fall was his favorite season, too. With the colorful array of leaves that crunched underfoot and the multi-colored canopy overhead, he loved the cool crisp air that made his nipples as hard as his cock. Whenever...

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...

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...

Halloween Cross-Dressing Bash Ch. 04

by BOSTONFICTIONWRITER on Sep 16, 2017
Transsexuals & Crossdressers

"If I knew you a bit better, I'd tell you the other half of the story relating to the name of the shop and what my ex-husband tricked me to do, but it's a bit risqué and I'm embarrassed that I fell for it," she said with a sexy laugh. "I'm too trusting and it's only something that I would do. I should have known better," she said hanging his dress back on th...

Planting Trees

by KaseyKlein on Sep 16, 2017
Transsexuals & Crossdressers

Author's introduction. I've not published to Literotia.com for long, with just two stories up. I'm pleased with the views, the hits my work gets. I'd like to see more comments. I've received some nice letters. I've been writing in open forums for about a decade, so I'm used to ignorant comments, somehow the reader mistaking my characters for me. I write s...

Hot Sex Instead of Dancing Ch. 08

by SusanJillParker on Sep 12, 2017
BDSM

Please give me the support of your vote. * Bound to the bed and blindfolded, instead of taking her dancing, Walter gives his wife, Linda, what she really wants, hot sex. With her on her back naked and helpless, Walter imagined his wife, Linda, tied to the bedposts at her wrists and ankles. In the way she was staring at him was the same way he imagined him...