Crossdressing Stories

1,097 results
Orientation
Length
Source
Infinite Scroll

The Chase

by thrillerauthor on Sep 16, 2017
Transsexuals & Crossdressers

I checked the contents of my purse one last time: lipstick, compact, some bobby pins, Altoids, tissues, hairbrush, cell phone, wallet, room key, car key, cigarettes and lighter. I added the case for the sunglasses which were gaily perched on top of my head. With that, I took a deep breath, and after a final glance at my hair and makeup in the mirror on the c...

Magic Dress - Michelle Pt. 05

by SlightlyRude on Mar 12, 2019
Transgender & Crossdressers

After my birthday my crossdressing became known at work, but I still went there as Michael. A few women said I should dress as Michelle, but I noticed some men had become standoffish with me, and did not wish to make a scene. I was also still shy, and only dressed under relatively protected conditions with my family or Anne or Kathy. Maurice said that there...

Julia, Ben and Lisa Ch. 10

by chloejacobs83 on Mar 9, 2020
Transgender & Crossdressers

Ch 10: Thursday More outfits and some girl-poses. A few quick notes: 1. this is the tenth chapter of a longish story, a novel in many chapters 2. everyone is 18+ 3. there is no safe sex here - cause it's a fantasy, not an instruction manual 4. crossdressing and gender bending, not everyone's cuppa tea - be forewarned I woke up with a smile, realizing...

Alex Struggles to Accept who He Is

by Shy_n_bi on Jul 29, 2019
Transgender & Crossdressers

Alex never thought he'd be living in this moment, a desire that he kept buried ‎deep within for his entire life and now a near reality! His eyes locked on her every move as his heart raced like he had never felt it race before and the battle between pleasure and guilt had all but began leading from his mind to the pit of his stomach! There he was, nervousl...

Driving Home - Getting Braver

by GeorgiaD on Jul 9, 2019
Transgender & Crossdressers

After my experiences meeting Steve on my way home (see Driving Home), I decided it was time for me to become braver, or rather less fearful of being out in public. Meeting Steve had exposed me to face to face contact with not only another actual human being, but a real guy, for the first time ever. I concluded that it had been Steve's patient, cool manner t...

Bra Zen

by ValoryG on Jul 10, 2019
Transgender & Crossdressers

Millions of women are familiar with the Bobby Braxton brand of bras (BBBB), one of the brands under the corporate ownership of Simone International. Where Simone's bras from all its lines cover the spectrum from teen training bras to 48DD harnesses, the Bobby Braxton line, Simone's most expensive, specializes in sexy, fancy, often elaborate brassieres rang...

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...

Beta Male Slave Academy Ch. 02

by Tazokm on Jul 13, 2020
BDSM

After being blown and locked, Miss Carly explained to me that the compound we were at had over a hundred rooms and approximately 50 current residents. She began walking me to a room where I was to keep myself preoccupied until they had prepared my sleeping arrangement. I walked butt naked behind Miss Carly down a high-ceilinged hallway. Her ass was absolutel...

Ugly Duckling to Sissy Princess Ch. 03

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

(Continued from Part 2) Wow! The kiss! Wow! Before I knew it, I was sitting on Ted's lap straddling him and we were French kissing in the most passionate and intense kiss of my life! I don't even know how I got up here. Maybe I climbed on his lap or maybe he grabbed me and pulled me up here. I was in bliss! The kissing was so amazing that my whole body j...

Prison Woman

by nancyvasquez on Sep 19, 2017
Transsexuals & Crossdressers

I get a lot of questions from men that I meet. Not all of them want to have sex with me; some just are curious about what I'm all about. A lot of people who know me know that I am an extremely feminized male who became a Queen when I went to prison due to alcohol related offenses. I always say that I became a woman in prison - and that is true. But I guess...