Crossdressing And Smoking Stories

359,753 results
Orientation
Length
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Infinite Scroll

Sissy, Hypnotized

by Slipperylock on Apr 8, 2019
Transgender & Crossdressers

It had taken six months to get to this point. As I stepped out of the bathroom, I caught sight of myself in the full-length mirror, and shivered. I was shaved below the eyebrows, hairless and smooth, except for a cute landing strip above my locked chastity cage. Other than the cage, I looked like a thoroughly average 21 year old boy, my small and skinny fram...

Biker Bitch Ch. 02

by MicheleNylons on Dec 21, 2017
Transsexuals & Crossdressers

Chapter Two: Caught With Consequences Cameron Rivers' first memory of feeling different to everyone else was when he was eight years old. The other boys liked to play with bikes and toy trucks and toy cars but he much preferred his younger sister's Barbie. But even then he was smart enough not to say so. He used the excuse that he had to play with her becau...

This to Keep Me Quiet Ch. 01

by MicheleNylons on Oct 5, 2020
Transgender & Crossdressers

Chapter One - It's Not Right Uncle John, For All Sorts of Reasons Author's Note: This is a little two-part tale similar to my early stories. It has all the trappings of a Michelle Nylons story: a little incest, a little blackmail, a lot of sex and a surprising ending. I hope you like it. Crystal Palace sat at the bar watching Melanie Starr singing The Cryi...

A Night to Remember Ch. 02

by Master_and_Sex_Kitten on Sep 16, 2017
Transsexuals & Crossdressers

Happy Birthday to me...Friday April 24th was my four year anniversary of joining Literotica.com, so as a special treat, four new stories in one go! * Author's note: If you haven't read part one -- A Night To Remember -- that might help provide a little context :P this is a transsexual story about love, confusion and exploring a new world of sex. Enjoy! --...

Barrack Room Betty Ch. 03

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Three -- Michele's Story The four Wrens of Collins Division woke at 'call the hands' at 0640. Doris had got out of bed at 0600 to prepare breakfast and was in the galley. She'd tried her best to do her makeup and dress like a Wren but she still looked like a 'scranbag'; not that it mattered, in the steam filled, greasy kitchen. Her hair was matted...

College Crossdressing Confessions

by wifetoy on Sep 11, 2017
Transsexuals & Crossdressers

My wife's control over me insures that I have no secrets from her no matter how depraved my hidden desires. She delights in my need to live under her feminizing control. As part of my training, she has ordered me to confess my prior deviant acts to the world. In this series, I confess my past experiences as a panty thieving college cross dresser. I have chan...

David and Jess Ch. 01

by TGDIB on Apr 20, 2020
Transgender & Crossdressers

This story is entirely fictitious. All names and likenesses are fabricated, and all characters depicted are over the age of 18. This story is multiple pages / chapters, and involves elements of romance and erotica. -------------------------------- Chapter One: "Have you ever thought about guys?" David inquired, sparking a tattered green bic lighter. "H...

Two Way Display

by seams_straight2me on Jun 9, 2020
Transgender & Crossdressers

Whilst writing this story I realised I am hoping to build and extend the worlds of the main characters. Suggestions and ideas would be very welcome. Zoe's view: Three weeks forced with my feet up due to a sporting injury, doctor's orders. No sport, no fun, no weight on it. And even worse, this unfortunately also put a stop to going out as a crossdresser. E...

David and Jess Ch. 02

by TGDIB on Apr 20, 2020
Transgender & Crossdressers

This story is entirely fictitious. All names and likenesses are fabricated, and all characters depicted are over the age of 18. This story is multiple pages / chapters, and involves elements of romance and erotica. -------------------------------- Chapter Two: Later that day I stood in my room, banging my head against the dresser. Not only had I ejaculat...

Webmeets Diary Ch. 03

by starbelliedboy on Sep 14, 2017
Transsexuals & Crossdressers

Note to the reader: In this diary I will tell the true stories of my sexual encounters that have come about thanks to the internet. Some more precise details such as names and places will be left out to protect mine and others privacy, and also because they don't matter, but otherwise I will try to be as accurate and truthful as possible. I'd been using the...