Start Smoking And Crossdressing Stories

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A Night of Surprises

by StephaniePlayland on Oct 16, 2018
Transgender & Crossdressers

Back story. I've been crossdressing for many years. The reasons for it are not really important however, I know I enjoy escaping being me, and getting to be softer, submissive and docile. My friend, Sir caught me crossdressing a long time ago, he has never really cared what I do as he has lots of women. We both enjoy the friendship and no judgements about a...

Rachel's Crossdressing Daddy

by randydaughterreborn on Mar 28, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. *** Hey, my name's Rachel and my story is a bit of an unusual one. Let's just say that one spring day, my whole world was turned upside down, but I loved every second of it. Just a little about my family: to this day, my parents are happily married. Mum is a loving woman, generally sup...

Life's What You Make It

by HYjaCK on Jun 7, 2020
Amateur

The first thing I see as I wake up is the blinding light coming through my curtains. Sadly, I couldn't afford blackout curtains due to my poorly-paying job that barely covered the bills, but I've slowly gotten used to it. I sit up and get off the sofa, stretching my back and neck. I also couldn't afford a large flat, so I had to make do with a single-room wi...

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The Devil You Know Ch. 01

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

Brian Davies sat on the hard toilet seat in a cubicle of the men's room on the twelfth floor of the building housing the large publishing company he worked for; he was reading the Daily Mail and trying to kill the last half hour before quitting time. As a middle-management employee he didn't really work mandated hours; he was expected to work whatever hours...

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...

Men and Women Cannot Be Friends

by chloevargas on Jul 15, 2020
Transgender & Crossdressers

"If this is what you want," she said, her tone even and controlled. I could tell she was disappointed. Perhaps she'd dreamed of a relationship or she'd fantasized of an emotional connection with me. She'd never hinted or remotely seemed interested. I thought she was happy with being friends. My few fumbling attempts to offer something more were rebuffed po...

Barrack Room Betty Ch. 09

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Nine - Pink Pussycats All good things come to an end and the six-week Reduced Operations Period at HMS Chelmsford ended on 15th January 1974. The Wrens and Leading Recruits were very busy as that day approached. The Depot needed to be de-winterised and preparations made for the return of the Ship's Company, the recruits, and the Wrens from their l...

Escapism: The Modern Man

by chasingrisque on Sep 13, 2017
Transsexuals & Crossdressers

*Synopsis: 25, in and out of relationships and one-night-stands. In debt, slightly overweight, unfulfilled at work and in life. Sick of his friends and routine, Alex accidentally reawakens feelings he has not had for a long time. Think Trainspotting for sissies - American Psycho without the violence and lot more lace, lip-gloss and high heels.* ESCAPISM:...

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...

All I Want for Christmas, Is You! Ch. 01

by grgy56 on Dec 17, 2017
Transsexuals & Crossdressers

"Open mine first!" Cheryl gleefully shouted as she handed me a beautifully wrapped Christmas present. It was a cold, crisp, white Christmas morning. But much later in the morning than I would usually get up for Christmas. For some reason, I slept in regardless of my excitement to open the presents under the tree. As a kid, we would open our gifts on Chris...