Crossdressing Stories

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Girlfriend with Testing Device Ch. 02

by Razmagurk on Jun 25, 2018
Transsexuals & Crossdressers

Author's Note: This is part two of my smutty little romantic comedy series. This chapter is probably the smuttiest of the early chapters, but its also the shortest because I was still kind of finding my stride when I wrote it. Please leave a comment! I love hearing from readers! A special Thank You to everyone who commented on part one! Its people like you...

Quinn Ch. 10

by 36FF_Tiki on Mar 5, 2018
Transsexuals & Crossdressers

Sorry for such a long delay on this. Real life has a will of its own and decides to intrude sometimes. I hope the story makes up for the wait. There are bound to be mistakes even with a good proofreading. I'm far from prefect. Still, I hope you enjoy it and feel compelled to leave a nice message and a high rating. It might be little slower moving than usual...

Fair Is Fair Ch. 04

by bgdddy_2000 on Sep 18, 2017
Transsexuals & Crossdressers

This is a story about crossdressing and bi sexual experience involving male on male contact. If you don't enjoy this kind of story, why would you read it? ***** His cock hit the back of my throat as he held my head, getting ready to fuck my mouth. I would have gagged, had I not had so much practice sucking cock recently. I relaxed my throat and let his coc...

From a Husband to a Dutiful Sissy Ch. 08

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Readers, I so hope you are enjoying my story here. It sort of allows me to live vicariously through my words as Chantel. This story has been outlined to allow me to write it in an encompassing and linear way. I try not to wing it but to paint a story that is life-like without being boring, well at least I hope it's not. I hope my characters are believable an...

Paul's Ultimate Fantasy

by kelsie on Sep 16, 2017
Transsexuals & Crossdressers

Paul couldn't walk fast enough. His heart was pounding and he kept checking the time on his iPhone every couple of minutes. It was only a ten minute walk to the hotel but it seemed to Paul that he would never get there. He knew that Marie has something very special planned for him and he couldn't wait to find out! The day started normally enough. Paul was u...

Nikki Goes to College

by Latexsissy69 on Sep 25, 2017
Transsexuals & Crossdressers

When I was younger I used to be a complete bully. I used to make fun of the poor people that couldn't afford to buy new clothes every school year. There were also times that I would make fun of girls that didn't want to participate in gym class because they were wearing a dress. I used to agitate so many people that I would get into fights almost daily. One...

Kasey's Confession Ch. 19

by KaseyLegs on Sep 13, 2017
Transsexuals & Crossdressers

I woke up very early in the morning, having fallen asleep in my bathtub. The water had turned ice cold, which along with the discomfort of having my head planted in the corner of the tiled wall, had jolted me into an early awakening. Tuesday was Lisa's funeral, and I had the day off for it. In the morning, after getting some more sleep back in my bed, I wou...

Michele and Buster: A Tranny Tale

by MicheleNylons on Sep 14, 2017
Illustrated

This is the continuation of my True Stories series, where I tell my readers about my real life adventures as a part time transvestite. In this instalment I will tell you about Buster, an admirer with whom I have I met up with a number of occasions. I warn you now that the story contains graphic sex, use of alcohol, mild bondage, use of recreational drugs and...

St. Clair Ladies Circle: Leonard

by 1946EW on Sep 16, 2017
Transsexuals & Crossdressers

Thelma and I were lunching at one of the St. Clairs' favorite restaurants, having just left the beauty salon. It had been three months since I had been with William. I still could not perform with Naomi as a man, although I ate her daily to orgasms. We had adjusted to our new lifestyle, opening a manufacturers' representative firm, Imhof Consultants, in a di...

Sissy Sidney and Sister

by FemFreak on Apr 17, 2019
Transgender & Crossdressers

Summary: Sidney is reluctantly persuaded into submitting to Ellen's humiliating wishes. His sister is along for the ride and gets to humiliate him a bit as well. In the end, Sydney questions his identity. All characters are 18 or older. Tags include feminization, crossdressing, pegging, femdom, mff, incest. ~~~~~ Angie loved to bully her little brother Si...