Crossdressing Bondage Stories

668 results
Orientation
Length
Category
Source
Infinite Scroll

Slave Ch. 09

by slaveheathen on Sep 25, 2017
Fetish

SLAVE Note: This is about a bisexual submissive man and his journey as he explores his sexuality. I put it in the fetish section because that seems to be the best fit. There is piss and scat. There is bondage and crossdressing. There is fisting. There is group, gay and bisexual sex. There is non-consensual and reluctant sex. There are even elements of reali...

Tony and Alicia Celebrate Halloween

by Ice_Tease on Sep 16, 2017
Fetish

Author's note: The Tony and Alicia stories are more about experimentation between a loving couple than hard core stories in a certain category. If you are looking for a hard core crossdressing story this is not the one for you. If you want a story of a guy who will do anything for his girl to include dressing as a hooker and strapon sex then please enjoy it!...

A Couple's Journey Into Depravity

by johncockenfurs on Sep 17, 2017
Loving Wives

I'd been slowly easing my wife Lisa into my fantasies for awhile now. We're in our early 40's and have been married almost 20 years, so we had to find ways to mix things up a bit. It started with her wearing leather and pvc clothing for me, allowing me to shoot photos of her and fucking. She's so fucking hot, even though she's in her 40's, she has the body o...

Shooting The Moon Ch. 04

by SEVERUSMAX on Nov 8, 2017
BDSM

"So, that's it. The new contract for Robert and me in our new life of bondage to you. I rather like it, in fact. It's making me wet, just thinking of how much we're both your sluts now. My hubby and I. We belong to you for life, by our own agreement. We will gladly serve you, as this contract stipulates, Master," Lindsay assured me, her silky hands caressing...

Evolving Sex Life Pt. 01

by slavecaro on Jul 14, 2020
BDSM

This story is part true but if chapters progress, it will evolve to include pure fantasy. It is about a husband and wife married for several years. The sex at the beginning is rare and boring for both. It will include many kinks but is starting out as wife humiliating a husband, denying him intercourse, and long nails. It can go a lot of places from here bec...

Slave Ch. 11

by slaveheathen on Sep 25, 2017
Fetish

SLAVE Note: I have no idea if a resort like the one in this chapter actually exists, but damn I'd love to go if it did! If you haven't read the previous chapters, I'd suggest you do, as it would help to understand the characters better. This story is about a bisexual man who has completely submitted to his Mistress. It contains scenes where he has sex with...

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...

Just a Girl

by katie_risita on Sep 18, 2017
Loving Wives

My name is Frank. OK, it WAS Frank, until recently, when things...changed. Now, more often than not, I answer to Katie. I know, I know. Yes, I am a guy, technically, but, well...to explain, it's gonna take a story, a loooong story...but not a boring one, I promise! I am a 33-year-old guy from Long Island. I have always been overweight, not great-looking, s...

Story Tags

by Literotica on Sep 18, 2017
How To

You've written your story, edited it within an inch of its life, and are all ready to show it to the world. You open a submission page and – what's this? Story Tags? What the bleep is a Story Tag? The larger any archive grows, the more important organization becomes. Separating stories into our current categories helps connect readers with stories they'll e...

You Never Know

by lipsticked on Sep 13, 2017
Fetish You Never Know

I moved to Los Angeles from New York about eight years ago, right after my divorce. The marriage didn't last long and ended bitterly. I now live a block from the beach in Santa Monica in a fairly exclusive high-rise apartment building. I quit my job as a graphic artist with a top advertising firm in NY, when I moved and started my own business here. I have a...