Bondage Crossdressing Stories

15,183 results
Orientation
Length
Source
Infinite Scroll

Pretty in Pink Ch. 02

by LeandraNyx on Sep 25, 2017
Transsexuals & Crossdressers

"Well, that's unusual," Susan purred, and the hairs on the back of my neck stood on end. "Our own powerhouse paralegal, all quiet and demure during the sound-off meeting? Now that just doesn't make sense." Grabbing both sides of my chair, Susan eased her obnoxious face into view. Personal space had never been her strong suit. Why god? Why? I asked the heav...

Be My Bitch

by purekink on Aug 20, 2019
Transgender & Crossdressers

I'm so glad you agreed to be my slut – I've been searching for a crossdressing hussy I can train to be my personal tart for some time now, and I'm certain I can teach you to fit the bill. I understand your fantasy is to be dressed as a sexy sissy and have your manhood and your cherry fucked right out of you. This pleases me, as I enjoy nothing better than u...

Feminine Fate Fulfilled

by mattpantyhose on Jun 15, 2020
Transsexual

Like all of my other stories this one had been already published on Literotica. You can find it here: https://www.literotica.com/s/feminine-fate-fulfilled__ For whatever reason Chyoa doesn't include Crossdressing in the category of Transsexual and doesn't have a separate category for that theme. This story does not include any transsexuals, but I considered...

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Sarah Had to Give a Blowjob

by SarahCD on Dec 18, 2018
Transgender & Crossdressers

I first published this story a few years ago. Since then, my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected some grammatical mistakes. ---------------------------- After collage, my girlfriend's best friend, Alison, and I found ourselves working in the same city and...

You Knew

by TwistedPanties on Mar 18, 2020
Transgender & Crossdressers

You had willingly searched and jerked off to sissy porn for years. You regularly read Literotica fiction and would love to stroke yourself for hours. It was not uncommon for you to chat or flirt with other bloggers or online friends. You sought out a deeper role. The hypnosis of online flirts and short sissy skirts led to cravings, stronger and stronger with...

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...

My New Daddy Ch. 07

by sissytoy20 on Mar 21, 2018
Transsexuals & Crossdressers

After Boss zipped up his freshly cleaned cock, glistening with my spit, he took me up to the 30th floor. My brain was still buzzing with my anal orgasm when he took my arm and basically forced me to walk out of the elevator. I stumbled on my heels beside him, reaching back to finger my cum-filled asscunt. I dug out some of Boss' load and licked it off my fin...

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...

A Halloween to Remember Ch. 02

by jealouscuck on May 7, 2019
Fetish

The morning after the Halloween party, we woke up as usual. I felt a little different under the covers until I remembered what had happened after we made love the night before. We had showered and then I picked out two pair of sexy panties. One for Jeff and one for me. I looked over at him as he started waking up. Jeff had been at home from work for a while...

Sarah has a Crossdressing Friend

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

I love to dress-up as a girl and get naughty with someone who understands the love of dressing as a girl. So I advertised on Craig's List for a crossdressing buddy; someone to play with and get naughty. A guy emailed me and we started exchanging emails and then a couple of phone calls. We discussed what we each liked to do. I love to kiss and cuddle before e...