Fisting Crossdresser Stories

4,986 results
Orientation
Length
Source
Infinite Scroll

Bra Zen

by ValoryG on Jul 10, 2019
Transgender & Crossdressers

Millions of women are familiar with the Bobby Braxton brand of bras (BBBB), one of the brands under the corporate ownership of Simone International. Where Simone's bras from all its lines cover the spectrum from teen training bras to 48DD harnesses, the Bobby Braxton line, Simone's most expensive, specializes in sexy, fancy, often elaborate brassieres rang...

Fisting and Wine Bottles

by 57hangar on May 12, 2020
Fetish

This is an account of a true event.... Started playing and stretching with a new friend recently. She contacted me through a website, talking about her desire to be fisted. We talked about our fantasies and experience. She really wanted to have her pussy fisted up to my wrist for the first time and have it stretched. Anal play was also something she wanted...

Into The Abyss: Vaginal Fisting

by Kael01 on Sep 26, 2017
How To

A bottle of water based lube and a pair of gloves. These are the basic tools that you need for a lot of different endeavors. Medical Play, anal play, putting new grips on your golf clubs, and replacing the washers on that leaky faucet are just some of the wonderful uses for these two tools. The one that we are going to discuss today is fisting, specifically...

One of My Favorite One-Offs

by slaveheathen on Nov 27, 2017
Fetish

This is a true story about one of my favorite one-off CL hookups. I had posted an ad, this being back when CL was still actually useful instead of the joke it is today. I mean, seriously, what's with all the time wasters these days? Anyway, I posted the ad; "non-passable crossdresser submissive, I suck cock, eat ass, love getting ass fucked, do ATM, swallo...

Asian Bimbo Sissy Slut Ch. 01

by melltsslut on Sep 14, 2017
Transsexuals & Crossdressers

Soo...where should I start? I'm sitting here now in liquid black leggings, a hot pink crop top, and a carefully teased wig, with D-cup breast forms glued onto my chest. Oh, as well as the special panties my girlfriend designed - for both of us! From the outside, they look like French briefs. On the inside, they're a little more special, if you get my drift....

Slave Tail

by Cyberweasel89 on Jul 11, 2020
Fantasy

In the kingdom of Pendragon, slavery is a burgeoning industry. Anyone can end up as one if they aren't strong or lucky enough. Slaves can be purchased, sold, and traded legally by anyone with the right business sense and magic. Slaves cannot be freed and are at the mercy of their current owner. Often kept naked to denote their sub-human status, some are cher...

Open in Reader

Sissy Academy

by Cynthia Sissy on Jan 2, 2019
Transsexual

(feel free to message me about anything! I'd love to hear from my readers :)) The alarm beeps away as you groan at the sound of it. A cool breeze rustles the curtains, letting the sun peek through. Pushing your hair to one side, you check the time. "Oh, it's still early," you say, pushing the sheets away to reveal your blue satin panties and chemis...

Open in Reader

Craigslist CD Hookup

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

I have been crossdressing since I was a kid. I started out with a pair of my mother's pantyhose, as most other crossdressers start out the same way. Once you get bit by the bug, you're hooked. This is my first story, but I have so much to tell that this certainly won't be my last. All of what I tell you here will be 100% true. I will not dramatize or sensati...

Vaginal Fisting

by Hand on Sep 26, 2017
How To

Editor's Note: The opinions and/or information in the how-to section are not those of Literotica.com, and anything you do with this information, you do at your own risk. Thank you for reading, and enjoy! There are many people who have never heard of fisting, or have no idea what is really involved. There are two types of fisting, vaginal and anal, this arti...

Crossdresser Gets Found Out

by leathertanya on Sep 16, 2017
Transsexuals & Crossdressers

This story is fiction and is written for my pleasure and any comments or suggestions that anyone would like to make. Any suggestions to the address in my profile. I adore the feel of leather, rubber, pvc and anything silky so it was no surprise to me that at an early age I liked the feel of certain female clothing. I am a perfectly straight male but my fant...