Sissy Bra Stories

144,731 results
Orientation
Length
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Infinite Scroll

In My Dad's Panties

by britneyfan on Sep 11, 2017
Transsexuals & Crossdressers

I knew my parents hadn't been getting along at all well recently and I had even begun to fear that they may some day be getting a divorce, but still the discovery that my father could be having an affair came as both a shock and something really quite distressing. It was the first time I had to confront the truth that my parents' split was a very real possib...

The Domme Club: The Fucking

by NancyPan on Sep 14, 2017
Fetish

This story will likely be most enjoyable if it is read after reading The Domme Club and one or two other stories in the series (for background of Tom and Monica's relationship and how Tom has previously been humiliated in front of the Domme Club.) Respectful comments are appreciated. ***** Mistress Monica left Tom the standard list of chores to do while s...

Sissy Pool Wager Pt. 01

by maxy007 on Sep 14, 2017
Transsexuals & Crossdressers

My name is Max, and I'm your typical high school graduate. White, short brown hair, blue eyes, skinny, and 6'4. I never had muscles or any masculine traits other than my lanky height. I had just finished high school, and had 4 months off before university to myself! As you could imagine, an 18-year-old horny boy like myself really got into my porn, which f...

Life With Miss Ida Ch. 04

by Sheermistress on Dec 2, 2017
Transsexuals & Crossdressers

As mentioned in Part 1, all Mistress and I had been waiting on was for the lease to run out on my place, so I could sort everything out and finally move into her place for good -- I had practically been living over the past few months anyway, so it really wasn't as big a move when it all came down to it. The entry way to our home, which was on the ground f...

Sissy Amy Loves Mummy Belinda Ch. 03

by Sissy Adele Howells on Sep 17, 2017
Fetish

Nurse Sue George sat opposite her best friend, Nurse Lynda Christopher. Both looked stunning in their royal, blue nurses uniforms. Lynda was a tall women in her middle forties, with dark, long hair, tied back in a bun. She wore glasses, but was attractive for her age. The best thing about Lynda Christopher, was that she sneezed frequently and enjoyed blowing...

Sissy's First

by CDJessie on Mar 7, 2018
Transsexuals & Crossdressers

This is a work of fantasy. (I wish my gf would do something like this to me.) *** I'm woken up to the blinding sun after Sarah rips open the curtains to our hotel room window. We were up half the night fucking our brains out, and I was pretty hangover "Fuck, you couldn't wake me up like a normal person instead of blinding me?" I ask. "Don't take that fuck...

Caught!

by centrum1000 on Sep 18, 2017
Transsexuals & Crossdressers

It all happened so quickly that I can barely remember the details. It was a Saturday afternoon and I was doing my laundry in the dorm laundry room when she came in. I've seen her around campus before and regularly pictured her naked body pressed against mine while I pleasured myself. Her name is Carrie. She is almost as tall as I am at about 5'7" with bleach...

Sissy's Decline into a Slut Pt. 01

by Sissy_Chantel on Sep 13, 2017
Transsexuals & Crossdressers

Hi, readers, here is a new hopefully erotic story series of a sissy's decline to that of playing a sissy slut and then without her knowing soon to be a enslaved sissy maid and slut, featuring your sissy girl Chantel. Enjoy... ************************ Chapter One: Sissy Crossdressing Play Time. I'm sitting inside my car, it's late, a faint drizzle falls a...

Ian's New Job Ch. 02

by SatinSlip on Dec 10, 2018
Fetish

Authors note- this story includes non-consensual, rough, and coerced sex. As well as straight and bi-sexual sex, crossdressing, and humiliation. ********** Wendy wore the shortest skirt she owned. A blue, pleated thing that stopped a few inches short of her knees. Underneath she wore red lace panties Ian had bought her for valentines a couple years ago, an...

Jamie's Descent Pt. 02

by nikkiesilk on Sep 18, 2017
Transsexuals & Crossdressers

'That's it, baby,' Vanessa purred as she snaked her hips forwards and back, gently sliding the strapon in and out of my mouth. I could no longer think rationally, as any self control I still had slipped away and trance like, my eyes closed, I sucked the rubber phallus in and out of my lips. 'Baby, you love this don't you?' Vanessa's voice took on a hypnoti...