White Sissy Stories

181,578 results
Orientation
Length
Source
Infinite Scroll

Sissy Meets Daddy

by lapitup_ on Jul 2, 2018
Transsexuals & Crossdressers

I never noticed in the moment, but I had been a sissy my whole life. Growing up I was always the shortest boy, always the weakest, I never had a girlfriend, and I wasn't good at any sports. My mom always told me I would grow into a man eventually, but that never happened, even during puberty my growth was minimal. By the time I finished high school I was a...

Halloween Pool Party Pt. 04

by sissymissyct on Sep 14, 2017
Fetish

Monday morning I was awakened early by Miss Annie releasing the air from my plug and swiftly pulling it from my bottom. I cried out from being so crudely awakened from my slumber and that got me a quick but hard smack on my already bruised bottom. "Good morning Brenda, time to shower and get ready for a big day", she informed me. "Thank you Mistress" I answ...

Mistress Shay Noir

by Samuelx on Sep 11, 2017
Group Sex

"Essential services, that's what I provide, like any good businesswoman, I know my clientele and their special needs," I smiled to myself as I read these words on the Temple of Noir website, which advertises my services to the entire world. There are a lot of Black dominatrix types out there but I, Mistress Shay Noir, am the only one catering to the hidden n...

Interracial Sissy

by nancyvasquez on Sep 16, 2017
Interracial Love

Remember how I told you the story my ex wife told me - of how that white prostitute at the strip club came out of the booth after having been in there with a black guy, and how she was flushed and proud and was telling all of the other hos about how proud she was to have been with that handsome black man? Well it happened to me tonight! I almost can't believ...

He said "Call me Daddy"

by yvetteinpanties on Sep 12, 2018
Transsexuals & Crossdressers

His personal ad said: dom top daddy seeking submissive, trannies and crossdressers preferred. When I answered his ad as a submissive sissy offering full service as requested, attaching a picture of me in a short camisole and wearing a slave chain between my collar and handcuffs, captioned with "submissive sissy cocksucker can swallow 7 inches. Boi pussy trai...

Being a Sissy for Viv Ch. 01

by Caron on Sep 25, 2017
Transsexuals & Crossdressers

"Even I had to tell my daughter off for looking at a sex site on the internet yesterday. A shame, it did look rather interesting. But even if she is nearly twenty, I really couldn't tell her now could I." "Oh, what was so interesting about it?" I asked. Viv paused for a moment, her eyes on the wine glass in her hands. "It was about turning men into maids....

Panty Posers Ch. 04

by EROTICbearscribe on Sep 21, 2020
Transgender & Crossdressers

I must tell you of an experience Daphne and I had one Saturday night. I know, I know. You're dying to find out if I ever finally met Daddy. All good come things to those who wait. I really am a sissy tease. Aren't I? I think you'll enjoy this side trip though. *** It was a lazy Sunday morning. Daphne and I were sipping coffee and nibbling on some danis...

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...

Panty Posers Ch. 05

by EROTICbearscribe on Oct 5, 2020
Transgender & Crossdressers

I certainly wasn't in Kansas. I was dressed as a private school girl tease and standing in front of an adult bookstore superstore. What did my sissy sister have in mind? I tried to find some sort of hint but his poker face offered no clues. We were certainly dressed for more than just shopping for DVD's. So I didn't think we were there for the sales. We ha...

Maid on Boxing Day

by Belongs2Beth on Sep 14, 2017
BDSM

Authors note: This story is an immediate sequel to my first story "Carol's Christmas". The events of this story deal with the younger man named Marcus who Mrs. Carson initiated into the mysteries of sex and submission in "Carol's Christmas". * Marcus was sweating bullets as he rang the door. He burned for Mrs. Carson...Mistress Carol...and needed to be wi...