Sissy Whore Stories

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Orientation
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Infinite Scroll

Jennifer Monroe & the Ladies Ch. 01

by corduroysissy on Dec 31, 2017
Transsexuals & Crossdressers

Jennifer Monroe & the Ladies -- Chapter one Jennifer held Debbie's hand as she led him down the stairs and into the finished basement. It was a large single room with a sofa, a few comfy chairs and a queen-sized bed at the far end. Seated on the sofa and chairs were five ladies, all of them dressed in corduroy outfits. Jennifer ignored them as she whisk...

Girl's Night Pt. 13

by DifferentBreed on Sep 14, 2017
Fetish

This is a culmination of an earlier story. It contains fetish themes of forced feminization, humiliation and other erotic themes that may not be to everyone's taste. If you enjoy these, please read on. Enjoy. - DB ***** Fisher minced after Eve, his skyhigh six inch heels whispering across the plush carpet of the hallway and then into the spacious living ro...

Mistress Commands Me in the Office Pt. 01

by Tracy69 on Dec 3, 2019
Transgender & Crossdressers

My phone buzzed, and chimed softly. But not with my normal text chime, with the soft, sexy whisper of my mistress, with the soft command "answer me now", and underneath that, the subliminal subtle trigger words "suck cock, panty girl". The app mistress had installed on my phone allowed her to choose the volume level, and select the chime, so I was grateful t...

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...

From Her Ex-Boss to her Bitch Pt. 03

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

This story contains extreme fantasies of Fem Domme, watersports, cock sucking, forced bi, if these aspects are likely to upset you please do not read on. ***** Pete had been taken in by Rachel, encouraged along the way, with a little titillation and confessions of her bisexuality. For a married man he had admitted too much and allowed himself to be taken f...

A Sissy's Forced Gangbang Pt. 02

by sissy77 on Dec 8, 2017
Transsexuals & Crossdressers

This story is a continuation of the part one of the series under the same title. If you haven't read part 1 already, I highly recommend you do so before reading this part. ***** After snapping out of harsh daddy's words and contemplating what more humiliation was planned out for me, I lifted my head off the bed and was welcomed to the sight of big daddy's...

Abducted and Turned Out Ch. 04

by dawnib66 on Sep 12, 2017
Transsexuals & Crossdressers

I let the landlord in and he immediately pushed me over the arm of my sofa and yanked my skirt up and pulled my panties down. I moaned and purred while he plunged his cock in and out of my pussy, fucking me furiously for about 5 minutes until he filled me with a nice hot creamy load. Then, without a word, he zipped up and left. I stayed there for a couple o...

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...

Sissy Crossdresser Needs to Please

by Interested4L8R on Dec 11, 2018
Transgender & Crossdressers

My wife is out shopping. I have just a couple of hours to indulge my fantasy before she returns. Yes, that fantasy. The same fantasy you have. The one in which I open my wife's closet and decide what clothing of hers I'm going to wear. I want to dress up. I want to dress up for you. And my little smooth, shaved cock is quivering in anticipation. What will I...

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...