Sissy Whore Stories

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Mistress Commands Me in the Office Pt. 02

by Tracy69 on Dec 3, 2019
Transgender & Crossdressers

Oh god, mistress, my dick is so hard in my panties now. At your command, in full view of the three vid-cams you made me install in my work cubicle, right here in the middle of my work day, with my associates working only feet away, on the other side of the cubical walls, you made me do it. Your commands, your training, your trigger words. My compliance. My s...

Unloading in Bristol

by DarkParamour on Sep 19, 2017
Transsexuals & Crossdressers

It had been a while since I last did the Bristol run. I texted Sonya from the services letting her knows I would be coming round. Now I have a few holes in several ports, but there aren't many like Sonya and Dave. The door wasn't on the latch like I had said, so I knocked impatiently. Dave answered, half hiding behind the door. "What the fuck?" I said imp...

England Pink

by Stillherer on Sep 16, 2017
Transsexuals & Crossdressers

Tanya knelt in the middle of the room rocking back on her haunches slightly stunned, struggling for breath. Cum. Cum coated her face. Cum dribbled from her mouth. Cum dripped from her chin. Cum. Cum slid down her forehead. Cum streaked her hair. She tasted cum. Breathed cum. Cum pooled in the cups of her pretty pink bra. Cum soaked her pink slip making it tr...

A Well Groomed Sissy Boy

by keptsissy on May 15, 2018
Transsexuals & Crossdressers

"If I receive any complaints I'll diaper you and put you in your dog cage for 48 yours, no exceptions. Do you understand?" He looks down at me. I feel his dominance over me. I see the look on his face. I start to cry hard. "Please, Daddy, no. Don't do that to me, please...I'll be good...please..." I stammer through sincere tears. "Well then, all you have...

Steve to Stevie to ?? Ch. 08

by gbr2004 on Sep 19, 2017
Fetish

Ms Storm has exposed me to my boss, showing her that I'm nothing but a sissy faggot. It was so embarrassing. Then she watched as my Mistress took my virgin asshole. Ms Storm talked to my boss, Ms Hunter, telling her that she wanted her to keep me in line at work and make sure that I remembered my place while at work. She gave Ms Hunter permission to use me i...

Girl's Night Pt. 04

by DifferentBreed on Sep 14, 2017
Fetish

"You want to cum too, don't you bitch?" Sophie said. "But pleasure is only reserved for Mistresses and Dommes. Not sissy whores like you." Sophie looked down at him, grinning evilly, turned on by the lips descending her body and the sight of him kneeling there in sexual servitude and agony. She let her hand fall lightly on the back of Jenny's head as she fel...

Instructional Jerkoff Sissy

by dirtywordygirl on Aug 19, 2017
Exhibitionist & Voyeur

Right now, I just want you to lay back on the bed and show me what you have down there... No! I DIDN'T SAY YOU COULD TOUCH IT! That's very naughty of you to do that. First you have to ask me, so let go of your cock and show it to me like a bad little girl...you're a very bad little girl, aren't you? Let's get you a little wet and slippery, ok? Ask me if y...

First Time Sissy Maid

by bart2077 on Sep 13, 2017
Transsexuals & Crossdressers

I had been fantasizing for many years about serving a dominant Mistress, watching lots of movies online, and generally lusting over the doms I saw posting ads. At the age of 28 I finally found the courage to answer a rather intriguing post by an older woman and her trans partner who were looking for a sissy maid for ongoing service. I answered the ad, includ...

Panty Jerkoff Encouragement

by dirtywordygirl on Sep 13, 2017
Exhibitionist & Voyeur

Right now, I just want you to lay back on the bed and show me what you have down there... No! I DIDN'T SAY YOU COULD TOUCH IT! That's very naughty of you to do that. First you have to ask me, so let go of your cock and show it to me like a bad little girl...you're a very bad little girl, aren't you? Let's get you a little wet and slippery, ok? Ask me if y...

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...