Sissy Caught Stories

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Orientation
Length
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Infinite Scroll

Discovering Amber Ch. 07

by Ms_Allison on Mar 25, 2019
Transgender & Crossdressers

Mistress notes: The morning after is always fun, people tend to get caught up in the moment, sissies included, and amber was no exception. The fact Jenn and I were there to remind her of all of it just made it better! The fact amber seemed to really enjoy humiliation only added to the whole experience. Ms. Allison ~~~~~~~~~~~~~~~~~~~~~~~~~~ The following...

Sammi Starts Camming

by Sissy_Sammi_ on Dec 3, 2017
Transsexuals & Crossdressers

Sam had always been rather small and feminine. As a guy puberty seemed to have missed him which left him in the rather uncomfortable position of being very girly. He was only about 5'8" with a womanly rounded face, smaller waist, and slightly larger hips. He had brunette hair, which for a guy was on the longer end. His lightly tanned white skin pieced with...

Invited to Interview

by Vramborne on Sep 16, 2017
Transsexuals & Crossdressers

'You are invited to interview. The Narrows, 7pm, do not be late. -Master Green and Mistress White' It didn't say how I should dress. It didn't tell me how I'd know who they were. They'd seen some pictures of me, sure, but I'd always blurred out my face. I sat on my bed staring at the screen in indecision watching the clock tick towards five. Should I go e...

From a Husband to a Dutiful Sissy Ch. 01

by Sissy_Chantel on Sep 25, 2017
Transsexuals & Crossdressers

Preface: Welcome to my next sissy story. This one is based around the exciting ideal of a married sissy, crossdresser. It will have many ideas based on my thoughts about how life could be for me as a married, crossdressing sissy maid. I hope you all enjoy it. ***** Chapter One: Sometimes one's most unique secrets do come out. My name is Phil and I've alwa...

The Drop-Off

by Longo_Afar on Nov 18, 2019
Transgender & Crossdressers

"Where's my comb, Mommy?" Margo sighed. Sissy could be so needy at times. And was there even a brain underneath that pile of blond curls? "I'm sure I saw it on your nightstand. But if you can't find it in all the junk you've piled up there, I'm not surprised!" Yes, Sissy's nightstand was a clutter of lipsticks, rouge, mascara and numerous other skin care...

Chuck

by wajawhiii on Jun 5, 2018
Erotic Couplings

My name is Marjerie. I'm thirty-nine years old. I was married to George when I was only twenty. He left when I was just twenty-three and Charles was only two. I got an uncontested divorce three years after he disappeared. Charles is the only thing George gave me and the best thing I've ever received. Charles is now eighteen and just graduated from high scho...

Ensnared by a Corset

by spinder on Sep 16, 2017
Transsexuals & Crossdressers

Warning: This story is a work of fiction and contains descriptions of explicit sexual acts between women. If this type of content offends you or you are under the age of 18 do not read it. Author's Note: This story is the property of the author. It can be downloaded for personal reading pleasure or sending to a friend, but if you wish to re-post them at you...

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...

Prankster Ch. 08

by Paris Waterman on Sep 15, 2017
Group Sex

Late the next afternoon, Tony met with Barely to set things up for that evening's session at Crazy's place. "You know," Barely said, "I came across something last night when I was editing the tapes." "What was that?" Tony asked. "It's best I show you, then you tell me if you want it back in. It was me, I'd keep it out. I just don't feel comfortable with...

Sissy

by rogue01 on Sep 19, 2017
Fetish

Sissy It happened at last that he was caught. His wife came home mid-afternoon with her friend Miriam and found him upstairs in the bedroom wearing a pair of her panties. Her reaction shocked him. In the hot instant of his overriding shame he was aghast to discover in her a persona he had not yet known existed. Him, a faintly domineering man, like so many...