Sissy Transformed Into Baby At A Dress Shop Stories Stories

371,963 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

My Phantom Lover

by DianeTG on Aug 21, 2018
Transsexuals & Crossdressers

Growing up, one of the things I hated was having to share a bedroom with my brother. Sharing with any brother would have sucked, but my brother was - well, I think the polite word is - an asshole. But I will admit that he was an asshole who was good at handyman stuff. So when our dad gave him permission to fix up an old shed we had at the back of our yard as...

Planet Pretty Sissy

by Hayleykim on Aug 18, 2017
Fetish

Louise ordered her kinky slave to stand naked in front of her. He was in his late forties, about eight years older than the pretty blonde, who had him like putty in her hands. "Welcome to your ultimate fantasy. We don't take passengers on this parallel planet. Is that perfectly understood?" said Louise. "Yes of course, Louise," he replied in a stuttering w...

Daddy's Sissy Staircase Ch. 03

by SissyLoniOR on Sep 28, 2020
Transgender & Crossdressers

This is part 3 of a 3-part series, to understand better, go back and read parts 1 and 2. Thanks for everyone's comments, this has been my first story here at Literotica, and I have ideas for many more. Please feel free to contact me with ideas for future submissive sissy slut stories! My visits to Daddy now typically involve more time than just during the...

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...

The Vixen

by TheEroticProspero on Oct 11, 2017
Transsexuals & Crossdressers

Simon first saw her as he walked through one of the rougher streets in town. He couldn't help but stare at her long red hair, sharp facial features, milky white skin and the tight velvet jacket she wore over an even tighter leather dress. He looked her up and down, admiring her modest but perky bust, her thin but shapely body and her simply perfect legs. Si...

Soames's Store

by justincbenedict on Sep 17, 2017
BDSM

Soames watched casually from behind the counter as Pangborn Mislaburski wandered through the aisles, looking unhappy. What could Pang want? Pang had been the "punk" of a series of muscular young men, supporting them royally as comptroller of a chain of coin laundries across the state. Soames was unsure how Pang did it, but he'd pick up a young man here...

Creating Ginger Ch. 06

by Ms_Allison on Jun 9, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into dominance and submission. If these are not topics you are interested in, then please move along. In the below story I refer to the male character several ways but try to maintain a consistent in referr...

Mommy and Goddess

by force_transitioned on Sep 12, 2017
Transsexuals & Crossdressers

Andrew never saw the noose. He was uncomfortable around his new mother in law - his wife's new step mom. And rightly so - he was, after all, going through the woman's intimates since the day she entered their lives, some two years ago, shortly after the marriage. Had he overcome his guilty reaction, he may have noticed a recurring theme in their conversa...

Subliminal Obsessions

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

Finding a place in the city is rough sometimes for a good place honestly and I spent two years in a real shitty studio apartment with not even a laundry room in the building and just no room or increasingly no room. And my luck turned around after I won money. Seriously there's a 50-50 draw at work and just sort of on a whim I put my name in and I won. Not...

Being a Sissy for Viv Ch. 05

by Caron on Sep 25, 2017
Transsexuals & Crossdressers

Mistress Viv wondered around the bed, filled with the most feminine and sissy items from my wardrobe. Her fingers stroking and examining various items in turn. The first things she picked up were some nylon panties. They were one of my earlier eBay purchases. A double layer of nylon ensured they always gave that nylon sliding on nylon feel even when worn on...