Sissy Caught Dressed In A Rubber Baby Romper Stories Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com
Create your own smut fantasy with AI

Wet Dream Pt. 03

by sissymissyct on Jan 28, 2020
Fetish

Gayle finished ordering items on line and checked the cam to be sure Georgia was asleep. The wetness in her panties told her what she needed to do. The payback for all those years that bastard cheated on her and how he had no idea what was coming to him, just made her pussy so wet. She was soon in bed enjoying her favorite toy. "I can't believe I slept so l...

A Sissy Saga Ch. 01

by Snurge on Sep 13, 2017
Novels and Novellas

The schoolgirl is wearing a gymslip of such a dark shade of blue it appears almost black. She is bending forward and stretching across a small table that boasts a cover of purple chenille, resting the flattened palms of her hands on the hard surface and pressing one side of her flushed face between them. The back of her skirt as been folded up to her waist a...

Las Vegas Best Friend Threesome

by SluttyBisexualGuy on Nov 21, 2017
Group Sex

Jenny and Noah and Elijah had been the three most inseparable friends all throughout high school. They'd grown up on the same cul-de-sac and their shared geography soon determined an easy grouping all throughout the following years. In high school, they each stood out in different but complimentary ways. Elijah filled the role of the three-sport athlete...

Don Venuto's Sissies

by marybethsanford on Aug 18, 2017
Fetish

Players: Capo De Matzo, counsel to Don Venuto. Don Venuto also known as the Godfather; Mario Venuto, son of Don Venuto; Ms. Rosa Cappella, professional dominatrix; Carol Evans, mother of Mark Evans; Mark Evans aka Martha Evans; Helen Andrews owner of the Little Miss Muffin Boutique; Ralph Summers, a friend of Mark, aka Robin; Steve Franks, friend of Mark, ak...

Marketing 101

by marybethsanford on Sep 16, 2017
Fetish

Players: Mark McLuhan, (Cindy Sue) first year college student and marketing intern at Little Miss Muffin, Inc.; Ms. Helen Pennyworth, owner and president of Little Miss Muffin Inc.; Carol Winters Vice President of Marking for LLM; Susan Evans, Product Manager of LLM; Julie Pennyworth, sister to Helen and professional dominatrix and practicing nurse. Tracy Ma...

Her Eyes Did The Talking

by GoneGray on Oct 8, 2019
Erotic Couplings

This is a story of a very special 25-year old woman, the man she falls for, and her special relationship with her virtual-sister/BFF/roommate. That is all the hints I am giving, except I would say the story has primary elements of Erotic Couplings and Romance, with bits of parallels to Group Sex & Loving Wives themes. The story came out longer than I e...

The Plumber's Daughter

by beagle9690 on Sep 13, 2017
Romance

September, 2010 Marie: I was nineteen when we married. My ex-husband, the Jerk, was twenty-five. I was madly in love with him, can you believe it? He was a third year Medical Student and I was an Art major. He was drop dead gorgeous handsome and could charm the Devil to let him out of hell. I dropped out of college and worked as a waitress to help suppo...

BDSM by the Book

by Stefani on Sep 11, 2017
BDSM

I was rather slow when it came to dating. My love life moved at glacial speed until I met my wife. In high school I was skinny and too short to be any good at sports. At school and in the town I grew up in outside Sioux City, I got pushed around a lot by other boys, all of which translated into a lack of confidence. Particularly around women. When I got to...

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...

A Sissy Saga Ch. 15

by Snurge on Sep 15, 2017
Novels and Novellas

A fine day, thick and hot making Miriam Hancock's face dewy with sweat. She gazed at the house. Was this the place? She checked the card in her hand. No mistake. It was an unimposing Edwardian terrace house in a street of equally unimposing houses, narrow fronted, three stories high, the windows heavily draped. She went up a set of steps to a porticoed door...