Literotica Wayward Stories

351,184 results
Orientation
Length
Source
Infinite Scroll

Dr. Thornbrush’s School for Wayward Girls

by Sassypants on Apr 22, 2025

Dave took another glance up at the monolithic facade of the “building” he and a few other guards had been hired to watch. There was the chain link fence perimeter several hundred yards away, with a couple more guards guarding the gate. Razor wire at the top and security cameras helped to secure a wide birth around the School for Wayward Girls. The building i...

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The Cream Doughnut

by Covatis on Sep 14, 2017
Exhibitionist & Voyeur

I've been a counselor at the Home for Wayward Women for five years. The behavioral indiscretions of the women at the Home range from kleptomania to nymphomania. Most of the women are sincerely trying to rehabilitate. But there are a few who have no intentions of changing their wayward ways. One of those few is Norma Hoffman. Norma came to the Home a year ag...

Wayward Schoolgirl

by WFEATHER on Sep 17, 2017
BDSM

It was a Thursday evening. Dinner was finished and My loving wife and slave was putting the last of the dishes away while I sat in the porch swing, reading a magazine article on the newest screenshots and news for Gran Turismo 4 while enjoying the final hour of daylight. I became so involved in the article that I did not notice the cessation of clinking soun...

Perspectives On Spousal Training

by MISTRESSTRESSA on Sep 16, 2017
BDSM

As a fifty year old career dominatrix, with nearly twenty five years in the business, I am often asked for my opinion on the topic of bondage discipline for wayward wives, or less commonly wayward husbands. Since spousal training is a lucrative and specialized endeavor, I have a vested interest in promoting it. However few prospective clients can afford my...

Granny Babette's House

by Samuelx on Mar 6, 2018
Mature

Meet Babette Grissom, also known as Granny Babette, a sixty-year-old black woman living in the City of Ottawa, Ontario. At first glance, Granny Babette looks like any of the charming old ladies you might run into your local black church. She's lovely, friendly, well-dressed, and deeply concerned about her community. Granny Babette doesn't have a family, so c...

2018 Christmas Letter

by JBEdwards on Dec 31, 2018
Humor & Satire

Our 2018 Christmas Letter Greetings friends and relatives! Before we forget like we did last year, Merry Christmas, Happy Hanukkah, Festive Kwanzaa, and anything else for which alternate side of the street parking rules are suspended! 2018 has been a momentous year for the Smithers family. Bill has been working hard, often very hard, when he has a job, an...

H. Bigguns - Victorian Scientist Vol. 01

by Paizuri_Pascal on Sep 14, 2017
Novels and Novellas

A rather dreary London day greeted me as I arose in the morning, the grey pale light yet another reminder of the rather depressing northern climes I had recently returned to, but never really escaped from in my thoughts. A late night out with friends after a most stimulating discussion at the London Scientific Foundation dinner the previous evening had rende...

The Wrong Way Road Trip Pt. 01

by SierraSprite on Oct 8, 2019
Novels and Novellas

Author's note: Please join Brian and Marigold on their fine adventure in many parts. This one begins on historic Route 66 in the California desert. ***** Chapter 1 - A Random Encounter I was wandering old Route 66 and stopped at an antique diner after a long day spent among the cactus in Anza Borrego park. The plastic badge on her ample chest said 'Milli...

Beautiful Boy Used By Women Ch. 01

by duranman on Sep 19, 2017
Mature

James was something of a loner. Although he excelled at sport and developed a wonderful strong physique, his peers seemed to shun him. Blond, tall, muscular and beautiful, there is no doubt he could have had the pick of the girls, yet he didn't seem interested, always preoccupied, almost troubled. This fact never escaped his mother, Jeannette. Her husband h...

Five Hundred

by WFEATHER on Sep 16, 2017
BDSM

Sitting on the back porch, Andrew sips His coffee, remaining quite dry as a cool spring shower falls upon the mountainside. Between the coffee, the sound of the rain, and the sight before him, the morning is definitely quite pleasant. Perhaps thirty feet away, kneeling in the grass, josephina fondles herself, as previously instructed. her clothes are soake...