Old Maid Stories

180,134 results
Orientation
Length
Source
Infinite Scroll

The Inquisitor Ch. 16

by theTCat on Sep 15, 2017
Novels and Novellas

The day passed as the rode along. They neither hurried, nor tarried, rather taking a leisurely pace. The device inside her played about, as if by whim, but the princess knew her master held the strings. She was amazed at the wizardry of his devices, and it pleasured her as they rode. The princess would have preferred an even slower pace, prolonging the ine...

Extra Towels

by doctor_d on Sep 12, 2017
Exhibitionist & Voyeur

The day was sunny and hot, just right for watching those bikini clad beauties down at the pool. But for me this would be a lonely day stuck in the hotel room with my computer working on the new specifications for the equipment my company had to install. This was a resort town and I was on vacation but my boss phoned me with an emergency, the client needed a...

From a Husband to a Dutiful Sissy Ch. 06

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Six will compress time a bit more forward in moving the story through time. It will be set two months forward from the original start date of the story in Chapter One, when Helen found out her husband Phil enjoyed crossdressing and fantasized about being sissy maid and a sissy slut. It all picks up with bit of recollecting from Phil who is now Chante...

Darling Ramona

by teddy2horse on Sep 16, 2017
Romance

'The House Guest' involves characters who appeared in my earlier offering, 'The Discipline Begins', and refers to events contained therein, but can be read as a stand alone story. * Florence Roberts' pretty ever-so slightly retroussé nose had been put out of joint. Sir Richard had invited a guest to stay at the Manse: Marsha Williams, best-selling popular...

The Idea Ch. 06

by niteowl2003 on Sep 15, 2017
Group Sex

How it all began. It all started with a crazy idea. Sat in a public bar, Mick and I were simply bouncing ideas off each other for possible ideal jobs. He turned to me and said "the best job in the world has to be filming those porno stars" to which I replied "No... The best job in the world would be filming everyday housewives and their dirty little fantasi...

The Family Business

by Mr James on Sep 17, 2017
BDSM

Amber stepped out of the shower and wrapped the towelling robe around her body. Her long blonde hair, darkened by the water hung down her back like a curtain of damp silk. In the mirror deep blue, almost violet, eyes looked at her, out of a lean, high cheek boned face. Her long fingers combed through the wet tresses, the action of lifting her arms pressing h...

The Maid Pt. 12

by Bumpinguglies on Nov 9, 2017
Erotic Couplings

When the old woman arrived home and opened the bedroom door, she was floored, Not at the sight of her husband and the maid together, that was a given. It was the sight of the maid's shaved pussy, looking so young between her open legs, sticky and wet with her husbands cum still seeping out of it. Pink and fresh, the lips glistening and parted, the hood of fl...

To the Manor Bound Ch. 04

by Nikki258 on Sep 26, 2017
Transsexuals & Crossdressers

This probably won't make too much sense unless you've read the other chapters first. Like the other chapters this includes forced feminisation, BDSM, and non-con, so it might not be your cup of tea. Regardless, do comment and email me to let me know what you think, or just to say hello! ***** Chapter 4 - Five Weeks After Transformation Peter held the d...

Sissy Maid Son Pt. 02

by Robyn228 on Jul 18, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Note: This story is entirely a work of fiction, and should only be viewed as a fantasy. Any similarities to actual events or people are entirely coincidental. All characters are over 18. ***** Peter wept on his mother's bed feeling violated and abused. The maid uniform still on...

David Shaw, Victorian Messenger Ch. 04

by Thorilla on Sep 19, 2017
Fetish

(It was 1892 and I, David Shaw, then aged 19 joined 'Maynard and Son, Purveyors to Gentlewomen and the Aristocracy' on Upper Richmond Road, Putney. The job involved providing 'underskirt services' to single women. This was my third day with the firm) *** I was given the following address by Mr. Maynard's secretary and arrived there promptly at half past tw...