First Time Lesbian Caned Sex Stories

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Infinite Scroll

Stranger Than Truth Ch. 02

by dweaver999 on Sep 16, 2017
BDSM

Chapter Two: The Screenwriters Before they left to meet the screenwriter at the Texan, Sally and Valerie packed a bag with clothes more appropriate for submitting to their Master. Both were lost in their thoughts on the drive. Valerie was still frustrated by how easily Milton Freeman, the producer, managed to make her mad. It wasn't going to help her deal w...

My First Thrashing

by spankedhusband on Feb 7, 2018
BDSM

My First Time With Another Woman Hi, I'm Melanie. I'm twenty-one and attending a local college - and still a virgin. I knew that my petite, pixie-like, small-breasted body, and my elfin face, framed by shoulder-length blonde hair, had drawn admiring looks from many boys and men; for that matter, I'd often noticed the looks of other women; especially in the...

First Interlude

by tovesslithy on Sep 14, 2017
BDSM

24 First Interlude Helen Shagton was forty-two years old. Despite this very adult age, she was nursing a very recently and well-caned bottom. She was just returning home by car. However, she had felt, as she so often did, that she really needed a good, hard, school caning style punishment herself. The Headmaster, had, naturally, been very happy to oblige h...

Claiming Katy Ch. 03

by CruelLines on Sep 19, 2017
BDSM

[Author's note: This story was originally posted in "Lesbian Sex", but due to the heavy sadomasochistic themes of the series, I have moved it to "BDSM".] ***** -Dr Isabella Pacetti's Notes: To recap: Sophie Burton has started a new job as assistant to a novelist, Marie Alderney. She has moved into the author's house and befriended her maid, Katy. Harbouri...

Claiming Katy Ch. 08

by CruelLines on Sep 25, 2017
BDSM

[Author's note: This story was originally posted in "Lesbian Sex", but due to the heavy sadomasochistic themes of the series, I have moved it to "BDSM".] ***** --Dr Isabella Pacetti's Notes: To recap: Katy has introduced Sophie to the cellar of Mrs Alderney's house, a room which is effectively a dungeon. Unable to explain her motivation, confused by her n...

A Taste of Slavery Ch. 58

by Thors_Fist on May 18, 2020
Novels and Novellas

This chapter has our slaves talking to Wendy about sex and introducing her to oral sex with men before Scott ushers her into her womanhood. This chapter contains oral sex, interracial sex, lesbian sex, and taboo sex. It is a first time story. As with other chapters, STD's don't exist in this fantasy world, nor does COVID-19. A Taste of Slavery, Ch 58 - Wend...

The First Book of the Merciful Nun

by snoopercharmbrights on Sep 12, 2017
Erotic Couplings

Author's Note: The author has asserted moral rights under sections 77 and 78 of the Copyright Designs and Patents Act 1988. This is a work of fiction. Any resemblance between any of the characters depicted herein and any real person, living or dead is wholly a matter of Nature imitating Art. There is not, and never was, a College of Correction and Redemptio...

Dirk and Roxy Pt. 03a

by PoeticallyChivalrous on Sep 14, 2017
BDSM

It was April first and you know what that means and the guys, Elaine, and I had a prank planned for the bosses secretary, Joyce. The boss had been fucking her almost daily for years I think. She was always sexily dressed but not over the top sexy. Elaine found a pair of her thongs in the bathroom trash can a few days earlier and came up with the devious plan...

The Astronaut Ch. 03

by mjar65 on Apr 24, 2018
Sci-Fi & Fantasy

For the next few days there was no more sex and little talk. It was a busy time on the farm and we all worked hard. I was happy for that. I needed a break and some time to process what was happening around me - and being done to me. I'd had so many violations forced on me. Then again, I was finding it easier to fit in with the culture of these strange peop...

The Day I Watched Them At It

by paulman on Sep 16, 2017
Fetish

When I first arrived in England and started living with Mandy my aunt, a few years back, Mandy had a carer coming in the daytime, to help with various things, as my aunt is elderly and disabled. Her carer, Jayde, was absolutely gorgeous. She made me feel good, and gave me the impression, maybe falsely, that she fancied me. A lot of flirting went on, and she'...