Schoolgirl Caning Stories

8,898 results
Orientation
Length
Source
Infinite Scroll

Return to "Weekend School" Ch. 14

by cynthiablaine7 on Oct 26, 2020
Transgender & Crossdressers

[This story involves bodily functions and sometimes severe disciplining, including caning and spanking, as well as crossdressing. If reading about those offends you, read no further. These stories may be read separately but do gain from being read in sequence.] Laura Franklin wasn't sure what kind of response she would receive when she sent out notices by m...

Learning the Art of CDD Ch. 03: Fun Time

by DonBrown on Jul 24, 2018
BDSM

Thought I would add a little of the fun side of CDD before highlighting the work of the cane or paddle. All couples have their favorite stimulation and sexual releases. These are a few accounts of ours over the years. We went on a rugby club holiday with 10 other young couples, children had never even been thought of by any of us. We were all of a simila...

Joan Takes Charge Ch. 05

by cynthiablaine7 on Aug 20, 2019
Fetish

[This story is part of a series, and you likely will enjoy it more if you read the earlier chapters. However, that is not mandatory, but the story does involve incest, bodily functions and spanking, as well as other fetishes. If any of this offends you, please read no further. All characters are 18 or older.] Andrea was still amazed that Joan, who had shown...

Master Thumbsy

by justincbenedict on Aug 6, 2019
BDSM

Noelle knelt before the two men, tears misting her eyes. The long lashes batted, and she wondered how this had happened, again. Still, it was incredibly hot to have your husband humiliate you before his least attractive employee. Marsden looked down at his beautiful, naked wife. She was a teensy bit chubby, a curvy Rubenesque figure, with heavy breasts that...

Margaret Visits the Headmaster

by Pimpleia on Feb 6, 2018
BDSM

'You haven't written anything for Literotica for a while.' It was Saturday and we were enjoying a late breakfast after a leisurely bout of summer morning lovemaking. Her face still aglow with post-orgasmic blush, Margaret dipped a finger into the honey jar and licked at the sticky sweetness with delicate dabs of her tongue, before sliding the whole finger i...

School's Out

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Steve asked me if I'd like to come to our school reunion. We were both twenty and being schoolmates seemed a long time ago. I agreed before he told me it was fancy dress. 'Your girlfriend, Sally's ok about this?' I ask dubiously. I knew Sally well, not that we got on particularly and she was phenomenally jealous. She would spin into a rage if Steve merely...

Jessica at the Finishing School Pt. 04

by MALIBUMAN666 on Sep 25, 2017
Fetish

This story was written in 2000, annoyingly I am having to transcribe it from a physical copy since that is all I have available. I hope you enjoy it and you think it worth my efforts. This is part four of five, since the feedback has been largely positive I am cracking on with the rewriting/transcribing and the last part should be done very soon. I'm postin...

Peeping Tom Photographer Punished

by Gizmo86 on Sep 19, 2017
BDSM

Samantha and Amanda, both attractive early-30 singletons, shared a rented house in a picturesque village on the south coast of England. Hard-working professionals in the stressful world of marketing, they didn't get to spend a great deal of time in the home they adored. But when they did, they made the most of the opportunity to forget about work and relax...

Letter from Tampa

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom, This morning Dawnette Erin McE____ came to see me. She's a slightly chubby blonde, busty deputy of the Hillsborough County Sheriff's Office, located midway along the. West Coast of Florida. Dawnie came in and I smiled at her,boredly. Of course I was smoking a bowl, and Dawnie was trying not to notice this as she reached into her purse, ha...

View From a Window Ch. 04

by Drmaxc on Sep 28, 2020
Exhibitionist & Voyeur

Three people in a car, travelling down little sun-drenched roads in search of a local beach. Graeme driving with Jill beside him and Mandy in the back. The air-conditioning on. "You all right there in the back, not too hot?" A day for the beach rather than sightseeing. The villa had a swimming pool so the sea was not essential for a cooling dip and they di...