Older Woman Spanking Stories

244,677 results
Orientation
Length
Source
Infinite Scroll

A3 - Younger Man with Older Woman

by SexyPillowTalker on May 27, 2019
Mature

All characters are over the age of 18. ***** Since Jeff's mother, Rose, allowed her son to have his incestuous, sexual fantasy with her naked body, as promised, Brianna arranged for Rose to experience her sexual fantasy by having sex with Jason, a man half her age. Brianna told her friend, Jennifer, about wanting to give her boyfriend, Jeff, his sexual fa...

Reading Material

by FeJuggler on Sep 1, 2017
Group Sex

Shelves of books loomed high above Marcie's head. Coupled with the dim light and near perfect silence, the bookstore reminded the forty year old of caves she'd visited earlier in the summer. Borrowing a small footstool from the next aisle, Marcie stepped up to one of her favorite sections of the shelves. The erotica section, naturally, was placed on the high...

Adult Women Discipline Series - Spanked

by tom6432 on Mar 26, 2019
BDSM

Adult Women Discipline Series - Spanked (This is a fantasy written by myself for fun. It contains spanking, humiliation and fetish; if this bothers you please seek other authors. All characters are 25 years old or older. If I have time this will become a series.)======= In our household two grown women are disciplined, if they disobey my rules. My wife, wh...

Sissy Lesbian Rita Meets Lisa

by maturesubmale_for_F on Apr 22, 2020
Transgender & Crossdressers

Dear readers, This is a continuation of my two already published stories: 'Miss Johnstone's Lesbian Sissy Slut' and 'Further Training as Sissy Lesbian'. I sincerely recommend reading these stories first as it provides background for this one. My stories have been well received and I would like to thank you all for the positive response! Enjoy and please ta...

Further Training as Sissy Lesbian

by maturesubmale_for_F on Apr 22, 2020
Transgender & Crossdressers

Dear readers, This is a continuation of my story 'Miss Johnstone's Lesbian Sissy Slut' and I sincerely recommend reading that story first as it provides background for this one. Enjoy and please take time to give me some feedback! Theo 3. Intermission: Further training Following the loss of my sissy virginity just after I had turned eighteen years old,...

My Journey to Submission Pt. 01

by davetoyboy on Sep 19, 2017
BDSM

I was a 20 year old senior at a large Midwestern university in the 1970s. I was shy and smart and beginning to explore my sexuality. I dated a few women but nothing special had yet developed. There was an older woman who I knew casually during my freshman year. She dated an older guy in my dorm. Her name was Karen. She was tall, slender and had a foxy face...

Carol Attends First Spanking Party

by reddbunnz on Sep 12, 2017
BDSM

Chapter One: Their First Party Before leaving after a night of spanking and sexual fun, Debbie told Ray and Joy that she would love for them to join their spanking club, and that their monthly meeting would be the coming weekend at a hotel located nearby. She explained that check-in begins at four, cocktails at five, but most members don't begin arriving un...

How I Spent My Vacation Ch. 01

by rembrandt on Sep 15, 2017
Fetish

Sophie was more then a little annoyed, at her age, to be forced by her parents to spend the entire summer vacation away at a summer camp like a little kid. Her friends would all be enjoying their summer vacations at beach houses, sunbaking and partying, or at the very least working back home and earning some real money. Even though she was eighteen, from the...

What Now, Sir? Ch. 02

by brahmin on Aug 30, 2017
Mature

Yes, I know. I've been the silent partner so far in this escapade. An ex-girlfriend used to call me Mr. T, because she said I was such a tease, so let that be my moniker for now. I'm in my early thirties, an average guy in looks, with perhaps a bit of a baby face, or so some have said. I stay in shape and women generally find me attractive, particularly the...

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...