Milf Chastity Stories

11,971 results
Orientation
Length
Source
Infinite Scroll

Delving into Femdom Ch. 01

by readytokneel2907 on Jun 1, 2020
BDSM

**Chapter 1. Growing up Oh my where to begin, I imagine it is best to start at the beginning (or as close to it as I can remember). I grew up in a relatively medium sized east coast city living what some may call a normal life with two sisters and both my parents. Growing up I was always into sports and when I entered middle school I had begun to focus on b...

Letter from Toledo

by justincbenedict on Sep 13, 2017
BDSM

Dear Shoeblossom: I really enjoyed "Letter from Los Angeles: Ms. Scunthorpe's Rebuttal" and also the story from the Time-Lock computer Mistress in "Letter from Greater Ponsonby ." I also have a paid key holder, Phyllis. I grew up in a strict Evangelical family, here in Ohio, and our parents were very primitive, sexually... Masturbation and copulation wer...

Becoming Melissa's Cuckold Pt. 04

by GreyMatterH on Sep 25, 2017
Fetish

The next morning I woke up feeling hopeful. I'd suffered a terrible humiliation but I think that I managed to talk myself out of it, and I was pretty sure that I could trust both Melissa and Victoria to not tell anyone else about what happened. I was also happy to learn that it seemed like Melissa was pretty open-minded about my panty fetish. Initially she...

True Desires Unleashed Pt. 05

by CuckedbyBBC on Aug 1, 2018
Interracial Love

As I watched Alice ingest cum from three black men she just fucked In front of me, I started to realized that this what she wants. Thoughts started to creep into my head that she would accept a totally submissive cuck husband. All of the secrets I kept from her, both what I had done and desired to do, I hid because society taught me that a husband must be do...

Adventures of a Super-Cuck Painslut Ch. 02

by lb404 on Nov 20, 2018
BDSM

DISCLAIMER: All characters in this story are 18+ years of age. All characters and events depicted are completely fictitious...obviously. CONTENT WARNING: If the title didn't already give it away, this is a BDSM story. It will include fetishes such as femdom, CBT, humiliation, and chastity just to name a few. Mainly though, it is a ballbusting story. Not onl...

Lois Lane's Night Out

by exxxidor456 on Aug 13, 2017
Fan Fiction

As with all my stories, I welcome other authors to add chapters! Remember to like and bookmark your favorite chapters! Regular chapters with 5+ likes get a sequel, chapters with 10+ likes get two. End chapters get an epilogue with 10+ likes. Chapters with the most likes & bookmarks get updated first! All characters in this story are at least 18 years old...

Open in Reader

My Chastity Story Pt. 01

by Digger66 on Oct 3, 2018
Fetish

[Massive re-write of this story. Good feedback. I flushed out the character's motivations.] * It all started because I jerk off too much. Every night, I would retreat to the basement after my wife, Kate, would go to bed early. Both of us are in our mid-forties. I often asked for sex, but my wife complained that I was never any good at it. She always said t...

Love Street Ch. 02

by Jason_NYC on Apr 17, 2018
Exhibitionist & Voyeur

An unfamiliar local number flashes on my cell-phone screen. "Hi, Mary. It's Wendy!" Someone has the wrong number. But the voice is young and pleasantly feminine with a familiar intonation. "Yes. This is Mary," I tease. "My, what a deep voice you have," Wendy quips. "All the better to please you with, My Dear," I reply. "And how exactly would you do tha...

Sissy for Mommy's Nipple Cream Ch. 04

by ppeaks42 on Feb 11, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Jaime clasped a hand over her mouth in horror, but it was too late and she knew it. Chills ran down her spine as Julia sauntered over with a wicked smile, then opened the door to reveal her sissy daughter sitting there wearing nothing but her lacy panties and her steel clitty cage...

Stretching the Boundaries

by morris40 on Sep 12, 2017
Group Sex

You have a better chance of appreciating this story if you have a large closet full of dresses that were carefully chosen to look professional and a small drawer of lace and silk originally intended for your husband alone. If you're a man who wants me to swallow a big load of cum by the second paragraph, then you'll get along with my husband; but you'll have...