Milf Chastity Stories

11,971 results
Orientation
Length
Source
Infinite Scroll

A Lesson for Lilah

by Ronin_Sundered on Sep 14, 2017
Sci-Fi & Fantasy

One of the elements of my life that had been, for so long, a thorn in my side recently has been resolved. You see, I am a doleramancer, or in the vulgar argot, a practitioner of pain magick. While theories on pain magick vary, I personally see it as what happens when sex magick grows up and gets nasty. To put it simply, the fuel for my most powerful works of...

Neighbourhood Terror to Sissy Pt. 08

by Fibaro on May 20, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** Chapter 9 Once off the bus Mark snuck to his house as good as he could. Hiding behind bushes and hedges whenever he spotted someone. He really didn't want to run in any of his neighbours with this big pink shopping bag. It would mean nothing but trouble since he realised f...

Happy Place

by Miguel59 on Jul 31, 2019
Loving Wives

We all have them. Some of them are locations. Some of them are activities. Some of them are done in solo while others involve people. Mine includes elements of all three. Today's happy place occurred in my house, specifically the living room. Drill down a bit deeper. On the couch in our living room. She took me to my happy place. Our relationship is symbi...

Mind Over Management Ch. 04

by SEVERUSMAX on Sep 15, 2017
Group Sex

I was balls deep inside Cheryl, with Jess sucking my balls and Jamie rimming Cheryl's ass, when Jen came through the door from work and immediately started to disrobe. Before I knew it, Jen's cunt was in Cheryl's face, and the blonde went to town on her snatch, licking away like nobody's business. We fucked for several more minutes, while Cheryl sucked Jen's...

From Charity to Chastity

by carrteun on Mar 10, 2020
First Time

This is my submission to the 2020 Valentine's Day contest. Please take a second to vote if you enjoy reading it. I've already enjoyed reading some of the submissions and look forward to reading more entries. Good luck to all the authors. * I almost felt like I didn't belong the first few weeks. Many of the faces were only a handful of years younger than me...

Before and After

by aanmetoo on Oct 19, 2020
Loving Wives

Reid's phone buzzed while he was having his "just got home from work piss." He carefully reached for his phone. Carefully, because 12 weeks before, his wife had locked a chastity cage on his dick and he had to be careful or he would pee all over everything, especially himself. He sat back upright, when a man wears a cock cage, there's no more stand up pissin...

Journey into Feminization Ch. 01

by KneelingNancy on Jul 14, 2020
BDSM

***Chapter 01 - The Beginning Like so many of our beginnings, mine started to what some would call a normal life. I grew up in on the west coast and would consider my family upper class. Both my parents had successful careers and my brother and I had a lot of great experiences growing up (private sports clubs, investment in the arts, etc.). During my chil...

A Relentless Teen Mistress Ch. 04

by JackFrostFire on Oct 5, 2020
BDSM

Introduction This is another chapter of Chloe's story, a tale of lesbian seduction and domination starring Chloe Sharpe, an 18-year old dominant or "domme" at Woodglen High School. The chapter's a bit of an experiment, since it's a first person account told through a series of emails. The emails are from Susannah Rush, the 43-year old principal of the sch...

Whore of the Dragon

by Conan The Librarian on Feb 19, 2020
Fantasy

There, amongst the remnants of the dead race, where their greatest queen reigned, two dragons lie dormant. One of pure evil, one of pure good, both yearning for a vessel, both lusting for a mate... She may be adequate for that purpose, our forlorn child... We shall see. "Silence, fools. We are close to the inner sanctum." The two mercenaries exch...

Open in Reader

A New Chapter Begins Pt. 02

by fearamouse on Mar 3, 2020
Fetish

My wife and I continued to see Doctor Stern in the months that followed. We learned how shifting our power dynamic can help her to cope with the childhood sexual trauma that had colored our sex life since we met. I had not even been aware of our dynamic until we explored it with Dr. Stern. She helped us to create a space where my wife was in control and felt...