Chastity Lipstick Stories

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Orientation
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Infinite Scroll

Anal Training Ch. 03

by Catchandrea2397 on Feb 3, 2020
Transgender & Crossdressers

Hello pet. Welcome back. Are you ready for the next stage in your training? Good. You're such an eager obedient pet aren't you? Such a slut. Today you are going to need the following items - Bra and panties - Stockings, ideally with suspender - Butt plug - Vibrator/dildo - Lipstick - Perfume You will also need plenty of time. I'm not going to...

The Perfect Pair Pt. 03

by ChangeYourPassword on Jul 6, 2020
Fetish

The Perfect Pair, Chapter 3 (fetish, chastity, consensual, cross dressing) By ChangeYourPassword Author's Note: This is a work of fiction. It is a story of sexual fantasies and fetishes. These sexual practices are not for everyone, but those of us who delve into them understand the allure. The characters in the story certainly do. If you enjoy this story...

Letter From Topeka

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: I come home from work, pulling up in my BMW Z4 Roadster, and the gardener greets me respectfully "Mr. Wegg, how are you?" I grin at him. Yes, Palmer Wegg is a hot shot in this thriving Midwestern city... and when I go in the house I am pleased to see my pretty wife Zenobia relaxing on the divan. "Hello, Pom." She greets me, smiling. Z...

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...

My Story of Degradation Ch. 03

by Philippasubmaid on Sep 10, 2018
Transsexuals & Crossdressers

This story involves BDSM and crossdressing, change of lifestyle and full submission both mentally and physically. If this is not for you feel free to read elsewhere, please. ***** "Yes." Was all I replied. I saw her nod to Cindy and felt Cindy behind me and the cold steel of the handcuffs go back on my wrists, Cindy shut them, and I heard the ratchets go...

Forced To Get Dumped

by footcucknerd on Sep 16, 2017
Transsexuals & Crossdressers

James looked at himself in the mirror and shuddered, wiping another tear from his eye. He had to refrain from crying today, it would only make everything worse. Crying would ruin his make up and earn him a stern punishment before bed. Not to mention, his Mother would probably make good on her threats if he didn't perform perfectly today, and there was no way...

Letter from Eugene

by justincbenedict on May 12, 2020
BDSM

Dear Shoeblossom: I did something that's rare--I was seeing a professional dominatrix, Goddess Octane of Eugene, Oregon, and recently we realized that we had a lot in common. We loved sailing, and opera, and sports, and we began dating. It helped a bit that I am relatively well off, my grandfather invented something or other that makes cars do whatever, it...

Katie vs. Melissa Day 05

by rifkinraf on Sep 26, 2017
Group Sex

"Get it off!" Melissa held the bathrobe she was wearing open from the waist down, showing the other two the chastity belt that Katie's would-be man locked her in the night before. Her copper hair stood wild like an electrocuted cartoon character, and even after an hour of scrubbing the 14 tallies on her forehead were still faintly visible. Rita couldn't ke...

Lucy's First Submission Ch. 06

by StrictDom on Sep 14, 2017
BDSM

I apologise for this instalment taking so long. I thank everyone who has pestered Me for more about Lucy's Domination, and as always, if anyone is interested in being the real life Lucy, feel free to get in touch! When I awoke, my Master was still sleeping. He looked so peaceful lying there, and I just lay there looking at Him. I love Him more than ever aft...

Pierced and Chained Chastity

by JulianDelacourt on Sep 13, 2017
BDSM

"Did you do what I asked?" asked my husband. "Yes," I said, pressing the phone against my ear to hear him above the city traffic. I shifted my rolled yoga mat over my shoulder as I maneuvered through the people on the sidewalk before entering our apartment building. "Make sure you're fresh for me," he said. "I will, honey." "See you when I get home." I...