Chastity Lipstick Stories

30,354 results
Orientation
Length
Source
Infinite Scroll

The Sexy Cuckold Couple Pt. 10

by cuckcpl4play on Sep 19, 2017
Fetish

After the crazy collaring weekend, our home life shifted slightly back to some form of normalcy. Master would send us occasional texts, orders, etc., but overall there was nothing significant that was transpiring and in fact Miss Jenny seemed sad that more activity was not taking place. At work it was a bit of a different story...Master was his typical domin...

Feminizing First Step Ch. 03

by antares34 on Oct 21, 2019
Transgender & Crossdressers

(All characters are age 18+) *** I felt like I was losing control. My body and mind were becoming less and less masculine with every passing day. And I was secretly ENJOYING it. I couldn't help myself. Every time I looked in the mirror, I found myself loving the ever-changing reflection. First, my dyed pixie haircut. Then, my bikinis. Then, my nose, ear, a...

Allure

by AMurphyWriting on Nov 22, 2017
BDSM

This is a standalone story for Halloween. I have left room for a potential second part, should I get enough requests. Let me know what you think in the comments. ***** "No, there's no way" I told my friend. "She is not staring at me." "I'm serious, she's eyeing you up." I glanced across the bar to see if this was true. Much to my surprise, the stunning,...

The Trouble with Roommates Ch. 06

by KaylaG on Sep 18, 2017
Transsexuals & Crossdressers

Now that Nicole had settled in, things around the house seemed much smoother. The chastity cage didn't hurt, either. Something about having her dick restricted and untouchable seemed to heighten the rest of her senses. She even started to kind of look forward to hearing Brian get home from work and calling for her to give him a kiss. When he'd pull her in an...

An Ever Changing Life Ch. 03

by Helenthemaid on Sep 16, 2017
Transsexuals & Crossdressers

Previously.... After several years, I was completely in their command, and when feeling particularly cruel they would invite several of their female friends around and introduce me as Jennifer, a cousin visiting for the weekend. Very soon I was getting invited to lots of girlie parties and events. Julie and Janet made sure I accepted every invite. I was alw...

A Week End with Mistress Pt. 01

by gasissynora on Oct 16, 2018
Transgender & Crossdressers

Dear readers this is my first story and I hope you enjoy it. Your comments and suggests will be most helpful. I am planning on continuing the story if the feedback is positive. This story is based in part on facts and part on fiction. I will leave it to the reader to decide which is which. ***** We had just finished dinner and I was in the den getting rea...

Milky Boy Ch. 06

by Subone1 on Sep 16, 2017
Toys & Masturbation

They left me alone the rest of that day and also that night. I drove to work the next day (Wednesday) with the chastity device in place, happy that my wife hadn't noticed it yet. Of course, the way our sex life had been going lately, she may not notice it for a while! When I walked in, my secretary was already at her desk. "Good morning, got milk?" she said...

Caged Pt. 01

by ToferSixoErotica on Feb 6, 2018
BDSM

James sat naked on the side of the bed. He blushed, unable to stop himself from having an erection. Elle sat between his legs, smiling. "You know, I'm never going to be able to get this thing on, if you can't control yourself" she told him, holding a small, plastic chastity cage in her hand. James had bought the cage a while ago, but had never had someone...

Maria's Life of Slavery

by StrictDom on Sep 19, 2017
BDSM

Maria is an absolute goddess. Her hair is blond, styled in a sexy messy way, her eyes are a gorgeous blue, her nose is cute and wrinkles slightly when she smiles. Her lips are full and soft. We have been seeing each other for a few months now, and talked for ages before then on the internet, where we met. Maria is My slave, in every way imaginable. I literal...

The Roommate Pt. 06 - Miranda

by ValoryG on Sep 16, 2017
Transsexuals & Crossdressers

Josh/Lori continued to endure a burning ass throughout most of the following day, but by the time he returned from teaching, the sting was more of a memory. He helped prepare the evening meal just as Miranda directed, reveling in his/Lori's long skirt, breasts, hairdo, earrings and bracelets, and slip-on sandals with heels. She had even applied a little li...