Chastity Lipstick Stories

30,354 results
Orientation
Length
Source
Infinite Scroll

The Roommate Pt. 09 - Miranda

by ValoryG on Sep 16, 2017
Transsexuals & Crossdressers

The summer's heat accompanied Miranda's heat. Her and Lori's apartment didn't have air conditioning, so fans were usually on, and the roommates wore shorts, cami tops, short skirts, sandals and clogs, and shorter hair. Lori was kept so unbalanced by Miranda that she didn't eat as much as she used to, pre-Miranda, and remained quite slim. Miranda finally de...

Laurie's House Slut Ch. 01

by royalrogue on Sep 25, 2017
BDSM

It was Friday. Two long weeks since Michael had last been under Laurie's control and teasing attentions. He had taken the day off and arrived at her house at mid-morning, letting himself in because she was at work. Carefully he followed the instructions she had left on the dining room table. His clothes and car keys were now securely locked in the cedar che...

Roland's Performance

by justincbenedict on Dec 17, 2018
BDSM

AFTER THE SHOW Tarique and Roland bowed and the curtain pulled close, shutting them off from the audience. Tarique grinned at her husband, as she tossed her ash blonde hair. "You think we did a pretty good performance, hon?" "Y-yes, Tarique, but you could have gone just a little easier. I think you broke a blister that you put on my butt from last week's...

Natalie Ch. 01

by the_proletariat on Mar 7, 2018
Romance

Natalie is a friend of mine, she's about forty years old, slightly resembles Minka Kelly. She enjoys wearing thin black tank tops that cling to her skin and outline her features like the landscape of the Sahara. It's hard to discern where the body ends and the tank top begins — along with it usually goes a small jacket of sorts and a pair of jeans. Her brown...

How I Make You My Toy Ch. 01

by SadistGoddess on Sep 14, 2017
BDSM

Chris exhales and winces as the spikes on the inside of the choke chain pinch his neck. It's not the first time he's been on a leash for his fiancee Natasha, but it's the first time it's not just metaphorical. "You sure that's safe?" Sebastian asks from the bed. His smirk doesn't do much in the way of concern. "Not too safe," Natasha says flatly. As if fo...

How I Became a Chastized Cuckold Ch. 03

by gizzard on Sep 19, 2017
Loving Wives

**Warning** This fantasy story series contains or will contain elements of Male Chastity, Orgasm Denial, Female Domination, Cuckolding, Interracial Sex, Bi-sexual Innuendo and Tendencies, Teasing, and BDSM Activities. If any of these topics are offensive you to, I recommend not reading. * Six very long days had gone by since the night I stood in front of m...

Halloween Pool Party Pt. 04

by sissymissyct on Sep 14, 2017
Fetish

Monday morning I was awakened early by Miss Annie releasing the air from my plug and swiftly pulling it from my bottom. I cried out from being so crudely awakened from my slumber and that got me a quick but hard smack on my already bruised bottom. "Good morning Brenda, time to shower and get ready for a big day", she informed me. "Thank you Mistress" I answ...

My Stroll outside the Car

by triffle64 on Sep 12, 2017
Transsexuals & Crossdressers

It was a beautiful evening in the spring of 1982. My wife and I were taking a drive up the coast of California for an evening stroll. She was driving. We had been married for about 5 years. She was 27, and I was 30. My wife is feminine, but she grew up as a tom boy. I had no idea that she would take so well to my submissive desires to be her sissy husband. T...

Rosa subrosa

by ValoryG on Apr 8, 2019
Transgender & Crossdressers

I first saw Rosa on a kinky-sex dating site. I, as a 35-year-old recent divorcee, had visited it "just out of curiosity" -- or was it rather because I sought a little titillation? I certainly never expected it to lead to anything. I just thought I'd peruse some photos and fantasize about meeting some off-beat women. I ended up beating off looking at a few of...

Letter from Raleigh

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: What will happen now? Yesterday, Pebbles summoned me from the closet (I undress and kneel there as soon as I come in from work) and instructed me to put on my pink panties and my pink and purple lacy floral print baby doll nightie and high heels. I walked into the living room, and there was Peb, and her sister Faye, and the six guys in my...