Chastity Lipstick Stories

30,354 results
Orientation
Length
Source
Infinite Scroll

Britney - Les Avocat

by call_me_dana on Sep 16, 2017
Transsexuals & Crossdressers

The Court awards Eight Million Euros ... The courtroom in Paris erupted all around though Britney Clark merely stood in place with a feint smile across her lips. She had won. She had expected to win. She almost always did. A couple hours after the verdict and having done the requisite press interviews, Britney was arriving at the offices of her firm with t...

Your Girl's Night Out

by aweatherly on Sep 16, 2017
Fetish

The night has well and truly fallen, but it's only just begun. You've been waiting in anticipation all day, part anxious and part (okay, a substantial part) turned on thinking about the events about to unfold. You watch as your girlfriend goes to the bedroom, and then as she emerges in the living room again, wearing only her skimpiest black g-string and a se...

The Perfect Pair Pt. 05

by ChangeYourPassword on Jul 13, 2020
Fetish

The Perfect Pair, Part 5 (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 and...

Letter from Jefferson City

by justincbenedict on Sep 16, 2017
BDSM

Dear Shoeblossom: Do you get many letters from Jeff City, or from Missouri at all? Harmon, my husband tells me we are the "silent majority" and no one cares about us, until the Presidential elections come around. Then we're considered the conservatives, I suppose. Harmon and I were at one of those Tea Party Town Hall events, and I remember reading an edito...

The Little Shop Ch. 05

by justincbenedict on Sep 17, 2017
BDSM

Now, Soapy stared at Melinda 109 as Webb kept babbling at her, holding her hand as if she was a real, live woman. Melinda had been in and out of The Little Shop a lot after Gridwell had reluctantly returned her... Most clients couldn't afford more than a half-hour visit, and Soapy would wince as he'd hear their agonized shrieks as Melinda caned them in th...

Adult Trip Pt. 02

by cuckcpl4play on Jul 3, 2018
Interracial Love

The trip back to the room was embarrassing given I was coated with the cum of my new Master. I rushed back and within seconds of arriving, my phone went off. The text read, Dearest white slut, please provide an inventory of the sex toys that were brought with you. It is now 4:00 and I expect you and your small dicked cuckold husband to join us on the beach...

Retired to a Whole New Life Ch. 02

by sissymissyct on Feb 11, 2019
BDSM

As my fate was now sealed by the lock, Mistress Michelle handed me the key and instructed me to put it on Cara's ankle bracelet. I gently undid the clasp and attached the key as instructed. I re-fit the bracelet and lovingly kissed her foot, and then Mistress Michelle's. They helped me too my feet and we went back out to the living room, Michelle locking th...

Letter from Coldstream Canyon

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: My cousin Glen is married to a dominant bitch called Jocelyn. When Glen and his brother Gavin, both free-wheeling, bimbo-chasing poker-playing drunkards met Jocelyn in a club, they had no idea that the icy blonde would tempt the two of them, and Glen's boss Monroe, into becoming her slave harem! Now Glen hasn't been out for a poker night...

Sissy Lauren Pt. 02

by CdJade on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Two: A New Girl It was the first day of February and almost six months into Freddie's jail sentence. Or at least it would be if Freddie still existed. On his second week inside, Freddie had been transformed into sissy Lauren, the girlfriend of E wing boss, Ronnie. Lauren had now learnt how to apply her make up to the style of most of the instructio...

Trapped and Trained Ch. 05

by SissyIndy on Sep 25, 2017
Transsexuals & Crossdressers

There I was, Saturday morning, back in the driveway of my quote/unquote "Master", as he liked to call himself. I turned off the key to the ignition of my car and prepared to step out. He had sent me an email the previous night telling me to show up in the outfit that I had left in during our last session. I looked down at myself and shivered as I saw the s...