Chastity Lipstick Stories

30,354 results
Orientation
Length
Source
Infinite Scroll

My Goth Girlfriend

by valkdragon on Sep 13, 2017
First Time

As my fingers run through the short dark brown hair on my head, I wonder just how I ended up here; sitting at my desk naked, next to my best friend of the last 20 years after having sex for the first time with her. I look down at Krissie and smile, twisting a lock of her jet-black hair in my fingers. My thoughts floating back over the last few months, trying...

Strapon Heaven

by tinaneesen on Sep 14, 2017
Erotic Couplings

I had bought the strapon ages ago when I was having an energetic affair with a fairly hard core lesbian. It was black and big; a good seven inches in length and more importantly about two and a half in radius. Those measurements meant that it provided an extremely good fuck, though I never quite understood what an avowed penis hating dyke got from me fucking...

Owned! Ch. 06

by MALIBUMAN666 on Sep 13, 2017
BDSM

Thankfully Mistress allowed me a few days to recover from my ordeal before making any strenuous demands of me. In fact she was unusually charitable, allowing me to lick her pussy and ass every day for the next few days. I was, of course, deliriously happy with this arrangement and wished that it could always be this way, but of course it couldn't. In the m...

Flyin the Friendly Skies

by Deviana on Apr 10, 2018
Transsexuals & Crossdressers

Michael didn't expect another trip to the corporate office as he had just presented his design plans for the company's latest product launch just the week prior. He and his team had spent months in product development, market research and testing, and the initial feedback from senior management was extremely positive. Still, they usually took months to make...

A Visit to the Doctor

by open_minded28 on Nov 2, 2017
Erotic Couplings

A fictional fantasy first conceived when my female general practitioner did cup my balls for a second to check them during a routine exam. ***** I was waiting nervously in my hospital johnny for the doctor to arrive. The room was a little chilly (aren't they always!) and I had been waiting for a while. I had a late afternoon appointment to begin with so i...

Finishing School For Ladies Ch. 03

by MicheleNylons on Oct 9, 2017
Transsexuals & Crossdressers

Chapter Three -- The Interview "So Valerie Swindon? Are you ready" Sally asked. Sally was still dressed in her bathrobe sitting at the coffee table in Valerie's expensive hotel room, sipping coffee and smoking. "You definitely not coming with me," Valerie pouted. "Yes! That's the look! Use that on the Dean," Sally teased. "Come on Valerie; you need to d...

Wicked Wife, Happy Life Pt. 01

by LetsStartAFire2Gether on Mar 6, 2018
Loving Wives

Hi everyone, After taking a break from writing for a few years, I've decided to try my talents at erotic literature. I'd value any and all feedback, especially from my target audience, which I guess I would say is the "Fifty Shades" crowd. So ladies, particularly married ladies, are invited to write me with ideas, critiques, and fantasies they would like to...

Biker Bitch Ch. 03

by MicheleNylons on Dec 25, 2017
Transsexuals & Crossdressers

Chapter Three: Super Glide Natalie Styles wore her usual uniform of tight-fitting navy blue business suit, cream silk blouse, heavy black mascara, bright-red lipstick, ultra-sheer pantyhose and Christian Louboutin high heels. "So here's the deal. We've made you into half a girl. You have the tits. The rest comes later if you cooperate and get us what we wa...

Online Only?

by LaceyLove on Nov 23, 2017
Loving Wives

Her eyes hovered over those words on the screen, "Maybe we should meet up." She just stared at them, trying to sort her racing thoughts. Did she even want this to turn into reality? She's been perfectly happy with their virtual relationship. It was supposed to just be an online thing, she never considered making it real. She really didn't know what to say...

Barrack Room Betty Ch. 08

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Eight - The Christmas Party Lieutenant Steven Winters was an extremely good-looking Navy fighter pilot whose last posting had been aboard the aircraft carrier HMS Ark Royal. There was some unpleasantness when, after a wardroom ladies dine-in night on board the ship, the rather portly Executive Officer had opened the door to a hangar workshop and fo...