Chastity Lipstick Stories

30,354 results
Orientation
Length
Source
Infinite Scroll

The Gender Pill Pt. 02

by MadisonWillow on Sep 14, 2020
Transgender & Crossdressers

**I highly recommend reading The Gender Pill: Part 1 to catch up on the storyline. To do so, view my works on my profile page, and please read my other works! Thanks for reading :) ** The Gender Pill: Part 2 I didn't always want to be a woman. Up until the age of 12, I don't remember ever wanting to try on female clothing or feeling as if I wasn't the boy...

Midway to McCarran Pt. 02

by eveashland on Oct 6, 2020
Interracial Love

~~~Chapter Eight~~~ We make it back to the hotel well before the eleven o'clock checkout time. Even when Nathan insisted that we sit down to eat the breakfast of scrambled eggs, fruit and coffee that he'd prepared while I was in the shower... His workday doesn't start until three pm but he showered and dressed for work as if there isn't still more than fiv...

TCCS Pt. 01 Ch. 04: Sister Nancy's Faith Exchange

by Stormbringer on Oct 31, 2017
Interracial Love

Based upon the Sister Nancy pinup by the Pit and the comic "Faith Exchange" written and illustrated by Rabies T Lagomorph. This follows events in the story "Sister Nancy of Coxville County" by SirSinn (found on literotica) and "Sister Nancy of Coxville County 2" by Thickwil (found on my blog). I had to do some rewriting to reconcile the events of the stories...

Trapped and Trained Ch. 03

by SissyIndy on Sep 25, 2017
Transsexuals & Crossdressers

The next few days felt like a lifetime for me. I couldn't sleep at night - every time I closed my eyes, all I could see were replays of myself, dressed like a whore, being strapped to a padded sawhorse while it fucked me from both sides. Everything I ate and drank had a horrid aftertaste of that bastard's cum - it was as if that taste was permanently embedde...

Best Girl Friends Ch. 04: Party Games!

by redjules on Sep 19, 2017
Group Sex

Party Games - Truth or Dare Part 4 of the Best Friends (Suzanne, Carla & Jack) series (Dedicated to my muse, J. You turn me on! xx) ***** Suzanne shut the door to Jack's office quietly and made her way back down to her room. Looking in the mirror the curvaceous redhead took in her somewhat dishevelled appearance, dilated pupils and flushed face. She was...

Ethan and Carrie Ch. 10

by jallen944 on Sep 12, 2017
First Time

Carrie bent over the counter to add the numbers again. She was never good at math and never trusted her own addition. If she didn't get the numbers right, the money would come out of her pay, or worse, she might lose her job, and she didn't want that. She liked working at the lingerie store. She especially liked the discounts. She was wearing her new, soft,...

When It's Gone

by melini on Sep 26, 2017
Interracial Love

"Can I make you another cranberry and vodka, ma'am?" The cute Puerto Rican smiled brightly and flirted lightly with the obviously sad woman. As much as he wanted to be the one to comfort her, he wanted to get a bigger tip even more. His deep brown eyes tried to bore into her soft, shy ones but clearly whoever she was supposed to be meeting was more than just...

Good Boy

by skyeomalley on Sep 14, 2017
Fetish

Before he comes home, I take a shower and straighten my hair. I get dressed in a black skirt, black tights, knee high black boots, and a white blouse. I look neat and professional, as though I'm going to work. I meet him at the door, and give him a long hug. "You smell nice," he says, and he kisses the top of my head. I hold him for a long time. Although I k...

Our Years of Sharing My Wife Ch. 01

by maturemadness3 on Sep 19, 2017
Loving Wives

Up until my wife turned 40, we had never broken our marriage vows. Turning 40, for me was not a big deal. Not so with Jan. It became the turning point in our lives, that continued for the next 17 years. We both had careers. She a teacher and I in the military. We only had one child, a daughter. Jan could not have anymore, because of complications during...

Burning Desire

by kitty_kitty_ on Sep 12, 2017
BDSM

I turn over, my legs tangling in the sheets which are now warm from my restless sleep. My eyes land on the pile of rope on the floor and I am instantly taken back to last night. My recollection is hazy, very hazy actually, but my stomach flips as I remember some merciless punishment is due to me today, cruelly my mind has not allowed me to forget that part....