Chastity Lipstick Stories

30,354 results
Orientation
Length
Source
Infinite Scroll

Jolene's Momma Pt. 01

by ValoryG on Jul 27, 2020
Transgender & Crossdressers

(The names and locations in this story are completely fictional and have no connection with any person living or dead.) My name's Chris. Wife Jolene and I have been married six years now. Live in the small city of Centertown, Ohio. It probably got that name because it's about half way between Columbus and Cincinnati. Being from a midwestern small town, the...

Simply Submissive

by cdnoir02 on Dec 16, 2019
Transgender & Crossdressers

It was an ordinary night, apart from the fact that I had something extra special planned. I had been talking to a man (we'll call him 'J') online for a few days now, and after exchanging some pictures and contact information we had agreed to meet up. I had gotten home from class around 9:30pm, and immediately went into the washroom with a razor to make sure...

The Mistress Ball Pt. 01

by mrbrightside88 on Sep 17, 2017
BDSM

I heard the crunching of gravel as the van stopped. My body swayed, I had to re position my knees on the hard floor of the van. I could hear voices as the van doors opened and closed, footsteps on the gravel. I felt so groggy, how long had I been out? How long had we driven? How far? My head hurt, my hands hurt. I was fixed to the side of the van somehow, my...

Candi's Conversion Ch. 02

by CandiCumminz on Sep 12, 2018
Transsexuals & Crossdressers

Please read chapter 1 first. - We join Candi, dressed to the nines as a sissy princess, sucking on her lipgloss tube and dancing like a slut. Her wife and her friend have just walked in on her, rubbing herself to orgasm. She's in for it now... - "What the fuck is happening here?" My wife stammered in disbelief. Her company, a friend named Lucy who I'd m...

The Facility Ch. 02

by spankmehard1984 on Sep 14, 2017
BDSM

I walked with Vanessa to the end of the block to where Blue's Diner was located. It was at the end of the same block, which had The Facility. Blue's Diner was your average greasy spoon that somehow survived in 2013 despite the big chain coffee shops. I opened and held the door open for Vanessa; she smiled and looked down as she walked in. I noticed she had r...

Teased, Denied and Sissified Ch. 03

by subbieman on Sep 12, 2017
Fetish

About a week passed since Ashley discovered my little panty fetish which was followed by our shopping trip. I was wearing panties daily and had found a couple bras that didn't show through my dress shirt at work. I started to grow quite used to, and fond of, wearing bra and panties everyday and mentioned as much to Ashley. "I thought you would," she smiled...

Found - Again

by BufordTJusticeTX on Sep 16, 2017
Transsexuals & Crossdressers

This story is a work of fiction, if it has any similarities it's all in your head. It does have graphic descriptions of sex; all participants are above legal age. This is the second story in the set, I encourage you to read part one, Found. I appreciate all feedback. ***** FOUND, AGAIN. Sally finished the evening by telling me to go home and get some res...

The Awakening of a Sissy Pt. 11

by sissyjolie4u on Jul 13, 2020
Transgender & Crossdressers

We had been driving in silence for about 10 minutes, with me reflecting on the changes to my home and the 2 men I was going to be meeting. I was both excited and nervous about meeting with Roy and Ronald. Mistress Di broke my thoughts stating "I think Nikki has done an excellent job with her house transformation work, don't you agree Jolie?" I looked over a...

First Time Sissy - The Bike Path

by Phillysissylexi on Jun 15, 2020
Transgender & Crossdressers

My roommates had gone away on a trip for a week, so I had the house to myself for a few days. I had been waiting for a moment like this. As soon as they left I went to my closet to find all my girly clothes, toys, makeup, heels, and lingerie. I couldn't contain myself. I was so excited to turn myself into a sissy. I turned on some sissy hypno to listen to wh...

Forgiving Wife Pt. 03

by manatdawnrise on Feb 1, 2018
Transsexuals & Crossdressers

The night was still early but with the combination of travelling, drinking on an empty stomach and the emotion of talking about my interest in crossdressing, I was exhausted. I suggested going to bed to which Mandy agreed. I stood behind her brushing my teeth wondering what was going to happen now my sordid secret was out. I caught Mandy's eye in the mirro...