Chastity Lipstick Stories

30,354 results
Orientation
Length
Source
Infinite Scroll

The King's Secret

by KittyAshleyy on Apr 22, 2020
Transgender & Crossdressers

King Mike was a great king, the people loved him, he had a beautiful queen, he ruled firmly but fairly and, at the age of 24, had a great reign ahead of him. He was tall and well built, keeping his lovely blonde hair short. He had blue eyes and a gentle smile. But he also had a secret. That secret was me, his concubine. He had picked me up off of the street...

Dani's Night Out

by Jemina004 on Sep 26, 2017
Transsexuals & Crossdressers

Danielle Winona was very nervous. Maybe it was because he was standing outside the door of a strange man's house at night in a mesh top, tiny skirt and thong panties. Maybe it was because he had just rang a stranger's doorbell and he had no idea of what awaited him inside. Whatever it was, and whether he enjoyed it or not, Dani had to be as pleasing and sexy...

My Transformation

by paige_silk on Sep 16, 2017
Transsexuals & Crossdressers

It all started during puberty as these things often do. I can distinctly remember watching a TV programme about a shop that would dress men up as a woman and getting really turned on by it but not really knowing too much more or what to do with myself. These feelings occasionally came back over the years but with the restrictions of living with parents the...

Luke Powers: Black Master Pt. 03

by scatwoman on Sep 16, 2017
Interracial Love

Brad's Ruined Honeymoon Starring: Brad Whitebread, Chastity Belle, Wesley Whitebread, Luke Powers and a special guest appearance by Mishi herself! (See the "XXX-Women" series, "Misadventures of Mishi" series and "The Perils of Greggie-Poo" for more Luke Powers & Mishi action!) Directed by Mishi. Most of you are familiar with Mishi favorite boytoy porno...

Willing Submission to a Dickgirl Ch. 01

by ArthurSummer2 on Dec 7, 2017
Fetish

Note to the reader: This story takes place in a futuristic world where body modifications and high technology are common place. Because of this, there are a subset of women who choose to have male genitalia attached to their bodies. These cocks and balls can be, and often are, much larger than natural male genitalia. So if you are not interested in futanari/...

Sissy Cristal Used by Mistress

by mistressandpussyboy on Jan 8, 2019
Transgender & Crossdressers

This is a real life story, another day in my life with my Mistress. We were ready to go out to run some errands, when Mistress addressed me. "Plans are canceled. I want to bang a hooker: get dressed for me." No sooner said than done, I was getting naked, opening my sissy suitcase. I put on a pretty panty, black stockings, a miniskirt and my high heels. M...

Madam Mary Ch. 02

by Danyale on Sep 12, 2017
BDSM

The story is a work of fiction. ***** Olga became the best friend of my wife, she started to visit us every day and she never entered our house without holding a present in her hand. Mary would send me to Olga's house on daily bases in the afternoon to clean it and follow her instructions. Mary didn't know that I served Olga's sexual needs, I was always lo...

Domestic Bliss

by SadistGoddess on May 1, 2018
BDSM

Every touch from Naomi reverberated with the precondition for pain. Liam knew that, but fuck her hand closing around his dick blocked out the warning from his brain. All thoughts melted away with the mere friction of her wrist stroking up and down the length of him. Naomi was barely even clenching her hand or working it in careful motion; just the feel of he...

Innocence Lost Ch. 19

by bradley_stoke on Sep 14, 2017
Novels and Novellas

In Which Alice rediscovers Innocence and learns the virtues of Purity; in which Innocence and Purity are shown in the practise of religious devotion; and in which Innocence leaves Chastity and Purity loses Innocence. The fruition of all plans is often much less than the ambitions associated with their formulation, and so it was with the vacation that Purity...

The Sexy Cuckold Couple Pt. 11

by cuckcpl4play on Sep 19, 2017
Fetish

This is part 11 of the series and it is about the fantasy we have as a cuckold couple. We have engaged in many acts of cuckoldry, but the story itself is fiction. If you are offended by this type of lifestyle than please don't read. It amazes me that we continue to get such negative comments to this series from people claiming that we are uneducated or despi...