Chastity Virgin Stories

50,051 results
Orientation
Length
Source
Infinite Scroll

Trudging The CessPonds

by MrFinesse on Apr 7, 2018
Fantasy

You are a penniless citizen in the kingdom of Gradrod. You are currently living in a large poor house with over twenty other people, taking odd jobs from the farms and plantations outside the kingdom's walls and barely making any money. You have always wanted to be an adventurer, but never knew where to look for treasure and even if you found a spot, it's us...

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Sissy, Hypnotized

by Slipperylock on Apr 8, 2019
Transgender & Crossdressers

It had taken six months to get to this point. As I stepped out of the bathroom, I caught sight of myself in the full-length mirror, and shivered. I was shaved below the eyebrows, hairless and smooth, except for a cute landing strip above my locked chastity cage. Other than the cage, I looked like a thoroughly average 21 year old boy, my small and skinny fram...

Miss A's New Play Thing Pt. 02

by Pornenthusiest on Dec 2, 2019
BDSM

Months before meeting Alex: Miss A stood in her living room her arms crossed with a smirk on her bright red lips and a twinkle in her blue eyes, her face framed by her straight as an arrow, jet black hair falling to her shoulders in a sexy bob cut. Her skin tight floral yoga pants seemingly painted on accentuating her legs and ass. Her low cut crop top show...

Mistress Kaderin

by justincbenedict on Jun 6, 2018
BDSM

Cameron breathed through his nose, his wrists carefully bound behind his back. Cameron was kneeling on a hard chair beside Kaderin's Princess bed. He'd bought the bed for her at Christmas, and let her have her own little room here, because she wasn't really comfortable sharing a bed yet, Cameron tossed around too much. Such a horny boy, she told him quite...

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...

Ella Cucks Her Patient Ch. 05

by CuckFantasy69 on Jun 17, 2019
Group Sex

I highly recommend you read the previous chapters for the full erotic experience. *********************************************** My 4th week of chastity was complete as I arrived at Ella's apartment eager for release. As I was about to knock on the door Ella opened it and threw herself on me. She gave me a big hug saying "I've missed you so freaking much...

Technically You are Still a Virgin...

by ElderDirt on Nov 25, 2017
Romance

When you first glanced at her face, Shari looked like she was fresh out of middle school instead of a twenty-year-old woman. Standing a petite five-feet, she had a pretty Chinese face that was framed with straight jet-black hair that fell to the middle of her back. When she giggled, her almond-shaped eyes twinkled, her cute nose wrinkled, and her sweet dimin...

My Initiation

by lockedupslut on Sep 13, 2017
Transsexuals & Crossdressers

(This story is a work of fiction. If you don't like erotic stories that contain cross dressing, heavy gay themes and water sports please just don't read it. Thank you.) * I was determined. This weekend it would happen. I would loose my gay virginity and complete manhood. The hard way. Tonight would change everything. Until now I've never had sex with a ma...

Innocent Lacey

by lanavelvet on Aug 27, 2019
BDSM

All characters in this story are over the age of 18. ***** The day I met Mr. Anders, I was sunbathing by the pool in Daddy's backyard. The sun was scorching hot through the thick layer of coconut oil on my slender body. My bikini was small, just three tiny black triangles. The top just barely covered my hard nipples, and the thong bottom showed off the hot...

My Old Guy Ch. 04

by anonentity on Sep 17, 2017
Mature

Chapter 04 Lusty, loving, little Tasty Tasha. "Dear Mister Old Guy, I just want to remember it forever ... my first real fuck ... with YOU! And giving me the Teddy Bear was a nice touch. It made me giggle and took me back in time to when I was a tiny teeny. I know you adore your sweet little girl. I can see it in your face every time you look at me. Miss...