Chastity Virgin Stories

50,051 results
Orientation
Length
Source
Infinite Scroll

Miss A's New Play Thing

by Pornenthusiest on Oct 8, 2019
BDSM

Chapter 1: Sexual Awakening Alex's morning ritual had changed lately. Typically he would start his day by slamming his alarm clock, getting out of bed, brewing coffee and taking a shower. But now, Alex was generally restless, always waking before his alarm could rouse him. He would rush to his computer immediately checking his messages, today was no differe...

Trophy - The Preys Story

by MissYellowPanties on Nov 26, 2017
Transsexuals & Crossdressers

The Beginning. I don't remember much of how I originally got myself into my current situation; it all seems so long ago and far away. All I'm really sure of is I was an IT geek working at a client site for a few months, I was staying at the local Marriot full time and only traveled home once every two weeks. It was a pretty miserable existence, people we...

The Business Trip

by OOAA on May 11, 2020
Fetish

My wife and I had been married for about 3 years when I first developed an interest in enforced male chastity. I had always had a very kinky and active fantasy life to fuel my almost daily masturbation habit. I was a 22-year-old virgin when I met Irene and I was looking to resolve that problem. Irene seemed like an exciting 20-year-old girl and I thought tha...

Locksmiths Have All the Fun

by JBEdwards on Feb 7, 2018
BDSM

I met Louise in my freshman year of college. She was the prettiest girl I had ever met, but she was special in another way. Unlike some pretty girls, who were stuck up, so to speak, Louise was charming and sweet. We dated for three months, but sexually I never got anywhere with her. We enjoyed some kissing and a little petting, but Louise was not really in...

Boyce Park

by kindmaster on Sep 26, 2017
BDSM

He was new to Pittsburgh, from the West Coast. Making a brand new start, without his family dropping in unannounced. But sadly, without his lover, who'd left him rather than leaving the coast. At the mysterious advice of a friend from the internet, he'd come to Boyce Park the day he got to Pittsburgh. Left everything parked, and his phone not working to come...

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The Halloween Party

by DMaster_14 on Sep 13, 2017
Erotic Couplings

The Halloween party was to start in 3 hours and my husband called me into our bedroom to get dressed. I had already showered and shaved so this was no problem. My costume was on the bed, what there was of it. We had decided that a pirate theme for this year would work for us. My husband would dress as a Captain and I would be the haughty noble woman captured...

Letter from Annapolis

by justincbenedict on Sep 26, 2017
BDSM

Dear Shoeblossom: I've always known I was a bad boy. My Mother used to get so mad at me...she'd want me to spend time with my sisters, and help polish the silverware...she'd shake her head because I didn't want to play with paper dolls...I wanted to be like my macho father. Mother had strawberry blonde hair in a bouffant hairdo, and what they used to call...

My Master

by SissyKaty on Mar 26, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** I pulled into the driveway to my house and I was disappointed to see my future mother-in-law's car in the driveway. "Oh great" I think sarcastically. I'm not looking forward to interacting with her so soon after getting off work. I had just come from a long day working in IT for...

Lucy's Revenge Ch. 03

by Cynthia_D on Sep 18, 2017
Transsexuals & Crossdressers

I got home late that night pretty much a broken man. I still couldn't believe what Lucy and Ranger Rick had put me through that day. I was humiliated beyond comprehension. Dressed as I was that day no one would believe I was straight and had never had sex with a man before but it was true till Lucy and Rick made that all change. My poor previously virgin as...

Head Lifted for a Neck Kiss Ch. 04

by CuteAndLovelyYetHorny on Jul 10, 2018
Fetish

Chapter one has been updated as of February 2018 Note: This story is a mix between a lovely romance and female domination, it belongs to the "gentle femdom" and "role reversal" category that emerged on reddit and tumblr a few years ago: extremely soft and caring femdom put into idealistic romance often marketed at teenage girls... ... ... except that point...