Chastity Surprise Stories

139,463 results
Orientation
Length
Source
Infinite Scroll

Family Business

by fantaseeboy on Jul 27, 2020
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** Laying on my bed in my room in my mom's trailer, my laptop was set on the table beside me with my webcam aimed where I lay. White, satin, bikini panties were looped around my left ankle. The snug-fitting, stretchy crop top clung to my narrow, smooth chest and left my midriff bare....

Innocence Lost Ch. 13

by bradley_stoke on Sep 14, 2017
Novels and Novellas

In Which we learn about the rewards and joy of unbridled pleasure, but also see how it may compromise the better virtues of Innocence and Chastity. What could be done about Null? wondered Kedi as she sat astride Innocence thrusting her crotch backwards and forwards on Innocence's wonderful penis. She was unable to avoid wondering about this as Null was sitt...

A Virgin released from Chastity

by ronron1818 on Nov 16, 2020
Fetish

It was time to move on... I will be graduating today, 4 years after moving in with Ruth, and tomorrow, I will be moving out to start my life as a grown up. I already found a job in my home town, and rented a small apartment near the new office place. Ruth came with me and my parents to the graduation event. My parents liked her a lot. For them, it was lik...

Innocence Lost Ch. 11

by bradley_stoke on Sep 14, 2017
Novels and Novellas

In Which Mouse appreciates Innocence and her thespian ambitions in equal measure; her performances help Kedi otherwise wedded to Chastity; but she affirms greater affection for the virtues of Innocence than those of Chastity. Mouse was passionately in love with Innocence, with a passion that burst through her tee-shirt and swelled her breasts. She could har...

Teased by My Neighbor Ch. 04

by randomer555 on Sep 21, 2020
Fetish

My heart raced with anticipation and my caged dick once again fought against its confines as I opened the text message from Beth. 'On second thought, I think we should start your punishment now. Come to my place ASAP,' the text read. I was torn between a mixture of excitement and angst. On one hand, I was glad I would get to see her again immediately. But...

A Cautionary Tale

by Mortice on Sep 17, 2017
BDSM

The bitch! I knew something was very amiss with our marriage for a long time, so when she told me she was seeing another man, it was no great surprise. I can imagine her, lying in bed with her new man, telling stories of our failed marriage and laughing. Laughing at me, of course. And no doubt one of the thing they'd be laughing at would be my bondage in...

Pleasing Princess

by JimmyHotpants on Sep 15, 2017
Fetish

Her fingers gently traced a path along my thigh and up, casually brushing the shaft of my small, hard cock. Princess paused her fingers at the head, brushed against the ring of my prince albert piercing and danced down the shaft. "I think you're all healed and better now, baby" she said, carefully lifting by balls and running her finger lightly over my vas...

Feminizing First Step Ch. 03

by antares34 on Oct 21, 2019
Transgender & Crossdressers

(All characters are age 18+) *** I felt like I was losing control. My body and mind were becoming less and less masculine with every passing day. And I was secretly ENJOYING it. I couldn't help myself. Every time I looked in the mirror, I found myself loving the ever-changing reflection. First, my dyed pixie haircut. Then, my bikinis. Then, my nose, ear, a...

Family Chastity Story Ch. 04

by antares34 on Aug 13, 2019
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. ***** My girlfriend Christina has been staying with me for the past sev...

Groupie for the women's college basketball team

by mzchandl on Apr 4, 2016
Group Sex

You had just started dating Chloe a few weeks ago and things had been going well. You, a tall 6'5" guy and her, a 5'11" chick with a fit body and curves to go crazy over. She often wore compression shorts that showed off her ass and legs. She almost had some sort of control over you with her sexiness. You started dating after talking casually with...

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