Chastity Surprise Stories

139,463 results
Orientation
Length
Source
Infinite Scroll

Mistress Kaderin's Welcome Home

by justincbenedict on Jul 29, 2019
BDSM

Cameron's penis strained in the chastity tube. It had been such a long trip, selling computer software in Connecticut, New York, Jersey, Delaware...it had been so frustrating. He'd asked Kadi to put him in the tube, and he'd said he loved the little games they played, but sometimes it might have gone a little far. The night before he'd left for his six-week...

Jake's Videos

by ChristopherDB on Sep 17, 2017
BDSM

Jake had just gotten home from work late Friday afternoon. He would only have a few hours before it was time to go out and play with his band at Neon's. Michael, the drummer, also booked the band and had been trying to get them into Neon's for a long time. Since it was such a popular nightspot, all the local bands were trying to get in. Despite the competiti...

Her Male Wife

by Zippeduptight on Nov 6, 2018
Transgender & Crossdressers

Sometimes I wonder how I got into this mess. The answer is obvious but it usually comes during the day when I pee. Carla's orders are to sit when I pee. I lift up my skirt, and tuck the exposed chastity device down, and relieve myself. Just like now. The shiny pink pvc sissy maid outfit she bought for me is locked on at the neck. I stand up and flush walking...

Chastity Vacation

by _Ashley_ on Oct 9, 2017
BDSM

Stephanie Her long, tanned legs stretched over the side of her bed as she rubbed the sleep out of her eyes. She took a few uneasy steps as she headed for the curtains. She gasped as she slowly drew them, temporarily blinding her deep green eyes. The sun was still partly blocked by trees but that didn't stop it from fighting through and melting the light cov...

Letter from Vines Village

by justincbenedict on Sep 17, 2017
BDSM

I drive a sterilized knitting needle through my son's left nipple. Sowell grimaces, but he is sucking on one of my bloody tampons, and his buttocks hurt from the vicious caning I gave him earlier. I surprise Sowell—when he's coming out of the tub, wet, naked and vulnerable, I charge in with my whippy cane and leave red, bloody streaks all over his slim whit...

Husband in Training Ch. 01

by Freakboy80 on Sep 15, 2017
BDSM

This is part 1 of a series. This story is "FICTIONAL." "Come in and have a seat Mrs. Jackson," Dr. Emerson said to her patient who was waiting in the waiting room. After sitting down, Dr. Emerson introduced herself to the patient. "Hello, I'm Dr. Emerson," As she put her hand out to shake Mrs. Jackson's hand. "Pleasure to meet you Dr. Emerson." "Pleasur...

Imperial Prostitute Tenel Ka Ch. 03

by HandcuffGirl on Sep 12, 2017
Celebrities & Fan Fiction

Authoress's notes: This story overlaps with the last chapter of Imperial Prostitute SX-51472 ZERO. It should be considered a sequel to that story. Please read and enjoy all of my stories! Also, please leave me feedback, public or via email. * Star Wars: Imperial Prostitute HC-00001 Chapter 3 of 5 When Tenel Ka arrived at her room, she found a pair of her...

Work Day, Fun Day

by manatdawnrise on Mar 28, 2018
Transsexuals & Crossdressers

Showering for work, I look down at my chastity bound cock, still struggling to come to terms with the events of the weekend. A sense of relief washes over me. The relief found when a lifelong secret had been broken. I was no longer wracked with guilt of my crossdressing dark side. No, I was now liberated in mind yet bound in a physical sense. My wife had a p...

Aphrodite's Curse Ch. 041

by Gaius8666 on Sep 15, 2017
BDSM

Chorea sat at her desk, head in her hands, staring intensely at the scroll in front of her, studying it despairingly. As owner of "Chorea's Exotic Dance Troupe" she was a successful business woman and had many gigs already booked on her calendar, as well as the prestige and cash flow that came from being the sole provider of dancing girls to the Palace. Ther...

Simon's Sluts

by Ellyce on Sep 16, 2017
Transsexuals & Crossdressers

Chapter One – Wake Up Call The alarm went off and I groped for the "snooze" switch out of habit. Then I remembered that I had day maid duty today and sleepily rolled out of bed. Wandering into the bathroom, I pulled the shortie nightgown over my head and observed myself in the full-length mirror starting at my red-painted toenails. My gaze wandered up my sh...