Chastity Surprise Stories

139,463 results
Orientation
Length
Source
Infinite Scroll

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...

Letter from Raleigh

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: What will happen now? Yesterday, Pebbles summoned me from the closet (I undress and kneel there as soon as I come in from work) and instructed me to put on my pink panties and my pink and purple lacy floral print baby doll nightie and high heels. I walked into the living room, and there was Peb, and her sister Faye, and the six guys in my...

Solo Submission Pt. 03

by Subkoksukr4u on Sep 23, 2019
Fetish

Debbie awoke the next morning refreshed. She was alone in the large California king bed. Cindy, already up but let Debbie sleep in a bit. It was Saturday and neither of them had anything to do but relax. Images of her husband sucking dildos and eating his own cum popped into some of her first thoughts. Having sex with Cindy convinced Debbie that someth...

Innocence Lost Ch. 29

by bradley_stoke on Sep 14, 2017
Novels and Novellas

In Which Une joins in the study of Algebra; the properties of Twelve are examined by Algebra; and Chastity returns to Innocence. After their one session of lovemaking, Algebra was disappointed to find that despite her attempts to repeat it Dodie was decidedly unenthusiastic to do so. Algebra soon came to conclude that her brief love affair with Dodie had fi...

Long Road to Ruin Ch. 05

by miss_js on Sep 16, 2017
BDSM

I emptied the grounds from my morning coffee, and added a new filter, filling it with French roast. I rinsed the pot, and added water to the machine. Once the coffee was on, I returned to the living room, and gathered the used toys, and transported them into the shower. Turning the water on, I pinned my hair up knowing I would not be allowed the time to dry...

From Charity to Chastity

by carrteun on Mar 10, 2020
First Time

This is my submission to the 2020 Valentine's Day contest. Please take a second to vote if you enjoy reading it. I've already enjoyed reading some of the submissions and look forward to reading more entries. Good luck to all the authors. * I almost felt like I didn't belong the first few weeks. Many of the faces were only a handful of years younger than me...

Mistress Katie Supervises Ch. 01

by royalrogue on Sep 18, 2017
BDSM

Three weeks. It had been a long three weeks for Michael since his last orgasm. Since Domina had strapped him to the bed, teased and milked him to an intense orgasm. She'd eased the thick prostate massager into his tight ass and used it to heighten his arousal. Smiling as his cock throbbed and dripped, while she played with only his nipples and his ass, teasi...

Anything for Her

by aweatherly on Sep 26, 2017
Fetish

DISCLAIMER: This story features a loving couple who participate in female domination, cuckolding, humiliation, chastity and cum-eating with the consent of both parties. If these themes offend you, feel free to discontinue reading now. Otherwise, I hope you enjoy the story. It almost feels like a dream when you're not in the middle of it. The days when you'r...

Cuckold Husband Ch. 01

by lace_lover on Sep 25, 2017
Loving Wives

This story contains cuckold, bisexual, interracial and female domination themes; if this is not your thing then please do not read on. I welcome comments but if criticising, please do so constructively - this is my first attempt at writing a story on Literotica. Abusive comments or emails will be deleted without being read. Otherwise, I hope you enjoy and le...

Jedi Submissive Ta'tan'ia II Ch. 03

by HandcuffGirl on Sep 14, 2017
Celebrities & Fan Fiction

Jedi Submissive Ta'tan'ia II "So, are you ready to move into DP's apartment," Chief Daala asked her once everything was cleaned and put away. "Um, not quite, Your Excellency," Ta'tan'ia answered politely. "I expect an answer soon, DJ" Chief Daala replied dismissively. "Yes, Your Excellency," Ta'tan'ia responded obediently. "And thank you very much for al...