Chastity Boy Stories

108,647 results
Orientation
Length
Source
Infinite Scroll

Vacation Expectation

by IPleaseYouTease on Oct 6, 2020
Fetish

The wife's side of a conversation with her husband as she gets packed to go on a 10-day vacation with her lover and leave him behind. ~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~ "Okay Dearie. Up on the bed. It's almost time for me to leave. I have a plane to catch. Don't you worry. I know that once you're done binding your hands and fee...

Maid on Boxing Day

by Belongs2Beth on Sep 14, 2017
BDSM

Authors note: This story is an immediate sequel to my first story "Carol's Christmas". The events of this story deal with the younger man named Marcus who Mrs. Carson initiated into the mysteries of sex and submission in "Carol's Christmas". * Marcus was sweating bullets as he rang the door. He burned for Mrs. Carson...Mistress Carol...and needed to be wi...

Charity Begins at Home

by justincbenedict on Aug 20, 2019
BDSM

"I don't know if I can afford it." Mooch looked just miserable. "Well, you did ask for this" Kiada said with a gentle smile. Kiada was a looker, and had once won a Gwen Stefani lookalike contest. Or was it Gwyneth Paltrow? Mooch knelt in front of Kia, who was resplendent in a tight rubber green bodysuit. She toyed with his burgeoning penis, and it dripped...

Letter from Newark

by justincbenedict on Jan 8, 2019
BDSM

Dear Shoeblossom, I am just an ex-cocktail waitress who married a troubled but worthwhile guy. Mom always told me to find someone classy like a dentist or a Buick dealer. "Mariah, it's as easy to fall in love with a rich guy as a broke guy." But I fell for Raymond Withers, Jr. hard, and I married him right before he went to Vietnam. Still, as in all marria...

Greg's Surprise Ch. 02

by SensualCurves on Sep 14, 2017
Fetish

(This is a continuation of a short story which was submitted to Literotica some time ago. Following a large reader feedback requesting further adventures of Greg and his Mistress Sasha, their story continues. If reading my work for the first time, this author respectfully suggests you read Part 1 first.) * Warm summer sunshine filtered through the bedroom...

Cruel Mistress Carnation

by justincbenedict on Sep 15, 2017
BDSM

JULY, 2005 Clausen Widdicombe pulled up just outside Enger Haverford's farm...She was the town dominatrix, and a bit weird, but Clausen had reasons for being here...he wanted to see Enger's niece, the wonderful Carnation!!!! Clausen got out of his little Miata convertible and sighed. Enger's youngest daughter, 20 year old Secondari (She and her sister Sel...

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...

The Dominatrix Order Pt. 01 Ch. 01

by Jwwsmith on Dec 12, 2018
BDSM

Nadia had heard of The Dominatrix Order of Femininus since she came of age. Femininus was a city governed by female supremacy in which women ruled over men and kept the men as their slaves. Nadia became aroused whenever she heard stories of the men being whipped, tortured, teased, locked in chastity, and brought to their knees by the Goddesses and Mistresses...

Secrets of the Deep Ch. 06

by Lady Malachite on Sep 15, 2017
Sci-Fi & Fantasy

Lena dropped out of the helicopter and glided down and into the crowd, landing softly, despite dropping some thirty meters, though her large bare breasts whacked her in the face as she crouched to dissipate the momentum. Everywhere around, there were piles of flesh and blood, the likes of which were rarely seen outside the most brutal of televised massacres...

The Palmist Ch. 09

by PeterOmez on Sep 14, 2017
Loving Wives

AUTHOR'S NOTE: Everyone in this story is at least 19 years of age. ******* "I'll be around No matter how you treat me now. I'll be around From now on. Your latest love Can never last, and when it's passed, I'll be around From now on." - Frank Sinatra ******* In the months following, Derek visited regularly, to see Megan, always staying at my house. Even...