Chastity Boyfriend Stories

60,738 results
Orientation
Length
Source
Infinite Scroll

Caged Pt. 02

by ToferSixoErotica on Feb 6, 2018
BDSM

James woke up to the painful feeling of his morning wood straining against a chastity cage. He groaned, reaching down to hold onto his caged member. It was a strange sensation, having a hard-on and not being able to touch it, like having an itch on your back that you can't scratch because it's just out reach. James sighed, sitting up to stretch and noticed E...

The Intern Ch. 04

by FrostShard on Mar 6, 2018
BDSM

The day after Mengxia had me listen in to her having sex with her boyfriend, I went back into work with some trepidation. Aroused from my three weeks denied orgasm, humiliated by the events of the previous evening and nervous about my meeting with Mengxia that evening, I could barely focus on work, and it seemed to take ages for 5 pm to roll around. At last...

Chaste Ch. 01

by vixxenFoxdragon on Sep 14, 2017
Romance

It was a beautiful day outside, and so the self-defense class was moved onto the back lawn. The class was comprised of 7 women and one reluctant boyfriend, most of the females being eighteen-year-olds, bored college students on break. A pair of the girls flirted with the instructor outrageously, and Chastity vowed to herself that she would never let her daug...

My Last Night of Freedom Ch. 03

by Sungmehetu on May 4, 2020
BDSM

Lindy The cussing from the basement was loud enough to reach the kitchen. Domina was upstairs, recently fed, and I spent an hour at church. Johanna came down stairs after her turn at church and relieving Domina's bladder. Two plates were on the floor with eggs and sausage on them. "Honey I need you. She filled me up." Johanna said. So I lay on the floor a...

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 Journey to Becoming a Mistress

by intofdom on Sep 13, 2017
BDSM

Note: This is pure fiction. It is not a real life experience. ***** It all began 8 years ago. I met this simple normal man through mutual friends. He was shy at first and I learnt that he was kind, calm and was very mature when I got to know him better. I on the other am a very outgoing, socializing confident woman. So naturally our attraction to each oth...

Celeste's Courier

by justincbenedict on Sep 17, 2017
BDSM

"Package for you, Harper" Ted stood up in his cubicle, but Brian just waved one muscular arm towards the reception area and walked off. The salesmen weren't very pally with him or the other accountants--sales guys were all jock types, funny and charming, and they didn't have a lot of energy for the numbers-crunchers. When they weren't selling insurance, th...

Dark Orchestrations

by David Phillips on Sep 16, 2017
Anal

It had been raining incessantly for months. Large dangerous puddles hid out of sight like fiendish hooded phantoms, eager to soak the unwary up to their knees. The persistent precipitation relented occasionally, but it always thundered back in sheets of big oily drops. The rueful inhabitants of Lawrence Cove mumbled and tried to look pleasant, but this wea...

Caged Pt. 03

by ToferSixoErotica on Mar 28, 2018
BDSM

"I'm home, honey!" James called out, excitedly, after coming home from a long day of work. Elle told him in the morning that she was planning a surprise for when he got home, and he couldn't wait to find out what it was. "I'm in the bedroom!" Elle called out. James eagerly rushed to her. When he entered their room, he was astonished to see an assortment of...

A Sissy Fantasy

by Sissy_Jeanette on Mar 30, 2020
Transgender & Crossdressers

My darkest fantasy has come true. I'm now a slave to a dominant couple. My ex-wife and her new boyfriend have taken me in, and in return I am dressed as a girl always and their maid and sex slave. Frilly panties, stockings and skirts, babydoll t-shirts, and a blonde wig are parts of my new uniform. Also I now wear a stainless steel chastity cage now encasing...