Chastity Surprise Stories

139,463 results
Orientation
Length
Source
Infinite Scroll

An Expensive Addiction Ch. 03

by NeverGuessWhatsNext on Sep 16, 2017
Transsexuals & Crossdressers

The Friday after my second encounter with English was just as eventful as I had thought it would be. My girlfriend got to town, and since we hadn't seen each other in weeks, she was hornier than hell. I picked her up from her parents house around 5 and we went straight back to my place to have sex before going to the party. A couple of months after we starte...

Come Sail Away With Me

by robertreams on Sep 13, 2017
Romance

Chastity, in a long, elegant evening dress of deep green satin, whirled around the dance floor with one man after another, thoroughly enjoying the swishing sound the dress made, the way it contrasted with her flaming hair. She was the official hostess of this dinner party. Since her mother had died four years earlier, when Chastity was only fifteen, Chastity...

A Femme Domme Tale Ch. 03

by melanieatplay on Sep 25, 2017
BDSM

It was incredibly difficult talking to my best friend Liz concerning the momentous changes in my marriage that occurred over the past two months. I had long suspected that she considered me a prude, or at the very least, sexually non-adventurous. Perhaps, compared to her, I was. I had only known Liz a little more than a year and both of us were quite reserv...

Brian Pumper Loves Lethal Lipps

by Samuelx on Sep 17, 2017
Celebrities & Fan Fiction

"Who's your strong Black goddess? Fool, speak up when you're spoken to," Lethal Lipps said sharply as she stood, hands on her hips, glaring down at the muscular, stocky and fit brother who knelt at her feet. The curvy, brown-skinned, dark-haired and sultry African American porn star licked her infamous lips, a smug smile on her lovely face. Impatiently she a...

You Took Everything

by playplay19722 on Sep 12, 2017
BDSM

Today you told me it has been a year since we first decided to get together 24/7. In that time you have taken everything from me and I have gladly given it. When we first started dating you put me in Chastity. That was the beginning. First you took my ability to say no to you. On our first weekend together you tied me spread eagle on the bed and began teasin...

Indian Femdom Story Ch. 04

by SundarSubmits on Nov 26, 2018
BDSM

Chapter 04 -- Komal, the Mild-mannered Lady | 3 years later, Present Day | For someone who was so mild-mannered, Komal was a very demanding lady, Sundar thought. She demanded punctuality, she demanded perfection in tasks she gave Sundar, she demanded Sundar keep to rigid timelines, and most of all she demanded financial tributes. Financial tributes were ve...

Platonic Chastity Ch. 02

by Cagedcompliance14 on Aug 24, 2020
BDSM

The roomates arrangement progress and they enjoy a night out... and then the rest of the night in. Platonic Chastity CH. 02 Taylor was unable to sleep in much past 7 in the morning due to the pressure created by the cage and Jacci forcing him to retire to bed early the night before. He was never an early riser but between the ache in his cage and 11 hour...

Senselessly Gangbanged

by Freedomslut on Sep 19, 2017
Group Sex

I had been in the BDSM scene for only a year or so. My "booty call" at the time had gotten me into it and had made me his submissive slave. We weren't going out exactly. We used each other for sex. It was great fun without the hassle of commitment or such things. One day he texted me, "5pm cum 2 my house, wear sundress only no bra no panties." I got off...

Sissy Maid to Be... Ch. 01

by missjennymaid on Sep 5, 2018
Transsexuals & Crossdressers

Prolog I have always had the desire to dress like a girl. It started at a young age when my mother used to have me try on dresses to "see if they would fit my cousin." As I got older I still had the desire and it got strong enough that I started going out in public in college. I was lucky enough to meet and marry a woman who was accepting of my "hobby". Liz...

A Woman's Chastity Belt Torment

by achillesthegreat on Sep 25, 2017
BDSM

At last I have you in my arms. We are together and naked. We kiss passionately on the bed, with me on top of you. I can feel the wetness between your legs and you can feel my raging hard-on, as I want you so badly. I turn over with you and you are now on top of me, ready to straddle me and shove my cock up inside of you and give you what you crave. Inste...