Surprise Chastity Stories

139,463 results
Orientation
Length
Source
Infinite Scroll

Survivor: Femdom

by pifan on Sep 13, 2017
Fetish

A dozen guys (including me) are picked up for a sex slave game. It pays a truckload of money so we sign a contract to be slaves for a year, disclaimers and all, and then are transported to a warm tropical paradise of an island. There are at least a dozen mistresses on the island probably more. Once we arrive, we are told about the rules for men. No clothes a...

Black MILF Femdom For Black Guys

by Samuelx on Aug 18, 2017
Fetish

Salutations, my name is Ginette Ambrose, and I'm a fifty-two-year-old African-American woman living in the City of Brockton, Massachusetts. One of the most diverse towns in all of New England, I swear. I'm five-foot-nine, chubby but still lovely in a wholesome kind of way, with dark brown skin and long Black hair. Thick Black mama with big tits and a big rou...

Mamma Mia - Forced Femme

by ppeaks42 on Sep 16, 2017
Transsexuals & Crossdressers

"We need a little more feminine energy around here." The words hung in the air as Tommy's devoted licking of Mia's ass slowed to a stop. "You mean another woman?" Mia hooked her legs behind Tommy's head and pulled his face back into her ass. "No, I mean you, you dumb sissy bitch." Once Tommy finished with pleasuring Mia, she led him into her closet. She...

Learning to Dance

by grizzley123 on Oct 19, 2020
BDSM

Dance Lessons It was a set up from the beginning. I had signed my daughter up for dance lessons for two reasons. First, she seemed to want to, and second, Erin, the studio owner was very direct in her approach, practically telling me to do so. Throw in the fact that the instructor was a hot young coed student of mine and the fact that Erin herself was damn...

Infidelity and Chastity Ch. 01

by rockbohunk on Sep 15, 2017
BDSM

Sara and Rick had been married for almost five years. For the most part, they were happy. They have had their share of bad times, but the good far out weighed the bad. Both were involved in the BDSM lifestyle, Rick being the Dom, and Sara the submissive. Rick worked full time in a managerial position at a local Home Depot. Sixty hours a week was very common...

Star Wars: Imperial Prostitute Ch. 07

by HandcuffGirl on Dec 24, 2019
Celebrities & Fan Fiction

Authoress's notes: The following story takes place soon after the conclusion of Legacy of the Force. This is the 10th Star Wars story that I have written. Please read and enjoy all of my stories, and vote me a five! Also, please leave me feedback, public or via email. Fifteen minutes later, they were both wearing their gym outfits, and walking out of S...

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...

A Fantasy with Lisa

by chastityfan on Sep 13, 2017
Fetish

I met Lisa for the first time just after finishing a workout at the local gym. Over the next few weeks we ran into each other on a regular basis and ended up going to out for a few pints. Spending time together eventually put us in bed together and we decided out relationship was best left as a friends with benefits situation. Over time we discussed each oth...

Helping Jess Pt. 05

by mski on Sep 25, 2017
BDSM

I slept well that Sunday night which surprised me, though I guess I was probably exhausted. I woke up with my normal hard-on a bit before 5am, well it would have been a hard-on but for the cage. My penis was certainly trying. I never found it an uncomfortable feeling, just frustrating that there is no ending and I could not jerk off, and now who knew what wa...

The Keyholder Ch. 04

by AndreaJordan on Sep 18, 2017
BDSM

What was she doing playing chastity games with a twenty something guy? She knew it was crazy, yet Amy was smiling to herself as she stepped off the bus and walked quickly to the address that Ben had given her, a two bedroom apartment in an upmarket development. She hadn't seen Ben since they'd made love at the hotel a week ago, but she could still remember...