Tricked Chastity Stories

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Orientation
Length
Source
Infinite Scroll

The Keyholder Ch. 16

by AndreaJordan on Mar 31, 2020
BDSM

Ben had been in chastity for several years and always under Amy's control. Her fantasies and sexual urges had long since dictated his life. She was currently going through a phase of chaining his chastity cage to things. Often immoveable objects that left him continually aroused yet totally stuck and dependent on her. "Amy, Sweetie?" Ben called again. Com...

Feminizing First Step Ch. 04

by antares34 on Dec 10, 2019
Transgender & Crossdressers

(All characters are age 18+) It has been months since my mom and therapist started my sissy transformation. So many changes have happened! Shortly after placing me in a chastity device, they revealed to me that the "male hormones" I thought I had been taking were in fact just the opposite -progestogen and testosterone blockers to be specific. To be honest...

Transgender Avis's Incredible Power

by justincbenedict on Jul 4, 2018
Transsexuals & Crossdressers

Skokie, Illinois, 2009 Aiken Aycock was sad to be losing her brother Aiden to the operation. He was a great guy, but he gave Aiken the beatings and torture she needed. But he'd finally gotten the money to do the big change. Aiken had really enjoyed supporting Aiden, letting him live in her apartment...stripping naked when she got home, and taking a few fro...

Sissy for Mommy's Nipple Cream Ch. 04

by ppeaks42 on Feb 11, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Jaime clasped a hand over her mouth in horror, but it was too late and she knew it. Chills ran down her spine as Julia sauntered over with a wicked smile, then opened the door to reveal her sissy daughter sitting there wearing nothing but her lacy panties and her steel clitty cage...

Sissified by Hypnosis

by Subkoksukr4u on Jul 16, 2019
Fetish

Reaching with just his tongue he licked the Big Black Cock in front of him. She was behind him, watching and fingering her moist pussy, reveling in his submission. He tasted the salty precum and let it linger on his tastebuds. It was his first cock of the night and he wanted to please his mistress. Being submissive did not come naturally for Matt or as he...

Accidental Cuckold Ch. 06

by Brass_ankle on Aug 31, 2020
Interracial Love

2009 Seattle, WA "Thomas! You're my lawyer!" Cassy said sternly to the very uncomfortable man across from her. "I need options, not problems!" "Ah... yes... ok..." Stammered the bald man as he adjusted his collar, Cassy had a way of getting him flustered. The petite black haired woman with a streak of red towards the front huffed as she paced his office...

Rosa subrosa

by ValoryG on Apr 8, 2019
Transgender & Crossdressers

I first saw Rosa on a kinky-sex dating site. I, as a 35-year-old recent divorcee, had visited it "just out of curiosity" -- or was it rather because I sought a little titillation? I certainly never expected it to lead to anything. I just thought I'd peruse some photos and fantasize about meeting some off-beat women. I ended up beating off looking at a few of...

Chastity Ch. 03

by wishfulthinking on Sep 18, 2017
Romance

King Garbin held his arm out straight through the bars, his fist clenched. Then his fingers straightened, and Kinlee's eyes widened. Dangling from a long, golden chain that glinted in the flickering torchlight, was a delicately formed, intricate key. It swayed, and her wide blue eyes followed the tantalizing movement as her mind calculated all the possibil...

Always Read Before You Sign

by Reaver90 on Apr 1, 2020
Transgender & Crossdressers

Sam had just got home from losing his retail job. His manager told him that the company had to make massive cuts and unfortunately for Sam, he was one of those people getting cut. Sam was 18 years old. He was five foot six with short black hair and blue eyes. His physical stature wasn't anything to write home about he was skinny with no muscle on him. "W...

Steak and Blowjob Day Ch. 01

by Shavvy3100 on Sep 25, 2017
BDSM

I'm still looking for a volunteer to review and edit my stories before they get posted here on literotica. I'm not a native English writer and my writing experience is also limited. If you feel you can improve my writing skills, eliminate typos, awkward wording, grammar mistakes... please send me a message. Advantage for you would be that: - you'll be able...