Chastity Lipstick Stories

30,354 results
Orientation
Length
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Infinite Scroll

Soames's submissives: Trevor

by justincbenedict on Sep 17, 2017
BDSM

Soames sipped his Beefeater Martini and contemplated wine. He didn't often get to restaurants like La Patisserie Chouquette , one of the ritzier French bistros in Buttermilk Falls. Soames looked with pleasure at the big man across the table from him...Trevor was sweating. And it was ruining the collar of his tailored micro striped poplin shirt. Once, when S...

The Roommate Pt. 12 - Miranda

by ValoryG on Sep 19, 2017
Transsexuals & Crossdressers

Chastened, Josh/Lori nursed her wounds for days, and little was said between her and Miranda, except when the dominant asked how Lori had opened her chastity when with Cassie. "I bought a master key on the Internet," answered Lori brightly. "Actually, my penis is getting a little irritated by the plastic over such a long time." "Give me the key. It obvious...

Forgiving Wife Pt. 02

by manatdawnrise on Jan 14, 2018
Transsexuals & Crossdressers

"Tonight just got more interesting" I said. "Oh, you don't even know the half of it yet," she beamed. Taking her drink to her lips like nothing had happened. Urges pulsed through me yet I couldn't do a thing here. Putting it simply, I needed to get her home, I needed her, my restricted erection felt unusual yet pleasurable . Finishing our drinks, we left...

Discovering Mistress Sarah's World Pt. 09

by oneguy4fun on Sep 14, 2017
Transsexuals & Crossdressers

Part 9 -- The Final Part Chapter 23 Leaving Work Josie's last week at work and concluding week of his normal life went quick. At work he spent time getting things in order for the next unlucky person to take over his job. Mentally he was already checked out of work. All he cared about was getting on with his new life. Miss May played a big part in ensuri...

Lonely Man Becomes a Sissy

by rebeldoll on Sep 12, 2017
Transsexuals & Crossdressers

I am a 28-year-old male. I'm single and live alone. I work days and usually sit at home at nights and watch movies, and talk online. I do small buying and selling on Ebay for extra cash that I stash away for a rainy day. So most of my time is spent online. I use to be into rock music a lot and have had long hair since I was a teenager. I some how lucked out...

Letter from Van Nuys

by justincbenedict on Oct 8, 2019
BDSM

Dear Shoeblossom, So I am a nice California girl, and when Kraven, my neighbor asked me to help him with his chastity belt training, I thought it was weird but kind of hilarious. I make a small living as a massager of sorts, my mom moved to Los Angeles to be a movie actress, and wound up in porn, and I got away from her and moved here to the San Fernando V...

Remaking a Boyfriend Pt. 03: Learning New Tricks

by her_every_command on Dec 3, 2019
BDSM

In contrast to the head-spinning events of the previous week, the next couple weeks were relatively uneventful for Ray. He had less trouble keeping his mind off of sex while his new piercing healed than he had been expecting. Both he and Allison were busy with work, and what time they had together they spent watching TV and talking. Ray continued running and...

Mistress Sage

by justincbenedict on Sep 19, 2017
BDSM

Manfred Wettington watched Sage leaving her apartment, holding hands with Figgins Clarke, her balding, geeky fiancée. Manny didn't know Fig well, but in the few conversations he'd had with Sage while they were walking their dogs in the front of the building where she was his tenant, he'd learned that Fig was "intelligent and talented" and was a Computation...

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...

Not so Sweet Release

by gbex on Jun 4, 2019
BDSM

It had been a long week. Work was a nightmare, and all I could think of was going home. To make matters worse, my wife Ana—oh I'm sorry, I guess I am supposed to refer to her as mistress now—my mistress locked me up. Not in the typical way like a cage, or well a cage, but not a normal one. She didn't lock me up or keep me hidden; I was able to function and d...