Chastity Clitty Stories

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Infinite Scroll

Taken Too Far Pt. 02

by SwitchSissy on Mar 10, 2020
Transgender & Crossdressers

"Good girl" He smiled in approval. "Now, I noticed something earlier, when I was clicking that new, secure padlock onto your clitty" he reminded me, pulling me up so I was now sat on the bed, my arms bound behind my back with duct tape. "You've written something there, and on your thighs. And I think I can also see something on your belly button too, you lit...

Bewitched, Bothered and Bewildered Ch. 03

by trevorm on Aug 30, 2017
Fetish

Part Three RULES OF THE GAME Where Vivian's mother lays out exactly what she expects from her son if he wants to keep her onside and help him to achieve his dream. Vivian went into the bedroom with a towel wrapped around his waist. He was whistling, there was a spring in his step. "You've been ages... hello, what's this?" His mother indicated the towel....

From Submissive to Slave Pt. 01

by HerBetaBoy on Sep 25, 2017
BDSM

So I sat there, my wrists and ankles bound to the chair I was sitting in. My mouth forced open by the pink ball gag wrapped around my head. My cock, as pitiful as it looked at the moment, was locked in its cage covered by pink lace panties. The view in front of me was both humiliating and exhilarating at the same time. My wife of 4 years was on her back, her...

Life according to Lizzie Ch. 02

by Lizziewannabe43 on Sep 15, 2017
Transsexuals & Crossdressers

Hello again everybody, I looked at most of the comments and took some of the advice. I really appreciate the feedback whether it was positive or negative I appreciate it all the same. Thank you and enjoy this second installment of "Life according to Lizzie," hopefully this one is a little bit more tolerable grammar wise. ***** Luke was awoken by the sound...

The Awakening of a Sissy Pt. 10

by sissyjolie4u on May 11, 2020
Transgender & Crossdressers

Best I could tell, neither one of us had moved an inch from the position that we fell asleep in. The urge to pee woke me quite early, like 4 AM early. A smile came to my face as I realized I was still holding Tim's cock. While barely awake, I made my way to the bathroom and took a seat to pee. While sitting there peeing, it hit me that I should probably do a...

Natalie Cleans Up After Mistress

by AngelSubmits on Sep 17, 2017
BDSM

I opened the car door and slid inside, wincing as the seat met my tender, well-fucked pussy. He leaned his head inside the car window and kissed me strongly, his tongue forcing its way inside my mouth. Mmmmm... Rob kissed like he fucked, taking what he wanted without asking. It had been a long time since I'd been with a man, and I had missed it like crazy. "...

Treva Makes the Perfect Man

by justincbenedict on Jun 19, 2018
BDSM

Shep shook his head as the door closed on Gibbon and his wife. "What happened, hon?" Shep smiled uncertainly at Treva. "Well, Gibbon had a deal going with his wife that if he sucked a certain number of cocks he could cum early... He's only entitled to two orgasms a year, but he earns a certain number more for how many men he services for his wife, say, 90...

Candi's Conversion Ch. 02

by CandiCumminz on Sep 12, 2018
Transsexuals & Crossdressers

Please read chapter 1 first. - We join Candi, dressed to the nines as a sissy princess, sucking on her lipgloss tube and dancing like a slut. Her wife and her friend have just walked in on her, rubbing herself to orgasm. She's in for it now... - "What the fuck is happening here?" My wife stammered in disbelief. Her company, a friend named Lucy who I'd m...

Suzy Lets me Join in

by Bakeboss on Sep 1, 2017
Group Sex

The first big change in our marriage was when my wife convinced me to wear a chastity device. She said it would heighten sexual feelings for both of us and as usual, she was right. The longer I go locked up the more attentive I am to her needs, which have gone from servicing her orally every night to doing most of the housework around the house. As for me th...

The Glory of Goddess Gabrielle

by justincbenedict on Feb 12, 2019
BDSM

When George Christopher Casemont, leader of the Frostburg Avenue Longboarders, got to take Gabrielle Abruzzi to the prom, his boys were impressed. As long as Casey, Flynn, Rod and "The Squirrel" had been running together, they'd never gotten much play from any of the Abruzzi sisters, who were kind of stuck up. But, time went by, and Casey moved to Seattle,...