Chastity Clitty Stories

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Descent into Submission Ch. 04

by Cyanlot on Mar 26, 2018
BDSM

Chapter 4: End of the Day Rewards When I got home, Charly was already there. Normally, she'd be in kitchen starting on dinner. We usually cooked together, but whoever got home first started. Tonight wasn't a normal night, though. Charly was in the living room, with a glass of wine in her hand. "What are you cooking me for dinner tonight, Honey?" she said a...

The Awakening of a Sissy Pt. 01

by sissyjolie4u on Jan 6, 2020
Transgender & Crossdressers

A little background about me. My name is/was Joe and I grew up in a small rural area, without a father figure around. There was just mom and 3 older sisters. As such, i ended up picking up a number of slightly femmie traits. It didn't help that i was also small and kind of wimpy. i was forever being harassed by the boys as i was walking home from school. I'm...

Young Greg Ch. 03: Loretta's Story

by StrattonChambers on Sep 28, 2020
Erotic Couplings

Finding myself in the neighborhood - well, I had planned to be - I arrived at Loretta's house just after four in the afternoon. I pushed the button, and Loretta answered the door, giving me a huge smile. "You came!" she exclaimed. I grinned and replied, "Yep. I wanted to come, so I thought I'd stop by and ring your bell." She gave me a big hug and said, "...

Thursday

by sissyfluff on Sep 16, 2017
First Time

Exactly one week later I got another phone call from Rina. "You come. Fix. "was all she said. "Listen you crazy bitch," I began "You come. Fix" she repeated. And then she hung up. "She's fucking' nuts if she thinks I'm going back over there for a repeat performance of last week." I thought to my self. But as I drove around I got to thinking about Benji's...

The Journey Ch. 02

by born2srvtv on Sep 19, 2017
Transsexuals & Crossdressers

(You may want to read The Journey before reading this so you will know the background of Tom/Tonya and Jason. These stories are a combination of real life and fiction. Thanks for sharing your comments.) Tonya was content as she stretched across Jason's lap. She had given Jason a long slow blow job and now Jason was rubbing his sissy slut's smooth ass a...

Delving into Femdom Ch. 01

by readytokneel2907 on Jun 1, 2020
BDSM

**Chapter 1. Growing up Oh my where to begin, I imagine it is best to start at the beginning (or as close to it as I can remember). I grew up in a relatively medium sized east coast city living what some may call a normal life with two sisters and both my parents. Growing up I was always into sports and when I entered middle school I had begun to focus on b...

Slow Descent into Sissy-Hood... Ch. 02

by Slipperylock on May 11, 2020
Transgender & Crossdressers

I started pretty slow. I'd wear it for at first hours, then a day, and then finally overnight. That one had been the hardest, no pun intended. I would wake up multiple times a night, locked in sweet torture between the inevitably erotic thoughts in my head and the bittersweet tightness between my legs. The first time I'd tried it, I'd made it till 2 a.m. bef...

The Office Sissy XX Ch. 02

by pennyjonestv on Sep 15, 2017
Transsexuals & Crossdressers

CHAPTER 3 The smell of Dannie's pheromones was making me giddy. It had been so long since I had last tastes sissy clitty; too long. My mind flashes back to boarding school, Gloucestershire. I was young, under age by English law. It was just after the summer play, and James had decided we should change costumes; boys wear the Shakespearean dresses of the gir...

Camboy's New Mistress

by pluggedforlife on Jun 5, 2018
Transsexuals & Crossdressers

His heart was pounding with passion. The big black dildo slid in and out of his well-lubed butthole, tickling his prostate. He could feel the large black penis glans squeeze out a drop of precum as he exhaled a moan of lust that was building up in his lungs. His steel chastity cage was flopping up and down, hitting his smoothly shaven crotch. His silver ho...

Halloween Pool Party Pt. 03

by sissymissyct on Sep 15, 2017
Fetish

I soon headed to town and told the apt manager that I was sorry but I would have to move out immediately. It was a family emergency and I would be leaving the area the next day. I asked if he knew anyone that would purchase my furniture, appliances and household stuff, and he asked to see it. It was all quality furniture and he said he would take it and offe...