Chastity Clitty Stories

10,475 results
Orientation
Length
Source
Infinite Scroll

Sissy's First

by CDJessie on Mar 7, 2018
Transsexuals & Crossdressers

This is a work of fantasy. (I wish my gf would do something like this to me.) *** I'm woken up to the blinding sun after Sarah rips open the curtains to our hotel room window. We were up half the night fucking our brains out, and I was pretty hangover "Fuck, you couldn't wake me up like a normal person instead of blinding me?" I ask. "Don't take that fuck...

Halloween Pool Party Pt. 08

by sissymissyct on Sep 14, 2017
Fetish

Friday morning cam and I was awakened with an electric shock that ran from my tits to my clit. My eyes flew open to see Miss Maddy and her girlfriend each with one of my nipples in their mouth. Pulling at the rings with their tongue, my high pitched squeal announced I was awake. My clitty tried to get hard but had no place to go. I reached to touch it and co...

The Journey

by born2srvtv on Sep 19, 2017
Transsexuals & Crossdressers

Tom couldn't believe he was wearing a CB-6000 chastity device while driving to Knoxville to actually meet face to face with Jason. He and Jason had been chatting on a kink oriented website for the last few months. Jason had asked him to buy the CB6000 and Tom found himself incredibly eager to comply with Jasons' desire. Jason had asked him to wear it while t...

Simon's Sluts

by Ellyce on Sep 16, 2017
Transsexuals & Crossdressers

Chapter One – Wake Up Call The alarm went off and I groped for the "snooze" switch out of habit. Then I remembered that I had day maid duty today and sleepily rolled out of bed. Wandering into the bathroom, I pulled the shortie nightgown over my head and observed myself in the full-length mirror starting at my red-painted toenails. My gaze wandered up my sh...

Simon’s Sluts

by Ellyce on Sep 16, 2017
Transsexuals & Crossdressers

Chapter One – Wake Up Call The alarm went off and I groped for the "snooze" switch out of habit. Then I remembered that I had day maid duty today and sleepily rolled out of bed. Wandering into the bathroom, I pulled the shortie nightgown over my head and observed myself in the full-length mirror starting at my red-painted toenails. My gaze wandered up my sh...

Wet Dream Pt. 03

by sissymissyct on Jan 28, 2020
Fetish

Gayle finished ordering items on line and checked the cam to be sure Georgia was asleep. The wetness in her panties told her what she needed to do. The payback for all those years that bastard cheated on her and how he had no idea what was coming to him, just made her pussy so wet. She was soon in bed enjoying her favorite toy. "I can't believe I slept so l...

A Perfect Birthday

by BelleBlack on Sep 14, 2020
Transgender & Crossdressers

Alex sighed as he woke up. Another birthday. He knew it was cliché, but he always hated his birthday. As petty as it sounded, he just wanted to spend time by himself, to have a day off, instead of being forced to go out and celebrate. He knew his friends and family always meant well, but couldn't he just have one birthday where he had time to do what he want...

Jerry becomes Jill Pt. 04a: Doctor

by gasissynora on Apr 27, 2020
Transgender & Crossdressers

Jerry becomes Jill: Part 4a: Summer - School This is the fourth part of my story about how I became Jill. Summer school continues with female hormones being introduced and a trip to the Doctor. Jill is looking forward to the month long break coming up at the end of the summer. Spring quarter ended with a short break, we started into the summer quarter. Not...

The Descent Ch. 03 - The Show

by pantywriter on Sep 28, 2020
Transgender & Crossdressers

She jarred me awake, destroying arguably the best slumber I had ever had. "Wh-what?" I managed. "Darling, you must get up, it's five AM and I have no wish for you to see me like this, yet," she softened her words. I blinked and rubbed my face with the palm of my hands. Sitting up still wearing incredibly sexy lingerie nearly made my clitty rise, but her...

Fifi's Long Wait

by Vertex on Sep 13, 2017
Transsexuals & Crossdressers

Around about 3 weeks ago, Sid had managed to acquire his very own maid; however, 'she' was not your normal run of the mill domestic worker. Oh no, Fifi liked to dress as a maid to fulfill her submissive cravings and the most notable difference was the fact that she had a penis. When working as a maid, she didn't call it that, tucked away in her silky panties...