Chastity Clitty Stories

10,475 results
Orientation
Length
Source
Infinite Scroll

Robillard's Pain

by justincbenedict on Sep 13, 2017
BDSM

POOR, PUDGY ROBILLARD! As he brushed and stroked his beautiful goddesses curls, Robie's penis nearly wrecked itself, locked in the tiny casing. Would he escape it today... maybe? Robillard St. Croix finished coming Autumn's cascading blonde hair. He'd given Autumn a great comb over, and massaged his pretty cousin's shoulders till Autumn had purred. She'd l...

Rene and Gene

by Bakeboss on Sep 16, 2017
Novels and Novellas

Part l My first Friday as Jean: Although I work at home, I still took the day off to make sure all the housework was done. Rene called on her lunch hour and said she bought a surprise for me, that she felt naughty and wanted us to spend the weekend doing naughty things. I was hard at the word naughty; my beautiful wife is such a tease and enjoys role-playi...

Business Trip - Day 01

by pantywriter on Dec 16, 2019
Transgender & Crossdressers

Day 1 At four-thirty in the morning, when you and your girlfriend are both up and screaming at each other to find this and that, because you both have flights leaving the airport within ten minutes of each other, and within ten minutes from six, sex is the very last thing on your mind. We woke on time and were generally getting along well but Emma was havin...

Mistress and Bitch

by hungry4femdom on Sep 18, 2017
BDSM

When they first met, there was electricity between them. When they gazed at one another, it was there, and when they touched, it was there. It almost goes without saying that this electricity was also present in their lovemaking. More than once he had said that he felt under her spell, totally captivated, and for him this was a good thing. Every day they m...

Zoey's Basement Transformation Pt. 02

by SissyStoryTime on Sep 11, 2017
Transsexuals & Crossdressers

"Stand up," the whip crack of Mia's voice caused Zoey to flinch, but she didn't move from where she kneeled. With a sigh, Mia grabbed the leash attached to her chastity cage and started to give it a firm pull. Zoey quickly found her motivation, legs scrambling beneath her to find purchase. In her haste she slipped, almost falling back down. "Slower," Mia sa...

The Awakening of a Sissy Pt. 07

by sissyjolie4u on Mar 9, 2020
Transgender & Crossdressers

I was a giddy as a school girl knowing that I would be sleeping with Tim, Curiosity was building inside me. I was going to sleep with a man for the very first time. What was the special surprise that Tim had planned for me. All night long, as we watched sissy porn, Mistress kept harassing my pussy with various levels of my trainer. I was happily enjoying us...

Candi is a Sissy Cam Girl Ch. 01

by CandiCumminz on Jan 15, 2019
Transgender & Crossdressers

This is the 6'th story in Candi's tale. Please read the Candi's conversion series and Candi Gets an Upgrade for the full picture of what's happened so far. - Hi! My name is Candi Cumminz and I'm your new favourite bimbo sex-doll. My camera's always on and I'm always horny so stop by any time for a good time! I love dressing up for my fans and putting o...

The Wedding Ch. 05

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

(Patti Cake part 3) Chapter 5 -- Femdom, Fucking and Femininity... At the end of our time spent with Ms. Walsh, I was left with a lot of questions and I wasn't sure how to deal or cope with any of it... But one thing was for certain, I was starting to see more of the old Patti bubbling back to the surface, being direct and without compromise... The whole d...

Pleasure with Driver Ch. 02

by sumantriguni on Sep 13, 2017
Erotic Couplings

After having a satisfying round of sex with my driver on that fateful day when I came back home, my looks were sufficient to raise some doubt in my sister-in-law's mind and I could not have continued to have regular sex with driver as long as she was there. I thought about this and finally came to conclusion that she also has to join us. I knew that she was...

Letter from Montgomery

by justincbenedict on Sep 24, 2019
Transgender & Crossdressers

Dear Shoeblossom, I didn't think there were any transgender men in Alabama, but apparently my husband and I got one as a client! This little convo was funny and somewhat arousing to friends of mine, so thus, I submit it. Syndi "Oh, thank you for letting me out, Syndi." "How was it, Won Joo? Let me sponge off those perky tits of yours." "Oh, that feels s...