Permanent Chastity Sissy Stories

27,304 results
Orientation
Length
Source
Infinite Scroll

Are You Kidding Me?

by Paniolo Boy on Feb 26, 2019
Erotic Couplings

"Are you kidding me?" I told Niki! Whoa! This was too much to handle. "Now James, I know it sounds kinky and weird, but would you do this for me? Puulllleeeeeaaaaassseeeee?" "But Niki ..." "Please James? I would be forever indebted to you. Puleeaase?" Shit! How can I refuse her? "Niki ..." I replied with a worried look, "this is going to be embarrassi...

Shadow Dance Ch. 01

by tame_goddess on Apr 10, 2019
First Time

I close my eyes as I grant the cherry at the end of my joint its vitality, letting the smoke billow around my head while the comforting scent of nature's medicine caresses my nostrils. Sitting cross-legged on my bed and topless, I lean forward slightly and rest one arm on my lap, the elbow of the other rested on my stocking covered knee as I pull the joint a...

Hotwife, Her Daddy, and Her Cuck

by fallstaffer on Jun 4, 2019
Group Sex

I come up behind Angie and gently slip off her thick Turkish terry cloth robe, letting it fall to the floor by her feet. Her husband sits on the gray pleather couch watching my hands kneed deep into his wife's large round breasts. They are thick and soft and heavy and her flesh craters as my fingers press into her. When I kiss her neck, she arches her back a...

Entrapment

by twistedwench on Dec 23, 2019
BDSM

Editor's note: this story contains scenes of non-consensual or reluctant sex. *** Kevin knew before he even swiped right, that she might be the best thing to ever happen to him. They talked for a few hours before deciding to meet up the next day. He couldn't stop thinking about her long hair, the way it would look so good wrapped around his fist as he......

Nico's Girlfriend Pt. 03

by SissyDemi99 on Oct 5, 2020
Transgender & Crossdressers

We arrived at the fields half an hour before we needed to and Kiera and Jerry pulled up next to us so they hopped in the Mercedes with Jill and I. Jill started talking, "So did you guys go get lunch together?" Jerry tried to say something, but Kiera spoke for him, "Well Jerry ate for sure, but mostly we just talked, it got quite emotional and Jerry got all...

Vegas Night Ch. 4

by malgbs on Oct 20, 2020
Erotic Couplings

I guess I hadn't slept long before Sandy's movements, sitting up in bed, stretching her arms high above her head and yawning loudly, disturbed me. I half opened my eyes and turned me head, drinking in the sight of her torso silhouetted against the soft silver moonlight streaming through the window. She'd still got her arms stretched high above her head, hand...

Begging for a Pegging

by Cirkle7 on Oct 12, 2020
Fetish

I'd like to first apologize for my extended absence! I became frustrated by anonymous critics who would pick my stories apart. So if this story is in no way interesting to you, please do not read all of it and then anonymously comment on how bad you thought it was.. I appreciate feedback and criticism but if I do not know the source then how could I trust it...

Becca is a Whore Ch. 01

by Prossie_Becca on Oct 19, 2020
Fetish

This is a story about BDSM and pleasure. Please understand everything done was consensual The scenes are no worse than you might see in the movies. There is no actual "snuffing." All of the women involved savored the experienced and had intense orgasms. This story is for your entertainment only. * Hello, my name is Becca. If you have read any of the storie...

My Twin Loves

by christo on Sep 25, 2017
Romance

Tell me your troubles, please. I want to hear, I want to help. You see, I'm a member of the fraternity, the brotherhood of unhappy men. Women consume our thoughts, don't they? We can't get girls to notice us, we don't know how to amuse them once we catch their eye, we don't know how to make them happy after they decide our sorry souls are worth their trouble...

Phone call interrupted Pt. 04

by ambise on Mar 9, 2020
Group Sex

Jill groaned as she started to release the nipple clamps, the blood flowed rapidly back into her nipples, she felt the exquisite pain she now relished. A new sensation surged through her clit, as under Jenna's instruction, she quickly pulled the new clamp off it, fortunately it comprised two small magnetic metal cones but she still screamed only partly in pa...