Chastity Prostate Stories

15,547 results
Orientation
Length
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Infinite Scroll

CFNM SCHOOL

by Tallywacker on Oct 30, 2018
Exhibitionist & Voyeur

New Horizons University of Female Supremacy (New Horizons for short) was founded by a group of rich and powerful women who were fed up with the chauvinism and toxic masculinity that permeated other tertiary establishments especially the Ivy League. So to ensure that their daughters would have bright futures and that their sons would not grow up to be misogyn...

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The Imprint

by thomas_dean on Aug 31, 2020
Exhibitionist & Voyeur

Editor's note: this story contains scenes of incest or incest content. ***** From my visit downstate to Father's house over the Christmas holidays, I ended up taking my brother Josh, a recent law grad, back to capital land with me. I knew my first day back would be hectic. But first, I had to dispose of a problem, my brother Josh I had been saddled with...

Teased and Denied Ch. 03

by bighouselover on Sep 25, 2017
BDSM

For the next three days life went on. We swam, talked; I cooked and cleaned, not to mention bringing my wife to orgasm with my mouth several times a day whenever she wanted. Sunday morning dawned clear and bright. After breakfast we showered together and I soaped and washed her beautiful body, then dried her off. We retired to the bedroom where she handed me...

Feminizing First Step Ch. 05

by antares34 on Mar 30, 2020
Transgender & Crossdressers

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. Chapter 5 Today began like any other. I awoke in my bed with my wireless earbuds still in my ears. The sissy hypnosis audio track was gently playing...

The Wedding Ch. 01

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

(Intro) This is the continuation in the life of Dale Horn and the never ending saga of both his pleasure-- and his plight while living in this new world of sexuality and discovery brought about through the hands of his caring, supportive Mother and as well, his long lost love Patti... Where we left off -and with every ones encouragement our Dale saw himself...

Chaste at Uni

by squeezi on Jun 1, 2020
Fetish

Edited by AtoMisery ---------------- Chapter 1 - Preparation ---------------- My hands ran up Sophie's loose, white t-shirt, making my way up her waist, as I aimed for her breasts. Over the bra, to start. It's not like I'd never felt them before. I had, a few times. But her parents were downstairs, somehow sending the vibes that they were listening to ev...

March Madness Ch. 09a

by jbirdman on Sep 13, 2017
Transsexuals & Crossdressers

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), teasing & denial, chastity training, mild bondage, creampies, cuckolding cross-dressing and a few other fantasies of mine. I hope you find it entertaining, but if you might be offe...

Just a School Project Ch. 01

by johnemerson30 on Sep 25, 2017
BDSM

Sara could feel her heart beating faster and her pussy moisten as she listened to her professor speak in her college human sexuality class. The class began with a mixed crowd of both female and male students, but had slowly dwindled to a small group of female students as the course was in its final week. The professor was in her late 40's, very attractive...

Becoming Hers

by rogueentity on Sep 13, 2017
BDSM

[Author's note: This is the first story I have written, so it's by no means 100% great. However I'm hoping it acts as good practice for me to start writing better, and to get some feedback.] *** We had only met last week, although it seemed like a lifetime ago. That first image of you walking into the bar, long sleek brown hair, tight fitting dress showing...

Loaned Out

by Valsslut on Sep 16, 2017
Fetish

Yesterday Lady Valerie loaned me out to her friend. Terrified beyond belief, I drove to a large hotel, rode the elevator up to a large suite and ordered to undo my pants and prove I was wearing panties at the door. I was scared about being scene in the hall worse the humiliation was turning me on so much my clit got hard. Lady Valerie had taken my chastity o...