Shrinking Chastity Stories

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Penis Shrinking from Chastity

by tinywhiteboi on Sep 19, 2017
BDSM

After losing my wife to her big dicked black lover I was pretty depressed. I knew that my 4 inch skinny penis was not big enough to satisfy any experienced women. Sure it was fine as a teenager fucking young girls, but in my mid thirties I figured pussy for me was likely to be rare. While reading pornography on the web I discovered stories about small penis...

Morning Service

by SadistGoddess on Feb 7, 2018
BDSM

You awaken to the soundless vibrations of a strap releasing gentle tingles through your balls and up the shaft of your dick. Why the strap is on your balls doesn't quite break the surface of your consciousness. You remember allowing it to be put on the night before, but why... you moan softly and roll over in the warm nest of bed sheets and the comforting bl...

An Obsession

by Marcus_Cicero on Jul 30, 2019
Transgender & Crossdressers

It would have been after that documentary. The one with a feature on online dominance-submission relationships on Fetlife. Because before that moment in time life had been so vanilla. Marcus had been queer and had had a boyfriend or two... or three since turning 18. Well, hell, he'd been to the bathhouses since turning 20. He'd even gone as far as to create...

Howie Hangs

by justincbenedict on Aug 7, 2019
BDSM

Giulia ran her long dark nails up and down Howie's swelling cock. He was hanging just above the floor with his hands tied to the rafters of the barn. Giulia and Howie loved going up to his parent's country place. Howie's folks summered in Miami now, and so the farm was deserted. Giulia shook her thick ash blonde hair and re-adjusted her sunglasses. She to...

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 Pump House

by AlinaX on May 11, 2020
Fetish

Inspired by an idea by enigma3 in the Forum. * They say size doesn't matter, but when you are - whether by length or girth - within the smallest five percent of the population, it's difficult not to feel self-conscious about it. It's difficult to talk to women without imagining their horror, their amusement, their mockery, their contempt. Easier to avoid r...

Carl & Chastity: 1st Date

by Ninjafish on Sep 14, 2017
Erotic Couplings

Carl got to the wine bar about ten minutes late, fortunately he arrived just before Chastity. One thing that he felt never looked good was making a lady wait especially on a first date. The date started a little awkwardly, as most dates do but this one was because Chastity couldn't remember what Carl looked like at all. Luckily for her, Carl more than made u...

Pleasing Princess

by JimmyHotpants on Sep 15, 2017
Fetish

Her fingers gently traced a path along my thigh and up, casually brushing the shaft of my small, hard cock. Princess paused her fingers at the head, brushed against the ring of my prince albert piercing and danced down the shaft. "I think you're all healed and better now, baby" she said, carefully lifting by balls and running her finger lightly over my vas...

Feminizing First Step Ch. 03

by antares34 on Oct 21, 2019
Transgender & Crossdressers

(All characters are age 18+) *** I felt like I was losing control. My body and mind were becoming less and less masculine with every passing day. And I was secretly ENJOYING it. I couldn't help myself. Every time I looked in the mirror, I found myself loving the ever-changing reflection. First, my dyed pixie haircut. Then, my bikinis. Then, my nose, ear, a...

A Valentines Gift for My Lady

by sissymissyct on Sep 1, 2017
Fetish

Her long flowing chestnut brown hair mixed with my long brown hair as we passionately embraced on the king-size four poster bed. I would catch a glimpse or two as I peered up between kisses. Mostly I saw her bright red lips as they neared my pink painted lips. She nibbled gently on my soft lips before driving her tongue into my mouth. Kissing me deeply as th...