Sissy Cage Stories

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Neighbourhood Terror to Sissy Pt. 07

by Fibaro on Apr 23, 2019
Transgender & Crossdressers

Mark regained consciousness when Stephanie pressed her lips against his and started pushing his load of cum in his mouth. He had only just sucked a load off of Linda's toes and now he was swallowing yet another one. Every time he came here he seemed to get stuck with a taste of cum in his mouth. Only made worse by the way in which he was fed the load. Well a...

Snap! to it Divina

by DivinaTellsAll on Feb 12, 2019
BDSM

Writer's note: The following story is 100% true THE DRIVE The drive to Austin was 8 hours in good weather. Today it had been raining, and it was going to be 11 hours in the car, by arrival time. I was acutely aware of how long the car ride had been so far, for several reasons. The biggest of which was the overly-tight pair of pink sissy panties, curren...

Family Chastity Story Ch. 02

by antares34 on Jul 3, 2019
BDSM

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+. ***** Having grown bored with how things were progressing with my sissy son, I have recently ventured into a new and fun project –filming and distribu...

Neighbourhood Terror to Sissy Pt. 06

by Fibaro on Apr 9, 2019
Transgender & Crossdressers

Mark's night ended up being a very restless one. The constant rubbing of his sheets against his nylon covered smooth legs as well as the feeling of the silky material of his panties all around his bottom and chest felt very sensual. He was embarrassed to admit it, but it actually turned him on. The worries combined with the horniness formed a potent combo to...

Pizza Delivery

by Spango on Sep 24, 2019
Transgender & Crossdressers

I could not believe that I was actually going to do it. I had been fantasizing about it for months. I was not really sure where I got the idea, but I had been watching a lot of sissy hypnosis videos online over the past few months, hoping to help release my inner girly girl, and perhaps the idea came from a scene in one of those videos. Anyway, it does not m...

Sissy's Shopping Trip Pt. 02

by SissyFaye on Jul 6, 2020
Transgender & Crossdressers

Hearing my beautiful mistress say that she needs to cum before continuing gets me excited. I have an idea of what she has in mind, but I'm not sure because this trip is different than any before. Mistress walks to the back passenger door and opens it, "Get in here on your back with your head on the edge of the seat," commands Mistress. As I comply, I not...

Transforming Brent Pt. 02

by sissymissyct on Jul 10, 2019
Loving Wives

Kept in Loving Wives to annoy the tiny dicked anonymous reviewers that love to trash everything they read (after they wank to it). *** I woke up Sunday morning with a painful erection in my chastity and the pumps still attached to my breasts. I reached down trying to find a way to ease the pain in my penis. Nothing seemed to help. Maybe Wendy will be up so...

The Cuckold's Babysitter

by yumacd on Sep 26, 2017
Loving Wives

Hi, I haven't written in a while. The set-up for the sex is probably too long. I'm thinking of continuing the story. Hope you enjoy it. YumaCD === My wife, Tami, has been cucking me for a couple of years now. Most of you Literotica readers have heard the story before... - It started when I revealed my fantasy of watching her with another man one night...

Cockland Island Pt. 04

by Sissyhalo1 on Dec 16, 2019
Transgender & Crossdressers

It was one of my first lessons as a sissy that I learned on my own. New girl only appealed for some men. And there were all sorts of hotter sissy girls there just working it in the food hall and other places. With real breasts or close enough, with great asses that were getting attention. And as femmed up my brain was there was still this sort of competi...

Seductress & Daemon: Sissy Pt. 01

by SeducedKnight on Sep 15, 2017
BDSM

After Eating out my Seductress for the last hour, we hear a knock at the hotel room door. "Go open it." I go to the door dressed only in my rubber wrist and ankle bands with heels and a pink crotchless panty, I have a plug in my ass and a cold metal cage on my cock. I open the door wide in my full nakedness to reveal a prettily dressed sissy outside. "...