Rubber Sissy Stories

28,680 results
Orientation
Length
Source
Infinite Scroll

Roommate Ch. 02

by corsetheelscollar on Sep 17, 2017
BDSM

The week had gone by. My legs were still smooth. I slid my hand inside my dressing gown and felt my hairless balls. I'd loved being forcibly dressed by Stephen and Shellie, but the vengeful man in me wanted to get my own back. How could I find a punishment that Stephen wouldn't enjoy? He was into all sorts of kink. I doubted that there was anything he would...

Dominating a Man

by Tosshhh_ on Aug 21, 2019
BDSM

Even I will admit this story is a little on the unusual side but it is 100% true. I have and will always consider myself a straight man. I think even to call myself bisexual is not entirely accurate. Being a natural and experienced dominant I was well accustomed to offering my services to women who I didn't find particularly attractive. I had never considere...

Sissifying Addictions

by Sissyhalo on Nov 25, 2017
Transsexuals & Crossdressers

They say you're born gay, they say you can't catch gay, that you can't be made into something you don't want to. That somewhere deep, deep down you really want it. It's somewhere in between and none of it either. It's actually so much like dominatingly slick, sinking, drowning...so very like that first time you sink into sweet sissy ass. It started for me...

Behavior Modification Institute Ch. 09

by NancyPan on Sep 12, 2017
Fetish

I want to finish the story since I have some avid readers and I don't want to leave you "hanging," so to speak. However, I've noted a significant drop in the number of votes and the rating of the last couple chapters - so if you want to encourage me or have constructive suggestions, please vote and/or leave a comment. ***** Confined to the cage and in tot...

Cockland Island Pt. 03

by Sissyhalo1 on Dec 23, 2019
Transgender & Crossdressers

I think my dreams that night were pleasant. I was kind of still just transforming back then. But when I woke up, I remember the feeling of my butt plug in my ass was pleasing and that my caged cock was perfectly sissy cute and I was good with that. It was kinda a trip to look in the mirror and see it all. And walking with the plug, sitting with the plug....

Mistress Joan Ch. 01: Punishment

by slutty_sissy_nikki on Mar 10, 2020
BDSM

BASED ON A TRUE STORY! All characters are over the age of 18. This is my first short story and I welcome constructive feedback. PRELUDE The cane cut through the air to deliver another mark onto my plump bum. I tried, unsuccessfully, not to flinch when I heard the wish sound of the cane travel through the air. Knowing it was coming was the worst part, or ra...

Sammi's Place in College

by Sissy_Sammi_ on Dec 17, 2017
Transsexuals & Crossdressers

Sammi was up at seven AM, as usual, fully dressed and dolled up and tidying up the suite. Something had broken in her brain at this point, she had been re-wired. Her life had taken some drastic turns, and who she was and what drove her had been completely replaced by something new. Sam, in the past, had been at the helm and would occasionally allow Sammi he...

Mother Dear Pt. 09

by keptsissy on Sep 13, 2017
Fetish

"I love this place, baby boy. Every time we dine here I think back to that one fateful dinner, the dinner where this all began. The dinner after I came to your home unannounced innocently enough, wanting to take you out to eat only to find you dressed like a girl and on your knees doing what we bad girls do, delightful." She winks at me over her wine glas...

The Sissy in the Loft

by Sissy_Sammi_ on Dec 31, 2018
Transgender & Crossdressers

*All characters are 18+ *** James grit his teeth and walked through the door, a bell ringing as he entered the store. It was getting late and the sun was setting outside. He had been waiting in his car for nearly 20 minutes, waiting for people to leave the shop and no longer be near the store. The lady running the shop looks at him with a strange look fro...

First Time as Sissy

by twofish73 on Sep 19, 2017
Transsexuals & Crossdressers

I'd had fantasies for years on and off about crossdressing, but I'd written them off as the same kind of fleeting idea like going to the moon, or racing formula one. I'm straight, I like women, but I also like pleasure and don't understand why some things are taboo even if they feel good. But those thoughts are best kept to oneself, at least they were where...