Sissy Rules Stories

46,352 results
Orientation
Length
Source
Infinite Scroll

Ultimate Sissy Weekend Ch. 06

by SissyTwinkleToes on Feb 4, 2020
Transgender & Crossdressers

Susie wonders if she'll ever get used to the horn honks. The gasps. The shouted comments. The whispers. The cruel laughter. She is stood with her sissy sister, Tinkerbell, in her pink OTT sissy dress she's been trapped in for over two days now, on the corner of the bad neighbourood where she now lives. It's 7:45, and she's been stood in public for almost two...

Panty Posers Ch. 04

by EROTICbearscribe on Sep 21, 2020
Transgender & Crossdressers

I must tell you of an experience Daphne and I had one Saturday night. I know, I know. You're dying to find out if I ever finally met Daddy. All good come things to those who wait. I really am a sissy tease. Aren't I? I think you'll enjoy this side trip though. *** It was a lazy Sunday morning. Daphne and I were sipping coffee and nibbling on some danis...

Julie is a Whore Ch. 05

by Pretty_Sissy_Julie on Jul 14, 2020
Fetish

Ch. 5 I am a sissy cross dresser that has been living as a woman in Madame's brothel for about 3 years now. During that time I have perfected my skills as a cock sucker and a top notch prostitute. I have my own room in the brothel where I live and entertain clients in other parts of the House. My sister, Becca, does not live in the brothel, but whenever she...

Neighbourhood Terror to Sissy Pt. 24

by Fibaro on Sep 14, 2020
Transgender & Crossdressers

Chapter 26 Marcy was a nerve wreck walking out in public dressed as she was carrying the big pink bags stuffed to the brink. The street was relatively calm yet coming out of the outrageous store with those bags she instantly drew everyone's attention. The bus stop was right outside the store and yet those few steps towards it were the most embarrassing step...

House of Kinks

by royal22erick on Dec 24, 2019
Fetish

The house of kinks is almost as old as the oldest profession in the history of mankind, its creation was founded upon three unrefutable principles. 1- There will always be a market for the pleasure of the flesh and the house of kink always need to be in touch with the populace needs. 2- No House of Kinks manager should seek power at the detriment of the hous...

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Quarantine Slave Ch. 01

by grizzley123 on Jun 9, 2020
Fetish

I was lonely. Only 4 days into the quarantine I was assigned to after testing positive for COVID-19. I was barely ill, but I didn't want to infect the world, and the world certainly didn't want me to share. I was supposed to stay out of the world and already I was going nuts. I was also horny as all hell. And then I got a text. Need Anything? I didn't kn...

My Wife Turns Me Out At Book Club

by Godscountry on Sep 26, 2017
Transsexuals & Crossdressers

It's been 3 days since the event, and my mind is still reeling. I can't believe my wife took me as far as she did in one night. Sharon had told me a few weeks ago that the neighborhood book club she attends was having a special couples night. Apparently the wives had discovered that their husbands enjoyed the idea of group sex and partner swapping, and eve...

My Life with Little Sparrow

by DomAlphamann on May 11, 2020
Fetish

I almost never come home early unless it's for a good reason. I have two reasons today; one of those being to keep you on your toes, of course, the other one is to give you news. If you followed the rules, as you should always, you might have heard the car pull up, but just in case you were busy doing anything for your own sake and enjoyment and didn't hear...

Julie's Collaring Ceremony Pt. 02

by julieaugust72 on Dec 25, 2019
BDSM

Welcome to my branding ceremony...Part 2 At this point I have just been branded. When my Master branded me I passed out and shit myself. I woke up with 2 women, Sue and Barbara, cleaning me and explaining the same thing happened to them when they got branded. What follows is the next part of the story. Enjoy and please send me comments. That is how I will l...

Jock Princess Ch. 01

by Sissyhalo on Sep 15, 2017
Transsexuals & Crossdressers

I'm Alex. And I got to admit that life's been kinda good. Cake actually. I'm a jock, left winger hockey player and all through high school it's done me pretty well. My family owns a good business in town actually a few of them. Grand dad on mom's side had a dairy farm and actually did okay, Mom's a registered nurse, my dad owns a big hardware store and ad...