Sissy Rules Stories

46,352 results
Orientation
Length
Source
Infinite Scroll

The Session

by davemacc65 on Sep 16, 2017
Transsexuals & Crossdressers

I arrive at the door of the hotel room, at the stated time. My feelings were mixed. Nervous, meeting you for the first time and excitement knowing that I would be in control of the situation, well at least for the moment. Just before the door opens I realise I will not recognise you! The only pictures I have seen of you, you are wearing a hood! The door open...

Halloween Pool Party Pt. 02

by sissymissyct on Sep 15, 2017
Fetish

Maddy Returns I noticed Miss Maddy getting dropped off at the main house around 10 am. I did a quick final check of the pool room and my "pink" room just in case I forgot anything and around 11 Miss Maddy came in. She greeted me warmly with a light peck on the cheek and asked, "How's Ronnie doing today? I have missed our time here in the pool house". Why do...

Jesse's Journey Down a Rabbit Hole Ch. 04

by sadkins116 on Sep 19, 2017
Illustrated

As I mentioned in the previous chapters, this story is a collaborative effort between me and Rebeccsm. She has provided the art, and a lot of the plot, god I love how her mind works, and me for the text. Please let us know how you feel about our efforts. Comments and votes are welcome. It is the only way we will know if you like our work. I would like to th...

My New Digs Ch. 02

by cuckytoher on Aug 21, 2018
Fetish

The ice cold water hit my tired body like a thousand stinging needles as the lights went on at 6 a.m. I jumped up from the floor to finish my shower in the two minutes allotted to me by Andrea and Marko. I quickly soaped myself up and rinsed myself down knowing the clock was ticking. If I lingered more than two minutes, the door would automatically lock and...

Reawakening

by magmaman on Aug 19, 2017
Exhibitionist & Voyeur

I married Lee because she was naughty, simple as that. I dated a lot prior to meeting her, never settling solidly on anyone. I don't even know what happened there for sure, I had no plans or even any inclination to hook up with any woman full time. Besides, she wasn't my type. Not my type at all. The first time I saw her she was up on a stage wearing nothi...

Life With Miss Ida Ch. 06

by Sheermistress on Dec 5, 2017
Transsexuals & Crossdressers

Life with Miss Ida – Part 6 - A New Development On most weekends Mistress and I would enjoy a nice wine or two with our evening meals however, on this particular Saturday, Mistress was enjoying more wine than she usually drinks – we had decided to do the twin, 'Schoolie-Slut' thing this evening, with both Mistress and I in matching, tartan mini-skirts, whi...

An Invitation

by Divadaze on Sep 16, 2017
Transsexuals & Crossdressers

"Oh come on,Sarah. There has to be a way." An innocuous enough statement, but that's how it all started. I'd just received an invite to Cressida's annual Christmas party which, maybe not on the Hollywood A list, was within the cognoscenti an occasion not to be missed. The soirees of this director and major shareholder of a left leaning and decidedly outré...

Young Master Ch. 05

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

I was running through the mansion, being chased by something so horrifying that I didn't dare to turn around and see what it was. I tried to find my room, but the once familiar hallways were now disjointed and strange, as if the building had be rearranged and some pieces had been replaced with imitations that had a sinisterly artificial look to them. My purs...

Neighbourhood Terror to Sissy Pt. 11

by Fibaro on Jul 2, 2019
Transgender & Crossdressers

Chapter 13 To Mark's huge relief he witnessed Lisa opening her shorts. Without the tight fly holding the dildo in place it would fall out, at least if Lisa hadn't taken a hold of it to put it neatly back on Mark's night stand. Lisa took off her shorts completely and her panties along with it. It was instantly clear that her neatly trimmed pussy was soppin...

Fran Johnson Ch. 09

by Heironymous on Sep 16, 2017
Letters & Transcripts

I made my husband, Bill, his favorite dinner. We ate mostly in silence, as the events of the past 24 hours were weighing heavily on both of us. Against my better judgement, my he had convinced me to have sex with another man so that he could watch. It had been his fantasy for years. When dinner was finished, I handed him the envelope containing this letter,...