Sissy Rules Stories

46,352 results
Orientation
Length
Source
Infinite Scroll

Neighbourhood Terror to Sissy Pt. 02

by Fibaro on Mar 11, 2019
Transgender & Crossdressers

When Mark woke up the next day his parents were already gone, as usual. He was no early riser after all. He made some breakfast, gamed a bit made lunch and went to the skate park. There didn't seem to be any signs that flyers or anything like that had been spread much to his relief. Yesterday had certainly been a scare, maybe it had just been a cruel prank....

Sissy Chantel, New Reality Ch. 06

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Six: On My Way to My New Life at The Agency. Well the day has come for my transition in my life to becoming another sissy maid and sissy slut (aka: comfort girl) to 'The Agency'. Over the last two hard and humiliating weeks Master Camron and Sir Gage now as paid agents to my joining the team at 'The Agency' have helped me sell, give away or toss o...

Lady's Sissy Bitch Ch. 01

by HorroticaWriterJCarter on Sep 16, 2017
BDSM

It was an exciting day. Lady was coming to visit and I knew I was in for a weekend of extreme pleasure mixed with extreme pain. It had only been ten months since we had met at a play party but it felt like she had known me my entire life. The minutes passed like hours and I could feel the desire growing inside of me like a wildfire. Lady was beautiful. Her...

House Rules Pt. 02

by GavinNuisance on Mar 16, 2020
Transgender & Crossdressers

Terry laid naked on Lana's couch, face down with his ass sticking up. Her cum had dried. Drowsy, and still a bit tired, Terry began to move, and stretched as he adjusted his eyes to light. He noticed the sun was setting and he was clearly there for at least a few hours. He rubbed his eyes, but noticed a peculiar feeling in his backside. "What the fuck?" He...

How Far Would He Go

by stories55 on Dec 29, 2017
BDSM

This story was inspired by a Domme that wanted me to write a story about being with a man. It was at first just a few paragraphs. She then wanted more and suggested I add various elements. She knew it embarrassed the hell out of me to write it. But then she knew how much I was a victim of my own sensuality and more would follow. She knew she just need to giv...

Meeting Miss Kate

by princess_nicole on Sep 16, 2017
Transsexuals & Crossdressers

been reading on this site a lot, my Mistress had me write a story of my own for Her, and i thought i'd post here. it's my first attempt, i know it's not terribly long, but hopefully some of Y/you will like it. ---------------------- i had been talking with my new Mistress online and via text message for about a month and a half now. my first Mistress reall...

The Sissy and The Gardener

by snorn on Sep 16, 2017
Transsexuals & Crossdressers

As I sit in my office, I am wearing my pink sissy uniform, watching the hired gardener dig up the weeds out front. I'm not supposed to expose myself to others, but my sissy rules state that I must be in uniform when nobody else is inside the house. I'm doing work, but all I can really concentrate on is the idea that I should be on my knees sucking cock, or b...

Further Training as Sissy Lesbian

by maturesubmale_for_F on Apr 22, 2020
Transgender & Crossdressers

Dear readers, This is a continuation of my story 'Miss Johnstone's Lesbian Sissy Slut' and I sincerely recommend reading that story first as it provides background for this one. Enjoy and please take time to give me some feedback! Theo 3. Intermission: Further training Following the loss of my sissy virginity just after I had turned eighteen years old,...

Danni

by Coder3445 on Jan 6, 2020
Transgender & Crossdressers

This story is a complete work of fiction. In said work all characters are at least 18 years if age. This is my first story so constructive criticism is welcomed. Enjoy or not don't let me tell you what to do. *** Daniel had an issue, the issue being that when he had first started watching porn he like any other cis-gendered male had started with a voluptu...

Ultimate Sissy Weekend Ch. 01

by SissyTwinkleToes on Dec 24, 2019
Transgender & Crossdressers

Dressed head to twinkle toes in beautiful baby pink, Sissy Susie nervously waits for her friend to arrive and the most humiliating weekend of her life to begin. She winces as her teeny clitty squirms in its pink prison, a chastity cage that's been on for four frustrating weeks. Her cage is safely tucked away in her pink ruffly panties, covered in sweet littl...