Sissy Rules Stories

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The Chastity Trap Ch. 01

by slavemalcom on Nov 23, 2017
BDSM

Malcom trudged out of the exam hall with the other students and sighed in relief, it was finally all over. He had just completed the final exam of his degree and could do nothing about the outcome now apart from wait and hope. He walked over to a group of his 'friends' who greeted him with high fives and cheers as they all stood around and dissected the exa...

Sissy Hubby

by rj1774 on Mar 18, 2020
Fetish

In case these are not the fetishes you like; this story features pegging, CEI, and sissy training. * It had been a very long week at work, but I had finally made it to Friday at 3pm and was excited to relax over the weekend. Then a text from my wife of five years came in that started the snowball rolling down a steep mountainside. "Hi! I have to run a few...

Goddess Rules Ch. 02

by sub_boi on Sep 17, 2017
BDSM

I take him into my mouth and suck him with My soft, wet lips. When he is near coming, I grab his balls and pull down hard, letting his little cock slip out of My mouth. He moans in pain as My hand squeezes harder on his balls. "Now, My little slut, I have a surprise for you." I go to the closet and pull out a sexy little pink camisole. "Put this on, slu...

'Cumshift' World Rules

by AlexRaymond22 on Apr 1, 2020
Reviews & Essays

So far as I can tell, I invented this world. It draws inspiration from a few other ideas, most of them based around the 'sissy' fetish and subculture, but I've never seen it anywhere else, so please accept my apology if the idea isn't as novel as I mistook it to be. The name is likewise made-up, if anything already has the name, I mean no offense by appropri...

Miss Samantha's Guest

by Sissy_Desire on May 11, 2020
BDSM

After the last text from Miss Samantha, I've been waiting anxiously to see her again. After getting home that night a few weeks ago watching the video she sent and reading "See ya next time for some more fun, sweetie" I've been wondering what our next encounter has in store. A knock at the door snaps me out of my daydream. Opening the door I see a small bo...

A Sissy Saga Ch. 13

by Snurge on Sep 15, 2017
Novels and Novellas

When not on duty on a Sunday Margaret Pardoe sometimes found herself at a loose end, and that particular Sunday she'd used up what enthusiasm she had for her embroidery project in the morning and had to settle for a stroll in the garden after lunch. Emma was on duty, but that didn't prevent Margaret from being watchful of the school rules or for taking reme...

New Rules Pt. 02

by skinnysailor on Sep 23, 2019
BDSM

"Shall we start with this?" The tip of her switch lifts my chin. She's an angel fallen to earth. I look into her beautiful blue eyes. Her long curly black hair tumbles to her shoulders. When she hugged me the satin and chiffon of her robe felt so good. She's blessed with a full figure, mature, but not fat. Her voice, like a soft caress tickled my ear. "You'...

A Sissy Saves the Neighbourhood

by JerkGently on Apr 22, 2025

You hung another dress on the line… basking in the bright sunshine for a moment. The fresh, Spring breeze cast your long, brown hair around your face, sending goosebumps rising across your bared stomach and thighs. You still felt a little nervous and exposed… standing out in your own backyard, dressed like this. Short-shorts and boob-tube all that stood betw...

Sissy Serendipity

by minc_04 on Apr 22, 2025

The past few weeks have been the hardest you can recall in your life. The series of events were kicked off by losing your job. You were far from happy at work, but at least your paycheck came through each week. Without it, or any savings, your girlfriend agreed to let you stay with her. Rachel was surprisingly hesitant at first, however, claiming that you we...

Sissy Boy Secretary

by Hotenuf4u on Sep 19, 2017
Fetish

As I sit here in the outer office space of the company CO, I look like an ordinary male secretary. On the inside I'm wearing a pair of pink lace panties, at my bosses request. You see I'm really a sissy inside and my boss takes advantage of this at every possible opportunity. I've worked here for 2 years now and it wasn't always this way. My boss, Elaine, a...