Sissy Life Stories

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Sissy life

by Kaori_chan on Jan 21, 2021
Fetish

So Ive always had this fetish. I love wearing panties. My name is Jake and Im a twin with my sister Jane. Ever since I was young I would sneak into the laundry room and wear my sisters panties. Being twins, we were always around the same size. She always had the cutest underwear. It was pink, frilly, and sometimes had cute designs all over them. My fetish de...

How to Become a Sissy/Cuckold

by Quietoldie on Sep 14, 2017
How To

This is a How To Guide for Sissies and Cuckolds. Please do not read this guide if you have no interest in the cuckold/sissy lifestyle. Like most couples these days both partners will be doing demanding full time jobs. Traditionally husbands have done gardening, cleaning the car, putting out the trash, performing do it yourself jobs around the house, drivi...

Black Sissy For White Goddess

by Samuelx on Sep 16, 2017
Interracial Love

Finally, I feel like I am where I belong. Picture this, if you will. A big and tall, muscular Black man clad in a pink tutu and frilly White panties, my face fully made up and my lips properly rouged. I am kneeling before a six-foot-tall, slender red-haired White chick and sucking her strap-on dildo. My Mistress Amelia Heinrich smiles at me as I suck her dil...

A Sissy Saga Ch. 04

by Snurge on Sep 15, 2017
Novels and Novellas

The highly polished writing table was uncluttered, the only item encroaching its pristine surface being the letter of application Miriam Hancock had received from Emma Twist, the young woman who now sat stiff backed in the chair facing her. Miss Hancock folded her hands over the pieces of paper and gave the impression of ignoring them as she assessed the ca...

I'm a Sissy!

by Queen_Diana on Apr 22, 2025

One day I woke up. Looked at my body, and thought to myself, I'd be way more sexy as a girl, I'd probably have more fun too. It's not like I'm overly girly, in fact, I'm quite masculine, girls can't have enough of me and I enjoy it. But there's this itch I can't scratch, I'm sure you know it too, a feeling of needing to be filled up and pumped full of, well...

Behavior Modification Institute Ch. 05

by NancyPan on Sep 12, 2017
Fetish

"I am so proud of you, Tom," Ms Jensen said warmly, approaching me and taking my hands in hers, "It will help you so much to accept this about yourself, Tom. We will help you turn the fantasy of being a sissy into the reality of sissy life. Ms. Panington will be pleased with this progress, and I am quite sure that Kelli will be pleased as well. Let's get you...

The Unsuspecting Candidate Ch. 02

by missvicky53 on Sep 11, 2017
Fetish

Part 2 Helen continues Mike's training, this time in a French Maid's uniform The aftershocks of his climax were still coursing through his body as I teased him. "Did you have a nice cum, sissy?" I cooed at his still bound form. "Do you want me to release you now?" "Yes, please," he replied. "I'd like to get dressed now." "And get dressed you shall," I tea...

Steph's Descent Ch. 09

by 62_goo on Aug 31, 2017
Fetish

Steph woke up and looked at the sleeping form next to her. Her first thought was of her husband, Phil. But a split second after that thought entered her head she realised that it was Amanda her girlfriend sleeping next to her. She thought about how much in love with Amanda she was and also of the situation she found herself in. It had started when she was f...

Domestic Bliss

by SadistGoddess on May 1, 2018
BDSM

Every touch from Naomi reverberated with the precondition for pain. Liam knew that, but fuck her hand closing around his dick blocked out the warning from his brain. All thoughts melted away with the mere friction of her wrist stroking up and down the length of him. Naomi was barely even clenching her hand or working it in careful motion; just the feel of he...

Kyle, The Party Dog

by Mixedwritings1993 on Sep 17, 2017
BDSM

After calling his little brother by his name, Brandon got a little pissed off when no one responded, "Damn, that boy is sleeping once again, man, can't he even stay awake for few hours at a stress?" He stomped on the floor hard on entering his little brother's room and was amazed to see even the loud stomping noise didn't wake up his brother, Kyle. Brandon...