Aw, look at you… already curious. You really think you’re ready for these sissy captions? Sweet, humiliating, and just the right amount of cruel — each one’s like a little reminder you’ll never be a real man. So go on, princess… scroll down, and let me ruin that last bit of pride you’re still holding onto.

New Girl

Bryan thought making friends at his new uni would be simple-share some notes, help with homework, maybe buy a few dinks.

But the guys had other plans. Now he's siting there in a skin, makeup perfect,

dressed up exactly how they wanted.

Homework was just the warm-up.. and something tells him they are only getting started.

Sissy Wife Secretary

The job market was brutal, so when I got a personal assistant chair, I jumped at it. The catch? Every shift I had to transform—curls, voice, everything—into exactly what my boss wanted. At first, it was just work.

But the longer I stayed in that role, the more it felt like me. Now I’ve asked to make it permanent, because being his perfect little “wife” feels like the job I was always meant for.

Real Men and Real Sissy

Look at them - broad shoulders, strong hands... and then there's you, in pink bra and panties.

You couldn't be further from a real man if you tried.

Sissy's Little Secret

Careful, sweetie your skirt’s riding up. Everyone might see your cute little secret.

Side Chick

He's only ever known me as the family's little sissy... all dolled up and harmless.

Guess that's why it was so easy for me to become his secret.

Now, when my sister can't keep him happy, he knows l'm just a call away.

All dressed up and ready to be his "other girl"

Messy Doll

Aww.. look at my messy little doll. Kneeling there in your lingerie, mascara running down your cheeks... you were so worried about smudging it earlier.

Now you just look exactly how a sissy should - used, flustered, and too pretty to care.