shamefulsissification

Happy birthday!

original caption by Kim

But won't the other boys make fun of me?

He tried to protest, but the gentle caresses of the ladies next door made him quite docile

I wanted mom & her friends to make me up 💄 They thought it was so funny and I looked so girly but then I’ll have to be a boy again 😥

"I love the way these new diapers improve your posture, Kyle! That extra padding between the thighs really helps with your that legs-apart waddle!"

Edward? Is that you? What has my daughter done to you now? Or should I call you Edwina, No, Tina sounds better. Yes, Tina, go and fetch my daughter for me and make it snappy, you little bitch.

Yes that my dream job

I think thats her plan.

One day as Jamie's was about to go over Mark's knee for a spanking, he looked pleadingly into Mark's eyes, and Mark responded, 'Don't worry mate, I'm sure our mums will get bored of this soon, but until then, this kind of fun. Now, over my knee sissy'.

In Trouble

Captions for sissy fags and their admirers!