teacher - Diaper Sissy

September 11, 2015

The boy was dressed in a pink sissy adult dress, high-heeled slippers, and stocks.

Published by Diaper Sissy at September 11, 2015

Teacher Takes Control

It was a normal day for me; I was in my classroom and working on the last of my paperwork when one of my students knocked on the door. I waved him in and couldn’t help but laugh when he entered the room wearing a frilly pink dress. He slowly walked up to me and started fumbling through some excuse about how he had lost a bet but I knew better.. He was a sissy, and no doubt, he was sent here for the humiliation he would endure walking through […]

March 14, 2010

Published by Diaper Sissy at March 14, 2010

Not in my classroom

I am a very strict teacher, there is not much I am willing to put up with. You think your the class clown, but I know a better way for you to entertain your peers and it is not with your foolish antics. I’ll make you the class clown alright but by my methods, I’ll spank you so hard that you’ll pee your pants and your peers will be laughing at the pathetic little pansy boy that now stands before them soaking wet, with a face as red as his […]

January 4, 2010

Published by Diaper Sissy at January 4, 2010

Punishment of the Day

Penelope and Verde are the biggest dimwits of my class. Always pushing the limit with me, thinking they will get away with it. Ha their little pea brains cant pull off any stunt without getting them caught. So to keep up with their dirty deeds, I am needing to up the anti on their punishments. One thing I know they hate the most and thats being humiliated in front of the entire class. Spankings from the Principal just aren’t getting results anymore. I think spankings in front of the whole […]