Some kind of gag or face-mask I guess. Stops him from crying probably :P

oooo owie
wtf? is the face thing?

Did you do the dare I gave you? :P

Alright...I dare you to spank yourself 30 times with a slipper (or something similar) and whisper after each spank 'I am a pathetic worm'

would if i had the money

I double-dare you to buy yourself a tawse and whip yourself with it :P (Only if you want to though)

aint done much but would like to try it

Cool, so you're into BDSM? The pain part or the humiliation part? Or both? Lol.

defo fun i like it

I have no idea, but it sounds fun to me lol. Probably some nice BDSM punishment. What do you think he means?