Butt plug
 

Decide how long I must wear a buttplug and comment what size it should be! I have a small, medium, and large and my master said I have to leave it in till dinner, sleep in it, or wear it till i get off work tomorrow!

I'd say you wear the small one until dinner, then the medium one until bedtime and the big one until you have to get to work tomorrow

Sleep in the medium one, and when you wake up, fuck your ass with it for 5 minutes, then insert the big one and get ready for the day with it in... Bonus points if you wear it to work XD