Answer:
My first master has four legs, my second master has two. My first I serve in life, my second I serve in death. Tough I am, yet soft beside. Against ladies cheeks I often reside.
A cowboy rode into Friday. He stayed in town for three days and rode back on friday. How is that possible?
I sleep by day, I fly by night. I have no feathers to aid my flight.
I am the greatest teacher out of them all, but alas in the end I kill my pupils.
What can be forever wound up but never annoyed?
My days are numbered. What am I?