This is Toronto slang meaning great and handsome

I skinny f*ckboy from sauga who send dicks to other male.

This slang was created in SJSS it was a name given to those mentally challenged students by the teachers. It was popularized to be a slang by non other than Tahseen.
Now days pip means dumb, disabled, retarded etc

a ruler and awesome at his job and his job is good looks