Assholes I've Known in My Life

I was randomly inspired to start a new series called "Assholes I've known in My Life." Thankfully I haven't known that many, but assholes make for funny comic subjects. So yeah. Anyway, here's a long foreword if you feel like reading it. If not, jump right into the first of the five assholes. (Wow, that sounds wrong. But funny. So I'm going to keep it like that. HA!)

*The names of the assholes have been changed to protect (or something like that) the privacy of the assholes.