What is Glasshole?
1.
A punk rocker hipster scene-ster type who wears horn rimmed, or Buddy Holly style glasses.
Usually accompanied with a zip-up hoodie, Dickies pants and Chuck Taylor shoes.
This person's perception of the world is pessimestic and/or sarcastic. Approach with caution because he's probably a jerk and think's he's much cooler than you, square.
Billy: "That guy's a creep, I said 'what up' and he snubbed me. What gives?"
Johnny: "Don't worry about him. He's just a glasshole."
2.
A glasshole refers to a woman's rectal orifice, when you fuck it without AsstroGlide.
Just before he blew his load, Jacques fucked Emmie's glasshole.
See
3.
Anything that is or can be unsatisfying
The movie was a glasshole.
See