Using a throwaway for this one.

I'm into fat chicks. Don't care if you make fun of me for it. It's not a self-esteem issue: I'm genuinely into them. I've been with a girl most guys would consider a 10 - skinny, amateur model - and couldn't get off.

Average looking guy, average height/weight, black (a surprise, I know), and not incredibly outgoing or successful with women: I have no problem talking to ones I'm interested in in public, but I have no idea how to indicate interest or take it to the next level.

I've heard all the stories about fat chicks supposedly being easy, but that hasn't been my experience. Self-esteem issues and inability to accept compliments/attraction has always been an issue.

Any advice?