Used as a form of negative reinforcement. A hand job where the giver covers their hand in vaseline, followed by dipping the hand in beach sand. This results in massive erosion of the penis.
Marco if you don't clean upyour shit, I'm going to give you the roughest sandy handy.
When having 3 way sex with a plump or fat girl doggie style, her friend or other participants give a handjob to the person penetrating the girl from behind while the sex is at its peak.
"I was nailin fat Suzy from behind and her friend jumped in and started stroking my shaft while we were getting it on"
Someone with very poor closing skills, or a person who is incapable of performing even simple tasks. This term originates in Colorado for someone who goes to a brothel and is unable to negotiate even a simple sex act, such as manual stimulation.
How do you expect to sell twenty insurance policies when you couldn't get a handy in a whorehouse?
A hand job given apathetically and out of pity. During the hand job things are often said such as "are you almost there?" and it's not uncommon to make a phone call, smoke a cigarette, or text a friend during the encounter.
I don't really like that guy, but I'd toss him a pity-handy if he asked.