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1.
Opposite of balls deep. During intercourse, only entering the tip of the penis. This may be for one of two reasons:

a) you are extremely well endowed

b) you are having sex with a child/small animal
a) Jemal: "Yo winston, check out that little blonde cheerleader. I'ma go tip deep in her wid my big black mamba"

b) Nigel: "Hey, Ronald, check out that dead fox on the road - I'll swing by later, scrape it up and we can take turns going tip deep on it!"
by Helmut von Dogbiscuit June 12, 2012