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Random
When a guy is really quick in bed
or
When you should only be getting to third base, but based on your skill, luck or some mistake, you get laid.
Girl: Wow, 5 seconds. Is that it?
Boy: Yeah, in the park home run. Sorry.
or
Wow, I totally wasn't expecting to get laid.
Having sexual relations in the bathroom of a bar. Called the inside the park home run because you're hooking up right there and then in the bar, whilst saving yourself the trouble of traveling to the others domicile.
"Damn! Did you hear Jerry hit an inside the park home run with that chick he just met over there on the dance floor?!"
An inside the park home run is incest.
When Cletus told us he'd scored an inside the park home run, we knew his sister "Ugly Jane" had lost her virginity.
When the chick you initially thought would ask you to pull out allows you to jizz inside her.
Oh yeahhhh...last night her Ludwig was so tight and I even hit an inside the park home run!
To successfully have sexual intercourse with your own sister.
Billy hit an inside the park home run last night, and now his mother is mortified.
The baseball themed innuendo equivalent to rape.
Bro #1: "Dude I totally ended last night with an Inside-the-park Home run."
Bro #2: "Isn't that illegal?"
Bro #1: "Not when the catcher's drunk!"
Bro #2: "Chyeah, brah!"
Doing a #2 in a public urinal.
From American Dad, season 12, episode 20, "Gift Me Liberty":
Stan: "I know you're hiding sonething!"
Dick: "(Sobs.) OK! OK! I'm the one taking dumps in the urinals. I call them 'inside-the-park home run'."