Up the skirt, undies still on. If this is as far as you get, its only slightly less frustrating than repeatedly taking a shovel to the head. Often resulting in blue balls. Stopping a guy at shortstop was ruled cruel and unusual punishment by the Geneva Convention of 1946.
In baseball, the shortstop is the field position between second and third base. So, in fooling around, shortstop is being masturbated by or masturbating your partner, as that's between feeling up and oral sex.
Margo finally let her boyfriend get to shortstop, but she used way too much lotion and he came on her shirt.