Halfway between 2nd (feeling up) and 3rd (oral). Involves the hand on the genitals. Is very frustrating if this is as far as you get, seeing as it results in blue balls.
damn, dude. Im so mad. I only got to shortstop last night. I had balls bluer than a naked eskimo.
by bassplayer91 September 11, 2009
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.

See also first and a half base.
I thought I was gonna get some poontang last night, but just as I was about to give her the Shocker she stopped me at shortstop. So I had to go home and play with my Trogdor.
by Anonymous March 17, 2003
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.
by Pauliver October 26, 2003
Street terminology for a hustler or a player.
I'm looking for a local shortstop to score some _____. Where can I find one?

(Usually is said to someone already involved in whatever ____ is.)
by Phaedrus4th March 9, 2012
Girl #1: me and ben went to shortstop last night!

Girl #2: whats shortstop?

by ATLCA August 21, 2010
In collaboration with the 3rd, 2nd, and 1st base, and Homerun terms for interaction with a partner. Shortstop is the area inbetween right before 2nd base, that includes (but is not limited to):

-Intense making out (including tounge)
-Hands on the ass, or up the others shirt, but not touching any thing (on purpose)
-hands running through hair
-rolling around on the floor
-making a scene in public

It is best NOT to do this public, unless its lonely there.
"Ya dude, she says that only her moms gonna be home, so we gotta stay on shortstop."
by Jar-Man August 3, 2008
The optional step between second and third base involving serious videochatting.
Chet: Dude, I heard you got to shortstop with Veronica.
Bret: Yeah we videochatted allllllll night.
by ScrubClub5 August 11, 2010