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1.
When someone is vomiting, usually invoked by drug or alcohol use, you sneak up behind them start fucking them doggie style. While this usually refers to male on female, it can also refer to male on male or anal as well.
Carolyn got so drunk last night, I gave her a Toledo Surprise in your bathroom.
by Cherrybomber5 December 06, 2010
 
2.
Sticking your dick inside a girl who is on her period and has a tampon already inserted
Dude...I tried to have sex with this girl last night when I realized she already had a tampon in and got a Toledo Surprise
by JookieAndSWoww November 03, 2013