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1.
A sexual act requiring the insertion of both the index finger and middle finger into the vagina, while inserting the pinkie and ring finger into the anus. In some circles this has been more commonly known as "The Spocker". The moniker used here relates to the catch phrase "We'll be back in two and two". As you are giving the willing recipient "Two and Two".
As commonly used "I've been known to Chuck Woolery a lady every now and again" or "This one girl had been spockered before, so I decided to introduce her to my man Chuck Woolery".

"On my dating game, I pull the Old Chuck Woolery, and I'm guaranteed a second date"
by TheycallmeCoxie December 01, 2009
23 2
 
2.
Taking two dumps before 2:00 pm, as in Chuck Woolery's catch phrase "We'll be back in 2 and 2."
Dan: I really need to crap. It's my second one and it's only 1:00.

Mark: Way to pull off the Chuck Woolery!
by RabbiDan August 27, 2009
3 11