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whale riding

When a man goes up to a women in a bar, gives her a hug and whispers in her ear that she is the fattest and ugliest thing in the world. Then he see's how long he can hold on to her for.
Winnner of whale riding is the person who holds on the longest!
(In a bar) man goes up to a women and says:

"you are the fattest thing in the room"

See's how long he can hold on

Friend: "you are the best at whale riding"
by Edward Mills March 11, 2009
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riding the whale

Engaging in sexual intercourse with an woman of considerable size.
John: You know how your sister is a little on the hefty side?
Chad: Yeah, why?
John: Consider me Ishmael.
Eric: You've been riding the whale?!
by Ortis Penbottom September 19, 2009
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