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1.
The act of having sex with a very large and fat woman in which the man must actually climb her to penetrate her.
Chubby B here loves the fat girls, hes been climbing the mountain for sex since he was 12.
by J-A Jewberg September 23, 2007
 
2.
Short guys pursuing taller women.

Often trying to compensate for their own height.
"Damn, that guy is only as tall as her boobs. Now that's what I call climbing the mountain."

"I don't date short men. If you're obsessed with climbing the mountain, go climb Mount Everest."
by lockedown January 21, 2010