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where the rubber meets the road 

An athlete can train all day, but the race is where the rubber meets the road and they'll know how good they really are.

tickling the rubber

to have sex with a person using a condom
sup bro was she tickling the rubber?

keep the rubber side down 

cycling slang for 'be safe'
on your next ride be sure to keep the rubber side down!

Stretch the rubber band 

This happens when you are having sex with a girl doggy style. You take one of your thumbs and rub her butthole until you loosen it up to penetrate her butthole with your thumb. Once you get her butthole looser then you insert your other thumb. So at this time you have both thumbs inserted into her butthole and you pull your thumbs in a east/west direction and stretch her butthole out. Now you have successfully stretched the rubber band.
Man last night I was having sex with ole girl and she let me stretch the rubber band!

Ring around the Rubber 

The ring that is embedded on your wallet from having a condom in there for a period of more than 6 months.

This happens when you try to prove to your friends, or anybody that you get laid. You occasionally pull it out to show someone, but stupidly put it back in the same place so it can make an indent in your wallet.

This is usually prevelent in the High School age group. For some reason, future computer science Majors and Dungeons and Dragons' Players seem to have a high instance.
My mom still does my laundry. I had to quickly get my wallet out of my pants before she saw the Ring around the Rubber.
Ring around the Rubber by jaymax45 January 15, 2011

The Ant and the Rubber Tree Plant 

The act of inserting the tip of a scoopula into one's anus to form a bridge into the orifice, then sprinkling bread crumbs along the scoopula. A box of camel crickets is then opened and coaxed to follow the bread crumb trail into the anus, leading to a chemical reaction inside the user's body that results in a wild, hallucinogenic experience.
I bought a box of camel crickets to do a little of The Ant and the Rubber Tree Plant and now I'm the sexiest man alive.