To bring male enhancement drugs ie. Viagra along on a trip or party to ensure that you will be able to perform sex regardless of your overall condition. These pills are not typically used by the person, but brought as dicksurance in anticipation of the savage debauchery of the event that may render his otherwise functioning penis useless.
Shawn: "Dude, we leave for Vegas in like a week!"
Alex: "I know, it's gonna be wild! I still gotta pick up some dicksurance from my doctor."
Jake: "Dude, that girl you left the party last night was smokin! Did you slay it?"
Shane: "Man, I was so wrecked that I had to dip into my dicksurance for the first time just so I could hit it proper."
Verb: When a girl is about to start her period and has sex, causing her to bleed a little during sex and start her period immediately after. The dicking kickstarts their menstruation.
I wasn't supposed to start my period for a couple of days, but we had sex and it dickstarted it.