Aside from the brand of cigarettes known as Virginia Slim, it is a term or slang word used to describe a lady of thin stature and possibly available for one night stands. Most likely made popular by the Americana Band KENNY AND THE ROOSTERS' song called VIRGINIA SLIM.
When at a club, one buys a carton of Virginia Slims and proceeds to smoke the entire carton at the club. This is usually done by an Italian who has never smoked in his life.
Kevin: Hey man, I thought you didn't smoke
John: I don't. I just wanted to start a Virginia Slim Massacre tonight. I'm thinking about putting a 12 inch filter on it as well.
When a man/boy with a 12 inch cock decides to buy a whole carton of Virginia Slims at a gas station before going to the local club. At the club he decides to light up, even though he has no idea how to smoke.
The man/boy is often then compared to cruella devil especially if he uses a 12 inch filter.
Playa 1: Yo bro why u smokin I thought u didn't do that shit?
Man/boy: I only do sometimes, specifically when I have the opportunity to ligth up a virginia slim.
Playa 1: Ok man just checkin I didn't know, but more power to you. Virginia Slims are the shit.
Man/boy: Yea dude u have to experience the virginia slim massacre at some point in your life. So next week u and me will hit up the local club and experience it.