“Six“ refers to behind you; your backside. Dining in the six refers to putting your mouth on someone’s anus. Thus “riding in the six” refers to anal sex
On the The Colbert Report (a show on Comedy Central at 11:30) episode "Wikiality", host Stephen Colbert asked viewers to add this sentence to Wikipedia, on the basis of wikiality, which means that if most people believe something to be true, then it becomes a fact. It can also be used randomly or as a joke.
Guy 1: "Hey wassup"
Guy 2: "The number of elephants has tripled in the last six months!"
six flags in the bedroom is when a man has many techniques during sex and will always pleasure anyone in the bed with him, if you meat a guy like this he will confuse you at first but really hit it off and you will probably want to stay with this man just because of his sex.
Johnny Threefingers: "Heard you're getting out of this craphole today."
Harry Hophead: "Pfft...well, I'll be back...you know me, man... ""I’ll be out the gate by eight / in the spoon by noon / fixed by six / and back in the pen by ten!”"
12 step recovery jargon referring to someone new who talks about how great life is, now that they'resober. Usually meaning that the person is out of touch with reality.
The new guy seems pretty happy for a dude who has no job, no money and no family. He must be on a pink cloud.