((A note to anyone reading: This roleplay is partially for character development, partially for muse therapy to get me back into the habit of writing. It will be weird.))
A young and prosperous businessman, a wealthy old drunkard, and a fourteen year old crossdresser walk into a bar. Not all at the same time, of course- how strange would that party be? Individually, each found their destination at a common place over a day's span of time. Other irrelevant individuals appeared in between these three's arrivals, but nevertheless, at the end of the day, there they met in a crusty old run-down bar.
The first to arrive was, of course, the wealthy old drunkard. He lived and breathed alcohol as any man of his type did, and stayed in the bar from opening to closing time (and sometimes a bit later). He was a regular, and as long as he had money to spend and didn't break anything, he was welcome.
"Greg! Good to see you again, what will it be today?" The greedy bartender called out, recognizing his main source of income as it walked through the thick wooden door. His exclamation was met with a forced, lopsided smile as the old man rasped out in reply, "The usual."
He took his regular seat at the far end of the bar and grabbed a regular mug of his regular choice of alcohol when it was offered to him. It was a regular day for the rich old drunkard man, and this was how he lived. He didn't come to peoplewatch, or socialize, or find a night's worth of love, he simply came to drink.
And drink he did, cleverly bringing only the amount of cash needed to fill his soul up and nothing more; he was experienced in the ways of being robbed blind while in a state of intoxication. He carried on his person no identification- the grey and white whiskers and sinking face proved his age to anyone questioning. No credit card, no wallet, no watch, no rings, nothing. Only cash. And what he had was enough to get where he wanted.