If all there were to do for unwholesome fun in New York City was go to clubs and shop for boots, we'd outdo every other city only in ennui and dejection. The fact remains that it's virtually impossible to get bored here. You don't even have to be especially imaginative about it. New York City has done most of the work for you.
It hardly matters what your particular interests are. If your primary fascination is with antiquity, there are are more and larger museums in New York City than perhaps any other city in the world; and an unusually large quantity of the exhibits are dedicated to the morbid and outré. If you are a media glutton, Hollywood may make it, but we are the biggest consumers of dark cinema and performance. If your imagination revolves around post-apocalyptic mayhem, there are regions throughout the city which could have been torn out of a vision of hell... and usually they're populated with people who fit right in with the motif, too. It is almost painfully easy to find talented friends or even partners to share disturbing insights and dubious creative achievements. Whatever your preoccupations are, you can find it in the Big (Poison) Apple.
Of course, sometimes all it takes to pass your hours in a grotesque and wickedly interesting way, is to simply be yourself in the most seemingly normal of surroundings. There are many opportunities to be covert. In fact, there's so much to do, that this section of the site acts as a "miscellaneous" category, and will continuously expand as your email contributions, continue to append and amend it with new discoveries and inventions.