His parents basement. The site of all of his milestone sexual exploits 

Like the first time he jerked off, the first time he touched another guys cock, or sucked a dick. The first time his buddy fucked his tight hole. The first time he got pimped out by his friend. The first time a train was run on his ass and his first gang bang. 

The separate entrance to his basement room made it easy for the schoolmates, teammates and friends that paid five dollars to fuck him in the ass to stop by at any time day or night.  His former friend and current pimp made a nice amount of money off him at five bucks a fuck.   

He made 25 cents each time a guy shot a load into his cunt.  He spent it all on jock straps and butt plugs. 

Inspired by and expanded upon captions from fraternity row and bi-a-piggy