FROM SCOOPS TO LOOPS
His pinpoint pupils followed the bark up the tree that grew past the collapsed rowhouse roof and through leafless branches. Dark clouds rained down upon him. The syringe still dangled from his vein before he slowly removed it. Partially dry vomit clung to the side of his mouth. Three empty wax bags with dragon stamps and a spoon rested on his rehab release papers.
Rogue springs stabbed through the discarded mattress against his flesh. Whoever he’d shot up with, left him there to die. He was now stripped of everything but his old dog tags, underwear, and ankle monitor. A pigeon glared at him from a leaning coatrack, before taking a shit on the floor. It flew away through the open roof.
His eyes and hands frantically scanned for his keys. He looked out a broken window, but the ice cream truck was gone.
His brother had given him one last chance to run the route. But this time, he’d gone far beyond being late, eating too much ice cream, or skimming a little cash. He’d grown tired of listening to “It’s a Small World” after all.
One rowhouse on the block was surrounded by all vacant homes and lots. It was painted robin’s egg blue with a soft yellow door. A crisp American flag flew over a cleanly swept stoop with potted flowers. An elderly woman collected mail from a passing letter carrier. She smiled and nodded, but quickly went inside.
The pavement was speckled with orange needle caps. Abandoned cars, furniture, appliances, and construction waste littered the block. A man leaned on an idling black Lincoln Town Car with matching vinyl roof. White wall tires covered golden spoke wheels. He watched over three scantily clad women pacing on the corner. One entered a wood-paneled station wagon before it drove off. Two kids passed on bicycles in a single lane. The ground shook as a fleeing train passed somewhere nearby.
Back inside, he picked up an old mildewed copy of TV Guide. The kid from “Leave it to Beaver” smiled from the cover of June 28th, 1958. It was unreadable, all of the pages stuck together. VHS home movies were plopped in a cardboard box, sitting on top of a broken TV. Bygone family photos smiled from crooked frames. Condoms, empty baggies, and cigarette butts were everywhere.
From the second floor, he heard rummaging and a loud crash below. With a broken 2x4 in hand, he descended the unstable staircase. There was no banister to grasp and a few missing steps.
A cat meowed before it ran off through the doorless kitchen. An overturned toaster still wobbled on the uneven floor.
On the counter, he saw a digital scale, razor blades, steel mallet, a faint powdery dusting, chunks of sheetrock, and hundreds of dragon stamped wax baggies. A ripped hole in the wall exposed remnants of removed copper pipes.
At this moment, he realized that the torn sheetrock was being crushed, mixed, and bagged with the heroin now in his bloodstream.

“ A pigeon glared at him from a leaning coatrack, before taking a shit on the floor. It flew away through the open roof.” Your imagery is always fucking badass!
I think this is your darkest one yet, and I enjoyed the sort of "nobody won but you lost the WORST" vibe here. Possibly?