Category: Harry

#Classic: Delivery Boy Harry’s Tip Costs Him Dearly

It’s been almost ten years since young Harry got waylaid by the Straight Hell Tops. The lanky young pizza delivery boy thought he was just dropping off a hot pie to a couple of douchey businessmen, but it turns out Stan and Terry were laying a trap for their own amusement. Seeing the pizza boy eyeing all of the cash they had stacked on the desk, Terry thought he might ask Harry what he might be willing to do for an extra tip.

It turns out, what Harry was willing to do and what Stan and Terry intended was miles apart. At first, Harry agreed to take off his shirt for the promise of an extra £20. And then he even took off his pants for another £20. But then Stan told him to start tugging on his wiener and Harry got freaked out. The older men in expensive suits aren’t keeping this request optional. It dawns on Harry that he’s not getting out of here unless he obeys every request.

Terry keeps promising money if he keeps submitting, and soon the terrified lad is bending over, sticking his ass in the air for a hard spanking from Stan with tears streaming down his face. Stan escalates the tension, using firm hand swats to discipline Harry, and then a clear acrylic paddle and then a riding crop. Harry squirms and begs to be freed, but Stan and Terry are just getting started with his sweet, cherry red ass. Click here to watch the full Straight Hell series featuring Harry getting turned into a CP bitch boy.

Watch Classic Straight Hell Videos Featuring Harry Here