How about some of his ex's get together and set him up.
They have a hot friend go pick him up in a bar and get him back to her place.
She says she wants to play kinky and cuffs him to the bed.
That's when the other girls come out.
They start out by making him plase them all, maybe they all straddle his face and ride his cock a little, but they've slapped a cock ring on him and he can;t cum.
They tease the shit out of him and have him licking pussy until he complains he can;t anymore.
They then flip him over and all don strap ons
They all fuck him in the ass and his cock stays hard because of the ring. They make him keep saying how much he loves it(when one isn't fucking his mouth with the strap on) at the end one of them jerks him off so he cums while getting fucked in the ass and saying he loves it.
They film the entire thing and put it on every amateur porn site they can find.
One of the ex's was a woman he worked with so on Monday morning when he limps into work he finds out a copy of the video has been e-mailed to everyone there.
"There is an expression; all men are created equal. This statement is a lie, no doubt created to help those who wallow in mediocrity feel better about themselves." The Lady Persephone, Grand Mistress of the Circle.