Cupcake SinClair, Stephen Lewis

Cupcake has the misfortune to be the long-suffering girlfriend of a degenerate gambler. This time he has outdone himself by losing a stack of money in a card game to Stephen Lewis, a dangerous gangster with a sadistic reputation. In lieu of the debt, and likely lethal consequences, Stephen has demanded that he send Cupcake to his hotel room.

In the sexy, slinky black dress Cupcake wears as a nightclub hostess, she enters Stephen’s hotel room thinking this is going to be purely for sex, seemingly confirmed as he humiliates her and orders her to strip. She knows well Stephen’s reputation; she’s frightened and wants this encounter to be over as quickly as possible. Stephen has other ideas. He has outfits for her to wear and he makes it very clear that Cupcake is going to suffer punishment for the financial loss her useless boyfriend has caused him.

As the story unfolds, Cupcake’s loyalty is severely tested, as well as how much punishment and humiliation she can take: a humiliating diaper position spanking in a school summer dress; a caning in sexy, silky lingerie, all the while being reminded how she ended up in this situation, and how much better her life could be…, should be.