Date Night in Hawaii As Debbie Wears Her Black Leather Skirt and Cum Filled Black Penny Love Kenny Stiletto Spiked Ankle Strapped Pumps 2. These are Debbie's tallest stiletto's measuring over 6 inches high. This evening, she's dolled up for date night in Maui as she puts on her skin tight black pleather mini dress with no bra or thong. She compliments this outfit with her stilettos and turned many heads as we enjoyed an evening out on the town. Best of all, I got to fuck her in this outfit at the end of the evening.