A Bottom As Red As My Heels – OTK Spanking For Sissy Maid Ft Miss Roper

In this scene, Miss Roper disciplines her sissy maid, determined to turn the maid’s pale bottom as crimson red as the bottom of her own heels. She commands the sissy to bend over her lap, pulling down the “sissy” marked silk underwear to expose the delicate cheeks.

Miss Roper starts with a warm-up using her open hand before escalating the punishment. She moves on to harsher implements, including a biting wooden ruler and a literal boot sole glued to a thick piece of hardwood. The sissy squirms but holds position, counting the strokes as Miss Roper lays claim to the flesh, all for her pleasure.