Bree Olson's anal punishment begins as she's ordered to strip and bend over, her tiny ass presented for discipline. A thick, black strap-on is attached to her tormentor, the cold, hard tip pressing against her quivering, untouched asshole. Bree whimpers, clenching her cheeks, but a sharp smack on her butt reminds her to comply. With a deep breath, she relaxes, allowing the massive shaft to breach her tight opening, crying out as it slides in, stretching her ass wide.