Today marks day 101 of our strap-on adventures, and we're celebrating with a hard pegging session. Our eager bottom is ready, his asshole twitching with anticipation. We start slow, teasing his tight entrance with a lollipop-shaped dildo, pushing it in and out, watching his face contort with pleasure-pain. As he moans, we pick up the pace, fucking his butt with increasing force, his screams filling the room. Our goal? To make him cum hands-free, prostate milked dry.