Milo Miles

Posted on October 20, 2026

Caged Jock took my fisting virginity! We met in Spain during the Grabbys and after he caught a glimpse of my cute little butt, he knew he had to take my fisting virginity. At the start, you can see just how tight my hole is, but he knows exactly how to open me up. He stretched my hole for a bit while keeping me engaged in conversation. In the beginning, his technique is slow, patient, and caring. But before I knew it, he pushed his entire fist in me! The feeling was so overwhelming, my body kind of went into shock, I started sweating all over, and I didn’t know what to do. I wanted him to pull his fist out…but he didn’t. He kept it inside me until I got used to it. The feeling was so intense, the anal orgasms were instant and never-ending. The intense pleasure made me cum hands-free through my chastity cage! Despite my moans, he doesn’t stop fisting me. He punches the piss out of me and makes me squirt all over. Eventually, he takes my cage off and I cum a second time.