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Kieran's Heels Up Spanking Kieran C 04/20/2026Kieran is an 18-year-old straight boy with a big, firm butt. This is his second spanking. It’s a position he probably couldn’t have imagined. He’s inverted on a couch with his heels and butt up. Tom spanks Kieran hard by hand and with various implements including a few paddles, a riding crop and...
Kyler's First Ever Spanking Kyler T. 04/13/2026Kyler is a good-looking 22-year-old straight boy with a firm, round butt. He is one of our favorite types of models in that he has never done videos or adult work of any type before. More than that, this is his first-ever spanking. He has never been physically disciplined.
Tom gets Kyler on the massage...
Heels Up Spanking Part 2 Josh Young 04/06/2026This spanking has been hard already, and Josh’s butt is quite red and sore. It’s much redder and much more sore than one might expect for the amount of spanking that he’s undergone. Our best guess is that this is mostly due to this position being such a great and ergonomic position for Tom. Josh’s...
