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Quizzing Darren
Darren Tate
12/16/2024
We haven’t seen Darren for quite a while. He’s always had a tendency to want to be convivial and chatty during his spankings. Tom doesn’t like that, and he clamps down hard on it today. Tom has been very surprised by how little most of the boys know about history and basic knowledge in general...

Tags: Hung Muscular
241213101-quizzing-darren
Rutger's First Spanking
Rutger H.
12/09/2024
Rutger is a blond young straight man with a smooth body and big, round butt. Before coming to us, he had never done any type of work in the adult sphere. This video begins with a brief interview in which Rutger discusses his history of physical discipline, which included getting paddled for misbehaving...

Tags: Blonds Bubble Butt First Contact Video Interview
240920102-rutgers-first-spanking
Quizzed Paddled Questioned and Tickled
Owen Thompson
12/02/2024
This was a hard day for Owen. It was a long shoot and an extra-long spanking. Owen spent almost one full hour in the stockade, which is anything but comfortable. In this final part of this video, Tom quizzes Owen to test his knowledge of his favorite subject (history). Tom then questions him about the...

Tags: Bent Over Bondage Bubble Butt College Student
180810103-quizzed-paddled-questioned-and-tickled
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More Updates
241213101-quizzing-darren Quizzing Darren
Darren Tate
13 min of video
12/16/2024
240920102-rutgers-first-spanking Rutger's First Spanking
Rutger H.
24 min of video
12/09/2024
230412101-some-boys-never-learn Some Boys Never Learn
Terry Loop
16 min of video
11/25/2024
240817102-scottys-shower-spanking Scotty's Shower Spanking
Scotty Mills
16 min of video
11/11/2024
240613101-vince-on-the-elliptical Vince on the Elliptical
Vince Enzo
11 min of video
11/04/2024
240721103-one-cheek-only One Cheek Only
Carter List
12 min of video
10/28/2024
241019101-tristans-first-spanking Tristan's First Spanking
Tristan K
15 min of video
10/21/2024
240519103-tom-goes-for-it Tom Goes for It
Cal Wheeler
12 min of video
10/14/2024
240731102-terry-breaks-down Terry Breaks Down
Terry Loop
12 min of video
10/07/2024
211203102-quick-not-easy Quick Not Easy
Russell Wall
10 min of video
09/30/2024
240522102-vince-in-the-stockade Vince in the Stockade
Vince Enzo
15 min of video
09/23/2024
210723101-greg-spanked-in-baseball-gear Greg Spanked in Baseball Gear
Greg Powell
15 min of video
09/16/2024
180222101-alexanders-first-spanking Alexander's First Spanking
Alexander Bryant
20 min of video
09/09/2024
240721102-carters-fucking-spanking Carter's Fucking Spanking
Carter List
38 min of video
09/02/2024
240731101-attitude-adjustment Attitude Adjustment
Terry Loop
11 min of video
08/26/2024
240817101-scottys-elliptical-spanking Scotty's Elliptical Spanking
Scotty Mills
21 min of video
08/19/2024
240809101-wedgie-fraud Wedgie Fraud
Darren Tate
14 min of video
08/12/2024
180810102-whipping-owen Whipping Owen
Owen Thompson
11 min of video
08/05/2024
240522101-vince-on-the-spanking-bench Vince on the Spanking Bench
Vince Enzo
15 min of video
07/29/2024
240721101-carters-new-bubble-butt Carter's New Bubble Butt
Carter List
11 min of video
07/22/2024
230131101-josh-upside-down Josh Upside Down
Josh Young
14 min of video
07/15/2024
231026102-caning-terry Caning Terry
Terry Loop
18 min of video
07/08/2024