Repeat Offender
Jason, one of our most popular models, is back for another spanking. A few days before this spanking, Jason asked Tom to send an Uber car to pick him up and bring him to Tom's. However, Jason never intended to show up. Instead, he redirected the Uber that Tom had paid for from Tom's to another destination. He then refused to answer calls, texts or emails. This was nothing short of fraud and theft. Given Jason's past frauds and failures to show, Tom wasn't particularly surprised by this deceit. But Tom was surprised that Jason would show up for a spanking so soon after ripping him off. Though the timing was ill-advised, you have to respect Jason for taking what he has coming in this video.
Jason was nervous when he arrived for this spanking. He knew he had done wrong and knew he had pissed Tom off. Jason suspected he was in for quite a spanking, and he was not wrong. Tom gives him a harsh spanking in this video. First he bends Jason completely over and locks his wrists and ankles to a spreader bar. This puts Jason in a fully subordinate, humiliating position that emphasizes the control he has relinquished.
After a few swats by hand, Tom gives Jason 11 hard whacks with the perforated wooden paddle. That paddle hurts, and Jason cries out repeatedly, but Tom is unsympathetic. Next Tom gives Jason 11 strokes of the cane. Jason continues to cry out and begins to shake uncontrollably. Tom then continues the caning as he lectures Jason and demands a sincere apology. Jason apologizes several times as he barely manages to avoid breaking down.
After the session is over, Tom unlocks Jason's restraints and tells him to get dressed. He then asks Jason why he stole, and what he was thinking when he did it. You'll see Jason apologize repeatedly and promise not to steal again. We think you'll agree that Jason is sincere when he apologizes and makes these promises. However, once he is away and the pain of the punishment fades in his memory, Jason is always likely to reoffend. Indeed, he has already stolen from Tom again (this time he requested money for a train ticket to come to town for another video, which he promptly spent on partying or whatever else he is up to).
Will Jason return? There's a good chance he will. And, if he does, he'll find Tom willing to discipline him again. Jason isn't a bad person. He's just very irresponsible. He wants to do what he wants to do when he wants to do it. Keeping him in line would be a full-time job.
Format: mp4
Duration: 14:46
Video: 1920x1080, AVC (H.264), 7632kbps
Audio: 303kbps
File size: 858.5 MB
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Sean's First Spanking Part 2
Sean, a 24-year-old straight military boy with a great ass, wanted a chance to earn more than a video would usually pay. However, he didn't want to also do a sexual video for our other site (RedHotStraightBoys), so the only option Tom could give him was to do a much longer, harder spanking.
The negotiations for this spanking were complex, and you can read a more detailed description of them in the narrative for the first part of this spanking (Sean's First Spanking). One interesting point of negotiation was that Sean wanted to remain clothed for the entire video! Of course, that was a non-starter for Tom and Sean had to give up on that goal.
In this video, you'll see Sean go back over Tom's knee for the second part of his spanking. What Sean didn't know was that he had really already had what amounted to a full first spanking in part one. If Sean wanted the full amount he might earn this day, he was going to have to endure quite a spanking. When Tom tells Sean he isn't even halfway through his spanking, Sean confidently states he won't give up on it. That's not a smart thing to say. It tells Tom that he should continue with a harsh spanking.
Sean has an increasingly tough time handling this spanking. He continues to bite/suck his thumb periodically and curses frequently under his breath. At one point, Tom stands him up for part of his spanking, and then orders him onto his knees for another. Sean obeys, though it's clear he doesn't want to.
Format: mp4
Duration: 18:20
Video: 1280x720, AVC (H.264), 4816kbps
Audio: 181kbps
File size: 671.7 MB
Download Sean's First Spanking Part 2