Spanking Straight Boys: Caning Terry
This is Terry’s first caning (it was shot before the caning he received in the previously released video “The Evil Eye”). He didn’t know he was in for a caning (although the boys can always ask as many questions as they want, they almost never do), and he didn’t even know what a caning was.
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Spanking Straight Boys: Basic Knowledge
Cal has come back for another spanking, something he says he thought he wouldn’t do. Tom delivers this spanking on the table.
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Spanking Straight Boys: Vince’s Wedgie Spanking
Though he doesn’t know it, Vince is in for a wedgie spanking today. He didn’t even know there was such a thing, or that Tom gives wedgie spankings. He’s confused by the clips dangling from the ceiling and can’t guess what they’re for. Watch the look on his face when Tom lets him know the clips are for a wedgie. Vince has never had a wedgie and is less than enthusiastic.
Tom has Vince put on a pair of vintage 1980s white briefs and then clips Vince to the wedgie machine and begins spanking him by hand and then with a leather strap and riding crop.
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Spanking Straight Boys: Philip’s First Ever Spanking
Philip is 27, straight, and has never been physically disciplined in his entire life. That changes today when Tom bends Philip over and spanks him by hand and with a leather slapper, leather strap, bamboo spatula, yardstick, PVC flog, martinet and a wooden paddle. Tom also canes him. It’s a rough session for a young man who has never before been spanked. Philip struggles with the sting of the punishment, but remains obedient.
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Spanking Straight Boys: Hunter’s First Spanking
This is Hunter’s first spanking video. Spanking Straight Boys already published a video in which Hunter is spanked, but that was his second spanking video. They were published out of order because, shortly before this video, Hunter had taken a shower and shaved his butt. He didn’t have a very hairy butt to begin with, but he decided to shave it with a blade razor, and that caused some red razor bumps to raise up on his butt. They look bad, so Tom was going to see if he could correct for that, but, in the end, the bumps just aren’t that bad, so Tom decided to publish this video now.
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Spanking Straight Boys: New Duds
Josh is 22 now. Tom decided he’d look great in some stylish new clothes, so he took Josh shopping. Josh didn’t seem to like the clothes Tom was showing him, so Tom told him he could keep the receipt and exchange them for ones he liked if he ultimately decided they weren’t his style. After the shoot, Josh apparently returned the whole lot and got a refund!
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Spanking Straight Boys: Near Tears
Terry, 21 and straight, is in a tough spot. He loaned his car to his brother, and his brother wrecked it. Terry’s car is only a few months old. It was too much car for him to begin with. It’s a very nice, new 2023 that he financed. His payment and insurance are about $1,000 per month, and that doesn’t include gas. Buying it was a bad idea.
Terry had an even worse idea. He was trying to be nice when he loaned his car to his brother, but his brother wrecked it and now Terry can’t afford to get it fixed. The insurance won’t cover the damage because his brother has no insurance of his own, and he isn’t listed on Terry’s insurance as a driver. So now Terry has a car that he can’t drive, with thousands of dollars of damage that he can’t afford to fix. It’s a terrible situation, and it’s sad because Terry was trying to be nice.
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Spanking Straight Boys: Part 2 of Vince Spanked in Baseball Gear
This is the second half of Vince’s spanking in a baseball uniform. His butt is already quite red. Tom breaks out the wooden spoon for a trip down memory lane. In his interview, Vince had revealed that he was subject to the spoon on many occasions when he was younger, and he is none too happy to see it now.
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Spanking Straight Boys: Owen in the Stockade
Owen is 21 and straight. Tom has spanked him with many implements in many positions. Today, Owen is in for some new experiences: being locked in a stockade and punished with a surprising new implement! In Colonial times, a person locked in a stockade (also known as a pillory) would likely face being pelted in the face with rotten fruit, or worse. Tom’s concentrates on the other end.
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Spanking Straight Boys: Russell On The Rail
When Russell first came to us, he was a mouthy young man with a bad attitude. Over the course of a series of spankings, Russell has learned to be obedient and respectful. Tom doesn’t believe this has changed Russell’s nature, but just teaching someone like Russell to conform is an accomplishment. Knowing when to hold your tongue and behave is important.
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