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Category Archives Spanking Straight Boys
Spanking Straight Boys: Carter’s Fucking Spanking

Posted on September 4, 2024 1:59 am by Ward Comment

Spanking Straight Boys: Carter’s Fucking Spanking

Straight boy Carter is back for another spanking. He walks in to see a bed with what he calls a “pocket pussy” and a cushion mount on it. He figures out he’ll be fucking the pocket pussy, and Tom tells him he’ll be getting spanked at the same time. Spanking Straight Boys have done this type of video a few times before, and it’s always great to see a straight boy try to perform sexually while getting spanked hard.

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Spanking Straight Boys: Attitude Adjustment

Posted on August 28, 2024 1:17 am by Ward Comment

Spanking Straight Boys: Attitude Adjustment

Terry is a cute, hung young straight guy with a great butt. He’s a nice young man, but he really resents being spanked. He knows he needs to be respectful and obedient to Tom, and he usually keeps his emotions under control. His spanking the day before this one was an exception.

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Spanking Straight Boys: Scotty’s Elliptical Spanking

Posted on August 21, 2024 2:52 am by Ward Comment

Spanking Straight Boys: Scotty’s Elliptical Spanking

Scotty is a fit, muscular straight boy. He works out every day, but he didn’t know he’d be working out during this shoot. Tom puts him on a lateral elliptical for a long, intense workout that has him sweating hard.

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Spanking Straight Boys: Wedgie Fraud

Posted on August 14, 2024 2:26 am by Ward 3 Comments

Spanking Straight Boys: Wedgie Fraud

Darren is a hot, hung and straight young man. He walked in for today’s spanking unaware that it would come with a wedgie. As the video opens, Darren tries to guess what the clamps suspended from the ceiling are for. He thinks they must be nipple clamps. When he realizes they are for a wedgie, he proceeds to tell Tom that he was offered money to do a private wedgie video, which he accepted. However, as he gleefully tells Tom, he had faked the wedgie so that the underwear wouldn’t really be riding up his butt (thus the title of this video).

Darren had made a big mistake in admitting his deception, as Tom immediately decides that this means Darren needs a very long and uncomfortable wedgie with today’s spanking.

There will be no wedgie fraud in Spanking Straight Boys videos!

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Spanking Straight Boys: Whipping Owen

Posted on August 7, 2024 2:04 am by Ward 4 Comments

Spanking Straight Boys: Whipping Owen

Owen is a 21-year-old straight boy who has an amazing body and beautiful face. He’s not conceited, but he is full of bravado, often saying he can handle two spankings in once visit. Today’s shoot tests that.

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Spanking Straight Boys: Vince On The Spanking Bench

Posted on July 31, 2024 2:06 am by Ward Comment

Spanking Straight Boys: Vince On The Spanking Bench

Vince hates being spanked. He always shows up with a look of dread on his face. It doesn’t help that he has so much butt to spank. It takes a lot of work to get it red.

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Spanking Straight Boys: Carter’s New Bubble Butt

Posted on July 24, 2024 1:06 am by Ward Comment

Spanking Straight Boys: Carter’s New Bubble Butt

It’s been a while since Carter’s last shoot. He’s 26 now, and he showed up with a surprise for Tom: a new bubble butt! Carter always had a nice butt with a decent amount of shape to it, but now he’s got a full-on bubble butt that looks and feels great!

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Spanking Straight Boys: Josh Upside Down

Posted on July 17, 2024 2:45 am by Ward Comment

Spanking Straight Boys: Josh Upside Down

Josh walked in today to find that he is going to be spanked upside down in a pair of vintage white briefs. Josh struggles with being upside down, and he seems to struggle with the spankings more and more as time goes on.

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Spanking Straight Boys: Caning Terry

Posted on July 10, 2024 1:33 am by Ward 1 Comment

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

Posted on July 3, 2024 3:17 am by Ward Comment

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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