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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: Vince’s Wedgie Spanking

Posted on June 26, 2024 3:18 am by Ward 1 Comment

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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📂This entry was posted in Male Spanking Spanking Straight Boys straight guys wedgie 📎and tagged Male Spanking Spanking Straight Boys wedgie
Spanking Straight Boys: Terry’s Wedgie Spanking

Posted on July 12, 2023 12:34 am by Ward Comment

Spanking Straight Boys: Terry’s Wedgie Spanking

Terry, 20 and straight, knew he was going to be spanked today, but he had no idea that he was going to get a wedgie, too. He is the first boy who ever looked at the clips hanging from a rope and immediately guessed they were for a wedgie. His only other guess was that maybe they were for his ears! (That would be painful.)

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📂This entry was posted in Spanking Straight Boys straight guys wedgie 📎and tagged Male Spanking Spanking Straight Boys wedgie
Spanking Straight Boys: Josh’s Wedgie Spanking

Posted on March 15, 2023 2:25 am by Ward 2 Comments

Spanking Straight Boys: Josh’s Wedgie Spanking

Josh is a 19-year-old straight boy who arrives to find a surprise today: two clips on a rope hanging from the ceiling. Tom asks Josh what he thinks the clips will be used for. Josh says maybe to attach to his feet or arms. Wrong!

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Spanking Straight Boys: Drake Von’s Wedgie Spanking

Posted on July 6, 2022 1:37 am by Ward Comment

Spanking Straight Boys: Drake Von’s Wedgie Spanking

Drake is a rare combination of cute and hot. Before coming to us, he had never done a spanking video. Now he’s back for another spanking. However, he has no idea that there will be a wedgie involved.

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Spanking Straight Boys: Carter’s Wedgie Spanking

Posted on May 11, 2022 12:52 am by Ward 3 Comments

Spanking Straight Boys: Carter’s Wedgie Spanking

Carter is a 23-year-old college boy with a lean, defined body and a beautiful face. Today he’s come in for another spanking, and, as is often the case, he has no idea what’s in store for him. Tom stands Carter beside a rope with two plastic clips and asks him if he knows what’s about to happen. He says he doesn’t. He examines the clips closely, and says maybe they are to hang him by his feet. It isn’t until Tom is about to clip them to his waistband that he realizes he’s about to get an extreme wedgie.

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📂This entry was posted in Male Spanking Spanking Straight Boys wedgie 📎and tagged Male Spanking Spanking Straight Boys wedgie
Spanking Straight Boys: Rich’s Wedgie Spanking

Posted on March 9, 2022 12:35 am by Ward Comment

Spanking Straight Boys: Rich’s Wedgie Spanking

Rich is back, and he’s in for a complete surprise! He has no idea he’s going to get the worst wedgie of his life today. Rich explains that he has no idea what the rope and clamps hanging from the ceiling are for. He only realizes when Tom pulls his pants down and begins to clamp the waistband of his tighty whities to the rope. Rich then begins to laugh hysterically as he repeats over and over that he does not want a wedgie.

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Spanking Straight Boys: Russell’s Wedgie Spanking

Posted on January 5, 2022 12:40 am by Ward 4 Comments

Spanking Straight Boys: Russell’s Wedgie Spanking

Russell is a young, cute twink. Today, he’s in for a surprise. He knows he’s going to be spanked, but has no idea the spanking will include a wedgie. He tells Tom he’s never had a wedgie, and that wedgies are “out of date.”

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Spanking Straight Boys: Mitch’s Wedgie Spanking

Posted on January 5, 2021 11:45 pm by Ward Comment

Spanking Straight Boys: Mitch’s Wedgie Spanking

Mitch is a muscleboy with a ripped physique and round butt. He knows he’s in for a surprise today, but doesn’t know anything about what that surprise is. He only learns the particulars as the video proceeds.

First Tom inserts a butt plug in Mitch’s ass, and then he gives him a wedgie with an industrial hoist.

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Spanking Straight Boys: Dustin’s Wedgie and Butt Plug Spanking

Posted on April 15, 2020 7:35 am by Ward 6 Comments

Spanking Straight Boys: Dustin’s Wedgie and Butt Plug Spanking

One of the most popular videos Spanking Straight Boys made was a wedgie and butt plug spanking video featuring Wes. Today they have another wedgie and butt plug spanking, this time featuring another very popular model, Dustin. Dustin is a United States Marine with a great body and a beautiful face.

He is a tough, masculine guy who knows how to fight. Today, however, he’ll be getting his ass whipped by Tom (with added discomfort and humiliation)

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📂This entry was posted in humiliation Male Spanking Sex Toy Spanking Straight Boys straight guys wedgie 📎and tagged humiliation Male Spanking sex toy Spanking Straight Boys wedgie

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