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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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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 He tells Tom he’s never had a wedgie, and that wedgies are “out of date.”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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Spanking Straight Boys: Owen’s Wedgie Spanking

Posted on December 12, 2017 10:12 pm by Ward 14 Comments

Spanking Straight Boys: Owen’s Wedgie Spanking

Owen, age 19, is back for his hardest spanking yet, and it has quite a twist. This is the first wedgie spanking video SSB has shot. They use an “ultra-wedgie machine,” as Owen himself describes it.

Tom attaches clips to the back of Owen’s white briefs. The clips are attached to a rope that is attached to Tom’s industrial hoist. The result is an embarrassing, uncomfortable, and increasingly revealing wedgie.

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