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.

Once Carter is clipped in and the wedgie begun, Tom spanks him with a riding crop, a leather strap and a leather belt. It’s a hard spanking that leaves Carter’s butt bright red.

However, more than that, this wedgie ends up like none we’ve done before. It goes farther because the briefs Carter is wearing are very high quality. For the first time, the waistband on the briefs doesn’t tear off. That leaves Carter fully suspended, off the floor, by his underwear, for some piñata-style spanking.

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.

Once Carter is clipped in and the wedgie begun, Tom spanks him with a riding crop, a leather strap and a leather belt. It’s a hard spanking that leaves Carter’s butt bright red.

However, more than that, this wedgie ends up like none we’ve done before. It goes farther because the briefs Carter is wearing are very high quality. For the first time, the waistband on the briefs doesn’t tear off. That leaves Carter fully suspended, off the floor, by his underwear, for some piñata-style spanking.

Charles' First Spanking.

Charles is a hot 20-year-old straight boy who, before today, had never been touched by a man or done any type of adult work. 

This video begins with a few minutes of interview footage during which Charles discusses his sex life (he’s straight) and his history of misbehavior and discipline. 

Tom then tells Charles to kneel on a chair and begins spanking him by hand and with a ping pong paddle and a flog. 

Charles finds the spanking hard to take. His eyes get very damp and glossy as his but gets redder. 

By the end of this video, Charles is shaking.

Charles' First Spanking.

Charles is a hot 20-year-old straight boy who, before today, had never been touched by a man or done any type of adult work. 

This video begins with a few minutes of interview footage during which Charles discusses his sex life (he’s straight) and his history of misbehavior and discipline. 

Tom then tells Charles to kneel on a chair and begins spanking him by hand and with a ping pong paddle and a flog. 

Charles finds the spanking hard to take. His eyes get very damp and glossy as his but gets redder. 

By the end of this video, Charles is shaking.

Ike in the Spanking Tower.

Ike is a hot 18-year-old straight boy with classic surfer-boy looks and one of the most perfect butts on the planet. He doesn’t like being spanked, but he agreed (maybe drop the “a”) to come in today for another spanking.

Ike has no idea that he’s going to be in the spanking tower. He doesn’t even know it exists. It’s hard to imagine what goes through an 18-year-old’s mind as he climbs into the tower and raises his legs above him, putting all of his private parts on display in a way they never have been before.

Tom spanks Ike by hand and with a ruler, hairbrush, flog, and a leather strap. Like most boys, Ike finds the spanking hurts much more in the stretched-tight position the spanking tower demands.

Like our model Owen, Ike’s butt doesn’t get very red, but, also like Owen, that doesn’t mean he feels the sting any less! He’s more than ready to be done by the end of the spanking. He tells Tom he doesn’t like the spanking tower.

Ike in the Spanking Tower.

Ike is a hot 18-year-old straight boy with classic surfer-boy looks and one of the most perfect butts on the planet. He doesn’t like being spanked, but he agreed (maybe drop the “a”) to come in today for another spanking.

Ike has no idea that he’s going to be in the spanking tower. He doesn’t even know it exists. It’s hard to imagine what goes through an 18-year-old’s mind as he climbs into the tower and raises his legs above him, putting all of his private parts on display in a way they never have been before.

Tom spanks Ike by hand and with a ruler, hairbrush, flog, and a leather strap. Like most boys, Ike finds the spanking hurts much more in the stretched-tight position the spanking tower demands.

Like our model Owen, Ike’s butt doesn’t get very red, but, also like Owen, that doesn’t mean he feels the sting any less! He’s more than ready to be done by the end of the spanking. He tells Tom he doesn’t like the spanking tower.

Darren’s Table Spanking

Darren is a tall, muscular and hung straight boy. Today he’s back for his second spanking. For this spanking, Tom has chosen an implement he rarely uses. It’s a leather gaucho whip from Argentina. It packs a mighty sting.

Tom orders Darren to strip and lie face down on the massage table. He then shows Darren the whip and gives him 30 hard lashes with it. 

There is a bit of spanking by hand, too, but today is primarily about the whip. Darren feels every bit of the whip’s sting and looks as though he might come to tears at various points.

At the end of the whipping, he is surprised to see how red his butt is. Still, he tells Tom he’s had worse. If he keeps coming back, he’ll have worse again.

Darren is muscular 23-year-old straight boy with a big cock. He is, in general, a good boy, which may be due to growing up in a strict family. He thought physical discipline was 

in his past, but then he came to us

Darren’s Table Spanking

Darren is a tall, muscular and hung straight boy. Today he’s back for his second spanking. For this spanking, Tom has chosen an implement he rarely uses. It’s a leather gaucho whip from Argentina. It packs a mighty sting.

Tom orders Darren to strip and lie face down on the massage table. He then shows Darren the whip and gives him 30 hard lashes with it. 

There is a bit of spanking by hand, too, but today is primarily about the whip. Darren feels every bit of the whip’s sting and looks as though he might come to tears at various points.

At the end of the whipping, he is surprised to see how red his butt is. Still, he tells Tom he’s had worse. If he keeps coming back, he’ll have worse again.

Darren is muscular 23-year-old straight boy with a big cock. He is, in general, a good boy, which may be due to growing up in a strict family. He thought physical discipline was 

in his past, but then he came to us