Darren is a hot, hung and straight young man. Because he never asks, Darren showed up 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 asked 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). Tom immediately decides that this...

Darren is a hot, hung and straight young man. Because he never asks, Darren showed up 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 asked 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). Tom immediately decides that this means Darren needs a very long and uncomfortable wedgie with today’s spanking. Tom picks a nice, strong pair of white briefs and clamps them to the wedgie machine. He then proceeds to spank Darren by hand, with a leather slapper, a leather paddle and a wooden paddle. It’s a long, hard spanking and wedgie that Darren will never forget. Sometimes the boys forget whether they’ve done a particular type of spanking (like the spanking bench or the spanking rail), but not even one boy has forgotten whether he’s done a wedgie spanking! (High Definition Version)