Keeping Good Company

Jack Bailey is one of those guys you can’t keep your eyes off of when he is getting fucked. He’s so sexy, and you can tell how much he appreciates a good dicking down. It seems like he’s met some good company in TJ Hughes, who has an equal passion not just for topping, but for anything remotely sexual. These […]

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Jack Bailey, Chapter 1: Top Training

“Have you ever had sex before?” Jack’s face flushed red. He didn’t know what to say that would sound right, so he just told the truth that he hadn’t. “Do you want some pointers?” Grandpa Lance asked, already beginning to remove his clothes. Jack could hardly believe what he was hearing and seeing. It became pretty apparent that this was […]

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Bad Grades, Bad Boy

Beefy stepdaddy Brian Bonds can’t believe how poorly his horny stepson Jack Bailey has been doing in school. To whip the boy into shape, he shoves his veiny stepdaddy dick into the little guy’s mouth before filling up his boy hole with man meat.        

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Jack Bailey, Jax Thirio Bottoms

Jax Thirio’s dominant demeanor and big daddy dick have more often than not led to him taking the top bunk in the bedroom – particularly with younger guys. But, in the latest scene from TwinkLoads, it seems all that’s about to change… Sexy Jax has found himself in a hotel room with the tall, flame-haired twink, Jack Bailey. The two […]

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Tom Bentley & Jack Bailey BAREBACK

Tom Bentley is a seriously sexy, pint-sized twink. He is thrilled to be able to meet up with Jack Bailey, a cute, flame-haired boy with a killer smile and a smooth, lean body. Rock hard and eager to play, the cameras turn on and the boys know exactly what to do. The guys strip naked. Tom may be small in […]

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Twink Fuck Hole

This is our second video with Jack Bailey, he was exactly as you would imagine, sweet cute and eager to get his hole crushed and filled with cum. His moaning and sub talking was so hot it made us both cum thick ropes of hot sticky cum deep in his sweet little twink ass. And yes you guessed it he […]

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Treesome

Most of us equate spanking with punishment. If you’re bad, you get spanked. And many spanking scenes are framed in this way. However, spanking can also be a playful, fun, romantic and focused on the bottom’s pleasure. And that’s what we see in this video, featuring Nico and Jack. Anchored by the massive trunk of an old growth American sycamore […]

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Ranger Danger

Featuring: Andre Donovan, Jack Bailey & MilkingCØACH In this video, a park ranger happens upon two men who are lost – and then joins in on an exciting adventure of pleasure and sexual discovery. This video is also a playful exploration of what might be hiding beneath his authority. This is the first of two videos featuring MilkingCØACH, who is […]

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Blaine Porter pounds Jack Bailey

While their buddies are out fishing, Jack Bailey and Blaine Porter sneak off to Blaine’s room to get to know each other a little better. As soon as they get in the bed, Blaine’s shorts come off and Jack turns into a cock connoisseur. After gobbling down Blaine’s thick meat, Jack gets the favored returned with Blaine deepthroating Jack’s pole. […]

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