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Jack Bailey

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Meet Jack

Sweet-faced Jack Bailey may look like a wholesome midwest boy, but rather he's a holesome, sexually driven cum-hungry bottom. Jack is a top-satisfying sub with a smile, happy & eager to take a big cock that comes his way and cums inside him. His social media profiles don't say much which should tell you that his actions speak louder than words. Jack is a real-go-getter, ambitiously going from social media to self-produced videos to studio work.

Featured In

Jack Bailey & Jacob Acosta

Jack Bailey & Lane Colten

Jack Bailey & Sean Xavier

Jack Bailey & Leo Louis

Jack Bailey & Kane Fox

DVD's

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Watch Jack Bailey & Jacob Acosta

Jack Bailey & Jacob Acosta New Release | 20 minutes Rating Rating Rating Rating Rating

Jack Bailey & Jacob Acosta

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Featuring: Jack Bailey & Jacob Acosta

Description: Jacob Acosta gets Jack Bailey alone in the woods to stretch his hole out with his ginormous cock! Jacob has cleverly camouflaged the outdoor bed at Camp CockyBoys to make sure he and Jack get it all to themselves. Jack is touched by this and the attention Jacob gives him, seducing him with kisses and super-pleasurable cock-sucking, making Jack much more eager to service Jacob's cock. Sucking Jacob and taking a little face-fucking is a small challenge for Jack--compared to getting fucked by Jacob's baseball bat. Jacob spit lubes Jack then with concentrated precision fucks him deep from behind and on his back. Jacob's quietly serious fucking is in sharp contrast to the visual and vocal way Jack articulates getting plowed. Finally though Jacob takes Jack sideways and opens him up to [more....]

Watch Jack Bailey & Lane Colten

Jack Bailey & Lane Colten New Release | 22 minutes Rating Rating Rating Rating Rating

Jack Bailey & Lane Colten

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Featuring: Jack Bailey & Lane Colten

Description: One lazy summer afternoon Jack Bailey and Lane Colten playfully cruise each other in the park, but once Lane gives Jack a sneak peek of his cock, they get make haste to get it on. Lane drives them to a secluded spot to park and when Jack gets a full look at his big dick, he proceeds to suck and stroke it, as well as make out with Lane. Jack can't get enough of Lane's huge cock, and as he gags on it, Lane reaches around to finger his hole. Soon, Lane insists Jack take out his cock so they can stroke each other while kissing and keeping an eye out. Lane takes a chance by going down Jack just outside the vehicle, then turns him around to eat his ass and begin fucking him from behind and plowing his hole. They get more brazen with a little acrobatic fucking in the open passenger door [more....]

Watch Jack Bailey & Sean Xavier

Jack Bailey & Sean Xavier New Release | 20 minutes Rating Rating Rating Rating Rating

Jack Bailey & Sean Xavier

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Featuring: Jack Bailey & Sean Xavier

Description: Award-winning star Sean Xavier makes his CockyBoys debut giving Jack Bailey some unforgettable sex that goes from a sensual beginning to a body--quivering climax. Sean takes the direct approach by rubbing his exposed cock against Jack and kissing his neck and while Jack is pleasantly excited, he's also semi-nervous by the feel of the huge cock. Sean reassures Jack to trust he will take care of him as he continues to kiss him and fondle his cute butt. Sean soon turns Jack over to feed him cock and though Jack swallows and gags on as much as he can, Sean doesn't give him more than he can handle. And, Sean periodically plies Jack with sweet kisses before giving him a break ---so Sean can concentrate on his hole. With Jack on his back and his legs bent all the way back, Sean eats and [more....]

Watch Jack Bailey & Leo Louis

Jack Bailey & Leo Louis New Release | 24 minutes Rating Rating Rating Rating Rating

Jack Bailey & Leo Louis

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Featuring: Jack Bailey & Leo Louis

Description: Guess what Leo Louis & Jack Bailey do when it's raining and they're stuck indoors bored, restless and looking for relief from the monotony? Jack isn't even excited playing with his cock, but he lights up right away when Leo joins him and reveals his jaw-dropping humongous cock. And while Jack's mouth is hanging open, Leo feeds it to him. Jack not only takes that fat veiny dick into his throat, he can't get enough of it--and Leo loves dominating him. Leo turns himself on more filming his blowjob, but he turns his attention to Jack's pink hole. Leo fingers it then bends over Jack and buries his mouth in his hole and it's not long before wide-eyed Jack is begging for his cock. He gets every inch and Leo is relentless about it, giving an instant training session to Jack who is thoroughly [more....]

Watch Jack Bailey & Kane Fox

Jack Bailey & Kane Fox New Release | 32 minutes Rating Rating Rating Rating Rating

Jack Bailey & Kane Fox

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Featuring: Jack Bailey & Kane Fox

Description: New Talent December continues with Jack Bailey making his CockyBoys debut with Kane Fox! Kane had been interested in insatiable bottom Jack from the start and after months of DMs they finally get to make it happen. Kane knows that Jack has a butt that's just waiting to be fucked and when Jack offers it up Kane wastes little time eating his hole and making him squirm with delight and moan with pleasure. The more Kane devours his hole the more Jack becomes his sub and begs to be fucked and bred. However, Kane teases him more before he gives Jack what he wants and drills him. Right away it's clear this exceeds both their expectations and the intensity builds as Kane goes harder on Jack. Before he goes over the edge though, Kane gives Jack the chance to show him how well he sucks [more....]

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2 Comments

Fantico on 12/31/2021 Ojalá este chico también lo pongan a grabar escena con Austin Wolf. Sería una escena súper candente. Musketcsa on 07/25/2022 Jack is such a beautiful man and id ravage him for days non stop

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Jack Bailey

Meet Jack

Featured In

DVD's

Jack Bailey & Jacob Acosta

Jack Bailey & Lane Colten

Jack Bailey & Sean Xavier

Jack Bailey & Leo Louis

Jack Bailey & Kane Fox

Join the Conversation

2 Comments

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