Jack Bailey

Gustavo Cruz Dominates Jack Bailey

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Synopsis

Jack Bailey is a handsome and sweet little twink by day, but by night, he has a darker and kinky side. This little sweetie loves submitting to men who are older and more masculine than him; he’s all about seeing how much he can stand up to their whims and will. The ultra-hung Gustavo Cruz has Jack Bailey bound and gagged with anal beads at the start of their encounter. But the beads have got to go when Gustavo whips out his enormous uncut manhood for oral and anal sex. Jack Bailey’s little pink hole takes some incredible anal punishment, you can bet on that!

Gustavo Cruz Dominates Jack Bailey

Gustavo Cruz
Gustavo Cruz

Jack Bailey
Jack Bailey

Lake Need – Sc. 1

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Synopsis

As the Johnny Rapid and his boys load onto a houseboat and head out on the water, Jack Bailey finds Johnny Rapid on the top deck and asks, ‘so when are you gonna fuck me?’ Johnny smirks and pulls his shorts down to reveal a rock-hard dick that Jack instantly goes down on. With spit dripping from his chin, Jack takes off his shorts so Johnny can dip his raw cock into Jack’s eager ass. On top of the boat and out in the open, Jack gets his hole reamed hard and bareback by Johnny. When Johnny wants Jack to do the work, he sits back to let Jack ride him. Switching positions one last time, Jack is on his back as Johnny piledrives his tight ass until Johnny jumps up and shoots his load right in Jack’s mouth.

Lake Need – Sc. 1 – Jack Bailey & Johnny Rapid

Johnny Rapid Studios

Jack Bailey
Jack Bailey

Johnny Rapid
Johnny Rapid

Pretty Young Thang

Pretty Young Thang – Alex Meyer, Jack Bailey & Johnny Rapid

Alex Meyer
Alex Meyer

Jack Bailey
Jack Bailey

Johnny Rapid
Johnny Rapid

Johnny walks in and find a perfect pair of twinks, blond Jack Bailey and black-haired Alex Meyers, kissing in their underwear without him. “Which one of you two sluts is gonna suck my dick?” he asks, and they give his favorite answer: both! Jack and Alex suck his cock and take turns deepthroating Johnny before he lubes up Jack’s hole. This pretty 22-year-old wants that dick, and he pulls his legs back as Johnny eases it in before he rides the top. Johnny fucks Jack in spoon and then cums on his face, and Jack makes sure to clean it all up.

Jack Bailey Bottoms For Dan Saxon

Jack Bailey Bottoms For Dan Saxon

Jack Bailey is is a smooth-faced, blond young twink who loves to get his ass pounded by a top with a huge cock—especially when the top knows how to use it! Jack Bailey introduces himself officially to the fans of Lucas Entertainment in an interview for “Bareback Auditions 24: Thrusted And Pumped.” After the chat, Jack Bailey strips down and shows off his smooth little body before Dan Saxon gives him one hell of a workout sucking dick and getting slammed up his ass!

Head in the Clouds with Jack Bailey

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Synopsis

Look at Jack Bailey. Headphones on. Grooving to music. On a bed. In a jockstrap. Oblivious to how his quivering ass might impact residents of the ColbyKnox compound. Mickey Knox sticks his head in the door and is transfixed. Can you blame him? 🙂 He pulls out his dick, which is already sticking out. After sneaking up to the bed, Mickey takes a taste of Jack’s hole. At first, Jack is surprised. However, he relaxes because his backside receives expert oral treatment. “Fuck. That feels so good,” Jack moans. Mickey licks, giving each butt cheek a playful slap. “So hot,” he observes. “Eat that fucking ass,” Jack whispers. Mickey enjoys making a roommate happy. He even plays with Jack’s jockstrap. All that booty tasting leads to dessert. “You want my cock,” Mickey wonders. “Oh, yes,” Jack replies. Mickey stands up, pointing his greased meat to Jack’s puckered hole. Once in, Mickey deeply drills down. “Take that fucking cock,” he orders. “Yes, sir,” Jack whispers. Mickey grabs the strap for leverage, pounding to the balls. “Nice and slow,” he says. “I want to feel every inch of you.” Jack’s eyes flutter when his spot is smashed. “Yes, sir,” he whimpers. “Pound that ass.” He gets on his side. “Stick it back in,” he pleads. Mickey resumes fucking. He and Jack kiss. “I love popping the strap so much,” Mickey notes. The camera focuses on Mickey’s tool slowly going in, and out, of Jack’s hole. “Open my ass up, sir,” he begs. Mickey can’t gaze enough at his shaft going inside Jack’s tender booty. He lifts up a leg to give Mickey all the access required. “I want to ride that dick,” Jack insists. After removing his jockstrap he gets on Mickey’s rod, facing the camera. Mickey pounds up. “That is so fucking good,” Jack moans. He takes control for a bit, taking Mickey’s shaft for a spin. “Ride that cock,” Mickey instructs. He grabs both of Jack’s cheeks, shaking them to his delight. Jack’s too. 🙂 All this time he’s been beating his meat. His load shoots out, landing on his hand and balls. “You came so much,” Mickey observes. “I want you to come,” Jack says. He gets on his stomach and Mickey resumes the fucking. Mickey slams inside of Jack, placing a hand between Jack’s shoulder blades. He pulls out, dumping a messy reward all over Jack’s back. Mickey eventually gets back inside Jack, nibbling his ear. “You’re the best roommate ever,” Jack exclaims. “No. You are,” Mickey counters. Both are right!

Head in the Clouds with Jack Bailey – Jack Bailey & Mickey Knox

Colby Knox

Jack Bailey
Jack Bailey

Mickey Knox
Mickey Knox

Twink Spit Roast


Twink Spit Roast – Jack Bailey, Cole Maverick & Hunter Maverick

Nothing hotter than an eager twink looking to get spit roasted by two top daddies. Jack Bailey is an all-American, blonde hair and blue eye, apple-pie kinda guy that you want to eat up and get deep inside of, so naturally we did. We loved having Jack come shoot with us! He’s a tall and lean sweetheart. We shot three videos with him and each is nasty and aggressive and hot; just the way Jack requested they be.

Am I Qualified?

Am I Qualified? – David Skylar & Jack Bailey

It’s Jack Bailey’s first day at the new job his stepdad David Skylar got Jack at his company. Jack knows he’s underqualified for the job, but it doesn’t seem to matter to David, who got him the job because he wanted to be around him more. He knows exactly what Jack is qualified to do…and damn is he good at it!