Jack’s room is under renovation, and while the paint dries, he’ll need to share a bed with his stepbrother, Damian. The issue is that Damian has never shared a bed before, and he knows Jack will disturb his sleep with his antics. Still, he can’t just deny his stepbrother and push him away. Things get weird when Jack wakes up to Damian stroking his own cock. Damian explains it’s a presleep ritual and that it’s the best. Jack is intrigued and wants to learn. The stepsiblings stroke each other’s dicks, and it’s clear they’re both getting turned on. They take a leap forward and start sucking each other off. It’s Jack’s first time having a cock in his mouth, but it feels so right, especially with his stepbrother - the familiarity of Damian makes it all the more sexy and exciting. Damian tops Jack and fills up his tight hole with a hot, sticky load that he’s been holding in. Next, it’s Jack’s turn to top. He’s already tired, but the sex is too good to stop, and he wants to show Damian how much he means to him by fucking him hard and giving him a load, too!
Cast: jack bailey
damian rose  
more BROTHER CRUSH updates 
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!
Cast:
gustavo cruz jack bailey  
more LUCAS ENTERTAINMENT updates 
Justin O'Neal's (Jack Bailey) family is exasperated by his behavior. They thought things would be better after he got home from Sam Gillis's program at the ranch. There was no change. In fact, Justin's gotten worse. They decide he should spend a day with a family friend Brandon Partridge (Colt Spence) in his garage. Maybe getting his hands dirty will finally make Justin a better man.
Cast: jack bailey
colt spence  
more DISRUPTIVE FILMS updates 
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!
Cast: jack bailey
dan saxon  
more LUCAS ENTERTAINMENT updates 
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!
Cast: jack bailey
mickey knox  
more COLBY KNOX updates