Join Jack Bailey and Gustavo Cruz in 'Penetrated & Pounded, Scene 2' on Lucas Entertainment for a thrilling encounter where Jack's sweet, submissive side meets Gustavo's dominant, ultra-hung presence. Starting with Jack bound and gagged, the scene escalates as Gustavo unveils his enormous uncut manhood, leading to intense oral and anal play. Witness Jack's resilience as his pink hole undergoes incredible anal punishment in this unforgettable Lucas Entertainment scene.

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Experience the gripping story of 'A Brat & A Gentleman' at Disruptive Films, featuring Justin O'Neal (Jack Bailey) and Brandon Partridge (Colt Spence). Watch as troubled Justin learns life lessons in Brandon's garage, leading to unexpected changes.

The post ASGmax’s Disruptive Films: Colt Spence Fucks Jack Bailey in ‘A Brat & A Gentleman’ appeared first on WAYBIG.

Discover Lucas Entertainment's newest star, Jack Bailey, receiving a powerful pounding from the well-endowed top, Dan Saxon. In his debut interview for “Bareback Auditions 24: Thrusted And Pumped,” Jack introduces himself to the fans, baring not only his smooth little body but also his passion for intense pleasure.

The post Lucas Entertainment: Jack Bailey Bottoms For Dan Saxon in ‘Bareback Auditions 24: Thrusted And Pumped, Scene 3’ appeared first on WAYBIG.

In this passionate scene from ColbyKnox, Jack Bailey catches the attention of Mickey Knox while lost in his music, wearing only a jockstrap on a bed. Mickey can't resist and enters the room, immediately engaging in some steamy action.

The post ColbyKnox: Jack Bailey Bottoms For Mickey Knox in ‘Head in the Clouds’ appeared first on WAYBIG.

Experience the return of Jack Bailey to the ColbyKnox house in this week's update. Join him as he explores the world of yoga with Colby Chambers by the pool. Witness the temptation, pleasure, and intense connection as they indulge in passionate acts of obedience. Get ready for a journey of pleasure where yoga and desire intertwine.

The post ColbyKnox: Colby Chambers Fucks Jack Bailey in ‘Yoga Fun: Namaste and Play’ appeared first on WAYBIG.

Lucas Entertainment: Babylon Prince, Brian Bonds, Bruno Galvez, Derek Kage, Gustavo Cruz, Harold Lopez, Jack Bailey, Kosta Viking and Santos in 'Lucas Men Extravaganza: Orgy'.

The post Lucas Entertainment: Babylon Prince, Brian Bonds, Bruno Galvez, Derek Kage, Gustavo Cruz, Harold Lopez, Jack Bailey, Kosta Viking and Santos in ‘Lucas Men Extravaganza: Orgy’ appeared first on WAYBIG.

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.

The post CockyBoys: Jacob Acosta Fucks Jack Bailey at ‘Camp Cockyboys’ appeared first on WAYBIG.

Raunchy Bastards: There's something very special about both Jack Bailey and Masyn Thorne. Sure, I know that they have done a good amount of porn, even well before I met them.

The post Raunchy Bastards #365: Clay, Jack Bailey and Masyn Thorne in ‘Sluts On Parade’ appeared first on WAYBIG.

When residents don't take their time in the Boys Halfway House seriously, it can lead to failed outcomes. Take this reject (Jack Bailey), for example: He had been a problem in the beginning, but had turned his act around.

The post Boys Halfway House: Jack Bailey Bottoms For Clay in ‘Turn For The Worse’ appeared first on WAYBIG.

Raunchy Bastards: Jack Bailey, of course, is one of my favorite Raunchy Bastards, and newbie Liam Addison is a perfect addition. Like Jack, Liam is a not-so-secret cock slut, and he loves fucking, getting fucked, sucking dick, getting sucked.

The post Raunchy Bastards #361: Clay Fucks Jack Bailey and Liam Addison in ‘Full-On Nympho Maniacs’ appeared first on WAYBIG.

NextDoorStudios: Michael Roman wants to help Jack Bailey celebrate finishing a tough semester at college, so he plans a nice dinner just the two of them.

The post NextDoorTABOO: Jack Bailey Bottoms Michael Roman in ‘Date with Step-Dad’ appeared first on WAYBIG.

TwinkLoads: Flame-haired, twink boy, Jack Bailey has made a beeline for the heavily-tattooed DILF, Romeo Davis, yet again. These two horny guys simply can’t stop hooking up, and they make a little bit of magic every time they meet!

The post Twink Loads: Romeo Davis Bottoms For Jack Bailey: Encounter 3 appeared first on WAYBIG.

Sketchy Sex: Some jealous assholes call us sloppy and call our cumdump house a "slop pad". Lol, little do they know their guys are always stopping in to dump a few loads. Guess we can't blame 'em for calling us sloppy sluts, probably hear us sucking dick from down the block. We know what these guys are missing and love giving them the kind of nut they need to bust. 

The post Sketchy Sex: MOUTH BREEDER [feat Grey Gold, Jack Bailey, Langley Gold and More…] appeared first on WAYBIG.

Sketchy Sex: DUMB DUMPSTER [feat Ethan Steel, Grey Gold, Jack Bailey, Langley Gold and More.

The post Sketchy Sex: DUMB DUMPSTER [feat Ethan Steel, Grey Gold, Jack Bailey, Langley Gold and More…] appeared first on WAYBIG.

Sketchy Sex: Gotta love when a night just comes together. Instead of a steady stream of tops ready to unload, they all showed up at once.

The post Sketchy Sex: Dick & Dash [feat Ethan Steel, Grey Gold, Jack Bailey, Langley Gold and Tattoo Guy] appeared first on WAYBIG.

DRIPPING DUMPS [feat. Langley Gold, Grey Gold, Jack Bailey and More...] at SketchySex.

The post Sketchy Sex: DRIPPING DUMPS [feat. Langley Gold, Grey Gold, Jack Bailey and More…] appeared first on WAYBIG.

Sketchy Sex: Langley Gold, Jack Bailey, Grey Gold, Ethan Steel and More in "Mouth Around".

The post Sketchy Sex: Langley Gold, Jack Bailey, Grey Gold, Ethan Steel and More… in “Mouth Around” appeared first on WAYBIG.

Twinkology 101 Class is in session! Carter DelRey, Jack Bailey, and Trevor Harris are hot for their teacher, Dakota Payne, as he instructs them on how to be the best twinks they can be! Enjoy this scholastic sexcapade written by our very own Dakota Payne!

The post NextDoorTWINK: Dakota Payne, Jack Bailey, Carter DelRey and Trevor Harris in ‘Twinkology 101’ appeared first on WAYBIG.

Raunchy Bastards: Matt Moss and Jack Bailey meet again, and this time these two horny bastards rim, suck, and fuck their way through a hot romp!

The post Raunchy Bastards #297: Matt Moss Fucks Jack Bailey in ‘Two Horny Bastards’ appeared first on WAYBIG.

New Talent December continues with Jack Bailey making his CockyBoys debut with Kane Fox!

The post CockyBoys: Jack Bailey Makes His Racy Debut With Kane Fox appeared first on WAYBIG.