Jack Bailey

Chock-Full of Jocks

Posted by

Videosxgays

Gay.xtapes

Gaycock4u

FXGGXT

Abyss

Photos

Chock-Full of Jocks - Amone Bane, Dereck Defendi, Jack Bailey, Michael Seraph, Tony Genius & Trent Marx

Synopsis

Jack Bailey, the last student to leave the classroom, grabs his backpack and is about to head out the door when one of the school’s football players, Tony Genius, comes in and asks Jack for tutoring. Tony says that his grades have reached a point where if he doesn’t get a B+ he’ll be held back a year, and there’s NO WAY that can happen.

While Jack is enthralled by Tony’s muscles, he explains that, unfortunately, at the moment he’s too busy. It’s nearing final exam time, so he’s had more tutoring requests than usual, and has to take them first-come-first-served. Tony, having caught Jack looking at his muscles and knowing that he’s gay, decides to try and use this to his advantage. He tries stretching to show off his abs while putting a hand on Jack’s shoulder, desperately adding that he’ll let Jack suck his dick if he helps out.

This is a dream come true for Jack, who milks the opportunity by saying that sounds good but he’s VERY busy, so he wants more than just sucking dick…

Soon enough, they are passionately fucking in the classroom but Jack’s shocked when Tony’s jock friends show up unannounced, also wanting help. Once Tony invites them to join, Jack’s over the moon! It looks like Jack’s in for a loooong weekend of tutoring.

Chock-Full of Jocks – Amone Bane, Dereck Defendi, Jack Bailey, Michael Seraph, Tony Genius & Trent Marx

Adult Time

Amone Bane
Amone Bane

Dereck Defendi
Dereck Defendi

Jack Bailey
Jack Bailey

Michael Seraph
Michael Seraph

Tony Genius
Tony Genius

Trent Marx
Trent Marx

Jack Bailey & Kane Fox

Posted by

Jack Bailey & Kane Fox

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 cock—which he does.

While feeding Jack his cock and gagging him, Kane also fingers the slobbering bottom to prep him for round two fucking. Finally, Kane gets Jack on all fours to pound him deep and put him in another state of sextasy. Still, Jack can’t get enough and asks Kane to fuck him on his back so he can watch him dump a load in him.

Kane soon slides into Jack on his back and sucks his cock & balls before going all in to fuck him every which way. Finally, Kane fucks a huge load out of Jack and keeps pounding him until he blows his load inside Jack and all over his hole. After Jack pushes out some of that load, Kane fucks it back into him. In the end they couldn’t be happier. If being called “Sir” wasn’t enough for Kane, Jack makes it clear he owns his hole now.

After the Sex – Secret Sexcapades 1

Posted by

After the Sex – Secret Sexcapades 1 – Stepdad With Benefits – Jack Bailey & Roman Todd

Jack Bailey has it bad for Roman Todd, which is…pretty bad considering Roman is Jack’s stepfather. Jack wants more than a ‘Stepdad With Benefits,’ which is all Roman is willing to give. After a passionate fuck, Jack lets Roman know how annoyed he is, and the friction between them only intensifies later that day when Roman attempts to act like nothing happened while Jack is playing video games with his best friend, Trevor Harris. Trevor ignores the tension as best he can, but with emotions boiling over, Jack leaves the house in a huff and Roman makes a swift exit to work off his aggravation in the gym. Arriving home amid the unrest, Jack’s dad, Jax Thirio, wonders what’s going on, and why Trevor was left alone on the couch. Will Jax be a good host to his visitor? Find out in Scene Two!

My Stepbro’s Dildo

Posted by

Boyfriendtv

Abyss

Photos

Synopsis

Jack Bailey is a naughty little stepbrother. When he finds his big stepbrother Justin Matthews’s dildo, he decides to give it a whirl. Justin finds Jack playing with the dildo and inserts the real thing.

My Stepbro’s Dildo – Justin Matthews & Jack Bailey

Next door Studios

Jack Bailey
Jack Bailey

Justin Matthews
Jack Bailey

I’ll Do Anything Else

Posted by

I’ll Do Anything Else – Jack Bailey & Jesse Bolton

When sexy stepbrothers Jesse Bolton and Jack Bailey start a gardening business together, they get into an argument over who has to do what while getting dirty in the backyard. Jesse plunges his delicious boner into his cute stepbro’s mouth and teaches him who’s boss before they get into some even nastier bareback action.