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.
Jack Bailey & Jacob Acosta
New Release
| 20 minutes
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....]
Jack Bailey & Lane Colten
New Release
| 22 minutes
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 chokes 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....]
Jack Bailey & Sean Xavier
New Release
| 20 minutes
Featuring: Jack Bailey & Sean Xavier
Description: Award-winning star Sean Xavier makes his CockyBoys debut giving Jack Bailey some unforgettable wake-up 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 [more....]
Jack Bailey & Leo Louis
New Release
| 24 minutes
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....]
Jack Bailey & Kane Fox
New Release
| 32 minutes
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....]
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
Cookies must be enabled to enjoy the full features of this website. Learn more about cookies and how to enable them by clicking here.
Be proud!
You are not a type. You are you.
“Cocky” does not mean rude.
Gay sex is not shameful. It is a blessing like a fine wine, a great meal, or a roller coaster ride. It is part of life and should be enjoyed.
Be safe. Be smart in all that you do. When in doubt, use the head holding up your ears!
Negativity only invites and creates more negativity.
Mutual respect is the path to true power. Power = pride. Pride = loving yourself. Love yourself and you can love another.
Gay is good.
CockyBoys are proud, confident men. At times funny, goofy, sometimes crazy, and shy.
They have dark days along with good. They like being admired. They do not succumb to cowardice. They love and want to be loved.
I am a CockyBoy!
I am a CockyBoy!
Please check your high horse at the door.
There is nothing wrong with being a “porn star.” It may not be your choice. Choice is freedom. So choose.
When having a bad day… stop. Think of five things you are grateful for….feel better?
Oscar Wilde said it best – “Humanity takes itself too seriously. It is the world’s original sin. If the caveman had known how to laugh, history would have been different.”
Love Always & Be Nice,
Jake Jaxson
There is something about the CockyBoys aesthetic that gets porn wheels turning—an ironic touch that’s light enough not to compromise the simple pleasures of whacking off.
— New York Magazine
The Walt Whitman of gay porn.
Jake Jaxson wants to revolutionize porn with an erotic documentary inspired by great poets and celebrating life.
In five short years, Jake Jaxson’s particular brand of arthouse erotica has propelled CockyBoys to the top of its industry.
— The Village VoiceCockyBoys.com is the most awarded gay studio, offering you unrivaled premium content with unlimited streaming as well as limited downloads. 100% Secure and Privacy Guaranteed!
Please read and comply with the following conditions before you continue: This website contains information, links, images and videos of sexually explicit material.If you are under the age of 21, if such material offends you or if it's illegal to view such material in your community please do not continue. Here is an excellent website to find something more to your tastes.Please read and comply with the following conditions before you continue:I am at least 21 years of age.The sexually explicit material I am viewing is for my own personal use and I will not expose minors to the material. I desire to receive/view sexually explicit material. I believe that as an adult it is my inalienable right to receive/view sexually explicit material. I believe that sexual acts between consenting adults are neither offensive nor obscene. The viewing, reading and downloading of sexually explicit materials does not violate the standards of my community, town, city, state or country. I am solely responsible for any false disclosures or legal ramifications of viewing, reading or downloading any material in this site. Furthermore this website nor its affiliates will be held responsible for any legal ramifications arising from fraudulent entry into or use of this website.
Enter CockyBoys