https://www.transhero.com/models/jack-bailey/ Tue 14 Apr 2026 19:16:58 +0200 https://www.transhero.com/videos/442897/next-door-taboo-college-twink-dreams-come-true-muscle-hunk-stepdilf-rails-hi/
Use code ASGDEAL for a FREE WEEK of NEXT DOOR TABOO! Featuring Jack Bailey, Michael Roman ]]> Fri 10 Apr 2026 19:58:39 +0200 https://www.transhero.com/videos/442897/next-door-taboo-college-twink-dreams-come-true-muscle-hunk-stepdilf-rails-hi/ https://www.transhero.com/videos/335945/dale-savage-jack-bailey-scott-finn-s-amazing-bareback-threesome/
After Toby (Jack Bailey) loses his virginity to his dad's best friend Carl (Dale Savage), Toby wants something serious with the older man. Unfortunately for Toby, Carl wanted a virgin, and now that Toby isn't one, Carl is not interested. That is, until Toby's father calls Carl to tell him that Toby and his best friend Will (Scott Finn) will be in Carl's town and they need a place to stay. Hearing that Will is coming with Carl gives Carl a bright idea. He opens his home to Toby and Will, and Toby will do whatever it takes to get back in Carl's good graces. ]]> Sat 21 Mar 2026 19:03:25 +0200 https://www.transhero.com/videos/335945/dale-savage-jack-bailey-scott-finn-s-amazing-bareback-threesome/ https://www.transhero.com/videos/331178/blacks-on-boys-jack-bailey-deepdicc-ray-diesel/
Jack has been wanting to get back to the gym but hates the way all the guys stare at him when he goes there. So instead Jack calls up his big crush Ray to see if he can come over and use his home gym. Ray is quick to invite the tasty dude over to let him do whatever he wants. Jack shows up with Ray and Deep already working up a sweat on the machines so he gets right to the weights. Ray and Deep are quick to encourage young Jack and once Jack bends over the bench Deep moves right in to help him with his form. Deep let's his hands wander to Jack's delight and once he pulls down Jack's little red shorts it was on. Ray, not one to miss a beat turns off his treadmill and pulls out his fat cock for Jack to focus on too. Once dicks are in both his holes Jack's true slutty nature comes right out. And with two fat creamy loads on his face Jack promises to come back for lot's of workouts. ]]> Tue 17 Mar 2026 12:46:19 +0200 https://www.transhero.com/videos/331178/blacks-on-boys-jack-bailey-deepdicc-ray-diesel/ https://www.transhero.com/videos/127631/jack-bailey-encounter-2-jax-thirio-bottoms/
When we put sweet-faced twink top Jack Bailey in a room with masculine bottom Jax Thirio, it was as if the cameras disappeared. ]]> Sun 15 Mar 2026 14:51:01 +0200 https://www.transhero.com/videos/127631/jack-bailey-encounter-2-jax-thirio-bottoms/ https://www.transhero.com/videos/184795/meet-sexy-young-twink-jack-jack-bailey/
Jack is an adorable young man who's more than ready to share everything with us. ]]> Sun 15 Mar 2026 12:35:57 +0200 https://www.transhero.com/videos/184795/meet-sexy-young-twink-jack-jack-bailey/ https://www.transhero.com/videos/144022/blond-twink-jack-bailey-seduced-and-fucked-by-greg-mckeon/
Young blond twink Jack Bailey is seduced by athletic yet dominant Greg McKeon who wanted to breed him the moment he saw him! ]]> Wed 11 Mar 2026 09:27:29 +0200 https://www.transhero.com/videos/144022/blond-twink-jack-bailey-seduced-and-fucked-by-greg-mckeon/ https://www.transhero.com/videos/302181/bored-stepbros/
Now and then, cute Alex Meyer and his stepbrother Jack Bailey get too bored for their own good. To liven things up, they please each other's tender cocks, sucking and fucking until they're drenched in each other's sticky semen. ]]> Mon 09 Mar 2026 18:04:03 +0200 https://www.transhero.com/videos/302181/bored-stepbros/ https://www.transhero.com/videos/327894/who-knew-these-guys-will-gay-around-as-much/
Since Jack Bailey is pissed at his 'stepfather with benefits' Roman Todd, he's off to see his favorite service top, Johnny Ford. Jack goes to Johnny when he wants his back broken and Johnny is happy to give the cutie his cock. ]]> Fri 06 Mar 2026 22:02:55 +0200 https://www.transhero.com/videos/327894/who-knew-these-guys-will-gay-around-as-much/ https://www.transhero.com/videos/261911/jock-stepuncle-dale-savage-pounds-twinks-jack-bailey-and-trevor-harris-raw-asses/
Jack Bailey and Trevor Harris thirst for *** leads them to c**e on Dale Savage’s big cock. ]]> Fri 06 Mar 2026 10:29:23 +0200 https://www.transhero.com/videos/261911/jock-stepuncle-dale-savage-pounds-twinks-jack-bailey-and-trevor-harris-raw-asses/ https://www.transhero.com/videos/166177/shoes-and-cock-shined-by-jack-bailey-feat-chris-damned/
As Chris Damned prepares for his big day, he makes one last stop to get his shoes shined by Jack Bailey. As Jack is buffing Chris' shoes, he can't help but eye the increasing bulge growing in Chris' pants. Without a word, Jack glances up at Chris and reaches for the cock in his face. Chris nods and unzips his trousers to reveal his uncut cock for Jack. He quickly switches from polishing the groom's shoes to polishing Chris' meat, while Chris works on shedding the rest of his suit. After shining his cock, Jack bends over to let Chris shine his hole with a deep rimming. Now that he's lubed up and ready to go, Chris bends Jack over a chair and works his pole deep into Jack's ass bareback. Since it's all about servicing the customer, Jack lays back and lets Chris pummel his hole until Chris shoots a thick load all over Jack's torso and sticks his cock back in the young, handsome stud. Covered in Chris' cum and stuffed with his cock, Jack rubs his cock out until his own shiny load is pooled on his stomach. ]]> Fri 06 Mar 2026 09:21:47 +0200 https://www.transhero.com/videos/166177/shoes-and-cock-shined-by-jack-bailey-feat-chris-damned/ https://www.transhero.com/videos/204702/cliff-jensen-and-jack-bailey-have-hardcore-anal-sex/
Justin O'Neal's family is sick of his spoiled and entitled behavior. They send Justin (Jack Bailey) to a remediation ranch to curb his destructive ways. At the ranch, Justin learns how to be a cowboy and a gentleman from ranch hand Sam Gillis (Cliff Jensen). Sam is sure he's gotten through to Justin, but old (bad) habits can't be kicked so easily. ]]> Thu 05 Mar 2026 23:54:07 +0200 https://www.transhero.com/videos/204702/cliff-jensen-and-jack-bailey-have-hardcore-anal-sex/ https://www.transhero.com/videos/220159/the-owner-can-t-resist-how-sexually-irresistable-this-house-boy/
Chris Damned and Jack Bailey explores the power dynamics of an owner and house boy. They look so good together in their sexual tension. ]]> Thu 05 Mar 2026 18:34:01 +0200 https://www.transhero.com/videos/220159/the-owner-can-t-resist-how-sexually-irresistable-this-house-boy/