Search Results for Jack Bailey in Videos
Videos where Jack Bailey is featured in the scene. — Total Matches: 58.
 | A Couch Fuck Next Door Studios | |
| Jack Bailey and Jesse Bolton don't waste any time and barely introduce themselves before getting down with the action. In a passionate homemade scene they fuck each other in exciting positions. Featuring Jesse Bolton, Jack Bailey. Original release date: January 2nd, 2021. | View Video | |
 | Good Game Bro Himeros TV | |
| This film is about bringing tenderness and affection into relationship to men's perception of power through balancing athletic prowess and "bro culture" with nurturance and attuning to each other's sensual needs. "Good Game, Bro" is a fantasy of what sports players long for from their teammates. Though these models look the part of athletes, we also see them open up t.... | View Video | |
 | Meet Jack Colby Knox | |
| In this week's new gay porn release from Colby Knox, we are thrilled to introduce Jack Bailey! Jack may have an innocent look about him, but he is a total freak in the sheets! Mickey Knox has really been looking forward to working with Jack, and the lusty excitement is written all over that smirking face of his from the very beginning of the scene. The two boys get wa.... | View Video | |
 | Rough Fuck Himeros TV | |
| BDSM is a power dynamic. By definition, the dominant exercises control over someone who submits to it. The sub strives to please his dom. Just as the dom derives pleasure from what he does to the sub, the sub takes pleasure from serving the dom -- a concept illustrated by this video. Featuring Chase Steele, Jack Bailey. Original release date: January 18th, 2021. | View Video | |
 | Colby Fucks Jack Colby Knox | |
| Colby Chambers gets to quench a months long thirst by fucking the brakes off of Jack Bailey's juicy ass! Jack may have a charming innocence about his look, but this boy is hardcore as fuck! He loves to have his hole used and wrecked by horny hung studs. Colby Chambers never disappoints to rise to just this occasion, giving us a very high tempo, passionate fuckathon fr.... | View Video | |
 | Jax Pounds Jack Next Door Studios | |
| Jax Thirio gives it to Jack Bailey good and hard and Jack loves it. These two guys get down and dirty in this homemade masterpiece. Featuring Jax Thirio, Jack Bailey. Original release date: February 20th, 2021. | View Video | |
 | Stepdad with Benefits Next Door Taboo | |
| 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 .... | View Video | |
 | Lake Need Scene 1 Naked Sword | |
| Johnny rounds up all his best buds and heads to 'Lake Need' for a boy's trip, but don't let the serene waters fool you, there's nonstop action on deck in this sun-drenched adventure. Critically acclaimed director Edward James captains a houseboat on 'Lake Need' filled with a cast of horny studs getting off with their best friends. Produced by: Naked Sword. Featuring J.... | View Video | |
 | Lake Need Scene 2 Naked Sword | |
| Johnny rounds up all his best buds and heads to 'Lake Need' for a boy's trip, but don't let the serene waters fool you, there's nonstop action on deck in this sun-drenched adventure. Critically acclaimed director Edward James captains a houseboat on 'Lake Need' filled with a cast of horny studs getting off with their best friends. Produced by: Naked Sword. Featuring B.... | View Video | |
 | Service Top Next Door Taboo | |
| 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. Featuring Johnny Ford, Jack Bailey. From the web series: Secret Sexcapades. Original release date: April 26th, 2021. | View Video | |
 | Lake Need Gay Empire | |
| Johnny Rapid rounds up all his best buds and heads to Lake Need for a boy's trip. But don't let the serene waters fool you - there's nonstop action on deck in this sun-drenched adventure. Acclaimed director Edward James captains a houseboat on Lake Need filled with a cast of horny studs getting off with their best friends. So, come on! Grab your bags and join the boys.... | View Video | |
 | Am I Qualified Next Door Twink | |
| It's Jack Bailey's first day at the new job his stepdad David Skylar got Jack at his company. Jack knows he's underqualified for the job, but it doesn't seem to matter to David, who got him the job because he wanted to be around him more. He knows exactly what Jack is qualified to do...and damn is he good at it! Featuring David Skylar, Jack Bailey. Original release da.... | View Video | |
 | My Stepbros Dildo Next Door Taboo | |
| 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. Featuring Justin Matthews, Jack Bailey. Original release date: August 27th, 2021. | View Video | |
 | A Virgin No More Disruptive Films | |
| Toby (Jack Bailey) is staying at his 'Uncle' Carl's apartment after a concert. As Toby's dad's best friend, Carl (Dale Savage) has always been in his life and has seen him grow up. He trusts Carl, and is looking forward to spending quality time with him. Carl is anticipating Toby's sleepover as well, but for a different reason. Now that Toby's eighteen, Carl's intenti.... | View Video | |
 | Shoe Shine Hot House | |
| 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 swit.... | View Video | |
 | Inseam Hot House | |
| Subtle glances, inviting looks, suggestive gestures and provocative signals define the art of sensual gay seduction in 'Inseam'. While preparing for his wedding, Chris Damned assembles the hottest wedding party and assistants, who help him prepare for the festivities by partaking in the silent persuasion that leads to the most intense action. Director Trenton Ducati e.... | View Video | |
 | Washboard Worship Next Door Twink | |
| Jack Bailey and Trevor Harris are thirsty and the only thing that can quench their thirst is getting a piece of their hot roommate Damien White. Featuring Damien White, Jack Bailey, Trevor Harris. Original release date: December 25th, 2021. | View Video | |
 | Twinkology 101 Next Door Twink | |
| 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! Featuring Dakota Payne, Jack Bailey, Carter DelRey, Trevor Harris. Original release date: February 4th, 2022. | View Video | |
 | Be Disruptive Films | |
| Years after graduating, Sam Romero (Jack Bailey) gets in touch with his former English teacher, Mr. Howard Dennison (Greg McKeon). After reconnecting on social media, they decide to meet up. Sam is grateful to Howard for allowing him to be himself with him and understand that it's okay to be who you are without apologies. Their affection and tenderness turns sexual as.... | View Video | |
 | Lake Need Scene 1 at Naked Sword | |
| As the Johnny Rapid and his boys load onto a houseboat and head out on the water, Jack Bailey finds Johnny Rapid on the top deck and asks, “so when are you gonna fuck me?” Johnny smirks and pulls his shorts down to reveal a rock-hard dick that Jack instantly goes down on. With spit dripping from his chin, Jack takes off his shorts so Johnny can dip his cock into J.... | View Video | |
 | Lake Need Scene 2 at Naked Sword | |
| While their buddies are out fishing, Jack Bailey and Blaine Porter sneak off to Blaine's room to get to know each other a little better. As soon as they get in the bed, Blaine's shorts come off and Jack turns into a cock connoisseur. After gobbling down Blaine's thick meat, Jack gets the favored returned with Blaine deep-throating Jack's pole. Now that both studs are .... | View Video | |
 | Lake Need AEBN | |
| Johnny Rapid rounds up all his best buds and heads to 'Lake Need' for a boy's trip, but don't let the serene waters fool you, there's nonstop action on deck in this sun-drenched adventure. Critically acclaimed director Edward James captains a houseboat on 'Lake Need' filled with a cast of horny studs getting off with their best friends. On their first day on the boat,.... | View Video | |
 | Sub Jack Top Fan Vids | |
| Description not available. Featuring Jack Bailey, Owen Hawk, David Eck. | View Video | |
 | Twink Trio Top Fan Vids | |
| I walk in and find this perfect pair of twinks, Jack Bailey and Alex Meyers, making out in their shorts. One dark-haired, one light-haired, and both sexy as fuck. Now, which one is gonna suck my cock!? How about both! Jack and Alex take turns deep-throating me before I lube up Jack before pounding him. Featuring Johnny Rapid, Jack Bailey, Alex Meyers. | View Video | |
 | Jack Attack Top Fan Vids | |
| Description not available. Featuring Jack Bailey, Ryan Carter. | View Video | |
 | Pretty Young Thang Johnny Rapid | |
| Johnny Rapid walks in and find a perfect pair of twinks, blonde Jack Bailey and black-haired Alex Meyers, kissing in their underwear without him. 'Which one of you two sluts is gonna suck my dick?' he asks, and they give his favorite answer: both! Jack and Alex suck his cock and take turns deep-throating Johnny before he lubes up Jack's hole. This pretty 22-year-old w.... | View Video | |
 | The Offering Disruptive Films | |
| 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 .... | View Video | |
 | Date with Step Dad Next Door Taboo | |
| 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. But, Jack wants to celebrate through other means. What could Jack possibly want? Featuring Jack Bailey, Michael Roman. Original release date: June 17th, 2022. | View Video | |
 | Fucking Jack Raunchy Bastards | |
| Masyn Thorne has been doing porn for a while now, and after seeing him in action, I'm not surprised. He's a great top. It was awesome getting to see him pound down my favorite bottom, Jack Bailey. When I first met him, I asked him if he could cum just from fucking, and he told me that he usually uses a video on his phone to get close. I laughed and told him that this .... | View Video | |
 | Nymphos 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. You name it! So, I knew before we began that I would have a lot of fun with these two. Turns out, we all had a blast as both Jack and Liam got fu.... | View Video | |
 | For the Worse Boys Halfway House | |
| When residents don't take their time in the House seriously, it can lead to failed outcomes. Take this reject, for example: He had been a problem in the beginning, but had turned his act around. Then, suddenly, he stopped going to his meetings. Well, this type of situation is not good, beccause it usually means that more trouble is on the way. So, of course out House .... | View Video | |
 | Get Off Raunchy Bastards | |
| Jack Bailey just might be the most slutty slut ever. He is different from a lot of the others, though. He's downright cheerful when you hook up with him. I love that. I love guys who smile when they are getting dicked down. I love it when the whore's facial expression lets you know you hit the right spot. And I love it when a guy is so damn proud of his asshole - how .... | View Video | |
 | Out of My Way Disruptive Films | |
| Description not available. Featuring Jack Bailey, Killian Knox. Original release date: August 26th, 2022. | View Video | |
 | Best of Justin Next Door Taboo | |
| Please enjoy this hot compilation of Justin Matthews! Featuring Justin Matthews, Brandon Anderson, Ricky Ridges, Trevor Ridge, Johnny Hills, Jim Fit, Dacotah Red, Jack Bailey, Dakotah Payne, Carter Woods, Alex Tanner. Original release date: September 16th, 2022. | View Video | |
 | Virgin Stepbrother Next Door Taboo | |
| Jack Bailey is catching up with stepbrother Jordan Starr when he finds out that Jordan is still a virgin. But when he offers to help Jordan lose his virginity, will Jordan take the bait? Or did Jack just make things more awkward? Featuring Jack Bailey, Jordan Starr. Original release date: October 7th, 2022. | View Video | |
 | Lake Need Naked Sword | |
| Description not available. Featuring Jack Bailey, Cyrus Stark, Jesse Bolton, Jax Thirio, Blaine Porter, Nic Sahara, Johnny Rapid. From the film: Lake Need. | View Video | |
 | Retaliation Disruptive Films | |
| Toby (Jack Bailey) has had enough of Uncle Carl's (Dale Savage) bullshit. He consults his computer whiz roommate (Trevor Harris) to hack into Uncle Carl's laptop and plant some incriminating items on the hard drive. When Toby and the roommate seduce Uncle Carl, Carl feels he's won the lottery. Little does he know they are fucking up his life by planting evidence and s.... | View Video | |
 | Best of Roman Next Door Taboo | |
| Please enjoy this compilation of Roman Todd's best moments! Featuring Roman Todd, Carter DelRay, Dale Savage, Trevor Harris, Jack Bailey, Trent Summers, Lance Ford, Greyson Lane, Elye Black, Princeton Price. Original release date: December 9th, 2022. | View Video | |
 | Split Me Open Scene 3 AEBN | |
| This collection of Cocky Boys scenes will have bottoms all over screaming "Split Me Open". Produced by: Cocky Boys. Featuring Jack Bailey, Leo Louis. From the film: Split Me Open. | View Video | |
 | Lake Need Gay Hot Movies | |
| Johnny Rapid rounds up all his best buds and heads to Lake Need for a boy's trip. But don't let the serene waters fool you - there's nonstop action on deck in this sun-drenched adventure. Acclaimed director Edward James captains a houseboat on Lake Need filled with a cast of horny studs getting off with their best friends. So, come on! Grab your bags and join the boys.... | View Video | |
 | Extravaganza Part 1 Lucas Entertainment | |
| Watch the first part (of two) of this gay orgy starring nine of the hottest gay porn models among the Lucas Men! You will not want to miss this, because the Lucas Men are about to have an unforgettable fuck party, and you have an all-access invite to check out the dick-sucking and hole-slamming action! Original title: Gay Porn Orgy Part 1. Featuring Kosta Viking, Baby.... | View Video | |
 | Extravaganza Part 2 Lucas Entertainment | |
| Watch the second part (of two) of this gay orgy starring nine of the sexiest and most cock-crazed gay porn models out of all the Lucas Men! You will not want to miss out, because the Lucas Men are about to have an unforgettable fuck party, and you have an all-access invite to check out the dick-sucking and hole-slamming gay action! Original title: Gay Porn Orgy Part 2.... | View Video | |
 | A Cowboy Disruptive Films | |
| Justin ONeal'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. Featuring Jack Bailey.... | View Video | |
 | Bailey Bottoms Lucas Entertainment | |
| 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 lit.... | View Video | |
 | Twink Jack Boy Crush | |
| Jack is an adorable young man who's more than ready to share everything with us. Original title: Meet Sexy Young Twink Jack. Featuring Jack Bailey. Original release date: January 15th, 2021. | View Video | |
 | At the Park from Men POV | |
| Pretty boy, Jack, gets horny for cock with playing badminton at the park. Original title: At the Park with Jack Bailey. Featuring Darron Bluu, Jack Bailey. Original release date: February 3rd, 2023. | View Video | |
 | Morning Pleasure Bare Twinks | |
| The first thing Jack and Carter need to start the day is some and hard young cock. Original title: Bare Boys Morning Pleasure. Featuring Jack Bailey, Carter Ford. Original release date: January 29th, 2021. | View Video | |
 | Dr Tapes 4 Scene 3 AEBN | |
| There are some doctors that specialize in the care of making sure boys become healthy men and their treatment comes in many forms. Doctor Tapes is an archive of these thorough exams. From the collection of semen samples to full rectal exams, these checkups have been recorded and are presented here to assist you in your own health and wellness! Full title: Doctor Tapes.... | View Video | |
 | Brat and Gentlemen Disruptive Films | |
| 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 Just.... | View Video | |
 | Cabin Fever Scene 6 Naked Sword | |
| Eight vignettes filmed in the forests of Big Bear and a stellar cast invite you to connect your sexuality to your partner's and the world around you. Produced by: Himeros TV. Featuring Nico Nova, Jack Bailey. From the film: Cabin Fever. | View Video | |
 | Namaste Colby Knox | |
| He's back! Jack Bailey has returned to the Colby Knox house. In this week's update, the sexy stud is learning about yoga from Colby Chambers. They are outside, by the pool, in the Sukhasana pose. The pair, both in black underwear, get on all fours. "Really arch your back," Colby suggests. He can't help himself. Seeing Jack's booty in that position causes him to pull J.... | View Video | |
 | Pair of Jacks Colby Knox | |
| This Colby Knox webcam video has a pair of Jacks: Jack Bailey and Jack Valor. They are on the studio's sofa with Colby Chambers. Jack B. slurps on Colby's cock. As for Jack V., his rod is attended to by Colby. Colby has a question for Jack B. "Want him to fuck you?” Jack B. likes this proposal. As the three lads get situated, Mickey Knox comes into the room. He adju.... | View Video | |
 | In the Clouds Colby Knox | |
| 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 Colby Knox 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 f.... | View Video | |
 | By Night Lucas Entertainment | |
| 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.... | View Video | |
 | Back in Town Gay Empire | |
| Nathaniel Arnold (Andre Donovan) is Back in Town for his father's funeral. The place is steeped in memories for him, and many of those memories include Tony Lyons (Adam Ramzi). The two had a clandestine relationship in high school. Though time has passed, there's still a connection between Nathaniel and Tony. They explore the relationship while exploring themselves. Y.... | View Video | |
 | The Recruit Gay Empire | |
| Tegan Young (Jkab Ethan Dale) is an army recruiter who recruits Colin Dillard (Trevor Harris) to enlist. Colin is a homeless, gay, eighteen-year-old who needs a place to stay. Tegan brings Colin back to his house where he lives with a fellow soldier, Rudy Vaughn (Roman Todd). Rudy is unimpressed with Colin and hates how sensitive Colin is when he has never faced the t.... | View Video | |
 | The Code Gay Empire | |
| When college morality officer George Meadows (Hans Berlin) catches wind that student Christian Grogan (Isaac Parker) has a fansite account where he sells naked pictures of himself to the masses, he knows he needs to crack down on the co-ed for breaking the morality code, also known as The Code (Disruptive Films). Twink Jack Bailey seduces his big, dicked stepdaddy, Ki.... | View Video | |
 | Not That Straight Next Door Studios | |
| Class in session. Carter Delrey, Jack Bailey and Trevor Harris are hot for their teache Dakota Payne. As he instructs them on how to be the best twinks they can be. Quentin is finding it hard to work on his career in acting due to the lack of respect his straight rooommate Jimmy shows. Featuring Carter DelRey, Dakota Payne, Dean Phoenix, Jack Bailey, Jimmy Clay, Mark .... | View Video | |
