Search Results for Jack Bailey in Videos
Videos where Jack Bailey is featured in the scene. — Total Matches: 94.
 | 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 | |
 | 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 | |
 | Teaching Tape 1 Carnal Plus | |
| From the outside, Jack's household seems perfectly ordinary. Close-knit, loving family with a handsome, all-star athlete boy. And in many ways, this is true. But what people might not assume is just how close-knit Jack is to the men in the family... particularly his grandpa, Lance. Grandpa Lance has always taken a special interest in Jack. The young man's bright, sunn.... | View Video | |
 | Teaching Tape 2 Carnal Plus | |
| Jack stepped into Lance's office, seeing the handsome man behind his desk, dressed in a perfectly tailored suit and looking like a total boss. Jack blushed, trying not to embarrass himself, but all Lance could do was look at him and gush. Lance walked Jack through some simple interview etiquette things such as proper eye contact, a confident handshake, and being intim.... | View Video | |
 | Teaching Tape 3 Carnal Plus | |
| Jack was pretty gutted when he didn't get the job he'd hoped for. His grandfather had done so much to help him and he really valued that time together. As his grandfather read the letter of rejection, he felt embarrassed that such a powerful and successful man as Mr. Charger had to be part of his failure. Mr. Charger pulled Jack over to him, letting him sit on his lap.... | View Video | |
 | Teaching Tape 4 Carnal Plus | |
| Becoming a man isn't about age. It's not about a birthday or losing your virginity or getting a job. It's none of the things that boys these days are told. For me and the other buyers, manhood means one thing: fucking. Being able to bend a slave over and leaving your seed inside his hole is the most natural and powerful way to claim that title. I know my grandson, Jac.... | View Video | |
 | Tom and Jack Chapter 1 Jock Breeders | |
| Tom Bentley is a seriously sexy, pint-sized twink. He is thrilled to be able to meet up with Jack Bailey, a cute, flame-haired boy with a killer smile and a smooth, lean body. Rock hard and eager to play, the cameras turn on and the boys know exactly what to do. The guys strip naked. Tom may be small in height, but his dick is huge. He relaxes as Jack shuffles down th.... | View Video | |
 | Tom and Jack Chapter 2 Jock Breeders | |
| Jack's backside is far too big for everyday underwear to contain, especially once he chubs ups making out with pierced twink Tom. That's why the orange and yellow jockstrap Jack wears is perfect for a good fucking session. They playfully make out first, exploring each other's smooth bodies. Their hands gently explore while their tongues intertwine, sending even more p.... | View Video | |
 | Jack and Killian Chapter 1 Jock Breeders | |
| How many times can one muscle daddy cum? When DILF Killian Knox pairs up with cute horny twink, Jack Bailey, the answer is "as many times as he wants!" The two begin with a hot makeout session and it's obvious from the start that Killian is very happy to see Jack! The two explore each other's muscles and mouths. Clothes come off as each guy gets more and more into the.... | View Video | |
 | Jax and Jack Chapter 1 Jock Breeders | |
| Jack Bailey has got a thing for older, beefy-jock type of guys. Turns out his good buddy Jax Thirio is exactly Jack's type. And it just so happens that Jax really wants to fuck the living daylights out of the young, sexy dude! Jack's hottest wet dream finally cums true when Jax, the veteran, muscle-bound stud pounds and breeds this tight, eager bottom. Full title: Jax.... | View Video | |
 | Jax and Jack Chapter 2 Jock Breeders | |
| Dream twink athlete Jack Bailey invites DILF muscle stud Jax Thirio over for another round of intense fucking! Jack is a real power bottom-he deep-throats his favorite jock daddy, then climbs aboard that huge cock and rides it. Jack bounces up-and-down on Jax's dick until the DILF launches a massive load deep inside the moaning twink's bubble butt! Full title: Jax Thi.... | View Video | |
 | Jack and Romeo Jock Breeders | |
| Some guys just know their role. Romeo Davis rips his shirt off to reveal his muscular, masculine inked-up body. Just the sight of this tall, hung top lights up Jack Bailey's eyes, and reduces him to putty in the dominant top's hands. Romeo makes this ginger jock his toy, eating him out then fucking his brains out with his big cock! Full title: Romeo Davis and Jack Bai.... | View Video | |
 | Jack and Killian Chapter 2 Jock Breeders | |
| The first time that Killian Knox, a thick, bearded picture of masculinity, paired up with cute twink-next-door Jack Bailey, he pounded the daylights out of the athletic boy. After that night, Killian didn't just ask Jack back in bed-he demanded it. Full title: Jack Bailey and Killian Knox Chapter 2. Featuring Jack Bailey, Killian Knox. From the web series: Jack Bailey.... | View Video | |
 | Tom and Jack Chapter 3 Jock Breeders | |
| Gorgeous twink legends Jack Bailey and Tom Bentley are at it again! Tom is in the mood for some passionate foreplay; he unabashedly sniffs and licks Jack's smooth armpits to young Jack's pure delight. Tom slaps Jack's ass as a sign of appreciation: Jack wore the jockstrap that always makes his dick rock hard. Full title: Tom Bentley and Jack Bailey Chapter 3. Featurin.... | View Video | |
 | Jack and Killian Chapter 3 Jock Breeders | |
| Killian Knox and Jack Bailey light up the screen! Killian eats this cute boy-next-door for breakfast, lunch and dinner, and Jack is more than eager to serve it up. They go full on daddy/boy, use my ass like fleshlight, sir. This masterclass in fucking leaves Jack limp on the bed, hole gaping open, and his eyes actually rolled back in his head. If these two guys aren't.... | View Video | |
 | Jack Bailey 1 Cum Dump Sluts | |
| This gay fucking sessions starts off right with big dick tops fucking bottoms such as Eddie Patrick and Braxton Cruz stretching Jack Bailey so good it leaves his hole gaping and eager for more cum. Dylan Tides, Kyler Drayke, T.D. Graham and Ethan Sinns all have their turn in this gay cumdump gangbang. Adam Snow, Ripley and Grant Ducati all use their big cocks to make .... | View Video | |
 | Scout Jack Bailey Chapter 1 Scout Boys | |
| On joining the Scouts, cute boy Jack B immediately developed an intense crush on Scoutmaster Dietrich. For the longest time, Dietrich didn't even know the young scout's name, but one night, as they toasted marsh-mallows around a fire, the scoutmaster noticed the blond boy's stunning smile and the sparks began to fly... The next day, Dietrich suggested that Jack join h.... | View Video | |
 | Troop Time Chapter 9 Scout Boys | |
| Scoutmaster Thirio is back. It seems that a single sip of forbidden fruit has turned this well-mannered gentleman into a raging sex machine. He's heard the rumors about Cole and Jack. These two horny boys have been caught with their pants down by most of this troop's scout leaders. While the rest of the gang are trekking on the other side of the wood, Thirio encourage.... | View Video | |
 | Scout Jack Bailey Chapter 2 Scout Boys | |
| Scoutmaster Smith is a sexy silver daddy who can make a young boy weak at the knees. For some time now, he's had his eye on Jack, a handsome, hairless twink with a winning smile and a glint in his eye. He finally gets the boy on his own in a tent in the forest and seduces him speedily. Jack instantly succumbs to the scoutmaster's sexy charms, and, within seconds, is d.... | View Video | |
 | Troop Time Chapter 11 Scout Boys | |
| Scoutmaster Legrand couldn't quite believe his eyes when he went to the other side of the campsite and found two of the boys going at it hammer and tongs! Marcus and Jack had said they weren't feeling well enough to go hiking that morning and the scoutmaster had made the somewhat altruistic, last-minute decision to stay behind at base camp to keep an eye on them. Ther.... | View Video | |
 | Jack and Jax 1 Twink Loads | |
| Jax Thirio's dominant demeanor and big daddy dick have more often than not led to him taking the top bunk in the bedroom -- particularly with younger guys. But, in the latest scene from TwinkLoads, it seems all that's about to change... Sexy Jax has found himself in a hotel room with the tall, flame-haired twink, Jack Bailey. The two men kiss passionately. Jack sits o.... | View Video | |
 | Buddy Check Chapter 6 Scout Boys | |
| Alone at base camp, two cute scout boys decide to have an arm wrestle. Cole is the taller and broader of the two so unsurprisingly wins, apparently without even breaking into a sweat! Undeterred, Jack foolishly challenges his friend to an actual wrestling match. Of course, it quickly becomes apparent that Jack is a wrestling rookie and, within seconds, the taller boy .... | View Video | |
 | Hot Trio Hung Fuckers | |
| Insatiable bottom twink Jack Bailey needs huge daddy dick deep inside his twink ass ASAP, and massively hung muscle tops Adam Snow and Eddie Patrick are ready to use that doll-faced slut's hole deep! Full title: Adam Snow, Eddie Patrick and Jack Bailey. Featuring Adam Snow, Eddie Patrick, Jack Bailey. Original release date: July 18th, 2024. | View Video | |
 | Jack and Romeo 1 Twink Loads | |
| Sexy, tattooed otter, Romeo Davis, is up for a real treat when he meets the seriously hot, baby-faced twink, Jack Bailey. Jack might look like a harmless angel, but his sex drive is off the charts and he's well into this rough, masculine hunk. The feeling is, of course, mutual. Romeo wouldn't normally go for a smooth, innocent-looking boy like Jack, but there's someth.... | View Video | |
 | Troop Time Chapter 14 Scout Boys | |
| The boys returned to camp in the middle of the afternoon looking filthy and disheveled. They needed to get out of their dirty uniforms pronto and be given a lesson in hand-washing clothes! I sent them into my tent and instructed them to remove their clothes. My eyes drifted hungrily from one scout to the next and my dick started pounding in my jeans. I imagined all th.... | View Video | |
 | Troop Time Chapter 15 Scout Boys | |
| It can get quite difficult to find a few minutes of alone time when you're in the great outdoors looking after a few dozen over-excited boy scouts! There's next-to-no privacy on the camp site and always someone yelling your name or sticking their head into your tent without any kind of warning. When it all gets too much, I like to wander off into the woods for what is.... | View Video | |
 | Jack and Killian 1 Twink Loads | |
| Cute, twink, Jack Bailey meets bearded, daddy-bear, Killian Knox in this all-raw, red hot encounter. The two men face each other on the bed, legs seductively wrapped around each other, grinding and writhing their sexy bodies together. Before long, they're tearing off clothes and kissing like their lives depend on it. Their looks of lustful desperation tell us how much.... | View Video | |
 | Jack and Romeo 2 Twink Loads | |
| It seems that Jack Bailey and Romeo Davis just can't get enough of each other! They say opposites attract, and these two guys couldn't be more different. Flame-haired cutie, Jack, is definitely the sort of boy you'd want your mom to meet, whereas heavily-tattooed, rough-guy Romeo would have her running for her life! They make out on a hotel bed, lips locked, tongues d.... | View Video | |
 | Eddie and Jack Hung Fuckers | |
| Jack Bailey and Eddie Patrick are clearly into each other, or maybe they are just very hungry horny guys. There is certainly a connection. The scene opens with the two of them sitting on a sofa kissing. Eddie's long uncut cock is clearly hard under his sweat pants and he jacks it with anticipation, until Jack takes over for him. Eddie stands up and Jack crawls over to.... | View Video | |
 | Jack Bailey Chapter 1 Twink Top | |
| Have you ever had sex before? Jack's face flushed red. He didn't know what to say that would sound right, so he just told the truth that he hadn't. "Do you want some pointers?" Grandpa Lance asked, already beginning to remove his clothes. Jack could hardly believe what he was hearing and seeing. It became pretty apparent that this was not going to be a usual birds and.... | View Video | |
 | Jack Bailey Chapter 2 Twink Top | |
| Dolf is no stranger to getting a hot young guy naked, and Jack was exactly his type. He loved his bright smile and pleasant demeanor, finding himself crushing on him harder and harder as the session progressed. Once Jack couldn't take anymore, he let the boy cool off, sitting beside him and showering him with compliments and encouragement. Jack loved it. He loved hear.... | View Video | |
 | Jack and Romeo 3 Twink Loads | |
| 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! They make out on a bed, tongues battling, legs interlocked, Romeo's hands wickedly squeezing the boy's delicate throat. Both smile expectantly. They k.... | View Video | |
 | Jack and Killian 2 Twink Loads | |
| Is there anything better than a bearded daddy going down on the cute twink-next-door? After Killian Knox wears out Jack Bailey's mouth with kisses, he strips them both, pushes the boy down on his bed, and worships every inch of his twink body. But getting worked over by the DILF's mouth just gets the twink worked up-and he takes charge by topping the daddy's hungry ho.... | View Video | |
 | Jack and Jax 2 Twink Loads | |
| When we put sweet-faced twink top Jack Bailey in a room with masculine bottom Jax Thirio, it was as if the cameras disappeared. They had laser-focus on each other; the only thing that mattered to Jack was getting his hard cock into Jax's warm, tight hole! Full title: Jack Bailey Encounter 2: Jax Thirio Bottoms. Featuring Jack Bailey, Jax Thirio. From the web series: J.... | View Video | |
 | Romeo and Jack Chapter 1 Raw Fuck Boys | |
| RawFuckBoys continues with a red hot dungeon fuck-fest featuring sandy-haired twink, Jack Bailey, and the tattoo-covered, dangerous-looking, Romeo Davis. The two guys kiss passionately, almost desperately. Romeo wraps his hands around Jack's neck. It's important the boy knows who's calling the shots... Jack licks and sucks on Romeo's nipples. The older dude smiles wic.... | View Video | |
 | Jack and Romeo Chapter 2 Raw Fuck Boys | |
| Jack Bailey and Romeo Davis meet again in the latest film from RawFuckBoys. They're an eccentric, yet incredibly sexy pairing. Davis, whose body is covered in tattoos, has a dark, brooding energy; the very antithesis of the sunny-haired, sunny-natured twink boy, Jack Bailey, who, in this film, is trussed up in a black leather collar. They kiss like hungry sluts. Romeo.... | View Video | |
 | Jack and Jax 3 Twink Loads | |
| Always naughty and always in the mood, horny twink Jack Bailey has got a hot idea in mind. All he needs is favorite DILF fuck-buddy Jax Thirio to come over and help him out! Once the tall, buff daddy arrives and gets on his back, Jack pulls out his phone and makes a private recording of just how insanely tight the moaning, begging daddy's hole is! Full title: Jack Bai.... | View Video | |
 | Jack and Romeo Chapter 3 Raw Fuck Boys | |
| As usual, their dick-tingling session takes off with some heavy-duty kissing, but Romeo instantly gets his hands wrapped around Jack's throat in a way which suggests he's in the mood for something sleazy. The kisses become wet and sloppy. Jack begs to be degraded. Romeo sits on a bench and Jack squats between his legs, hungrily servicing the older man's giant, throbbi.... | View Video | |
 | Jack and Killian 3 Twink Loads | |
| Hungry, horny twink Jack Bailey always gets such a huge boner whenever beefy daddy Killian Knox comes around. The steamy kissing and foreplay is always super hot, but what really gets Killian revved up and ready to go is knowing that Jack is going to take that long, thick hardon and nail his DILF hole with it. Full title: Jack Bailey Encounter 3: Killian Knox Bottoms..... | View Video | |
