All gay porn sex pics and gay porn sex videos of twink Boy Jack Bailey. Gay porn star Jack Bailey is naked jerking his huge young cock cumming all over his ripped six-pack abs.
Hair Color: Brown
Sign: Unknown
Eye Color: Brown
Dick Size: 8-inch dick
Height: 5’9″
Cut / Uncut: Cut / Circumcised
Weight: 165lbs
Sexual Positions: Versatile
Jack Bailey gay porn scenes at Raging Stallion
Tattooed muscle hunk Chris Damned’s huge uncut dick bareback fucked by Jack Bailey’s bubble ass.
As Chris prepares for his big day, he makes one last stop to get his shoes shined by Jack. 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 ass 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.Join them!
Jack Bailey gay porn scenes at Next Door Taboo
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The college year is finally done and Michael Roman wants to help Jack Bailey celebrate finishing a tough semester, so he plans a nice meal for them both.
But, Jack wants to celebrate through other means. What could Jack possibly want?Join them!
Jack Bailey gay porn scenes at Raw Fuck Boys
Smooth twink Jack Bailey and bearded tattooed hunk Romeo Davis meet again in the latest gay porn movie from RawFuckBoys. They’re an eccentric, yet incredibly sexy pairing.
Romeo’s hot body is covered in tattoos, and he has a dark, brooding air about him; the very opposite of the sexy young twink boy, Jack Bailey, who is trussed up in a black leather collar and tight black jockstrap.
They kiss like hungry sluts. Romeo pulls Jack’s hair and grabs him by the throat. The boy beams with the lustful excitement of a corrupted innocent. Romeo will enjoy using this boy tonight, and he’s gonna use him hard.
Romeo aggressively pushes Jack to his knees and insists the boy take his dick right to the back of his hungry little mouth. Romeo’s huge, pervy cock makes the boy choke. Endless strings of saliva stream helplessly from his well-used throat.
Romeo orders Jack onto a bench and preps his tight hole for deep, raw penetration, the sort of ride only a sleazy daddy would know how to give. Jack groans with pleasure and quivers with anticipation, begging for the DILF’s horny dick.
Romeo stands and slides his raw meat into the boy. Jack begins to whimper, then yell as the strokes get harder and faster. Before long, Romeo finds himself banging the screaming boy like a living sex doll, using his dick like a devastating weapon of mass destruction.
Jack’s hole is soon a wrecked, gaping, sloppy mess, oozing with saliva and slimy pre-cum. With every brutal stroke, Romeo inches closer to orgasm, finally letting go with a depraved roar and an epic explosion of semen deep inside Jack’s raw asshole. The spent boy can do nothing but thank his master repeatedly.Join them!
Jack Bailey gay porn scenes at Scout Boys
Sexy young scout boys Cole Blue and Jack Bailey have returned early from their hike, their muscles tired and aching.
But all alone on base camp, and a little bored, the cute boys decide to have some fun with arm-wrestling.
Cole knows he’s way stronger than Jack and thinks he can get his hot new mate into some hot pleasurably compromising positions
As the two boys wrestle with each other on the floor of their tent Cole presses against Jack’s crotch and can feel that Jack’s soft dick is becoming erect through his shorts.
The thought of sucking his young mate’s huge cock turns Cole on and he feels his own huge monster 9-inch dick growing and tenting against his tight undies.
Before long, the two boys are excitedly pulling their dicks out of their shorts to compare hard-ons. Cole reaches across and grabs ahold of Jack’s beautiful 8-inch monster. Jack immediately returns the favor and, within seconds, they’re seductively rubbing and fondling each others’ huge erections with precum dripping all over.
Off with their shorts now, the two boys start to make out, kissing deeply. Cole is desperate to show off some of the sexual tricks he’s learned from dirty encounters with the other horny straight Scoutmasters.
Jack squats down and starts to suck on Cole’s massive thick dick, and he doesn’t have to wait long before Cole is forcing his nine-inch tool deep into his tight bubble butt asshole.
The tall scout fucks his best friend from behind with slow, brutal, bareback thrusts. Jack just loves the feeling of Cole’s massive thick dick moving deep inside his raw hole.
The sexy scout boys switch up positions a number of times with Cole each time getting himself balls deep into Jack’s soft pink asshole, making his moan with delight.
Without warning, Cole can hold off his orgasm no longer and he pulls out and explodes violently with jizz spraying out all over Jack’s scout uniform.
Seeing his friend’s cum all over his clothes, Jack lets rip with a massive cum shot spraying both horny boys with his seed before they lean across for a post fuck cummy kiss.Join them!
Jack Bailey gay porn scenes at 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 understands that it’s okay to be who you are without apologies.
Their affection and tenderness turns sexual as they realize that their growing feelings are mutual.Join them!
Jack Bailey gay porn scenes at 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.Join them!
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.Join them!
Jack Bailey gay porn scenes at 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 they want each other and just how steamy this boy-meets-dad hook-up is gonna get.
Jack pulls down his boxers and his huge, solid dick bounces up, slapping forcefully against his belly button.
This twink is ready for action! Daddy Killian instantly gets to work, wrapping his hungry lips around Jack’s shaft and tickling his balls with his beard.
Jack’s eyes roll back in his head. He’s never felt anything this good before.
Killian gets naked and squats on the bed, pointing his perfectly-sculpted daddy butt towards the excited boy. Jack immediately gets his tongue busy, exploring every inch of Killian’s tight, tasty hole.
Jack spits into the palm of his hand and rubs it on his dick before plunging his rod deep into Killian.
The intensity and speed of Jack’s strokes blow Killian’s mind.
He grits his teeth and winces as Jack delivers blow after internal blow, ruthlessly rearranging the daddy bear’s internal organs in a frenzy of brutal thrusting.Join them!
Jack Bailey gay porn scenes at Twink Top
Dolf Dietrich looks like a badass, but he’s really a big softy at heart. He’s got the energy of a supportive big brother that motivates his athletes to push themselves.
Despite being a 6’6” giant and looking like a total DILF, he loves being able to relate with the younger guys and make them feel comfortable.
This was especially helpful for Jack Bailey. When he first met the big guy, he saw his complete opposite. Jack had a fairer complexion, looked like a little boy, and had no sense of what he was doing in his exercises. As much as he was intimidated by the older man, he wanted to impress him as well.
So much of Jack’s personality was wrapped in wanting to succeed and be seen as achieving. With that, he gave it his all in their training session.
Dolf put him through the usual routinestretches, cardio, situps, pushups, pullups, etc. He wanted to get a sense of what the young man’s baseline was so he could track his progress. He wanted to go easy on the younger guy but found Jack’s eagerness to continue unflappable.
Even as Jack began to get sweaty and winded, he seemed to need Dolf to tell him to stop. The older man admired his determination… as well as the pump the young guy was getting.
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 hearing the positive feedback from his trainer, but also found himself increasingly attracted to him.
Once he realized he wasn’t as scary as he first imagined, he saw the exuberant, friendly, even playful personality of the older trainer. Dolf pressed his hands on Jack’s chest, feeling for the swelling and pump of his young muscles.
It was common for him to do so with his athletes, but when it came to Jack, his own heart started racing as if he’d done a series of pushups. The chemistry between them seemed to increase with each passing second. As Dolf’s hands moved over Jack’s body, Jack opened himself up to allow the older man to explore further.
Dolf was not shy about putting his big hands up Jack’s thighs to feel his groin. Jack was rock hard within seconds, tenting up his shorts in a way that Dolf could not ignore.
Dolf brought Jack in close, feeling up his chest before telling him to take off his shirt. Jack did without hesitation. Seeing Jack’s response, he asked him to take off his shorts as well.
Jack’s cock swelled up even tighter as he got down to just his jock. He didn’t anticipate anything like this happening, but he was more than happy to see where things could go.Join them!
Jack Bailey gay porn scenes at Next Door Studios
Jax Thirio has his hands full with a whole lot of hot ass. Jax takes care of Jack Bailey and Troye Jacobs in this homemade hornfest.Join them!
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….Join them!
