Jack Bailey Blog

GayDemon's Blog: On this page you can find all gay porn posts related to Jack Bailey listed in order they where published.


Twink Jack Bailey Fucks & Breeds Trans Guy Luke Hudson

27 Mar 2024

Twink Jack Bailey Fucks & Breeds Trans Guy Luke Hudson

Jack Bailey kisses Luke Hudson's toned torso, slowly working his lips down towards Luke's bonus hole in this new Jock Pussy video. The two engage in verbal play and Luke deep-throats the horny stud.

Things get even hotter when Luke rides Jack's rock-hard cock, sending the twink's eyes rolling in the back of his skull. The bearded bottom encourages Jack to keep fucking, working his pussy on stud's throbbing meat. When he can't take another minute, Jack deposits his large cum load into Luke's hungry hole.

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Trans Guy Gets Filled With Big Twink Cock & Cum

29 Jan 2024

Trans Guy Gets Filled With Big Twink Cock & Cum

Jack Bailey and Luke Hudson don't waste any time diving into some deep kissing in this new Jock Pussy video. T-shirts and cargo shirts go flying. Luke pounces on Jack's fat juicy cock and makes the twink moan. Jack is hungry, too, and rolls Luke over to chow down on the trans guy's pussy. 

Jack tongues the T-dick until he has his sexy man begging for cock, which he's happy to offer. Jack slides into that tight hole with a satisfied moan.

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Unruly Twink Gets Serviced By The Family Mechanic

28 Jan 2024

Unruly Twink Gets Serviced By The Family Mechanic

Justin O'Neal's (Jack Bailey) family sent him to a remediation camp in an attempt to curb his unruly and entitled behavior. They thought things would be better after he got home from the ranch, but there's been no change, in fact, Justin is worse than ever.

In A Brat & A Gentleman at Disruptive Films, Justin's father thinks spending a day with a family friend Brandon Partridge (Colt Spence) in the mechanic's garage will help. Maybe getting his hands dirty will finally make Justin a better man.

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Man Shoves Butt Plug in Twink's Ass & Milks His Cock

5 Nov 2023

Man Shoves Butt Plug in Twink's Ass & Milks His Cock

In The Breakdown over at Him Eros, Andre Donovan and his twink lover Jack Bailey have broken down and they're standing at Coach's door asking to use his phone. While Andre makes the call for roadside assistance, Coach gets Jack naked and plays with the twink's cock.

When Andre enters the kitchen, he finds his lover on all fours on the kitchen counter with a butt plug in his ass and Coach is showing the milking technique he's perfected -- and it drives guys crazy. Andre pulls out his cock and watches the man working over his lover's stiff cock.

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Devious Twinks Get Retaliation on Dirty Uncle Carl

1 Dec 2022

Devious Twinks Get Retaliation on Dirty Uncle Carl

Do you remember dirty Uncle Carl? He seduced his best friend's son, Toby (Jack Bailey), in Virgin No More at Disruptive Films. When Toby tried to pursue something romantic with the sexy older man, Carl rebuffed him saying that he only fucks virgins. His tune changed when Toby and his friend Will (Scott Finn) needed a place to spend the night after a concert.

Toby is back with another friend, Nick (Trevor Harris). Does Uncle Carl get into Nick's ass, too? Come inside and see what happens.

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Twink Helps His Stepbrother Pop His Virginity

16 Oct 2022

Twink Helps His Stepbrother Pop His Virginity

Jack Bailey is hanging out with his stepbrother, Jordan Starr, and the conversation turns intimate. Jordan has been dating a guy and they nearly went all the way the other night, but didn't. Jack asks why and Jordan confesses that he's a virgin and is nervous

"Would it be a good idea if you lost your virginity with me?" Jack asks. "But we're stepbrothers," Jordan says. Jack shrugs it off saying that it would be more comfortable with him than a stranger.

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Twink's Crush on His Stepfather Takes a Chilling Turn

30 Aug 2022

Twink's Crush on His Stepfather Takes a Chilling Turn

Jack Bailey has been crushing on Killian Knox ever since his mother started bringing him around. But the boy's crush gets out of hand and when Jack's mother announces Killian is her fiance, Bailey loses it. 

In Disruptive Films' Out of My Way, Jack tries to convince his stepfather-to-be that they could be happy together, he even crawls into bed and takes care of the man's cock. But as Killian continues to rebuff the boy, Jack takes things to a chilling level. "There was no denying that my mother was in the way," Jack writes in his journal.

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Dirty Old Man Fucks Two Nympho Twinks

20 Jun 2022

Dirty Old Man Fucks Two Nympho Twinks

Dirty old pornographer Clay loves Jack Bailey and he's fucked the blond twink many times before on Raunchy Bastards. In Full-On Nympho Maniacs, Clay brings in newcomer Liam Addison who loves fucking, getting fucked, sucking dick, getting sucked ... you name it!

"I knew before we began that I would have a lot of fun with these two. Turns out, we all had a blast and I fucked both boys."

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Scoutmaster Catches Two Scouts Playing in the Woods

13 Jun 2022

Scoutmaster Catches Two Scouts Playing in the Woods

Scouts Troye Jacobs and Jack Bailey are hiking in the woods in Catching Scoutmaster at Scout Boys. They're on the lookout for a spot where they can do some dick sucking. They set their packs down by a tree and fall into a passionate kiss. 

They didn't notice Scoutmaster Charger was only a few feet away jerking his cock. He, too, was craving a bit of alone time. He quietly walks over, dick in hand, and surprises the boys. What happens next? It's probably not what you're thinking ...

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Really Slow ... I Want You to Take Your Time!

7 Jun 2022

Really Slow ... I Want You to Take Your Time!

Nico Nova returns from a walk when Rough Oral opens over at HIM Eros. Jack Bailey is exactly where he left him - blindfolded and lying on the couch with his hands bound behind his back. "Are you ready to show me how much you love me?" Nico asks. 

He pulls at Jack's underwear revealing the boy's soft ass cheeks, then he kisses and nibbles them. Nico orders his blindfolded boy to suck his cock. Before he lets his boy feed, Nico says, "Really slow ... I want you to take your time."

Watch Nico Drain His Balls Into Jack's Hungry Mouth!

Big-Dicked Jock Delivers a Delicious Creampie

1 Jun 2022

Big-Dicked Jock Delivers a Delicious Creampie

Dirty old porngrapher Clay brought gay porn regular Masym Thorne over to Raunchy Bastards for a new scene called Breeding Jack Bailey. Since Masyn hadn't filmed with the site, Clay asked if he was able to cum while fucking a guy's ass. 

Masyn said that he usually uses a video on his phone to get close. "We don't work that way here," Clay says. So Masyn took on the new challenge and after pounding the daylights out of Jack's tight hole, he delivered a beautiful creampie in the boy's ass.

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Scoutmaster Plows 3 Scouts Face Down Ass Up!

1 Jun 2022

Scoutmaster Plows 3 Scouts Face Down Ass Up!

In Troop Time at Scout Boys, three scouts return to camp filthy and disheveled. Their leader sends them into the tent to get out of their dirty uniforms for a lesson in hand-washing their clothes. Instead, once the boys have stripped down to their underwear, Scoutmaster Kipling encourages two of the boys to kiss. "It's just a game," he says.

Minutes later, after all the scouts have kissed one another, the leader tells Troye to put his mouth on Marcus' cock. "My mouth?" he asks. "Yes, it's just a game." Indeed, and a game Scout Jacobs excels at. Come inside and see how far this goes ...

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Trio of Horny School Boys Bend Over for Their Teacher

20 Feb 2022

Trio of Horny School Boys Bend Over for Their Teacher

Professor Payne ... it has a deliciously nasty ring to it, doesn't it? Twinkology 101 is a new scene from Next Door Twink featuring Carter DelRey, Jack Bailey, and Trevor Harris who are hot for their teacher, Dakota Payne.

Trevor and Jack get into an argument during class, and Trevor says, "If you want to kiss the teacher's ass so much, why don't you go pulls down his pants?" That gives the professor an idea, so he locks the classroom door.

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