There are 64 posts for Jack Bailey, the oldest from November 11, 2020.
Jack Bailey, a young and obedient new face in the church, has a follow-up interview with the president, Johnny B. Willing to do anything for a promising role, Jack shows the leader just how obedient he actually is.
Continue with “Say Uncle | Missionary Boys: Jack Bailey and Johnny B”
This is the second video with Jack Bailey, and he was exactly as you would imagine, sweet, cute and eager to get his hole crushed and filled with cum. His moaning and sub talking was so hot it made both of the guys cum thick ropes of hot, sticky cum deep in his sweet little twink ass. And yes you guessed it he wanted more, so they gave it to him with both barrels….Maverick Men style lol. He is the quintessential YES SIR twink!
Continue with “Maverick Men: Jack Bailey”
Jack Bailey is being naughty for the webcam when his stepdad Brian Bonds walks in on him. Jack is startled at first but Brian likes what he sees and asks if he can join him. Turns out Jack’s fans really love seeing him fuck his stepdad!
Continue with “Say Uncle | Family Dick: Jack Bailey and Brian Bonds”
Most of us equate spanking with punishment. If you’re bad, you get spanked. And many spanking scenes are framed in this way. However, spanking can also be a playful, fun, romantic and focused on the bottom’s pleasure. And that’s what we see in this video, featuring Nico and Jack.
Anchored by the massive trunk of an old growth American sycamore tree, we see a deep connection between the boys and the nature that surrounds them. As the scene unfolds, the boundaries between Nico, Jack and the world around them, become blurred – and a deep sense of connection is felt by all.
Continue with “Himeros: Jack Bailey and Nico Nova – Treesome”
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.
Continue with “NextDoorStudios: Jax Thirio, Jack Bailey and Troye Jacobs”
President Johnny B meets with missionary boy Jack Bailey for his worthiness review. After asking him a few questions he confesses that he’s had impure thoughts and has masturbated several times. President Johnny understands the boy’s urges and decides to reward his good behavior by fulfilling all his naughty cravings!
Continue with “Say Uncle | Missionary Boys: Johnny B and Jack Bailey”
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.
Continue with “NextDoorTaboo: Johnny Ford and Jack Bailey”
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.
Continue with “Brother Crush: Alex Meyer and Jack Bailey”
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.
Continue with “NextDoorStudios: Jax Thirio and Jack Bailey”
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 raw cock into Jack’s eager ass.
Continue with “Naked Sword: Johnny Rapid and Jack Bailey”
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 from start to finish.
Continue with “Colby Knox: Jack Bailey”
In this weeks release from Colby Knox, we are thrilled to meet 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.
Continue with “Colby Knox: Meet Jack Bailey”
Blonde twink stepbrothers Daniel Hausser and Jack Bailey are working a pool job when suddenly Daniel playfully pushes Jack into the water! Once Jack is out, he gets his revenge by pushing Daniel in with his pants and shoes on. When Jack suggests that Daniel take off his clothes to lay them out to dry, he wasn’t expecting his dick to be so out there. Daniel then challenges Jack to “do something about it” and the boys get busy by the pool.
Continue with “Brother Crush: Jack Bailey and Daniel Hausser”
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.
Continue with “NextDoorStudios: Jack Bailey and Jesse Bolton”
When sexy stepbrothers Jesse Bolton and Jack Bailey start a gardening business together, they get into an argument over who has to do what while getting dirty in the backyard. Jesse plunges his delicious boner into his cute stepbro’s mouth and teaches him who’s boss before they get into some even nastier bareback action.
Continue with “Brother Crush: Jesse Bolton and Jack Bailey”
A couple of cute boys, Jesse Bolton and Jack Bailey, are always a welcome sight at horny Jax Thirio’s house. After a hard day’s work in the garden, the boys are invited inside to enjoy a raw anal threesome with the pervy guy, and the fun ends in a creamy mess!
Continue with “Brother Crush: Jesse Bolton, Jack Bailey, Jax Thirio”