https://www.429men.com/models/jack-bailey/ Sun 19 Apr 2026 16:08:47 +0200 https://www.429men.com/videos/432026/next-door-taboo-college-twink-dreams-come-true-muscle-hunk-stepdilf-rails-hi/
Use code ASGDEAL for a FREE WEEK of NEXT DOOR TABOO! Featuring Jack Bailey, Michael Roman ]]> Thu 19 Mar 2026 14:32:23 +0200 https://www.429men.com/videos/432026/next-door-taboo-college-twink-dreams-come-true-muscle-hunk-stepdilf-rails-hi/ https://www.429men.com/videos/436039/next-door-taboo-horny-stepbro-jack-bailey-pops-virgin-jordan-starr-s-tight-che/
Use code ASGDEAL for a FREE WEEK of NEXT DOOR TABOO! Featuring Jack Bailey, Jordan Starr ]]> Sat 07 Mar 2026 23:13:12 +0200 https://www.429men.com/videos/436039/next-door-taboo-horny-stepbro-jack-bailey-pops-virgin-jordan-starr-s-tight-che/ https://www.429men.com/videos/66896/stepdad-michael-roman-pounds-jack-bailey-tight-asshole/
Michael Roman is eager to give Jack Bailey a special treat for finishing a college semester, so Jack asks for his giant cock! ]]> Tue 07 Oct 2025 21:49:00 +0200 https://www.429men.com/videos/66896/stepdad-michael-roman-pounds-jack-bailey-tight-asshole/ https://www.429men.com/videos/109879/chock-full-of-jocks/
Jack Bailey, the last student to leave the classroom, grabs his backpack and is about to head out the door when one of the school's football players, Tony Genius, comes in and asks Jack for tutoring. Tony says that his grades have reached a point where if he doesn't get a B+ he'll be held back a year, and there's NO WAY that can happen. ]]> Thu 04 Sep 2025 00:50:30 +0200 https://www.429men.com/videos/109879/chock-full-of-jocks/ https://www.429men.com/videos/39786/a-bonding-moment/
Jax invites his old college friend Max for a nice getaway. He’s sure that his stepson and Max’s boy will get along well too. Truth be told, Jax and Max did more than study in college, so when their stepsons Andy and Jack are not around, the two jump at each other for a horny plow. Jack and Andy suddenly barge in and demand explanations, so Max and Jax invite the boys to join them for an amazing four-way. ]]> Sun 25 May 2025 09:00:40 +0200 https://www.429men.com/videos/39786/a-bonding-moment/ https://www.429men.com/videos/39788/horny-horror-movie-night/
Jax and Max’s horny getaway weekend continues as the two friends spend some time with their stepsons, Andy and Jack. Jax is a bit concerned about how Max wants to have sex with Jack once more. They agreed it would be a one-time thing, but both Max and Jack are ready for a second round. When the four gather for a horror-movie night, Max takes a dildo and starts playing with Jack’s ass in front of Jax and Andy. Jax initially wants to stop them, but Andy convinces him to join the other two for a hot foursome. One more fuck sesh can’t hurt anyone! ]]> Mon 12 May 2025 09:00:43 +0200 https://www.429men.com/videos/39788/horny-horror-movie-night/ https://www.429men.com/videos/34105/adam-snow-eddie-patrick-and-jack-bailey/
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! ]]> Fri 20 Dec 2024 11:08:40 +0200 https://www.429men.com/videos/34105/adam-snow-eddie-patrick-and-jack-bailey/ https://www.429men.com/videos/33980/jack-bailey-encounter-3-killian-knox-bottoms2/
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. ]]> Wed 20 Nov 2024 12:56:19 +0200 https://www.429men.com/videos/33980/jack-bailey-encounter-3-killian-knox-bottoms2/ https://www.429men.com/videos/34022/adam-snow-eddie-patrick-and-jack-bailey2/
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! ]]> Mon 18 Nov 2024 12:57:11 +0200 https://www.429men.com/videos/34022/adam-snow-eddie-patrick-and-jack-bailey2/ https://www.429men.com/videos/33828/luke-hudson-and-jack-bailey-chapter-5/
Toned-up twink Jack Bailey has been pumping FTM stud Luke Hudson full of his loads for a while now. The trans hunk doesn't shy away from begging Jack for more DNA, either! ]]> Fri 15 Nov 2024 12:46:09 +0200 https://www.429men.com/videos/33828/luke-hudson-and-jack-bailey-chapter-5/ https://www.429men.com/videos/33726/jack-bailey-encounter-2-jax-thirio-bottoms/
When we put sweet-faced twink top Jack Bailey in a room with masculine bottom Jax Thirio, it was as if the cameras disappeared. ]]> Tue 12 Nov 2024 07:17:01 +0200 https://www.429men.com/videos/33726/jack-bailey-encounter-2-jax-thirio-bottoms/ https://www.429men.com/videos/35668/relaxin-with-jax/
While they have the house to themselves, Jax wants to spend some time with his stepson, Jack. At first, Jack is preoccupied with his phone, but when he sees Jax has other plans, he quickly comes around. Jax fucks his stepson’s sweet feet before pounding him from behind. Jack likes having his ass eaten, but he likes having his tight hole pounded even more. ]]> Tue 05 Nov 2024 11:45:04 +0200 https://www.429men.com/videos/35668/relaxin-with-jax/