Jack Bailey - Over 100 files at GayFilesMonster!
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| Type | Title |
| Videos | JasonSparksLive - Tom Bentley and Jack Bailey Chapter 2 1080p - 2022 - Bareback |
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| Videos | Disruptive Films - A Virgin No More - The Offering - Dale Savage, Scott Finn |
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| Videos | Disruptive Films - Dale Savage, Jack Bailey and Scott Finn - The Offering - 2022 - Big Dick, Blowjob |
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| Videos | Next Door Taboo - Secret Sexcapades - Keeping Him Busy - 2022 - Trevor Harris, Jax Thirio - kissing, bareback |
| Movies | Eight is Enough - 2008 - Chase Himmel, Bradley Thomas - dildo, Rimming |
| Movies | Drunk On Cum Pt.6 Hard Training - Treasure Island - 2013 - Chris Perry, Nick Moretti |
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| Movies | Eight is Enough - 2008 - Aiden Starr, Jake Jensen - Dildo, Rimming |
| Videos | Getting In Touch With Nature - Colton McKeon, Jack Bailey and Greg McKeo - 2022 - Bareback |
| Videos | Boys At Camp - Getting In Touch With Nature - Greg McKeon, Jack Bailey |
| Videos | Next Door Taboo - Secret Sexcapades Part 1 - 2022 - Roman Todd, Jack Bailey - bareback, kissing |
| Videos | SayUncle - Colton McKeon, Jack Bailey and Greg McKeon - 2022 - Bareback, Big Dick |
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| Videos | Remember When We Used To Do This - Max Lorde And Jack Bailey |
| Videos | Colton McKeon, Jack Bailey and Greg McKeon - Getting In Touch With Nature |
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| Videos | Rhyheim Shabazz and Jack Bailey - 2021 - hardcore, Amateur |
| Videos | Naked Sword - Lake Need Scene 4 - 2021 - Jax Thirio, Nic Sahara - bareback, kissing |
| Movies | Viral Loads - 2014 - Noah Paris, Brad McGuire - Muscle, Cumshot |
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| Videos | Naked Sword - Lake Need Scene 3 - 2021 - Johnny Rapid, Cyrus Stark - bareback, kissing |
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| Videos | Max Lorde and Jack Bailey – Remember When We Used To Do This - 2022 - Bareback |
| Videos | Rhyheim Shabazz and Jack Bailey - 2021 - Amateur sex, Blowjob |
| Videos | Remember When We Used To Do This (720p,1080p) - Jack Bailey, Max Lorde - Bareback, Oral Sex |
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| Videos | SayUncle - Max Lorde and Jack Bailey - Remember When We Used To Do This - 2022 - Bareback, Big Dick |
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| Videos | Jason Sparks Live - Tom Bentley and Jack Bailey Chapter 1 - 2022 - kissing, bareback |
| Videos | Jason Sparks Live - Tom Bentley and Jack Bailey Chapter 2 - 2022 - kissing, bareback |
| Videos | Remember When We Used To Do This - Max Lorde and Jack Bailey (1080p) |
| Videos | Next Door Homemade - Jax Thirio Pounds Jack Bailey - 2022 - kissing, bareback |
| Movies | Drunk On Cum Blowjob Training - 2013 - Truckee, Keiran - Cum Eating, Facial |
| Videos | Naked Sword - Lake Need Scene 1 - 2021 - Johnny Rapid, Jack Bailey - bareback, kissing |
| Videos | JasonSparksLive - Tom Bentley and Jack Bailey - 2022 - Big Dick, Bareback |
| Videos | Tom Bentley and Jack Bailey, Chapter 2 |
| Videos | Tom Bentley fucks Jack Baileys asshole Ch.1 720p - Oral Sex, Anal Sex |
| Videos | Jason Sparks Live - Tom Bentley and Jack Bailey Chapter 1 |
| Videos | Tom Bentley and Jack Bailey, Chapter 1 |
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| Videos | Tom Bentley and Jack Bailey Chapter 2 - 2022 - Bareback |
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| Videos | Jason Sparks Live - Tom Bentley and Jack Bailey Chapter 2 |
| Videos | SayUncle - Workout On The Balcony - Jax and Jack 1080p - 2022 - Jack Bailey, Jax Thirio - Bareback |
| Videos | Say - Crush - This Is How It Feels - Jack Bailey and Max Lorde |
| Videos | Jack Bailey and Romeo Davis Chapter part 2 - 2022 |
| Videos | Max Lorde fucks Jack Baileys asshole 4K - Anal Sex, Oral Sex |
| Videos | RawFuckBoys Jack Bailey and Romeo Davis Chapter 2 |
| Videos | This Is How It Feels - Jack Bailey and Max Lorde 4K |
| Movies | Butt Snack - 2013 - Drew Sebastian, Blake Daniels - Masturbation, Rimming |
| Videos | A Virgin No More - 2019 - Hairy, Cumshots |
| Videos | Missionary Boys - Ashton Silvers and Jack Bailey - 2022 - bareback, kissing |
| Videos | Jack Bailey and Dale Savage - 2022 - Pierce Paris, Jordan Lake - Masturbation, Tattoos |
| Videos | BrotherCrush - Daniel Hausser and Jack Bailey - 2022 - bareback |
| Videos | Ricky Larkin and Michael Del Ray - 2022 - Jack Bailey, Dale Savage - Masturbation, Cumshots |
| Videos | Next Door Twink - Washboard Worship - 2021 - Trevor Harris, Jack Bailey - group, threesome |
| Movies | Drunk On Cum vol.6 Hard Training - 2013 - Brad McGuire, Sven Norse - Cum Eating, Facial |
| Videos | Say Uncle - Boys at Camp - Whip em Out - Jack Bailey, Greg McKeon |
| Videos | Raw Fuck Boys - Jack Bailey and Romeo Davis Part 1 - 2022 - kissing, bareback |
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| Videos | Missionary Boys - Assigned Companions - 2021 - Ashton Silvers, Jack Bailey - kissing, bareback |
| Videos | OnlyFans - Jack Bailey Videos, Part 3 |
| Videos | OnlyFans - Jack Bailey Videos, Part 2 |
| Videos | OnlyFans - Jack Bailey Videos, Part 1 |
| Videos | This Is How It Feels - Max Lorde and Jack Bailey - 2022 - Bareback |
| Videos | Only Fans - Jack Bailey - 2022 - Bareback |
| Videos | Twink Loads - Killian Knox Bottoms - Jack Bailey Part 1 - 2021 - kissing, bareback |
| Videos | Twink Top - Getting Pumped - Jack Bailey Chapter 2 - 2021 - Dolf Dietrich - bareback, kissing |
| Videos | SayUncle - Max Lorde and Jack Bailey - 2022 - bareback, kissing |
| Videos | Boy For Sale - The Buyers Group - Chapter 8 - Party Favor - 2021 - Marcus Rivers, Cole Blue - bareback |
| Videos | GayCest - Teaching My Grandson - Hard Lessons Part 3 - 2022 - Lance Charger, Jack Bailey - bareback, kissing |
| Videos | Doctor Tapes - The Doctors Orders - Johnny Ford and Jack Bailey (1080p) |
| Videos | Jack Bailey - Episode 37 |
| Videos | Jack Bailey - Episode 38 |
| Videos | Jack Bailey - Episode 35 |
| Videos | Jack Bailey - Episode 36 |
| Videos | Jack Bailey - Episode 33 |
| Videos | Jack Bailey - Episode 34 |
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