Jack Bailey - Over 100 files at GayFilesMonster!
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| Type | Title |
| Videos | Virgin No More - Retaliation - Dale Savage, Jack Bailey and Trevor Harris |
| Videos | Doctor Tapes - The Doctors Orders - Johnny Ford and Jack Bailey 720p - 2021 |
| Movies | Butt Snack - 2013 - Dominic Sol, Drew Sebastian - Rimming, Masturbation |
| Movies | Drunk On Cum vol.6 Hard Training - 2013 - Fyerfli, Chad Brock - Facial, Cum Eating |
| Videos | FamilyDick - The Perfect Pool Day - 2022 - Isaac Parker, Taylor Reign - kissing, bareback |
| Videos | Scout Boys - Scout Jack Bailey - Chapter 1 - A Walk In The Woods 1080p - 2022 |
| Videos | Scout Boys - Scout Jack Bailey - Chapter 2 - Lessons in Discretion 1080p - 2022 |
| Videos | The Doctors Orders - Johnny Ford and Jack Bailey - 2022 |
| Videos | Disruptive Films - Virgin No More - Retaliation - 2022 - Dale Savage, Jack Bailey - rimming, bareback |
| Videos | Virgin No More - Retaliation - Dale Savage, Jack Bailey, Trevor Harris |
| Videos | DF2 - Virgin No More Retaliation Dale Savage, Jack Bailey and Trevor Harris Bareback |
| Videos | Virgin No More Retaliation 720p - Jack Bailey, Dale Savage - Bareback, Anal Sex |
| Videos | Disruptive films - Virgin No More |
| Videos | Disruptive films - Dale Savage, Jack Bailey and Trevor Harris |
| Videos | Dale Savage, Jack Bailey and Trevor Harris |
| Videos | ColbyKnox - Colby Chambers Fucks Jack Bailey Bareback - 2022 - rimming, kissing |
| Videos | Getting in Touch With Nature - Greg McKeon, Jack Bailey and Colton McKeon 720p |
| Videos | Scout Jack Bailey - Chapter 1 - A Walk In The Woods 720p |
| Videos | Camp Guessing Games - Greg McKeon, Jack Bailey, Colton McKeon and Grey Gold 720p |
| Videos | Before Leaving Camp - Greg McKeon, Jack Bailey and Colton McKeon 720p |
| Videos | Scout Jack Bailey - Chapter 1 - A Walk In The Woods - 2022 |
| Videos | Scout Jack Bailey - Chapter 2 - Lessons in Discretion 720p |
| Videos | Whip em Out - Greg McKeon, Jack Bailey and Grey Gold 720p |
| Videos | Scout Jack Bailey - Chapter 2 - Lessons in Discretion - 2022 |
| Videos | Next Door Films - Writers Block - Jack Bailey and Nico Coopa (4K) |
| Videos | Getting My Wet Daniel Hausser and Jack Bailey |
| Videos | Bored StepBros Alex Meyer and Jack Bailey |
| Videos | Cannonball Contest Taylor Reign and Jack Bailey |
| Videos | Next Door Taboo - Date With Step-Dad - 2022 - Michael Roman, Jack Bailey - kissing, bareback |
| Videos | Next Door Films - Writers Block - 2022 - Nico Coopa, Jack Bailey - smooth, bareback |
| Videos | Next Door Films - Writers Block - Jack Bailey and Nico Coopa (720p) |
| Videos | NextDoorFilms Writers Block - Jack Bailey and Nico Coopa |
| Videos | Writers Block Jack Bailey and Nico Coopa 4K - Bareback, Oral Sex |
| Videos | Jack Bailey and Nico Coopa - Writers Block |
| Videos | Next Door Films - Writers Block - Jack Bailey and Nico Coopa (1080p) |
| Videos | Jack Bailey and Nico Coopa |
| Videos | Before Leaving Camp Greg McKeon Jack Bailey and Colton McKeon |
| Videos | Camp Guessing Games Greg McKeon Jack Bailey Colton McKeon |
| Videos | Getting in Touch With Nature Greg McKeon Jack Bailey Colton McKeon |
| Videos | The Perfect Pool Day Ch 3 - Isaac Parker, Jack Bailey and Derek Allen - 2022 |
| BDSM | Himeros - Rough Oral - 2022 - Jack Bailey, Nico Nova - ropes, kissing |
| Videos | Too Horny To Behave - Jack Bailey and Derek Allen - 2022 |
| Videos | Stepdad Joins The Show - Jack Bailey and Brian Bonds - 2022 |
| Videos | Twink Loads - Romeo Davis Bottoms With Jack Bailey Encounter 3 - 2022 - bareback, kissing |
| Videos | Lets Share A Bath - Jax Thirio, Jack Bailey and Max Lorde - 2022 |
| Movies | Viral Loads - 2014 - Austin Shadow, Drew Sebastian - Muscle, Cumshot |
| Videos | Fighting For His Attention - Max Lorde, Jack Bailey and Jax Thirio - 2022 |
| Videos | Flying the Nest - Jack Bailey and Jax Thirio - 2022 |
| Videos | Disruptive Films - Out of my way |
| Videos | Disruptive Films - Out Of My Way - 2022 - Jack Bailey, Killian Fox - bareback |
| Videos | Getting in Touch With Nature - Greg McKeon, Jack Bailey and Colton McKeon - 2022 |
| Videos | Bad Grades, Bad Boy - Brian Bonds, Jack Bailey - 2022 |
| Videos | DisruptiveFilms Out of my way - Jack Bailey and Killian Fox |
| Videos | Jack Bailey and Killian Fox |
| Videos | Out Of My Way Killian Fox fucks Jack Baileys asshole (720p,1080p) - Oral Sex, Anal Sex |
| Videos | Out Of My Way - Jack Bailey and Killian Knox 1080p |
| Videos | Whip em Out - Greg McKeon, Jack Bailey and Grey Gold - 2022 |
| Videos | Before Leaving Camp - Greg McKeon, Jack Bailey and Colton McKeon - 2022 |
| Videos | Camp Guessing Games - Greg McKeon, Jack Bailey - 2022 |
| Videos | Disruptive - Out Of My Way - Jack Bailey and Knox 1080p |
| Videos | Bad Grades, Bad Boy - Jack Bailey and Brian Bonds - 2022 |
| Videos | BrotherCrush - Getting My Stepbrother Wet - 2021 - Daniel Hausser, Jack Bailey - bareback |
| Videos | Scout Boys - Troop Time - Chapter 15 After Camping - 2022 - Marcus Rivers, Mr Smith - kissing, bareback |
| Videos | Missionary Boys SayUncle - Authority Granted - 2022 - Jack Bailey, Ashton Silvers - kissing, bareback |
| Videos | NextDoorTaboo - Virgin - Jack and Jordan 720p - 2022 - Jordan Starr, Jack Bailey - Bareback |
| Videos | Next Door Twink - Washboard Worship - 2021 - Trevor Harris, Jack Bailey - group, bareback |
| Videos | Adult Time - Accidental Gangbang - Chock-Full Of Jocks - 2022 - Tony Genius, Michael Seraph - rimming, bareback |
| Videos | Family Dick - Stepdad Joins the Show - Brian Bonds, Jack Bailey 2160p - 2022 |
| Videos | Family Dick - Workout on the Balcony - Jack Bailey, Jax Thirio 2160p - 2022 |
| Videos | Fighting For His Attention - Max Lorde, Jack Bailey and Jax Thirio 1080p - 2022 |
| Videos | Adult Time - Accidental Gangbang - Chock-Full Of Jocks (1080p) - Trent Marx, Tony Genius |
| Videos | Chock-Full Of Jocks - Trent Marx, Amone Bane, Jack Bailey, Tony Genius |
| Videos | Stepdad Joins The Show - Jack Bailey and Brian Bonds 1080p - 2022 |
| Videos | The Perfect Pool Day Ch 2 - Isaac Parker, Jack Bailey and Derek Allen 1080p - 2022 |
| Videos | Accidental Gangbang - Chock-Full Of Jocks - 2022 - bareback porn |
| Videos | Chock-Full Of Jocks - Trent Marx, Amone Bane and Jack Bailey |
| Videos | Family Dick - Fighting for His Attention - Jack Bailey, Jax Thirio, Max Lorde 2160p - 2022 |
| Videos | Family Dick - Bad Grades, Bad Boy - Brian Bonds, Jack Bailey 2160p - 2022 |
| Videos | Accidental Gangbang Chock-Full Of Jocks 1080p - Tony Genius, Michael Seraph - Bareback, Anal Sex |
| Videos | Adult Time - Accidental Gangbang - Chock-Full Of Jocks (1080p) |
| Videos | Flying the Nest - Jack Bailey and Jax Thirio 1080p - 2022 |
| Videos | Accidental Gangbang Chock-Full Of Jocks |
| Videos | Bad Grades, Bad Boy - Jack Bailey and Brian Bonds 1080p - 2022 |
| Videos | Jack Bailey and Jordan Starr – Virgin - bareback porn |
| Videos | Missionary Boys SayUncle - Assigned Companions - 2022 - Jack Bailey, Ashton Silvers - bareback, kissing |
| Videos | Jack Bailey and Jordan Starr - Virgin Stepbrother |
| Videos | Disruptive Films - A Virgin No More - The Offering - 2022 - Scott Finn, Jack Bailey - group, threesome |
| Videos | Twink Top - Jack Bailey Chapter 2 - Getting Pumped - 2022 - Dolf Dietrich - kissing, bareback |
| Videos | Himeros - Backseat Driver - 2022 - Peyton Key, Andre Donovan - bareback, group |
| Videos | HimerosTV - Backseat Driver - Andre Donovan, Jack Bailey and Peyton Key |
| Videos | Andre Donovan, Jack Bailey and Peyton Key |
| Videos | Next Door Taboo - Virgin |
| Videos | GayCest - Teaching My Grandson Tape 3 - Hard Lessons - 2022 - Jack Bailey, Lance Charger - kissing, bareback |
| Movies | D.O.C. vol.6 - 2013 - Jay Elliott, Rowdy Gaines - Facial, Cum Eating |
| Videos | Boy For Sale - The Buyers Group - Chapter 8 - Party Favor - 2021 - Korzak Kipling, Jack Bailey - bareback |
| Videos | Scout Boys - Scout Jack Bailey - Chapter 2 - Lessons in Discretion - 2022 - Scoutmaster Smith - bareback, kissing |
| Videos | Too Horny To Behave - Jack Bailey and Derek Allen - 2022 - muscle, big dick |
| Videos | Nakedsword - Lake Need - Scene 1 - 2022 - Jack Bailey, Johnny Rapid - Big Dick, doggy style |
| Videos | Boys At Camp - Getting In Touch With Nature - 2022 - Jack Bailey, Greg McKeon - threesome, group |
| Videos | Scout Jack B Pt 2 - Lessons in Discretion - Jack Bailey, Korzark Kipl - 2022 - bareback porn |
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