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GayRoom – Detention Wedgie – Reese Rideout & Jack Bailey

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FamilyDick – The Perfect Pool Day – Taylor Reign, Isaac Parker, Jack Bailey & Derek Allen

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DadCreep – Relaxin with Jax – Jax Thirio & Jack Bailey

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TroopSex – Massage In The Barracks – Darron Bluu & Jack Waters

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Secret Sexcapades Scene 1 – Stepdad With Benefits – Roman Todd & Jack Bailey

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BoysAtCamp – Getting In Touch With Nature – Colton McKeon, Jack Bailey & Greg McKeon

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NextDoorTaboo – Date with Step-Dad – Jack Bailey & Michael Roman

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FamilyDick – The Perfect Pool Day, Part 2 – Isaac Parker, Jack Bailey & Derek Allen

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ColbyKnox – Head in the Clouds with Jack Bailey – Jack Bailey & Mickey Knox

ColbyKnox – Head in the Clouds with Jack Bailey – Jack Bailey & Mickey Knox

CumDumpSluts – Jack Bailey – Cumdump #1

CumDumpSluts – Jack Bailey – Cumdump #1

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BlackOnBoys – Jack Bailey, Deepdicc & Ray Diesel

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HungFuckers – Adam Snow & Eddie Patrick tag Jack Bailey

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JasonSparksLive – Tom Bentley & Jack Bailey, Chapter 1

HimErosTV – Backseat Driver – Andre Donovan, Jack Bailey & Peyton Key

HimErosTV – Backseat Driver – Andre Donovan, Jack Bailey & Peyton Key

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RFC – 11 Inch Stuffing – 11Inch King & Jack Bailey

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NextDoorTaboo – Virgin Stepbrother – Jack Bailey & Jordan Starr

GayCest – Hard Lessons – Lance Charger & Jack Bailey

GayCest – Hard Lessons – Lance Charger & Jack Bailey

BrotherCrush – Remember When We Used To Do This – Jack Bailey & Max Lorde

BrotherCrush – Remember When We Used To Do This – Jack Bailey & Max Lorde

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TwinkLoads – Encounter 1 – Killian Knox Bottoms – Jack Bailey, Killian Knox

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FamliyDick – Fighting For His Attention – Jack Bailey & Jax Thirio & Max Lorde

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TwinkTop – Getting Pumped – Jack Bailey, Dolf Dietrich

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NextDoorHomemade – Jax Stacks Troye And Jack – Jax Thirio, Jack Bailey & Troye Jacobs

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FamilyDick – Too Horny To Behave – Jack Bailey & Derek Allen

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RawFuckBoys – Jack Bailey & Romeo Davis – Chapter 2

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CockyBoys – Jack Bailey & Lane Colten

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ScoutBoys – After Camping – Marcus Rivers, Jack Bailey & Troye Jacobs

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OnlyFans – Zayne Bright & Jack Bailey Flip Fuck

OnlyFans – Zayne Bright & Jack Bailey Flip Fuck

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FamilyDick – Flying the Nest – Jax Thirio and Jack Bailey

TherapyDick – The Perfect Roleplay – Johnny Ford & Jack Bailey

TherapyDick – The Perfect Roleplay – Johnny Ford & Jack Bailey

LucasEntertainment – Jack Bailey Bottoms For Dan Saxon

LucasEntertainment – Jack Bailey Bottoms For Dan Saxon

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OnlyFans – Jack Bailey & Jaylen Thomas

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LucasRaunch – Gustavo Cruz Puts Jack Bailey In Bondage

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RaunchyBastards – Breeding Jack Bailey – Jack Bailey & Masyn Thorne

LucasEntertainment – Gustavo Cruz Dominates Jack Bailey

LucasEntertainment – Gustavo Cruz Dominates Jack Bailey

HotHouse – Inseam- Chris Damned & Jack Bailey

HotHouse – Inseam- Chris Damned & Jack Bailey

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DisruptiveFilms – A Virgin No More, The Offering – Dale Savage, Jack Bailey & Scott Finn

RaunchyBastards – I’m Not Gay But His Ass Made Me Cum – Daniel Dean & Jack Bailey

RaunchyBastards – I’m Not Gay But His Ass Made Me Cum – Daniel Dean & Jack Bailey

ColbyKnox – Namaste and Play – Colby Chambers & Jack Bailey

ColbyKnox – Namaste and Play – Colby Chambers & Jack Bailey

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MissionaryBoys – Authority Granted – Ashton Silvers & Jack Bailey

AdultTime – Accidental Gangbang – Chock-Full Of Jocks – Trent Marx, Amone Bane, Jack Bailey, Tony Genius, Michael Seraph & Dereck Defendi

AdultTime – Accidental Gangbang – Chock-Full Of Jocks – Trent Marx, Amone Bane, Jack Bailey, Tony Genius, Michael Seraph & Dereck Defendi

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RaunchyBastards – Too Horny – Jack Bailey & Liam Addison

BoysAtCamp – Whip em Out – Greg McKeon, Jack Bailey & Grey Gold

BoysAtCamp – Whip em Out – Greg McKeon, Jack Bailey & Grey Gold

OnlyFans – Nick Cranston & Jack Bailey

OnlyFans – Nick Cranston & Jack Bailey

RaunchyBastards – Sluts On Parade – Clay, Jack Bailey & Masyn Thorne

RaunchyBastards – Sluts On Parade – Clay, Jack Bailey & Masyn Thorne

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