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CockyBoys – Jack Bailey & Sean Xavier

CockyBoys – Jack Bailey & Sean Xavier

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CockyBoys – Jack Bailey & Leo Louis

CockyBoys – Jack Bailey & Jacob Acosta

CockyBoys – Jack Bailey & Jacob Acosta

CockyBoys – Jack Bailey & Lane Colten

CockyBoys – Jack Bailey & Lane Colten

CockyBoys – Bailey Zane & Jordan Starr

CockyBoys – Bailey Zane & Jordan Starr

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FamilyDick – Bad Grades, Bad Boy – Jack Bailey and Brian Bonds

CockyBoys – Love Happens – Austin Avery, Kane Fox and Adrian Hart

CockyBoys – Love Happens – Austin Avery, Kane Fox and Adrian Hart

TherapyDick – The Perfect Roleplay – Johnny Ford & Jack Bailey

TherapyDick – The Perfect Roleplay – Johnny Ford & Jack Bailey

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FamilyDick – Flying the Nest – Jax Thirio and Jack Bailey

CockyBoys – Just A Perfect Day – Jack Valor & Lyle Isara

CockyBoys – Just A Perfect Day – Jack Valor & Lyle Isara

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

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

GayCest – Hard Lessons – Lance Charger & Jack Bailey

GayCest – Hard Lessons – Lance Charger & Jack Bailey

RaunchyBastards – Too Horny – Jack Bailey & Liam Addison

RaunchyBastards – Too Horny – Jack Bailey & Liam Addison

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

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

OnlyFans – Jack Bailey & Jaylen Thomas

OnlyFans – Jack Bailey & Jaylen Thomas

DisruptiveFilms – Virgin No More: Retaliation – Dale Savage, Jack Bailey & Trevor Harris

DisruptiveFilms – Virgin No More: Retaliation – Dale Savage, Jack Bailey & Trevor Harris

CockyBoys – Ari Avanti and Kane Fox

CockyBoys – Ari Avanti and Kane Fox

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LucasEntertainment – Jack Bailey Bottoms For Dan Saxon

CockyBoys – Jack Aries & Jake Mathews

CockyBoys – Jack Aries & Jake Mathews

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

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

RawFuckBoys – Jack Bailey & Romeo Davis – Chapter 2

RawFuckBoys – Jack Bailey & Romeo Davis – Chapter 2

TwinkTop – Getting Pumped – Jack Bailey, Dolf Dietrich

TwinkTop – Getting Pumped – Jack Bailey, Dolf Dietrich

BrotherCrush – This Is How It Feels – Max Lorde & Jack Bailey

BrotherCrush – This Is How It Feels – Max Lorde & Jack Bailey

RaunchyBastards – Breeding Jack Bailey – Jack Bailey & Masyn Thorne

RaunchyBastards – Breeding Jack Bailey – Jack Bailey & Masyn Thorne

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

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CockyBoys – Flynn Fenix & Jack Aries

CockyBoys – Evan Knoxx & Kane Fox

CockyBoys – Evan Knoxx & Kane Fox

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HotHouse – Inseam- Chris Damned & Jack Bailey

JasonSparksLive – Tom Bentley & Jack Bailey, Chapter 1

JasonSparksLive – Tom Bentley & Jack Bailey, Chapter 1

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

CockyBoys – Alex Gonzalez & Kane Fox

CockyBoys – Alex Gonzalez & Kane Fox

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LucasEntertainment – Gustavo Cruz Dominates Jack Bailey

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CockyBoys – Gage Palmer & Kane Fox

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BrotherCrush – Cannonball Contest – Taylor Reign & Jack Bailey

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JasonSparksLive – Tom Bentley & Jack Bailey, Chapter 2

CumDumpSluts – Jack Bailey – Cumdump #1

CumDumpSluts – Jack Bailey – Cumdump #1

NextDoorTwink – Twinkology 101 – Dakota Payne, Jack Bailey, Carter DelRey, Trevor Harris

NextDoorTwink – Twinkology 101 – Dakota Payne, Jack Bailey, Carter DelRey, Trevor Harris

NextDoorTaboo – Virgin Stepbrother – Jack Bailey & Jordan Starr

NextDoorTaboo – Virgin Stepbrother – Jack Bailey & Jordan Starr

HungFuckers – Adam Snow & Eddie Patrick tag Jack Bailey

HungFuckers – Adam Snow & Eddie Patrick tag Jack Bailey

CockyBoys – Kane Fox & Oliver Carter

CockyBoys – Kane Fox & Oliver Carter

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

FamilyDick – Workout On The Balcony – Jack Bailey and Jax Thirio

FamilyDick – Workout On The Balcony – Jack Bailey and Jax Thirio

CockyBoys – Alfonso Osnaya & Jack Waters

CockyBoys – Alfonso Osnaya & Jack Waters

TwinkTrade – A Bonding Moment – Jax Thirio, Jack Bailey, Max Romano, Andy Adler

TwinkTrade – A Bonding Moment – Jax Thirio, Jack Bailey, Max Romano, Andy Adler

CockyBoys – Kane Fox & Max Mabry

CockyBoys – Kane Fox & Max Mabry

DisruptiveFilms – Be – Jack Bailey & Greg McKeon

DisruptiveFilms – Be – Jack Bailey & Greg McKeon

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CockyBoys – Kane Fox & Tristan Hunter

BoysAtCamp – Camp Guessing Games – Colton McKeon, Grey Gold, Greg McKeon & Jack Bailey

BoysAtCamp – Camp Guessing Games – Colton McKeon, Grey Gold, Greg McKeon & Jack Bailey

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