Jack Bailey Longest Videos

3 years ago Writer’s Block – Jack Bailey & Nico Coopa
58 min

Writer’s Block – Jack Bailey & Nico Coopa

NextDoorStudios 704
4 years ago A Virgin No More – Dale Savage & Jack Bailey
56 min

A Virgin No More – Dale Savage & Jack Bailey

DisruptiveFilms 633
4 years ago Washboard Worship – Damien White, Jack Bailey & Trevor Harris
53 min

Washboard Worship – Damien White, Jack Bailey & Trevor Harris

NextDoorStudios 138
4 years ago A Virgin No More: The Offering – Jack Bailey, Scott Finn & Dale Savage
49 min

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

DisruptiveFilms 415
4 years ago Twinkology 101 – Dakota Payne, Jack Bailey, Carter DelRey & Trevor Harris
47 min

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

NextDoorStudios 5.3K
2 years ago A Brat & A Gentleman – Jack Bailey & Colt Spence
46 min

A Brat & A Gentleman – Jack Bailey & Colt Spence

DisruptiveFilms 6.6K
4 years ago Be – Greg McKeon & Jack Bailey
46 min

Be – Greg McKeon & Jack Bailey

DisruptiveFilms 467
1 year ago Chock-Full Of Jocks – Jack Bailey, Tony Genius, Trent Marx, Amone Bane, Dereck Defendi & Michael Seraph
45 min

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

AdultTime 5.3K
3 years ago You Missed a Spot – Taylor Reign & Jack Bailey
45 min

You Missed a Spot – Taylor Reign & Jack Bailey

BrotherCrush 330
4 years ago The Perfect Roleplay – Johnny Ford & Jack Bailey
40 min

The Perfect Roleplay – Johnny Ford & Jack Bailey

TherapyDick 7.4K
3 years ago Virgin No More: Retaliation – Dale Savage, Jack Bailey & Trevor Harris
39 min

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

DisruptiveFilms 584
4 years ago Let’s Share A Bath – Jax Thirio, Jack Bailey & Max Lorde
38 min

Let’s Share A Bath – Jax Thirio, Jack Bailey & Max Lorde

FamilyDick 403
4 years ago Flying the Nest – Jax Thirio & Jack Bailey
37 min

Flying the Nest – Jax Thirio & Jack Bailey

FamilyDick 231
5 years ago Secret Sexcapades: Stepdad With Benefits – Roman Todd & Jack Bailey
37 min

Secret Sexcapades: Stepdad With Benefits – Roman Todd & Jack Bailey

NextDoorStudios 179
3 years ago Too Horny To Behave – Jack Bailey & Derek Allen
36 min

Too Horny To Behave – Jack Bailey & Derek Allen

FamilyDick 398
2 years ago Pair of Jacks – Colby Chambers, Jack Bailey, Jack Valor & Mickey Knox
36 min

Pair of Jacks – Colby Chambers, Jack Bailey, Jack Valor & Mickey Knox

ColbyKnox 434
3 years ago The Perfect Pool Day – Taylor Reign, Isaac Parker, Jack Bailey & Derek Allen
36 min

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

FamilyDick 466
3 years ago The Perfect Pool Day Part 2 – Isaac Parker, Jack Bailey & Derek Allen
36 min

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

FamilyDick 286
4 years ago Workout on the Balcony – Jax Thirio & Jack Bailey
34 min

Workout on the Balcony – Jax Thirio & Jack Bailey

FamilyDick 339
3 years ago Camp Guessing Games – Greg McKeon, Jack Bailey, Colton McKeon & Grey Gold
34 min

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

BoysAtCamp 209
4 years ago Jack Bailey & Lance Charger – The Grooming
33 min

Jack Bailey & Lance Charger – The Grooming

BoyForSale 354
4 years ago Jack Bailey & Kane Fox
33 min

Jack Bailey & Kane Fox

CockyBoys 128
3 years ago Virgin Stepbrother – Jack Bailey & Jordan Starr
33 min

Virgin Stepbrother – Jack Bailey & Jordan Starr

NextDoorStudios 429
2 years ago Relaxin’ With Jax – Jax Thirio & Jack Bailey
33 min

Relaxin’ With Jax – Jax Thirio & Jack Bailey

DadCreep 6.8K