Jack Bailey Longest Videos

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

Writer’s Block – Jack Bailey & Nico Coopa

NextDoorStudios 600
3 years ago A Virgin No More – Dale Savage & Jack Bailey
56 min

A Virgin No More – Dale Savage & Jack Bailey

DisruptiveFilms 474
3 years ago Washboard Worship – Damien White, Jack Bailey & Trevor Harris
53 min

Washboard Worship – Damien White, Jack Bailey & Trevor Harris

NextDoorStudios 91
3 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 303
3 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 148
3 years ago Be – Greg McKeon & Jack Bailey
46 min

Be – Greg McKeon & Jack Bailey

DisruptiveFilms 352
11 months ago A Brat & A Gentleman – Jack Bailey & Colt Spence
46 min

A Brat & A Gentleman – Jack Bailey & Colt Spence

DisruptiveFilms 6.2K
5 months 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 4.8K
2 years ago You Missed a Spot – Taylor Reign & Jack Bailey
45 min

You Missed a Spot – Taylor Reign & Jack Bailey

BrotherCrush 238
3 years ago The Perfect Roleplay – Johnny Ford & Jack Bailey
40 min

The Perfect Roleplay – Johnny Ford & Jack Bailey

TherapyDick 185
2 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 445
3 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 308
3 years ago Flying the Nest – Jax Thirio & Jack Bailey
37 min

Flying the Nest – Jax Thirio & Jack Bailey

FamilyDick 198
4 years ago Secret Sexcapades: Stepdad With Benefits – Roman Todd & Jack Bailey
37 min

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

NextDoorStudios 138
2 years ago Too Horny To Behave – Jack Bailey & Derek Allen
36 min

Too Horny To Behave – Jack Bailey & Derek Allen

FamilyDick 289
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 370
2 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 346
2 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 174
2 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 141
3 years ago Workout on the Balcony – Jax Thirio & Jack Bailey
34 min

Workout on the Balcony – Jax Thirio & Jack Bailey

FamilyDick 299