Jack Bailey Latest Videos

3 years ago At The Park with Jack Bailey & Darron Bluu
29 min

At The Park with Jack Bailey & Darron Bluu

GayRoom 3.6K
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 588
3 years ago Writer’s Block – Jack Bailey & Nico Coopa
58 min

Writer’s Block – Jack Bailey & Nico Coopa

NextDoorStudios 707
3 years ago Jack Bailey & Jacob Acosta
21 min

Jack Bailey & Jacob Acosta

CockyBoys 348
3 years ago Backseat Driver – Andre Donovan, Jack Bailey & Andrew Connor
14 min

Backseat Driver – Andre Donovan, Jack Bailey & Andrew Connor

Himeros 418
3 years ago Virgin Stepbrother – Jack Bailey & Jordan Starr
33 min

Virgin Stepbrother – Jack Bailey & Jordan Starr

NextDoorStudios 431
3 years ago Jack Bailey & Lane Colten
23 min

Jack Bailey & Lane Colten

CockyBoys 281
3 years ago Jack Bailey & Sean Xavier
21 min

Jack Bailey & Sean Xavier

CockyBoys 335
3 years ago Before Leaving Camp – Greg McKeon, Jack Bailey & Colton McKeon
23 min

Before Leaving Camp – Greg McKeon, Jack Bailey & Colton McKeon

BoysAtCamp 372
3 years ago Grand Promise – Andre Donovan & Jack Bailey
15 min

Grand Promise – Andre Donovan & Jack Bailey

Himeros 353
3 years ago You Missed a Spot – Taylor Reign & Jack Bailey
45 min

You Missed a Spot – Taylor Reign & Jack Bailey

BrotherCrush 333
3 years ago Jack Bailey & Leo Louis
24 min

Jack Bailey & Leo Louis

CockyBoys 1.4K
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 218
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 289
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 467
3 years ago Too Horny To Behave – Jack Bailey & Derek Allen
36 min

Too Horny To Behave – Jack Bailey & Derek Allen

FamilyDick 403
3 years ago Cannonball Contest – Taylor Reign & Jack Bailey
30 min

Cannonball Contest – Taylor Reign & Jack Bailey

BrotherCrush 180
4 years ago Date with Step-Dad – Jack Bailey & Michael Roman
32 min

Date with Step-Dad – Jack Bailey & Michael Roman

NextDoorStudios 488
4 years ago Incident 335: Turn For The Worse – Jack Bailey
20 min

Incident 335: Turn For The Worse – Jack Bailey

BoysHalfwayHouse 466
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 424
4 years ago Getting In Touch With Nature – Colton McKeon, Jack Bailey & Greg McKeon
31 min

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

BoysAtCamp 146
4 years ago Remember When We Used To Do This? – Jack Bailey & Max Lorde
31 min

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

BrotherCrush 3.2K
4 years ago Horsing Around – Jack Bailey & Benjamin Blue
21 min

Horsing Around – Jack Bailey & Benjamin Blue

ScoutBoys 366
4 years ago The Doctor’s Orders – Jack Bailey & Johnny Ford
31 min

The Doctor’s Orders – Jack Bailey & Johnny Ford

DoctorTapes 421