Jack Bailey Longest Videos

1 year ago Relaxin’ With Jax – Jax Thirio & Jack Bailey
33 min

Relaxin’ With Jax – Jax Thirio & Jack Bailey

DadCreep 6.6K
3 years ago We Met At The PrEP Clinic 2 – Jax Thirio, Jack Bailey & Jack Valor
33 min

We Met At The PrEP Clinic 2 – Jax Thirio, Jack Bailey & Jack Valor

NextDoorStudios 68
4 years ago The Garden Boys – Jesse Bolton, Jack Bailey & Jax Thirio
33 min

The Garden Boys – Jesse Bolton, Jack Bailey & Jax Thirio

BrotherCrush 99
3 years ago Jack Bailey & Lance Charger – The Grooming
33 min

Jack Bailey & Lance Charger – The Grooming

BoyForSale 283
3 years ago Jack Bailey & Kane Fox
33 min

Jack Bailey & Kane Fox

CockyBoys 77
2 years ago Virgin Stepbrother – Jack Bailey & Jordan Starr
33 min

Virgin Stepbrother – Jack Bailey & Jordan Starr

NextDoorStudios 340
3 years ago Date with Step-Dad – Jack Bailey & Michael Roman
32 min

Date with Step-Dad – Jack Bailey & Michael Roman

NextDoorStudios 370
4 years ago Jax Thirio Pounds Jack Bailey
32 min

Jax Thirio Pounds Jack Bailey

NextDoorStudios 255
3 years ago The Doctor’s Orders – Jack Bailey & Johnny Ford
31 min

The Doctor’s Orders – Jack Bailey & Johnny Ford

DoctorTapes 321
3 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 109
1 year ago Trick or Treat Gangbang Part 1
31 min

Trick or Treat Gangbang Part 1

RawFuckClub 6.8K
3 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 101
4 years ago Secret Sexcapades: Service Top – Johnny Ford & Jack Bailey
31 min

Secret Sexcapades: Service Top – Johnny Ford & Jack Bailey

NextDoorStudios 135
1 year ago Trick or Treat Gangbang Part 2
31 min

Trick or Treat Gangbang Part 2

RawFuckClub 4.3K
3 years ago Jax Thirio Stacks Jack Bailey & Troye Jacobs
31 min

Jax Thirio Stacks Jack Bailey & Troye Jacobs

NextDoorStudios 214
3 years ago Cannonball Contest – Taylor Reign & Jack Bailey
30 min

Cannonball Contest – Taylor Reign & Jack Bailey

BrotherCrush 119
2 years ago At The Park with Jack Bailey & Darron Bluu
29 min

At The Park with Jack Bailey & Darron Bluu

GayRoom 3.5K
2 years ago A Bonding Moment – Jax Thirio, Jack Bailey, Max Romano & Andy Adler
29 min

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

TwinkTrade 537
3 years ago Am I Qualified? – David Skylar & Jack Bailey
28 min

Am I Qualified? – David Skylar & Jack Bailey

NextDoorStudios 135
4 years ago Jack Bailey, Deepdicc & Ray Diesel
28 min

Jack Bailey, Deepdicc & Ray Diesel

DownlowBoys 233