Jack Bailey Videos

3 years ago The Worthiness Review – Jack Bailey & Johnny B
26 min

The Worthiness Review – Jack Bailey & Johnny B

MissionaryBoys 80
3 years ago Incident #307: Collaborators Will Be Fucked – Jack Bailey
25 min

Incident #307: Collaborators Will Be Fucked – Jack Bailey

BoysHalfwayHouse 204
4 years ago Jack’s Muscle Daddy Gang Bang
26 min

Jack’s Muscle Daddy Gang Bang

RawFuckClub 351
4 years ago Hot Daddy Nights – Jack Bailey & Tristan Jaxx
20 min

Hot Daddy Nights – Jack Bailey & Tristan Jaxx

RawFuckClub 520
4 years ago Secret Sexcapades: Service Top – Johnny Ford & Jack Bailey
31 min

Secret Sexcapades: Service Top – Johnny Ford & Jack Bailey

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

Jack Bailey, Deepdicc & Ray Diesel

DownlowBoys 232
4 years ago Incident 282: A Mouth Made For Sucking – Jack B
12 min

Incident 282: A Mouth Made For Sucking – Jack B

BoysHalfwayHouse 424
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
4 years ago Bored StepBros – Alex Meyer & Jack Bailey
21 min

Bored StepBros – Alex Meyer & Jack Bailey

BrotherCrush 287
4 years ago Pretty Young Thang – Johnny Rapid, Alex Meyer & Jack Bailey
21 min

Pretty Young Thang – Johnny Rapid, Alex Meyer & Jack Bailey

JohnnyRapid 109
4 years ago Jack Bailey & Blaine Porter – Lake Need
22 min

Jack Bailey & Blaine Porter – Lake Need

NakedSword 128
4 years ago Jax Thirio Pounds Jack Bailey
32 min

Jax Thirio Pounds Jack Bailey

NextDoorStudios 255
4 years ago Johnny Rapid & Jack Bailey – Lake Need
22 min

Johnny Rapid & Jack Bailey – Lake Need

NakedSword 92
4 years ago Getting My Stepbrother Wet – Jack Bailey & Daniel Hausser
19 min

Getting My Stepbrother Wet – Jack Bailey & Daniel Hausser

BrotherCrush 110
4 years ago Jesse Bolton & Jack Bailey’s Couch Fuck
19 min

Jesse Bolton & Jack Bailey’s Couch Fuck

NextDoorStudios 94
4 years ago I’ll Do Anything Else – Jack Bailey & Jesse Bolton
22 min

I’ll Do Anything Else – Jack Bailey & Jesse Bolton

BrotherCrush 134
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