Jack Bailey Most Viewed Videos

3 years ago Jack Bailey & Lane Colten
23 min

Jack Bailey & Lane Colten

CockyBoys 279
4 years ago Twink Fuck Hole with Jack Bailey
25 min

Twink Fuck Hole with Jack Bailey

MaverickMen 276
4 years ago Incident #307: Collaborators Will Be Fucked – Jack Bailey
25 min

Incident #307: Collaborators Will Be Fucked – Jack Bailey

BoysHalfwayHouse 262
4 years ago Jax Thirio Stacks Jack Bailey & Troye Jacobs
31 min

Jax Thirio Stacks Jack Bailey & Troye Jacobs

NextDoorStudios 262
4 years ago Bad Grades, Bad Boy – Jack Bailey & Brian Bonds
15 min

Bad Grades, Bad Boy – Jack Bailey & Brian Bonds

FamilyDick 245
5 years ago I’ll Do Anything Else – Jack Bailey & Jesse Bolton
22 min

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

BrotherCrush 234
4 years ago Flying the Nest – Jax Thirio & Jack Bailey
37 min

Flying the Nest – Jax Thirio & Jack Bailey

FamilyDick 231
4 years ago Whip ‘em Out – Greg McKeon, Jack Bailey & Grey Gold
27 min

Whip ‘em Out – Greg McKeon, Jack Bailey & Grey Gold

BoysAtCamp 224
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 Chris Damned & Jack Bailey – Inseam
25 min

Chris Damned & Jack Bailey – Inseam

HotHouse 206
5 years ago Secret Sexcapades: Service Top – Johnny Ford & Jack Bailey
31 min

Secret Sexcapades: Service Top – Johnny Ford & Jack Bailey

NextDoorStudios 181
5 years ago Jack Bailey & Blaine Porter – Lake Need
22 min

Jack Bailey & Blaine Porter – Lake Need

NakedSword 180
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 Cannonball Contest – Taylor Reign & Jack Bailey
30 min

Cannonball Contest – Taylor Reign & Jack Bailey

BrotherCrush 177
5 years ago Getting My Stepbrother Wet – Jack Bailey & Daniel Hausser
19 min

Getting My Stepbrother Wet – Jack Bailey & Daniel Hausser

BrotherCrush 162
4 years ago Assigned Companions – Ashton Silvers & Jack Bailey
19 min

Assigned Companions – Ashton Silvers & Jack Bailey

MissionaryBoys 152
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 145
4 years ago Washboard Worship – Damien White, Jack Bailey & Trevor Harris
53 min

Washboard Worship – Damien White, Jack Bailey & Trevor Harris

NextDoorStudios 138
5 years ago Pretty Young Thang – Johnny Rapid, Alex Meyer & Jack Bailey
21 min

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

JohnnyRapid 136
4 years ago Jack Bailey & Kane Fox
33 min

Jack Bailey & Kane Fox

CockyBoys 128
4 years ago Let’s Share A Bath – Jax Thirio, Jack Bailey & Max Lorde
28 min

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

FamilyDick 127
5 years ago The Garden Boys – Jesse Bolton, Jack Bailey & Jax Thirio
33 min

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

BrotherCrush 125
5 years ago Jesse Bolton & Jack Bailey’s Couch Fuck
19 min

Jesse Bolton & Jack Bailey’s Couch Fuck

NextDoorStudios 123
5 years ago Johnny Rapid & Jack Bailey – Lake Need
22 min

Johnny Rapid & Jack Bailey – Lake Need

NakedSword 117