Jack Bailey Most Liked Videos

3 years ago This Is How It Feels – Jack Bailey & Max Lorde
25 min

This Is How It Feels – Jack Bailey & Max Lorde

BrotherCrush 109
1 year ago Relaxin’ With Jax – Jax Thirio & Jack Bailey
33 min

Relaxin’ With Jax – Jax Thirio & Jack Bailey

DadCreep 6.6K
1 year ago The Breakdown – Jack Bailey, Andre Donovan & Milking Coach
14 min

The Breakdown – Jack Bailey, Andre Donovan & Milking Coach

Himeros 3.3K
2 years ago Jack Bailey & Sean Xavier
21 min

Jack Bailey & Sean Xavier

CockyBoys 279
3 years ago Incident #307: Collaborators Will Be Fucked – Jack Bailey
25 min

Incident #307: Collaborators Will Be Fucked – Jack Bailey

BoysHalfwayHouse 204
2 years ago Jack Bailey & Jacob Acosta
21 min

Jack Bailey & Jacob Acosta

CockyBoys 264
3 years ago A Walk In The Woods – Jack Bailey & Dolf Dietrich
17 min

A Walk In The Woods – Jack Bailey & Dolf Dietrich

ScoutBoys 828
1 year ago Jack Bailey Bottoms For Dan Saxon
27 min

Jack Bailey Bottoms For Dan Saxon

LucasEntertainment 1.4K
3 years ago Jack Bailey & Lance Charger – Teaching My Grandson
19 min

Jack Bailey & Lance Charger – Teaching My Grandson

GayCest 277
4 years ago Jax Thirio Pounds Jack Bailey
32 min

Jax Thirio Pounds Jack Bailey

NextDoorStudios 255
7 months ago This Will Make You Feel Better – Jack Bailey & Jack Valor
25 min

This Will Make You Feel Better – Jack Bailey & Jack Valor

BrotherCrush 4.3K
4 years ago Secret Sexcapades: Stepdad With Benefits – Roman Todd & Jack Bailey
37 min

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

NextDoorStudios 139
3 years ago Jack Bailey & Lance Charger – Interview Prep
24 min

Jack Bailey & Lance Charger – Interview Prep

GayCest 189
2 years ago Grand Promise – Andre Donovan & Jack Bailey
15 min

Grand Promise – Andre Donovan & Jack Bailey

Himeros 279
4 years ago Getting My Stepbrother Wet – Jack Bailey & Daniel Hausser
19 min

Getting My Stepbrother Wet – Jack Bailey & Daniel Hausser

BrotherCrush 110
11 months ago A Brat & A Gentleman – Jack Bailey & Colt Spence
46 min

A Brat & A Gentleman – Jack Bailey & Colt Spence

DisruptiveFilms 6.2K
2 years ago Namaste and Play – Colby Chambers & Jack Bailey
28 min

Namaste and Play – Colby Chambers & Jack Bailey

ColbyKnox 524
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
3 years ago Authority Granted – Jack Bailey & Ashton Silvers
23 min

Authority Granted – Jack Bailey & Ashton Silvers

MissionaryBoys 265
4 years ago Jesse Bolton & Jack Bailey’s Couch Fuck
19 min

Jesse Bolton & Jack Bailey’s Couch Fuck

NextDoorStudios 94