Jack Bailey Longest Videos

2 years ago First Time Sharing a Bed – Jack Bailey & Damian Rose
27 min

First Time Sharing a Bed – Jack Bailey & Damian Rose

BrotherCrush 3.9K
3 years ago Jack Bailey Bottoms For Dan Saxon
27 min

Jack Bailey Bottoms For Dan Saxon

LucasEntertainment 1.6K
3 years ago Babylon Prince, Brian Bonds, Bruno Galvez, Derek Kage, Gustavo Cruz, Harold Lopez, Jack Bailey, Kosta Viking & Santos – Lucas Men Extravaganza Gay Orgy Part 2
27 min

Babylon Prince, Brian Bonds, Bruno Galvez, Derek Kage, Gustavo Cruz, Harold Lopez, Jack Bailey, Kosta Viking & Santos – Lucas Men Extravaganza Gay Orgy Part 2

LucasEntertainment 522
5 years ago Jack’s Muscle Daddy Gang Bang
26 min

Jack’s Muscle Daddy Gang Bang

RawFuckClub 534
5 years ago The Worthiness Review – Jack Bailey & Johnny B
26 min

The Worthiness Review – Jack Bailey & Johnny B

MissionaryBoys 128
4 years ago Killian Knox Bottoms for Jack Bailey
25 min

Killian Knox Bottoms for Jack Bailey

TwinkLoads 411
5 years ago Incident #307: Collaborators Will Be Fucked – Jack Bailey
25 min

Incident #307: Collaborators Will Be Fucked – Jack Bailey

BoysHalfwayHouse 277
2 years ago This Will Make You Feel Better – Jack Bailey & Jack Valor
25 min

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

BrotherCrush 4.7K
4 years ago This Is How It Feels – Jack Bailey & Max Lorde
25 min

This Is How It Feels – Jack Bailey & Max Lorde

BrotherCrush 3.2K
5 years ago Twink Fuck Hole with Jack Bailey
25 min

Twink Fuck Hole with Jack Bailey

MaverickMen 364
4 years ago Chris Damned & Jack Bailey – Inseam
25 min

Chris Damned & Jack Bailey – Inseam

HotHouse 251
2 years ago Jack’s Gratitude – Jack Bailey & Damian Rose
24 min

Jack’s Gratitude – Jack Bailey & Damian Rose

BrotherCrush 3.9K
4 years ago Jack Bailey & Leo Louis
24 min

Jack Bailey & Leo Louis

CockyBoys 1.4K
3 years ago Making Daddy Proud – Bama Romello, Chase Steele, Jack Bailey, Nate Grimes & Nico Nova
24 min

Making Daddy Proud – Bama Romello, Chase Steele, Jack Bailey, Nate Grimes & Nico Nova

Himeros 8.6K
5 years ago Jack Bailey & Lance Charger – Interview Prep
24 min

Jack Bailey & Lance Charger – Interview Prep

GayCest 342
4 years ago Romeo Davis Bottoms: Encounter 1 – Jack Bailey
24 min

Romeo Davis Bottoms: Encounter 1 – Jack Bailey

TwinkLoads 347
4 years ago Jack Bailey & Lane Colten
23 min

Jack Bailey & Lane Colten

CockyBoys 299
4 years ago Authority Granted – Jack Bailey & Ashton Silvers
23 min

Authority Granted – Jack Bailey & Ashton Silvers

MissionaryBoys 315
3 years ago Babylon Prince, Brian Bonds, Bruno Galvez, Derek Kage, Gustavo Cruz, Harold Lopez, Jack Bailey, Kosta Viking & Santos – Lucas Men Extravaganza Gay Orgy Part 1
23 min

Babylon Prince, Brian Bonds, Bruno Galvez, Derek Kage, Gustavo Cruz, Harold Lopez, Jack Bailey, Kosta Viking & Santos – Lucas Men Extravaganza Gay Orgy Part 1

LucasEntertainment 507
4 years ago Before Leaving Camp – Greg McKeon, Jack Bailey & Colton McKeon
23 min

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

BoysAtCamp 409
5 years ago I’ll Do Anything Else – Jack Bailey & Jesse Bolton
22 min

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

BrotherCrush 252
4 years ago Dolf Dietrich & Jack Bailey – Getting Pumped
22 min

Dolf Dietrich & Jack Bailey – Getting Pumped

TwinkTop 466
5 years ago Johnny Rapid & Jack Bailey – Lake Need
22 min

Johnny Rapid & Jack Bailey – Lake Need

NakedSword 134
5 years ago Jack Bailey & Blaine Porter – Lake Need
22 min

Jack Bailey & Blaine Porter – Lake Need

NakedSword 194