Jack Bailey Longest Videos

1 year 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 8.2K
3 years ago Jack Bailey & Lance Charger – Interview Prep
24 min

Jack Bailey & Lance Charger – Interview Prep

GayCest 190
3 years ago Romeo Davis Bottoms: Encounter 1 – Jack Bailey
24 min

Romeo Davis Bottoms: Encounter 1 – Jack Bailey

TwinkLoads 206
2 years ago Before Leaving Camp – Greg McKeon, Jack Bailey & Colton McKeon
23 min

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

BoysAtCamp 266
2 years ago Jack Bailey & Lane Colten
23 min

Jack Bailey & Lane Colten

CockyBoys 219
3 years ago Authority Granted – Jack Bailey & Ashton Silvers
23 min

Authority Granted – Jack Bailey & Ashton Silvers

MissionaryBoys 265
2 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 359
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 Johnny Rapid & Jack Bailey – Lake Need
22 min

Johnny Rapid & Jack Bailey – Lake Need

NakedSword 92
3 years ago Dolf Dietrich & Jack Bailey – Getting Pumped
22 min

Dolf Dietrich & Jack Bailey – Getting Pumped

TwinkTop 368
4 years ago Jack Bailey & Blaine Porter – Lake Need
22 min

Jack Bailey & Blaine Porter – Lake Need

NakedSword 128
3 years ago Romeo Davis Bottoms for Jack Bailey
22 min

Romeo Davis Bottoms for Jack Bailey

TwinkLoads 265
3 years ago An Obedient Ordination – Jack Bailey & Johnny B
22 min

An Obedient Ordination – Jack Bailey & Johnny B

MissionaryBoys 86
2 years ago Jack Bailey & Sean Xavier
21 min

Jack Bailey & Sean Xavier

CockyBoys 280
2 years ago Jack Bailey & Jacob Acosta
21 min

Jack Bailey & Jacob Acosta

CockyBoys 264
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 Stepdad Joins The Show – Brian Bonds & Jack Bailey
21 min

Stepdad Joins The Show – Brian Bonds & Jack Bailey

FamilyDick 330
4 years ago Bored StepBros – Alex Meyer & Jack Bailey
21 min

Bored StepBros – Alex Meyer & Jack Bailey

BrotherCrush 287
3 years ago Horsing Around – Jack Bailey & Benjamin Blue
21 min

Horsing Around – Jack Bailey & Benjamin Blue

ScoutBoys 229
4 years ago Hot Daddy Nights – Jack Bailey & Tristan Jaxx
20 min

Hot Daddy Nights – Jack Bailey & Tristan Jaxx

RawFuckClub 520