Jack Bailey Most Liked Videos

4 years ago A Virgin No More – Dale Savage & Jack Bailey
56 min

A Virgin No More – Dale Savage & Jack Bailey

DisruptiveFilms 634
4 years ago My Stepbro’s Dildo – Justin Matthews & Jack Bailey
28 min

My Stepbro’s Dildo – Justin Matthews & Jack Bailey

NextDoorStudios 331
4 years ago Am I Qualified? – David Skylar & Jack Bailey
28 min

Am I Qualified? – David Skylar & Jack Bailey

NextDoorStudios 4.5K
4 years ago Let’s Share A Bath – Jax Thirio, Jack Bailey & Max Lorde
38 min

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

FamilyDick 403
5 years ago Jack’s Muscle Daddy Gang Bang
26 min

Jack’s Muscle Daddy Gang Bang

RawFuckClub 448
3 years ago Writer’s Block – Jack Bailey & Nico Coopa
58 min

Writer’s Block – Jack Bailey & Nico Coopa

NextDoorStudios 704
4 years ago Stepdad Joins The Show – Brian Bonds & Jack Bailey
21 min

Stepdad Joins The Show – Brian Bonds & Jack Bailey

FamilyDick 451
4 years ago Bad Grades, Bad Boy – Jack Bailey & Brian Bonds
15 min

Bad Grades, Bad Boy – Jack Bailey & Brian Bonds

FamilyDick 245
3 years ago Jack Bailey & Lane Colten
23 min

Jack Bailey & Lane Colten

CockyBoys 279
4 years ago Romeo Davis Bottoms: Encounter 1 – Jack Bailey
24 min

Romeo Davis Bottoms: Encounter 1 – Jack Bailey

TwinkLoads 309
5 years ago Hot Daddy Nights – Jack Bailey & Tristan Jaxx
20 min

Hot Daddy Nights – Jack Bailey & Tristan Jaxx

RawFuckClub 573
4 years ago Be – Greg McKeon & Jack Bailey
46 min

Be – Greg McKeon & Jack Bailey

DisruptiveFilms 467
3 years ago Jack Bailey & Leo Louis
24 min

Jack Bailey & Leo Louis

CockyBoys 1.4K
3 years ago You Missed a Spot – Taylor Reign & Jack Bailey
45 min

You Missed a Spot – Taylor Reign & Jack Bailey

BrotherCrush 330
4 years ago Horsing Around – Jack Bailey & Benjamin Blue
21 min

Horsing Around – Jack Bailey & Benjamin Blue

ScoutBoys 355
4 years ago Chris Damned & Jack Bailey – Inseam
25 min

Chris Damned & Jack Bailey – Inseam

HotHouse 206
2 years ago Trick or Treat Gangbang Part 1
31 min

Trick or Treat Gangbang Part 1

RawFuckClub 7.1K
5 years ago Secret Sexcapades: Service Top – Johnny Ford & Jack Bailey
31 min

Secret Sexcapades: Service Top – Johnny Ford & Jack Bailey

NextDoorStudios 181
2 years ago Trick or Treat Gangbang Part 2
31 min

Trick or Treat Gangbang Part 2

RawFuckClub 4.5K
4 years ago The Worthiness Review – Jack Bailey & Johnny B
26 min

The Worthiness Review – Jack Bailey & Johnny B

MissionaryBoys 111
3 years ago The Perfect Pool Day – Taylor Reign, Isaac Parker, Jack Bailey & Derek Allen
36 min

The Perfect Pool Day – Taylor Reign, Isaac Parker, Jack Bailey & Derek Allen

FamilyDick 466
4 years ago A Virgin No More: The Offering – Jack Bailey, Scott Finn & Dale Savage
49 min

A Virgin No More: The Offering – Jack Bailey, Scott Finn & Dale Savage

DisruptiveFilms 416
5 years ago Bored StepBros – Alex Meyer & Jack Bailey
21 min

Bored StepBros – Alex Meyer & Jack Bailey

BrotherCrush 3.4K
4 years ago The Doctor’s Orders – Jack Bailey & Johnny Ford
31 min

The Doctor’s Orders – Jack Bailey & Johnny Ford

DoctorTapes 416