Jack Bailey Most Viewed 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 8.1K
1 year ago Trick or Treat Gangbang Part 1
31 min

Trick or Treat Gangbang Part 1

RawFuckClub 6.8K
1 year ago Relaxin’ With Jax – Jax Thirio & Jack Bailey
33 min

Relaxin’ With Jax – Jax Thirio & Jack Bailey

DadCreep 6.6K
11 months ago A Brat & A Gentleman – Jack Bailey & Colt Spence
46 min

A Brat & A Gentleman – Jack Bailey & Colt Spence

DisruptiveFilms 6.2K
5 months ago Chock-Full Of Jocks – Jack Bailey, Tony Genius, Trent Marx, Amone Bane, Dereck Defendi & Michael Seraph
45 min

Chock-Full Of Jocks – Jack Bailey, Tony Genius, Trent Marx, Amone Bane, Dereck Defendi & Michael Seraph

AdultTime 4.8K
10 months ago Gustavo Cruz Dominates Jack Bailey – Penetrated And Pounded
28 min

Gustavo Cruz Dominates Jack Bailey – Penetrated And Pounded

LucasEntertainment 4.5K
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
1 year ago Trick or Treat Gangbang Part 2
31 min

Trick or Treat Gangbang Part 2

RawFuckClub 4.3K
5 months ago Jack’s Gratitude – Jack Bailey & Damian Rose
24 min

Jack’s Gratitude – Jack Bailey & Damian Rose

BrotherCrush 3.6K
6 months ago First Time Sharing a Bed – Jack Bailey & Damian Rose
27 min

First Time Sharing a Bed – Jack Bailey & Damian Rose

BrotherCrush 3.5K
2 years ago At The Park with Jack Bailey & Darron Bluu
29 min

At The Park with Jack Bailey & Darron Bluu

GayRoom 3.5K
1 year ago The Breakdown – Jack Bailey, Andre Donovan & Milking Coach
14 min

The Breakdown – Jack Bailey, Andre Donovan & Milking Coach

Himeros 3.3K
1 year ago 11 Inch Stuffing – Jack Bailey & 11inchking
28 min

11 Inch Stuffing – Jack Bailey & 11inchking

RawFuckClub 3.2K
1 year ago Jack Bailey Bottoms For Dan Saxon
27 min

Jack Bailey Bottoms For Dan Saxon

LucasEntertainment 1.4K
2 years ago Jack Bailey & Leo Louis
24 min

Jack Bailey & Leo Louis

CockyBoys 1.2K
3 years ago A Walk In The Woods – Jack Bailey & Dolf Dietrich
17 min

A Walk In The Woods – Jack Bailey & Dolf Dietrich

ScoutBoys 825
2 years ago Horny Horror Movie Night – Jack Bailey, Max Romano, Jax Thirio & Andy Adler
27 min

Horny Horror Movie Night – Jack Bailey, Max Romano, Jax Thirio & Andy Adler

TwinkTrade 788
4 months ago TRANSMAN Red – Jack Bailey, Edward Terrant & Noah Way
13 min

Red – Jack Bailey, Edward Terrant & Noah Way

Himeros 777
2 years ago Writer’s Block – Jack Bailey & Nico Coopa
58 min

Writer’s Block – Jack Bailey & Nico Coopa

NextDoorStudios 600
2 years ago A Bonding Moment – Jax Thirio, Jack Bailey, Max Romano & Andy Adler
29 min

A Bonding Moment – Jax Thirio, Jack Bailey, Max Romano & Andy Adler

TwinkTrade 537