Jack Bailey Most Viewed Videos

2 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 8.3K
2 years ago Trick or Treat Gangbang Part 1
31 min

Trick or Treat Gangbang Part 1

RawFuckClub 6.9K
2 years ago Relaxin’ With Jax – Jax Thirio & Jack Bailey
33 min

Relaxin’ With Jax – Jax Thirio & Jack Bailey

DadCreep 6.6K
1 year ago A Brat & A Gentleman – Jack Bailey & Colt Spence
46 min

A Brat & A Gentleman – Jack Bailey & Colt Spence

DisruptiveFilms 6.4K
3 years ago Twinkology 101 – Dakota Payne, Jack Bailey, Carter DelRey & Trevor Harris
47 min

Twinkology 101 – Dakota Payne, Jack Bailey, Carter DelRey & Trevor Harris

NextDoorStudios 5.2K
9 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 5K
1 year ago Gustavo Cruz Dominates Jack Bailey – Penetrated And Pounded
28 min

Gustavo Cruz Dominates Jack Bailey – Penetrated And Pounded

LucasEntertainment 4.6K
12 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 4.5K
4 years ago Am I Qualified? – David Skylar & Jack Bailey
28 min

Am I Qualified? – David Skylar & Jack Bailey

NextDoorStudios 4.4K
2 years ago Trick or Treat Gangbang Part 2
31 min

Trick or Treat Gangbang Part 2

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

Jack’s Gratitude – Jack Bailey & Damian Rose

BrotherCrush 3.8K
10 months ago First Time Sharing a Bed – Jack Bailey & Damian Rose
27 min

First Time Sharing a Bed – Jack Bailey & Damian Rose

BrotherCrush 3.7K
2 years ago The Breakdown – Jack Bailey, Andre Donovan & Milking Coach
14 min

The Breakdown – Jack Bailey, Andre Donovan & Milking Coach

Himeros 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 11 Inch Stuffing – Jack Bailey & 11inchking
28 min

11 Inch Stuffing – Jack Bailey & 11inchking

RawFuckClub 3.3K
2 years ago Jack Bailey Bottoms For Dan Saxon
27 min

Jack Bailey Bottoms For Dan Saxon

LucasEntertainment 1.5K
3 years ago Jack Bailey & Leo Louis
24 min

Jack Bailey & Leo Louis

CockyBoys 1.3K
9 months ago TRANSMAN Red – Jack Bailey, Edward Terrant & Noah Way
13 min

Red – Jack Bailey, Edward Terrant & Noah Way

Himeros 978
4 years ago A Walk In The Woods – Jack Bailey & Dolf Dietrich
17 min

A Walk In The Woods – Jack Bailey & Dolf Dietrich

ScoutBoys 902
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 837