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 8.6K
4 years ago The Perfect Roleplay – Johnny Ford & Jack Bailey
40 min

The Perfect Roleplay – Johnny Ford & Jack Bailey

TherapyDick 7.4K
2 years ago Trick or Treat Gangbang Part 1
31 min

Trick or Treat Gangbang Part 1

RawFuckClub 7.1K
2 years ago Relaxin’ With Jax – Jax Thirio & Jack Bailey
33 min

Relaxin’ With Jax – Jax Thirio & Jack Bailey

DadCreep 6.8K
2 years ago A Brat & A Gentleman – Jack Bailey & Colt Spence
46 min

A Brat & A Gentleman – Jack Bailey & Colt Spence

DisruptiveFilms 6.7K
4 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 5.3K
1 year 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 5.3K
2 years ago Gustavo Cruz Dominates Jack Bailey – Penetrated And Pounded
28 min

Gustavo Cruz Dominates Jack Bailey – Penetrated And Pounded

LucasEntertainment 4.8K
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 4.6K
4 years ago Am I Qualified? – David Skylar & Jack Bailey
28 min

Am I Qualified? – David Skylar & Jack Bailey

NextDoorStudios 4.6K
2 years ago Trick or Treat Gangbang Part 2
31 min

Trick or Treat Gangbang Part 2

RawFuckClub 4.5K
9 months ago Detention Wedgie – Reese Rideout & Jack Bailey
29 min

Detention Wedgie – Reese Rideout & Jack Bailey

GayRoom 4K
2 years ago Jack’s Gratitude – Jack Bailey & Damian Rose
24 min

Jack’s Gratitude – Jack Bailey & Damian Rose

BrotherCrush 3.9K
2 years ago First Time Sharing a Bed – Jack Bailey & Damian Rose
27 min

First Time Sharing a Bed – Jack Bailey & Damian Rose

BrotherCrush 3.8K
2 years ago The Breakdown – Jack Bailey, Andre Donovan & Milking Coach
14 min

The Breakdown – Jack Bailey, Andre Donovan & Milking Coach

Himeros 3.8K
3 years ago At The Park with Jack Bailey & Darron Bluu
29 min

At The Park with Jack Bailey & Darron Bluu

GayRoom 3.6K
2 years ago 11 Inch Stuffing – Jack Bailey & 11inchking
28 min

11 Inch Stuffing – Jack Bailey & 11inchking

RawFuckClub 3.5K
5 years ago Bored StepBros – Alex Meyer & Jack Bailey
21 min

Bored StepBros – Alex Meyer & Jack Bailey

BrotherCrush 3.4K
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
4 years ago Remember When We Used To Do This? – Jack Bailey & Max Lorde
31 min

Remember When We Used To Do This? – Jack Bailey & Max Lorde

BrotherCrush 3.2K
8 months ago TRANSMAN The Parachute – Jack Bailey & Noah Way
15 min

The Parachute – Jack Bailey & Noah Way

Himeros 1.9K
3 years ago Jack Bailey Bottoms For Dan Saxon
27 min

Jack Bailey Bottoms For Dan Saxon

LucasEntertainment 1.6K
4 years ago Jack Bailey & Leo Louis
24 min

Jack Bailey & Leo Louis

CockyBoys 1.4K
1 year ago TRANSMAN Red – Jack Bailey, Edward Terrant & Noah Way
13 min

Red – Jack Bailey, Edward Terrant & Noah Way

Himeros 1.2K