Jack Bailey Latest Videos

11 months ago TRANSMAN The Parachute – Jack Bailey & Noah Way
15 min

The Parachute – Jack Bailey & Noah Way

Himeros 2K
12 months ago Detention Wedgie – Reese Rideout & Jack Bailey
29 min

Detention Wedgie – Reese Rideout & Jack Bailey

GayRoom 4.1K
2 years ago TRANSMAN Red – Jack Bailey, Edward Terrant & Noah Way
13 min

Red – Jack Bailey, Edward Terrant & Noah Way

Himeros 1.2K
2 years 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 5.4K
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 3.9K
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 4.7K
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 A Brat & A Gentleman – Jack Bailey & Colt Spence
46 min

A Brat & A Gentleman – Jack Bailey & Colt Spence

DisruptiveFilms 6.7K
2 years ago 11 Inch Stuffing – Jack Bailey & 11inchking
28 min

11 Inch Stuffing – Jack Bailey & 11inchking

RawFuckClub 3.6K
2 years ago Trick or Treat Gangbang Part 2
31 min

Trick or Treat Gangbang Part 2

RawFuckClub 4.6K
2 years ago The Breakdown – Jack Bailey, Andre Donovan & Milking Coach
14 min

The Breakdown – Jack Bailey, Andre Donovan & Milking Coach

Himeros 3.8K
2 years ago Trick or Treat Gangbang Part 1
31 min

Trick or Treat Gangbang Part 1

RawFuckClub 7.2K
3 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
3 years ago Relaxin’ With Jax – Jax Thirio & Jack Bailey
33 min

Relaxin’ With Jax – Jax Thirio & Jack Bailey

DadCreep 6.9K
3 years ago Jack Bailey Bottoms For Dan Saxon
27 min

Jack Bailey Bottoms For Dan Saxon

LucasEntertainment 1.6K
3 years ago Head in the Clouds with Jack Bailey
20 min

Head in the Clouds with Jack Bailey

ColbyKnox 479
3 years ago Pair of Jacks – Colby Chambers, Jack Bailey, Jack Valor & Mickey Knox
36 min

Pair of Jacks – Colby Chambers, Jack Bailey, Jack Valor & Mickey Knox

ColbyKnox 441
3 years ago Namaste and Play – Colby Chambers & Jack Bailey
28 min

Namaste and Play – Colby Chambers & Jack Bailey

ColbyKnox 596
3 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 1K
3 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 679
3 years ago Yellow – Jack Bailey, Derek Cline & Nico Nova
19 min

Yellow – Jack Bailey, Derek Cline & Nico Nova

Himeros 588
3 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 2
27 min

Babylon Prince, Brian Bonds, Bruno Galvez, Derek Kage, Gustavo Cruz, Harold Lopez, Jack Bailey, Kosta Viking & Santos – Lucas Men Extravaganza Gay Orgy Part 2

LucasEntertainment 522
3 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 507