Jack Bailey Videos

11 Inch Stuffing – Jack Bailey & 11inchking

11 Inch Stuffing – Jack Bailey & 11inchking

1.1K views 28 min
1 day ago RawFuckClub
Trick or Treat Gangbang Part 2

Trick or Treat Gangbang Part 2

2.7K views 31 min
3 weeks ago RawFuckClub
The Breakdown – Jack Bailey, Andre Donovan & Milking Coach

The Breakdown – Jack Bailey, Andre Donovan & Milking Coach

2.2K views 14 min
3 weeks ago Himeros
Trick or Treat Gangbang Part 1

Trick or Treat Gangbang Part 1

4.9K views 31 min
4 weeks ago RawFuckClub
Making Daddy Proud – Bama Romello, Chase Steele, Jack Bailey, Nate Grimes & Nico Nova

Making Daddy Proud – Bama Romello, Chase Steele, Jack Bailey, Nate Grimes & Nico Nova

6.7K views 24 min
2 months ago Himeros
Relaxin’ With Jax – Jax Thirio & Jack Bailey

Relaxin’ With Jax – Jax Thirio & Jack Bailey

5.6K views 33 min
4 months ago DadCreep
Jack Bailey Bottoms For Dan Saxon

Jack Bailey Bottoms For Dan Saxon

626 views 27 min
4 months ago LucasEntertainment
Head in the Clouds with Jack Bailey

Head in the Clouds with Jack Bailey

191 views 20 min
5 months ago ColbyKnox
Pair of Jacks – Colby Chambers, Jack Bailey, Jack Valor & Mickey Knox

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

210 views 36 min
6 months ago ColbyKnox
Namaste and Play – Colby Chambers & Jack Bailey

Namaste and Play – Colby Chambers & Jack Bailey

213 views 28 min
6 months ago ColbyKnox
Horny Horror Movie Night – Jack Bailey, Max Romano, Jax Thirio & Andy Adler

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

359 views 27 min
7 months ago TwinkTrade
A Bonding Moment – Jax Thirio, Jack Bailey, Max Romano & Andy Adler

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

205 views 29 min
7 months ago TwinkTrade
Yellow – Jack Bailey, Derek Cline & Nico Nova

Yellow – Jack Bailey, Derek Cline & Nico Nova

194 views 19 min
9 months ago Himeros
Babylon Prince, Brian Bonds, Bruno Galvez, Derek Kage, Gustavo Cruz, Harold Lopez, Jack Bailey, Kosta Viking & Santos – Lucas Men Extravaganza Gay Orgy Part 2

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

106 views 27 min
9 months ago LucasEntertainment
Babylon Prince, Brian Bonds, Bruno Galvez, Derek Kage, Gustavo Cruz, Harold Lopez, Jack Bailey, Kosta Viking & Santos – Lucas Men Extravaganza Gay Orgy Part 1

Babylon Prince, Brian Bonds, Bruno Galvez, Derek Kage, Gustavo Cruz, Harold Lopez, Jack Bailey, Kosta Viking & Santos – Lucas Men Extravaganza Gay Orgy Part 1

138 views 23 min
9 months ago LucasEntertainment
At The Park with Jack Bailey & Darron Bluu

At The Park with Jack Bailey & Darron Bluu

203 views 29 min
10 months ago GayRoom
Virgin No More: Retaliation – Dale Savage, Jack Bailey & Trevor Harris

Virgin No More: Retaliation – Dale Savage, Jack Bailey & Trevor Harris

128 views 39 min
12 months ago DisruptiveFilms
Writer’s Block – Jack Bailey & Nico Coopa

Writer’s Block – Jack Bailey & Nico Coopa

203 views 58 min
1 year ago NextDoorStudios
Jack Bailey & Jacob Acosta

Jack Bailey & Jacob Acosta

71 views 21 min
1 year ago CockyBoys
Backseat Driver – Andre Donovan, Jack Bailey & Andrew Connor

Backseat Driver – Andre Donovan, Jack Bailey & Andrew Connor

152 views 14 min
1 year ago Himeros