Jack Bailey Videos

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

Red – Jack Bailey, Edward Terrant & Noah Way

Himeros 774
4 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
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
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
10 months ago Gustavo Cruz Dominates Jack Bailey – Penetrated And Pounded
28 min

Gustavo Cruz Dominates Jack Bailey – Penetrated And Pounded

LucasEntertainment 4.5K
11 months ago A Brat & A Gentleman – Jack Bailey & Colt Spence
46 min

A Brat & A Gentleman – Jack Bailey & Colt Spence

DisruptiveFilms 6.2K
1 year ago 11 Inch Stuffing – Jack Bailey & 11inchking
28 min

11 Inch Stuffing – Jack Bailey & 11inchking

RawFuckClub 3.2K
1 year ago Trick or Treat Gangbang Part 2
31 min

Trick or Treat Gangbang Part 2

RawFuckClub 4.3K
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 Trick or Treat Gangbang Part 1
31 min

Trick or Treat Gangbang Part 1

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

Relaxin’ With Jax – Jax Thirio & Jack Bailey

DadCreep 6.6K
1 year ago Jack Bailey Bottoms For Dan Saxon
27 min

Jack Bailey Bottoms For Dan Saxon

LucasEntertainment 1.4K
1 year ago Head in the Clouds with Jack Bailey
20 min

Head in the Clouds with Jack Bailey

ColbyKnox 404
2 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 370
2 years ago Namaste and Play – Colby Chambers & Jack Bailey
28 min

Namaste and Play – Colby Chambers & Jack Bailey

ColbyKnox 523
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 786
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 536
2 years ago Yellow – Jack Bailey, Derek Cline & Nico Nova
19 min

Yellow – Jack Bailey, Derek Cline & Nico Nova

Himeros 467