Jack Bailey Most Viewed Videos

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

A Walk In The Woods – Jack Bailey & Dolf Dietrich

ScoutBoys 973
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 918
3 years ago Writer’s Block – Jack Bailey & Nico Coopa
58 min

Writer’s Block – Jack Bailey & Nico Coopa

NextDoorStudios 704
4 years ago A Virgin No More – Dale Savage & Jack Bailey
56 min

A Virgin No More – Dale Savage & Jack Bailey

DisruptiveFilms 634
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 624
3 years ago Virgin No More: Retaliation – Dale Savage, Jack Bailey & Trevor Harris
39 min

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

DisruptiveFilms 584
3 years ago Namaste and Play – Colby Chambers & Jack Bailey
28 min

Namaste and Play – Colby Chambers & Jack Bailey

ColbyKnox 576
5 years ago Hot Daddy Nights – Jack Bailey & Tristan Jaxx
20 min

Hot Daddy Nights – Jack Bailey & Tristan Jaxx

RawFuckClub 573
3 years ago Yellow – Jack Bailey, Derek Cline & Nico Nova
19 min

Yellow – Jack Bailey, Derek Cline & Nico Nova

Himeros 565
5 years ago Incident 282: A Mouth Made For Sucking – Jack B
12 min

Incident 282: A Mouth Made For Sucking – Jack B

BoysHalfwayHouse 488
3 years ago Date with Step-Dad – Jack Bailey & Michael Roman
32 min

Date with Step-Dad – Jack Bailey & Michael Roman

NextDoorStudios 487
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 482
4 years ago Be – Greg McKeon & Jack Bailey
46 min

Be – Greg McKeon & Jack Bailey

DisruptiveFilms 467
3 years ago The Perfect Pool Day – Taylor Reign, Isaac Parker, Jack Bailey & Derek Allen
36 min

The Perfect Pool Day – Taylor Reign, Isaac Parker, Jack Bailey & Derek Allen

FamilyDick 466
3 years ago Incident 335: Turn For The Worse – Jack Bailey
20 min

Incident 335: Turn For The Worse – Jack Bailey

BoysHalfwayHouse 465
2 years ago Head in the Clouds with Jack Bailey
20 min

Head in the Clouds with Jack Bailey

ColbyKnox 453
4 years ago Stepdad Joins The Show – Brian Bonds & Jack Bailey
21 min

Stepdad Joins The Show – Brian Bonds & Jack Bailey

FamilyDick 451
4 years ago Jack Bailey & Lance Charger – Teaching My Grandson
19 min

Jack Bailey & Lance Charger – Teaching My Grandson

GayCest 450
5 years ago Jack’s Muscle Daddy Gang Bang
26 min

Jack’s Muscle Daddy Gang Bang

RawFuckClub 448
4 years ago The Master’s Grandson – Jack Bailey, Lance Charger & Cole Blue
20 min

The Master’s Grandson – Jack Bailey, Lance Charger & Cole Blue

BoyForSale 447
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 444
4 years ago Dolf Dietrich & Jack Bailey – Getting Pumped
22 min

Dolf Dietrich & Jack Bailey – Getting Pumped

TwinkTop 437
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 434
3 years ago Virgin Stepbrother – Jack Bailey & Jordan Starr
33 min

Virgin Stepbrother – Jack Bailey & Jordan Starr

NextDoorStudios 429