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 935
3 years ago Writer’s Block – Jack Bailey & Nico Coopa
58 min

Writer’s Block – Jack Bailey & Nico Coopa

NextDoorStudios 707
4 years ago A Virgin No More – Dale Savage & Jack Bailey
56 min

A Virgin No More – Dale Savage & Jack Bailey

DisruptiveFilms 645
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 630
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 588
3 years ago Namaste and Play – Colby Chambers & Jack Bailey
28 min

Namaste and Play – Colby Chambers & Jack Bailey

ColbyKnox 577
5 years ago Hot Daddy Nights – Jack Bailey & Tristan Jaxx
20 min

Hot Daddy Nights – Jack Bailey & Tristan Jaxx

RawFuckClub 576
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 495
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 490
4 years ago Date with Step-Dad – Jack Bailey & Michael Roman
32 min

Date with Step-Dad – Jack Bailey & Michael Roman

NextDoorStudios 488
4 years ago Be – Greg McKeon & Jack Bailey
46 min

Be – Greg McKeon & Jack Bailey

DisruptiveFilms 469
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 467
4 years ago Incident 335: Turn For The Worse – Jack Bailey
20 min

Incident 335: Turn For The Worse – Jack Bailey

BoysHalfwayHouse 466
5 years ago Jack’s Muscle Daddy Gang Bang
26 min

Jack’s Muscle Daddy Gang Bang

RawFuckClub 460
4 years ago Jack Bailey & Lance Charger – Teaching My Grandson
19 min

Jack Bailey & Lance Charger – Teaching My Grandson

GayCest 458
4 years ago Stepdad Joins The Show – Brian Bonds & Jack Bailey
21 min

Stepdad Joins The Show – Brian Bonds & Jack Bailey

FamilyDick 458
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 455
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 453
2 years ago Head in the Clouds with Jack Bailey
20 min

Head in the Clouds with Jack Bailey

ColbyKnox 453
4 years ago Dolf Dietrich & Jack Bailey – Getting Pumped
22 min

Dolf Dietrich & Jack Bailey – Getting Pumped

TwinkTop 443
4 years ago Jack Bailey & Lance Charger – Top Training
19 min

Jack Bailey & Lance Charger – Top Training

TwinkTop 436
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 434