Jack Bailey

Jack’s Gratitude – Jack Bailey and Damian Rose
Brother Crush
24:29 HD
Jack’s Gratitude – Jack Bailey and Damian Rose
6 months ago 5,207 views
First Time Sharing a Bed – Jack Bailey and Damian Rose
Brother Crush
26:38 HD
First Time Sharing a Bed – Jack Bailey and Damian Rose
7 months ago 4,685 views
This Will Make You Feel Better – Jack Bailey and Jack Valor
Brother Crush
25:07 HD
This Will Make You Feel Better – Jack Bailey and Jack Valor
8 months ago 6,755 views
Penetrated And Pounded, Scene 2 – Gustavo Cruz and Jack Bailey
Lucas Entertainment
27:50 HD
Penetrated And Pounded, Scene 2 – Gustavo Cruz and Jack Bailey
11 months ago 4,264 views
A Brat and A Gentleman – Jack Bailey and Colt Spence
Disruptive Films
46:29 HD
A Brat and A Gentleman – Jack Bailey and Colt Spence
12 months ago 7,716 views
Relaxin with Jax – Jax Thirio and Jack Bailey
Dad Creep
33:25 HD
Relaxin with Jax – Jax Thirio and Jack Bailey
1 year ago 9,237 views
Bareback Auditions 24, Thrusted And Pumped Scene 3 – Jack Bailey and Dan Saxon
Lucas Entertainment
27:19 HD
Bareback Auditions 24, Thrusted And Pumped Scene 3 – Jack Bailey and Dan Saxon
1 year ago 4,934 views
Head in the Clouds with Jack Bailey
Colby Knox
19:39 HD
Head in the Clouds with Jack Bailey
2 years ago 3,529 views
Pair of Jacks
Colby Knox
36:15 HD
Pair of Jacks
2 years ago 2,954 views
Namaste and Play – Colby Chambers and Jack Bailey
Colby Knox
27:51 HD
Namaste and Play – Colby Chambers and Jack Bailey
2 years ago 3,985 views
Horny Horror Movie Night – Jack Bailey, Max Romano, Jax Thirio and Andy Adler
Twink Trade
26:59 FHD
Horny Horror Movie Night – Jack Bailey, Max Romano, Jax Thirio and Andy Adler
2 years ago 10,608 views
A Bonding Moment – Jax Thirio, Jack Bailey, Max Romano and Andy Adler
Twink Trade
28:37 FHD
A Bonding Moment – Jax Thirio, Jack Bailey, Max Romano and Andy Adler
2 years ago 5,292 views
Lucas Men Extravaganza – Gay Porn Orgy, Part 02
Lucas Entertainment
26:53 FHD
Lucas Men Extravaganza – Gay Porn Orgy, Part 02
2 years ago 4,776 views
MenPOV, At The Park With Jack Bailey – Darron Bluu and Jack Bailey
Gay Room
29:30 HD
MenPOV, At The Park With Jack Bailey – Darron Bluu and Jack Bailey
2 years ago 5,205 views
Virgin No More, Retaliation – Dale Savage, Jack Bailey and Trevor Harris
Disruptive Films
39:29 HD
Virgin No More, Retaliation – Dale Savage, Jack Bailey and Trevor Harris
2 years ago 10,259 views
Writer’s Block – Jack Bailey and Nico Coopa
Next Door Films
58:19 HD
Writer’s Block – Jack Bailey and Nico Coopa
2 years ago 10,322 views
Out of my way – Jack Bailey and Killian Fox
Disruptive Films
41:14 HD
Out of my way – Jack Bailey and Killian Fox
2 years ago 12,050 views
Jack Bailey and Jacob Acosta
CockyBoys
20:49 HD
Jack Bailey and Jacob Acosta
2 years ago 4,301 views
Backseat Driver – Andre Donovan, Jack Bailey and Peyton Key
HimerosTV
13:37 HD
Backseat Driver – Andre Donovan, Jack Bailey and Peyton Key
2 years ago 3,371 views
Virgin Stepbrother – Jack Bailey and Jordan Starr
Next Door Taboo
33:19 HD
Virgin Stepbrother – Jack Bailey and Jordan Starr
2 years ago 13,005 views
Jack Bailey and Lane Colten
CockyBoys
22:54 HD
Jack Bailey and Lane Colten
2 years ago 6,688 views
Jack Bailey and Sean Xavier
CockyBoys
20:50 HD
Jack Bailey and Sean Xavier
2 years ago 6,127 views
Before Leaving Camp – Greg McKeon, Jack Bailey and Colton McKeon
Boys At Camp
23:33 HD
Before Leaving Camp – Greg McKeon, Jack Bailey and Colton McKeon
2 years ago 3,215 views
You Missed a Spot – Taylor Reign and Jack Bailey
Brother Crush
44:40 HD
You Missed a Spot – Taylor Reign and Jack Bailey
2 years ago 10,183 views
Jack Bailey and Leo Louis
CockyBoys
24:13 HD
Jack Bailey and Leo Louis
2 years ago 6,766 views
The Perfect Pool Day, Part 3 – Isaac Parker, Jack Bailey and Derek Allen
Family Dick
35:00 HD
The Perfect Pool Day, Part 3 – Isaac Parker, Jack Bailey and Derek Allen
3 years ago 5,069 views
Camp Guessing Games – Colton McKeon, Grey Gold, Greg McKeon and Jack Bailey
Boys At Camp
34:05 HD
Camp Guessing Games – Colton McKeon, Grey Gold, Greg McKeon and Jack Bailey
3 years ago 3,738 views
The Perfect Pool Day, Part 2 – Isaac Parker, Jack Bailey and Derek Allen
Family Dick
36:17 HD
The Perfect Pool Day, Part 2 – Isaac Parker, Jack Bailey and Derek Allen
3 years ago 7,333 views
Cannonball Contest – Taylor Reign and Jack Bailey
Brother Crush
30:13 HD
Cannonball Contest – Taylor Reign and Jack Bailey
3 years ago 7,536 views
The Perfect Pool Day – Taylor Reign, Isaac Parker, Jack Bailey and Derek Allen
Family Dick
36:29 HD
The Perfect Pool Day – Taylor Reign, Isaac Parker, Jack Bailey and Derek Allen
3 years ago 8,627 views
Too Horny To Behave – Jack Bailey and Derek Allen
Family Dick
35:34 HD
Too Horny To Behave – Jack Bailey and Derek Allen
3 years ago 7,075 views
Date with Step-Dad – Jack Bailey and Michael Roman
Next Door Taboo
32:26 HD
Date with Step-Dad – Jack Bailey and Michael Roman
3 years ago 7,705 views
Jack Bailey Encounter 3, Romeo Davis Bottoms – Davis Bottoms and Jack Bailey
Twink Loads
23:20 HD
Jack Bailey Encounter 3, Romeo Davis Bottoms – Davis Bottoms and Jack Bailey
3 years ago 6,262 views
Troop Time Chapter 16, Catching Scoutmaster – Jack Bailey, Troye Jacobs and Lance Charger
Scout Boys
19:11 HD
Troop Time Chapter 16, Catching Scoutmaster – Jack Bailey, Troye Jacobs and Lance Charger
3 years ago 3,564 views
Troop Time Chapter 15, After Camping – Marcus Rivers, Jack Bailey, Troye Jacobs and Korzark Kipling
Scout Boys
30:58 HD
Troop Time Chapter 15, After Camping – Marcus Rivers, Jack Bailey, Troye Jacobs and Korzark Kipling
3 years ago 5,912 views
A Virgin No More, The Offering – Dale Savage, Jack Bailey and Scott Finn
Disruptive Films
49:16 HD
A Virgin No More, The Offering – Dale Savage, Jack Bailey and Scott Finn
3 years ago 11,315 views
Getting In Touch With Nature – Colton McKeon, Jack Bailey and Greg McKeon
Boys At Camp
31:00 HD
Getting In Touch With Nature – Colton McKeon, Jack Bailey and Greg McKeon
3 years ago 2,562 views
Remember When We Used To Do This – Jack Bailey and Max Lorde
Brother Crush
31:13 HD
Remember When We Used To Do This – Jack Bailey and Max Lorde
3 years ago 6,789 views
Tom Bentley and Jack Bailey, Chapter 2
Jason Sparks Live
24:36 HD
Tom Bentley and Jack Bailey, Chapter 2
3 years ago 2,753 views
Tom Bentley and Jack Bailey, Chapter 1
Jason Sparks Live
23:58 HD
Tom Bentley and Jack Bailey, Chapter 1
3 years ago 2,364 views