Jack Bailey

Jack’s Gratitude – Jack Bailey and Damian Rose
Brother Crush
24:29 HD
Jack’s Gratitude – Jack Bailey and Damian Rose
9 months ago 5,615 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
10 months ago 5,145 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
11 months ago 7,160 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
1 year ago 4,387 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
1 year ago 8,022 views
Relaxin with Jax – Jax Thirio and Jack Bailey
Dad Creep
33:25 HD
Relaxin with Jax – Jax Thirio and Jack Bailey
2 years ago 9,413 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
2 years ago 5,021 views
Head in the Clouds with Jack Bailey
Colby Knox
19:39 HD
Head in the Clouds with Jack Bailey
2 years ago 3,623 views
Pair of Jacks
Colby Knox
36:15 HD
Pair of Jacks
2 years ago 3,053 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 4,109 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 10,852 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 5,453 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 4,893 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 5,337 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 10,534 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 10,461 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 12,339 views
Jack Bailey and Jacob Acosta
CockyBoys
20:49 HD
Jack Bailey and Jacob Acosta
2 years ago 4,417 views
Backseat Driver – Andre Donovan, Jack Bailey and Peyton Key
HimerosTV
13:37 HD
Backseat Driver – Andre Donovan, Jack Bailey and Peyton Key
3 years ago 3,472 views
Virgin Stepbrother – Jack Bailey and Jordan Starr
Next Door Taboo
33:19 HD
Virgin Stepbrother – Jack Bailey and Jordan Starr
3 years ago 13,281 views
Jack Bailey and Lane Colten
CockyBoys
22:54 HD
Jack Bailey and Lane Colten
3 years ago 6,805 views
Jack Bailey and Sean Xavier
CockyBoys
20:50 HD
Jack Bailey and Sean Xavier
3 years ago 6,208 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
3 years ago 3,344 views
You Missed a Spot – Taylor Reign and Jack Bailey
Brother Crush
44:40 HD
You Missed a Spot – Taylor Reign and Jack Bailey
3 years ago 10,304 views
Jack Bailey and Leo Louis
CockyBoys
24:13 HD
Jack Bailey and Leo Louis
3 years ago 6,881 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 5,189 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 3,906 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 7,572 views
Cannonball Contest – Taylor Reign and Jack Bailey
Brother Crush
30:13 HD
Cannonball Contest – Taylor Reign and Jack Bailey
3 years ago 7,637 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 8,789 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 7,160 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 7,868 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 6,384 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 3,693 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 6,054 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 11,499 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 2,644 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 6,903 views
Tom Bentley and Jack Bailey, Chapter 2
Jason Sparks Live
24:36 HD
Tom Bentley and Jack Bailey, Chapter 2
3 years ago 2,839 views
Tom Bentley and Jack Bailey, Chapter 1
Jason Sparks Live
23:58 HD
Tom Bentley and Jack Bailey, Chapter 1
3 years ago 2,446 views