Jack Bailey Most Liked Videos

5 years ago Bored StepBros – Alex Meyer & Jack Bailey
21 min

Bored StepBros – Alex Meyer & Jack Bailey

BrotherCrush 3.5K
5 years ago The Garden Boys – Jesse Bolton, Jack Bailey & Jax Thirio
33 min

The Garden Boys – Jesse Bolton, Jack Bailey & Jax Thirio

BrotherCrush 99.8K
5 years ago Jack Bailey & Lance Charger – Top Training
19 min

Jack Bailey & Lance Charger – Top Training

TwinkTop 492
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 616
4 years ago Twinkology 101 – Dakota Payne, Jack Bailey, Carter DelRey & Trevor Harris
47 min

Twinkology 101 – Dakota Payne, Jack Bailey, Carter DelRey & Trevor Harris

NextDoorStudios 5.3K
4 years ago The Perfect Roleplay – Johnny Ford & Jack Bailey
40 min

The Perfect Roleplay – Johnny Ford & Jack Bailey

TherapyDick 7.4K
4 years ago Virgin Stepbrother – Jack Bailey & Jordan Starr
33 min

Virgin Stepbrother – Jack Bailey & Jordan Starr

NextDoorStudios 453
4 years ago Too Horny To Behave – Jack Bailey & Derek Allen
36 min

Too Horny To Behave – Jack Bailey & Derek Allen

FamilyDick 424
3 years 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 8.6K
4 years ago Date with Step-Dad – Jack Bailey & Michael Roman
32 min

Date with Step-Dad – Jack Bailey & Michael Roman

NextDoorStudios 525
5 years ago Jack Bailey, Deepdicc & Ray Diesel
28 min

Jack Bailey, Deepdicc & Ray Diesel

DownlowBoys 372
4 years ago Incident 335: Turn For The Worse – Jack Bailey
20 min

Incident 335: Turn For The Worse – Jack Bailey

BoysHalfwayHouse 485
4 years ago Cannonball Contest – Taylor Reign & Jack Bailey
30 min

Cannonball Contest – Taylor Reign & Jack Bailey

BrotherCrush 201
5 years ago Jax Thirio Stacks Jack Bailey & Troye Jacobs
31 min

Jax Thirio Stacks Jack Bailey & Troye Jacobs

NextDoorStudios 288
3 years ago Relaxin’ With Jax – Jax Thirio & Jack Bailey
33 min

Relaxin’ With Jax – Jax Thirio & Jack Bailey

DadCreep 6.9K
4 years ago Jack Bailey & Sean Xavier
21 min

Jack Bailey & Sean Xavier

CockyBoys 357
2 years ago A Brat & A Gentleman – Jack Bailey & Colt Spence
46 min

A Brat & A Gentleman – Jack Bailey & Colt Spence

DisruptiveFilms 6.7K
4 years ago Killian Knox Bottoms for Jack Bailey
25 min

Killian Knox Bottoms for Jack Bailey

TwinkLoads 411
5 years ago Flying the Nest – Jax Thirio & Jack Bailey
37 min

Flying the Nest – Jax Thirio & Jack Bailey

FamilyDick 260
4 years ago This Is How It Feels – Jack Bailey & Max Lorde
25 min

This Is How It Feels – Jack Bailey & Max Lorde

BrotherCrush 3.2K
12 months ago Detention Wedgie – Reese Rideout & Jack Bailey
29 min

Detention Wedgie – Reese Rideout & Jack Bailey

GayRoom 4.1K
2 years ago The Breakdown – Jack Bailey, Andre Donovan & Milking Coach
14 min

The Breakdown – Jack Bailey, Andre Donovan & Milking Coach

Himeros 3.8K
5 years ago Incident #307: Collaborators Will Be Fucked – Jack Bailey
25 min

Incident #307: Collaborators Will Be Fucked – Jack Bailey

BoysHalfwayHouse 277
3 years ago Jack Bailey & Jacob Acosta
21 min

Jack Bailey & Jacob Acosta

CockyBoys 372