Jack Bailey in Brother Crush

All Videos Jack Bailey Often appears with Damian Rose Max Lorde Jesse Bolton Jack Valor Alex Meyer Daniel Hausser Also with male performers Taylor Reign Jax Thirio

The Garden Boys

17.2K • Nov 11, 2020

The Garden Boys

Jesse Bolton, Jack Bailey, Jax Thirio

I’ll Do Anything Else

16.3K • Dec 9, 2020

I’ll Do Anything Else

Jesse Bolton, Jack Bailey

Getting My Stepbrother Wet

13.5K • Jan 6, 2021

Getting My Stepbrother Wet

Daniel Hausser, Jack Bailey

This Is How It Feels

13.3K • Mar 24, 2022

This Is How It Feels

Max Lorde, Jack Bailey

This Will Make You Feel Better

13K • May 30, 2024

This Will Make You Feel Better

Jack Valor, Jack Bailey

Bored StepBros

11.9K • Mar 3, 2021

Alex Meyer, Jack Bailey

Cannonball Contest

11.7K • Jul 7, 2022

Cannonball Contest

Jack Bailey, Taylor Reign

Remember When We Used To Do This?

10.8K • Apr 21, 2022

Remember When We Used To Do This?

Max Lorde, Jack Bailey

You Missed a Spot

10.4K • Aug 14, 2022

You Missed a Spot

Jack Bailey, Taylor Reign

First Time Sharing a Bed

9.3K • Jul 4, 2024

First Time Sharing a Bed

Damian Rose, Jack Bailey

Jack’s Gratitude

7.4K • Aug 1, 2024

Jack’s Gratitude

Damian Rose, Jack Bailey

See The Best Of Jack Bailey At Brother Crush