Jack Bailey Most Liked 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
2 years ago Jack Bailey Bottoms For Dan Saxon
27 min

Jack Bailey Bottoms For Dan Saxon

LucasEntertainment 1.6K
4 years ago Jack Bailey & Lance Charger – Teaching My Grandson
19 min

Jack Bailey & Lance Charger – Teaching My Grandson

GayCest 450
3 years ago Grand Promise – Andre Donovan & Jack Bailey
15 min

Grand Promise – Andre Donovan & Jack Bailey

Himeros 352
5 years ago Jax Thirio Pounds Jack Bailey
32 min

Jax Thirio Pounds Jack Bailey

NextDoorStudios 281
2 years ago This Will Make You Feel Better – Jack Bailey & Jack Valor
25 min

This Will Make You Feel Better – Jack Bailey & Jack Valor

BrotherCrush 4.6K
5 years ago Secret Sexcapades: Stepdad With Benefits – Roman Todd & Jack Bailey
37 min

Secret Sexcapades: Stepdad With Benefits – Roman Todd & Jack Bailey

NextDoorStudios 179
4 years ago Jack Bailey & Lance Charger – Interview Prep
24 min

Jack Bailey & Lance Charger – Interview Prep

GayCest 303
5 years ago Jesse Bolton & Jack Bailey’s Couch Fuck
19 min

Jesse Bolton & Jack Bailey’s Couch Fuck

NextDoorStudios 123
5 years ago Getting My Stepbrother Wet – Jack Bailey & Daniel Hausser
19 min

Getting My Stepbrother Wet – Jack Bailey & Daniel Hausser

BrotherCrush 162
3 years ago Namaste and Play – Colby Chambers & Jack Bailey
28 min

Namaste and Play – Colby Chambers & Jack Bailey

ColbyKnox 576
5 years ago Pretty Young Thang – Johnny Rapid, Alex Meyer & Jack Bailey
21 min

Pretty Young Thang – Johnny Rapid, Alex Meyer & Jack Bailey

JohnnyRapid 137
4 years ago Authority Granted – Jack Bailey & Ashton Silvers
23 min

Authority Granted – Jack Bailey & Ashton Silvers

MissionaryBoys 299
1 year ago Chock-Full Of Jocks – Jack Bailey, Tony Genius, Trent Marx, Amone Bane, Dereck Defendi & Michael Seraph
45 min

Chock-Full Of Jocks – Jack Bailey, Tony Genius, Trent Marx, Amone Bane, Dereck Defendi & Michael Seraph

AdultTime 5.3K
4 years ago We Met At The PrEP Clinic 2 – Jax Thirio, Jack Bailey & Jack Valor
33 min

We Met At The PrEP Clinic 2 – Jax Thirio, Jack Bailey & Jack Valor

NextDoorStudios 106
4 years ago Remember When We Used To Do This? – Jack Bailey & Max Lorde
31 min

Remember When We Used To Do This? – Jack Bailey & Max Lorde

BrotherCrush 3.2K
5 years ago I’ll Do Anything Else – Jack Bailey & Jesse Bolton
22 min

I’ll Do Anything Else – Jack Bailey & Jesse Bolton

BrotherCrush 234
4 years ago Whip ‘em Out – Greg McKeon, Jack Bailey & Grey Gold
27 min

Whip ‘em Out – Greg McKeon, Jack Bailey & Grey Gold

BoysAtCamp 224
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 918
3 years ago The Perfect Pool Day Part 2 – Isaac Parker, Jack Bailey & Derek Allen
36 min

The Perfect Pool Day Part 2 – Isaac Parker, Jack Bailey & Derek Allen

FamilyDick 286
1 year ago First Time Sharing a Bed – Jack Bailey & Damian Rose
27 min

First Time Sharing a Bed – Jack Bailey & Damian Rose

BrotherCrush 3.8K
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 482
3 years ago Yellow – Jack Bailey, Derek Cline & Nico Nova
19 min

Yellow – Jack Bailey, Derek Cline & Nico Nova

Himeros 565
2 years ago 11 Inch Stuffing – Jack Bailey & 11inchking
28 min

11 Inch Stuffing – Jack Bailey & 11inchking

RawFuckClub 3.5K