Jack Bailey Latest Videos

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
4 years ago The Master’s Grandson – Jack Bailey, Lance Charger & Cole Blue
20 min

The Master’s Grandson – Jack Bailey, Lance Charger & Cole Blue

BoyForSale 488
4 years ago Let’s Share A Bath – Jax Thirio, Jack Bailey & Max Lorde
28 min

Let’s Share A Bath – Jax Thirio, Jack Bailey & Max Lorde

FamilyDick 148
4 years ago Be – Greg McKeon & Jack Bailey
46 min

Be – Greg McKeon & Jack Bailey

DisruptiveFilms 505
4 years ago Whip ‘em Out – Greg McKeon, Jack Bailey & Grey Gold
27 min

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

BoysAtCamp 257
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 Let’s Share A Bath – Jax Thirio, Jack Bailey & Max Lorde
38 min

Let’s Share A Bath – Jax Thirio, Jack Bailey & Max Lorde

FamilyDick 446
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 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 127
4 years ago Romeo Davis Bottoms for Jack Bailey
22 min

Romeo Davis Bottoms for Jack Bailey

TwinkLoads 412
4 years ago Authority Granted – Jack Bailey & Ashton Silvers
23 min

Authority Granted – Jack Bailey & Ashton Silvers

MissionaryBoys 315
4 years ago Washboard Worship – Damien White, Jack Bailey & Trevor Harris
53 min

Washboard Worship – Damien White, Jack Bailey & Trevor Harris

NextDoorStudios 149
4 years ago Assigned Companions – Ashton Silvers & Jack Bailey
19 min

Assigned Companions – Ashton Silvers & Jack Bailey

MissionaryBoys 169
4 years ago Dolf Dietrich & Jack Bailey – Getting Pumped
22 min

Dolf Dietrich & Jack Bailey – Getting Pumped

TwinkTop 466
4 years ago Killian Knox Bottoms for Jack Bailey
25 min

Killian Knox Bottoms for Jack Bailey

TwinkLoads 411
4 years ago Jack Bailey & Kane Fox
33 min

Jack Bailey & Kane Fox

CockyBoys 142
4 years ago Jack Bailey & Lance Charger – The Grooming
33 min

Jack Bailey & Lance Charger – The Grooming

BoyForSale 418
4 years ago Chris Damned & Jack Bailey – Inseam
25 min

Chris Damned & Jack Bailey – Inseam

HotHouse 251
4 years ago Romeo Davis Bottoms: Encounter 1 – Jack Bailey
24 min

Romeo Davis Bottoms: Encounter 1 – Jack Bailey

TwinkLoads 347
5 years ago Jack Bailey & Lance Charger – Interview Prep
24 min

Jack Bailey & Lance Charger – Interview Prep

GayCest 342
5 years ago Jack Bailey & Lance Charger – Teaching My Grandson
19 min

Jack Bailey & Lance Charger – Teaching My Grandson

GayCest 534
5 years ago Jack Bailey & Lance Charger – Top Training
19 min

Jack Bailey & Lance Charger – Top Training

TwinkTop 492
5 years ago A Walk In The Woods – Jack Bailey & Dolf Dietrich
17 min

A Walk In The Woods – Jack Bailey & Dolf Dietrich

ScoutBoys 1K
5 years ago Flying the Nest – Jax Thirio & Jack Bailey
37 min

Flying the Nest – Jax Thirio & Jack Bailey

FamilyDick 260