Jack Bailey Videos

3 years ago Killian Knox Bottoms for Jack Bailey
25 min

Killian Knox Bottoms for Jack Bailey

TwinkLoads 280
3 years ago Jack Bailey & Kane Fox
33 min

Jack Bailey & Kane Fox

CockyBoys 92
3 years ago Jack Bailey & Lance Charger – The Grooming
33 min

Jack Bailey & Lance Charger – The Grooming

BoyForSale 303
3 years ago Chris Damned & Jack Bailey – Inseam
25 min

Chris Damned & Jack Bailey – Inseam

HotHouse 125
3 years ago Romeo Davis Bottoms: Encounter 1 – Jack Bailey
24 min

Romeo Davis Bottoms: Encounter 1 – Jack Bailey

TwinkLoads 231
3 years ago Jack Bailey & Lance Charger – Interview Prep
24 min

Jack Bailey & Lance Charger – Interview Prep

GayCest 225
3 years ago Jack Bailey & Lance Charger – Teaching My Grandson
19 min

Jack Bailey & Lance Charger – Teaching My Grandson

GayCest 307
3 years ago Jack Bailey & Lance Charger – Top Training
19 min

Jack Bailey & Lance Charger – Top Training

TwinkTop 288
3 years ago A Walk In The Woods – Jack Bailey & Dolf Dietrich
17 min

A Walk In The Woods – Jack Bailey & Dolf Dietrich

ScoutBoys 867
3 years ago Flying the Nest – Jax Thirio & Jack Bailey
37 min

Flying the Nest – Jax Thirio & Jack Bailey

FamilyDick 202
3 years ago Jax Thirio Bottoms: Encounter 1 – Jack Bailey
16 min

Jax Thirio Bottoms: Encounter 1 – Jack Bailey

TwinkLoads 325
3 years ago Workout on the Balcony – Jax Thirio & Jack Bailey
34 min

Workout on the Balcony – Jax Thirio & Jack Bailey

FamilyDick 304
3 years ago A Virgin No More – Dale Savage & Jack Bailey
56 min

A Virgin No More – Dale Savage & Jack Bailey

DisruptiveFilms 504
4 years ago Bad Grades, Bad Boy – Jack Bailey & Brian Bonds
15 min

Bad Grades, Bad Boy – Jack Bailey & Brian Bonds

FamilyDick 193
4 years ago My Stepbro’s Dildo – Justin Matthews & Jack Bailey
28 min

My Stepbro’s Dildo – Justin Matthews & Jack Bailey

NextDoorStudios 280
4 years ago Am I Qualified? – David Skylar & Jack Bailey
28 min

Am I Qualified? – David Skylar & Jack Bailey

NextDoorStudios 150
4 years ago An Obedient Ordination – Jack Bailey & Johnny B
22 min

An Obedient Ordination – Jack Bailey & Johnny B

MissionaryBoys 90
4 years ago Twink Fuck Hole with Jack Bailey
25 min

Twink Fuck Hole with Jack Bailey

MaverickMen 196
4 years ago Stepdad Joins The Show – Brian Bonds & Jack Bailey
21 min

Stepdad Joins The Show – Brian Bonds & Jack Bailey

FamilyDick 344
4 years ago Jax Thirio Stacks Jack Bailey & Troye Jacobs
31 min

Jax Thirio Stacks Jack Bailey & Troye Jacobs

NextDoorStudios 224