Jack Bailey Most Viewed Videos

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

Jax Thirio Bottoms: Encounter 1 – Jack Bailey

TwinkLoads 321
3 years ago The Doctor’s Orders – Jack Bailey & Johnny Ford
31 min

The Doctor’s Orders – Jack Bailey & Johnny Ford

DoctorTapes 321
3 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 308
3 years ago A Virgin No More: The Offering – Jack Bailey, Scott Finn & Dale Savage
49 min

A Virgin No More: The Offering – Jack Bailey, Scott Finn & Dale Savage

DisruptiveFilms 303
3 years ago Workout on the Balcony – Jax Thirio & Jack Bailey
34 min

Workout on the Balcony – Jax Thirio & Jack Bailey

FamilyDick 299
2 years ago Too Horny To Behave – Jack Bailey & Derek Allen
36 min

Too Horny To Behave – Jack Bailey & Derek Allen

FamilyDick 289
4 years ago Bored StepBros – Alex Meyer & Jack Bailey
21 min

Bored StepBros – Alex Meyer & Jack Bailey

BrotherCrush 287
3 years ago Jack Bailey & Lance Charger – The Grooming
33 min

Jack Bailey & Lance Charger – The Grooming

BoyForSale 283
2 years ago Grand Promise – Andre Donovan & Jack Bailey
15 min

Grand Promise – Andre Donovan & Jack Bailey

Himeros 279
2 years ago Jack Bailey & Sean Xavier
21 min

Jack Bailey & Sean Xavier

CockyBoys 279
3 years ago Jack Bailey & Lance Charger – Top Training
19 min

Jack Bailey & Lance Charger – Top Training

TwinkTop 277
3 years ago Jack Bailey & Lance Charger – Teaching My Grandson
19 min

Jack Bailey & Lance Charger – Teaching My Grandson

GayCest 277
3 years ago Authority Granted – Jack Bailey & Ashton Silvers
23 min

Authority Granted – Jack Bailey & Ashton Silvers

MissionaryBoys 265
3 years ago Romeo Davis Bottoms for Jack Bailey
22 min

Romeo Davis Bottoms for Jack Bailey

TwinkLoads 265
3 years ago My Stepbro’s Dildo – Justin Matthews & Jack Bailey
28 min

My Stepbro’s Dildo – Justin Matthews & Jack Bailey

NextDoorStudios 265
2 years ago Before Leaving Camp – Greg McKeon, Jack Bailey & Colton McKeon
23 min

Before Leaving Camp – Greg McKeon, Jack Bailey & Colton McKeon

BoysAtCamp 265
2 years ago Jack Bailey & Jacob Acosta
21 min

Jack Bailey & Jacob Acosta

CockyBoys 264
4 years ago Jax Thirio Pounds Jack Bailey
32 min

Jax Thirio Pounds Jack Bailey

NextDoorStudios 255
3 years ago Killian Knox Bottoms for Jack Bailey
25 min

Killian Knox Bottoms for Jack Bailey

TwinkLoads 247
2 years ago You Missed a Spot – Taylor Reign & Jack Bailey
45 min

You Missed a Spot – Taylor Reign & Jack Bailey

BrotherCrush 238