Jack Bailey Most Viewed Videos

4 years ago Jack Bailey & Lance Charger – Top Training
19 min

Jack Bailey & Lance Charger – Top Training

TwinkTop 427
3 years ago Backseat Driver – Andre Donovan, Jack Bailey & Andrew Connor
14 min

Backseat Driver – Andre Donovan, Jack Bailey & Andrew Connor

Himeros 417
4 years ago The Doctor’s Orders – Jack Bailey & Johnny Ford
31 min

The Doctor’s Orders – Jack Bailey & Johnny Ford

DoctorTapes 416
4 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 415
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 403
3 years ago Too Horny To Behave – Jack Bailey & Derek Allen
36 min

Too Horny To Behave – Jack Bailey & Derek Allen

FamilyDick 398
4 years ago Killian Knox Bottoms for Jack Bailey
25 min

Killian Knox Bottoms for Jack Bailey

TwinkLoads 378
4 years ago Romeo Davis Bottoms for Jack Bailey
22 min

Romeo Davis Bottoms for Jack Bailey

TwinkLoads 361
3 years ago Before Leaving Camp – Greg McKeon, Jack Bailey & Colton McKeon
23 min

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

BoysAtCamp 358
4 years ago Jax Thirio Bottoms: Encounter 1 – Jack Bailey
16 min

Jax Thirio Bottoms: Encounter 1 – Jack Bailey

TwinkLoads 355
4 years ago Horsing Around – Jack Bailey & Benjamin Blue
21 min

Horsing Around – Jack Bailey & Benjamin Blue

ScoutBoys 355
4 years ago Jack Bailey & Lance Charger – The Grooming
33 min

Jack Bailey & Lance Charger – The Grooming

BoyForSale 354
3 years ago Grand Promise – Andre Donovan & Jack Bailey
15 min

Grand Promise – Andre Donovan & Jack Bailey

Himeros 352
3 years ago Jack Bailey & Jacob Acosta
21 min

Jack Bailey & Jacob Acosta

CockyBoys 345
4 years ago Workout on the Balcony – Jax Thirio & Jack Bailey
34 min

Workout on the Balcony – Jax Thirio & Jack Bailey

FamilyDick 339
5 years ago Jack Bailey, Deepdicc & Ray Diesel
28 min

Jack Bailey, Deepdicc & Ray Diesel

DownlowBoys 331
4 years ago My Stepbro’s Dildo – Justin Matthews & Jack Bailey
28 min

My Stepbro’s Dildo – Justin Matthews & Jack Bailey

NextDoorStudios 331
3 years ago Jack Bailey & Sean Xavier
21 min

Jack Bailey & Sean Xavier

CockyBoys 330
3 years ago You Missed a Spot – Taylor Reign & Jack Bailey
45 min

You Missed a Spot – Taylor Reign & Jack Bailey

BrotherCrush 330
4 years ago Romeo Davis Bottoms: Encounter 1 – Jack Bailey
24 min

Romeo Davis Bottoms: Encounter 1 – Jack Bailey

TwinkLoads 309
4 years ago Jack Bailey & Lance Charger – Interview Prep
24 min

Jack Bailey & Lance Charger – Interview Prep

GayCest 303
4 years ago Authority Granted – Jack Bailey & Ashton Silvers
23 min

Authority Granted – Jack Bailey & Ashton Silvers

MissionaryBoys 299
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
5 years ago Jax Thirio Pounds Jack Bailey
32 min

Jax Thirio Pounds Jack Bailey

NextDoorStudios 281