Jack Bailey Most Viewed Videos

3 years ago Virgin Stepbrother – Jack Bailey & Jordan Starr
33 min

Virgin Stepbrother – Jack Bailey & Jordan Starr

NextDoorStudios 447
3 years ago Pair of Jacks – Colby Chambers, Jack Bailey, Jack Valor & Mickey Knox
36 min

Pair of Jacks – Colby Chambers, Jack Bailey, Jack Valor & Mickey Knox

ColbyKnox 439
4 years ago The Doctor’s Orders – Jack Bailey & Johnny Ford
31 min

The Doctor’s Orders – Jack Bailey & Johnny Ford

DoctorTapes 438
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 429
3 years ago Backseat Driver – Andre Donovan, Jack Bailey & Andrew Connor
14 min

Backseat Driver – Andre Donovan, Jack Bailey & Andrew Connor

Himeros 425
4 years ago Too Horny To Behave – Jack Bailey & Derek Allen
36 min

Too Horny To Behave – Jack Bailey & Derek Allen

FamilyDick 416
4 years ago Horsing Around – Jack Bailey & Benjamin Blue
21 min

Horsing Around – Jack Bailey & Benjamin Blue

ScoutBoys 412
4 years ago Killian Knox Bottoms for Jack Bailey
25 min

Killian Knox Bottoms for Jack Bailey

TwinkLoads 404
4 years ago Romeo Davis Bottoms for Jack Bailey
22 min

Romeo Davis Bottoms for Jack Bailey

TwinkLoads 397
4 years ago Before Leaving Camp – Greg McKeon, Jack Bailey & Colton McKeon
23 min

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

BoysAtCamp 389
4 years ago Jax Thirio Bottoms: Encounter 1 – Jack Bailey
16 min

Jax Thirio Bottoms: Encounter 1 – Jack Bailey

TwinkLoads 383
4 years ago Jack Bailey & Lance Charger – The Grooming
33 min

Jack Bailey & Lance Charger – The Grooming

BoyForSale 382
4 years ago Grand Promise – Andre Donovan & Jack Bailey
15 min

Grand Promise – Andre Donovan & Jack Bailey

Himeros 362
3 years ago Jack Bailey & Jacob Acosta
21 min

Jack Bailey & Jacob Acosta

CockyBoys 359
4 years ago My Stepbro’s Dildo – Justin Matthews & Jack Bailey
28 min

My Stepbro’s Dildo – Justin Matthews & Jack Bailey

NextDoorStudios 357
5 years ago Jack Bailey, Deepdicc & Ray Diesel
28 min

Jack Bailey, Deepdicc & Ray Diesel

DownlowBoys 355
4 years ago You Missed a Spot – Taylor Reign & Jack Bailey
45 min

You Missed a Spot – Taylor Reign & Jack Bailey

BrotherCrush 352
4 years ago Workout on the Balcony – Jax Thirio & Jack Bailey
34 min

Workout on the Balcony – Jax Thirio & Jack Bailey

FamilyDick 351
3 years ago Jack Bailey & Sean Xavier
21 min

Jack Bailey & Sean Xavier

CockyBoys 347
5 years ago Twink Fuck Hole with Jack Bailey
25 min

Twink Fuck Hole with Jack Bailey

MaverickMen 336
4 years ago Romeo Davis Bottoms: Encounter 1 – Jack Bailey
24 min

Romeo Davis Bottoms: Encounter 1 – Jack Bailey

TwinkLoads 328
4 years ago Jack Bailey & Lance Charger – Interview Prep
24 min

Jack Bailey & Lance Charger – Interview Prep

GayCest 324
4 years ago Authority Granted – Jack Bailey & Ashton Silvers
23 min

Authority Granted – Jack Bailey & Ashton Silvers

MissionaryBoys 311
4 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 305