Jack Bailey Longest Videos

4 years ago Romeo Davis Bottoms for Jack Bailey
22 min

Romeo Davis Bottoms for Jack Bailey

TwinkLoads 361
4 years ago An Obedient Ordination – Jack Bailey & Johnny B
22 min

An Obedient Ordination – Jack Bailey & Johnny B

MissionaryBoys 99
3 years ago Jack Bailey & Sean Xavier
21 min

Jack Bailey & Sean Xavier

CockyBoys 330
3 years ago Jack Bailey & Jacob Acosta
21 min

Jack Bailey & Jacob Acosta

CockyBoys 345
5 years ago Pretty Young Thang – Johnny Rapid, Alex Meyer & Jack Bailey
21 min

Pretty Young Thang – Johnny Rapid, Alex Meyer & Jack Bailey

JohnnyRapid 137
4 years ago Stepdad Joins The Show – Brian Bonds & Jack Bailey
21 min

Stepdad Joins The Show – Brian Bonds & Jack Bailey

FamilyDick 451
5 years ago Bored StepBros – Alex Meyer & Jack Bailey
21 min

Bored StepBros – Alex Meyer & Jack Bailey

BrotherCrush 3.4K
4 years ago Horsing Around – Jack Bailey & Benjamin Blue
21 min

Horsing Around – Jack Bailey & Benjamin Blue

ScoutBoys 355
5 years ago Hot Daddy Nights – Jack Bailey & Tristan Jaxx
20 min

Hot Daddy Nights – Jack Bailey & Tristan Jaxx

RawFuckClub 573
3 years ago Incident 335: Turn For The Worse – Jack Bailey
20 min

Incident 335: Turn For The Worse – Jack Bailey

BoysHalfwayHouse 465
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 447
2 years ago Head in the Clouds with Jack Bailey
20 min

Head in the Clouds with Jack Bailey

ColbyKnox 453
3 years ago Yellow – Jack Bailey, Derek Cline & Nico Nova
19 min

Yellow – Jack Bailey, Derek Cline & Nico Nova

Himeros 565
5 years ago Jesse Bolton & Jack Bailey’s Couch Fuck
19 min

Jesse Bolton & Jack Bailey’s Couch Fuck

NextDoorStudios 123
5 years ago Getting My Stepbrother Wet – Jack Bailey & Daniel Hausser
19 min

Getting My Stepbrother Wet – Jack Bailey & Daniel Hausser

BrotherCrush 162
4 years ago Assigned Companions – Ashton Silvers & Jack Bailey
19 min

Assigned Companions – Ashton Silvers & Jack Bailey

MissionaryBoys 152
4 years ago Jack Bailey & Lance Charger – Top Training
19 min

Jack Bailey & Lance Charger – Top Training

TwinkTop 427
4 years ago Jack Bailey & Lance Charger – Teaching My Grandson
19 min

Jack Bailey & Lance Charger – Teaching My Grandson

GayCest 450
4 years ago A Walk In The Woods – Jack Bailey & Dolf Dietrich
17 min

A Walk In The Woods – Jack Bailey & Dolf Dietrich

ScoutBoys 973
4 years ago Jax Thirio Bottoms: Encounter 1 – Jack Bailey
16 min

Jax Thirio Bottoms: Encounter 1 – Jack Bailey

TwinkLoads 355
3 years ago Grand Promise – Andre Donovan & Jack Bailey
15 min

Grand Promise – Andre Donovan & Jack Bailey

Himeros 352
7 months ago TRANSMAN The Parachute – Jack Bailey & Noah Way
15 min

The Parachute – Jack Bailey & Noah Way

Himeros 1.8K
4 years ago Bad Grades, Bad Boy – Jack Bailey & Brian Bonds
15 min

Bad Grades, Bad Boy – Jack Bailey & Brian Bonds

FamilyDick 245
2 years ago The Breakdown – Jack Bailey, Andre Donovan & Milking Coach
14 min

The Breakdown – Jack Bailey, Andre Donovan & Milking Coach

Himeros 3.7K