Jack Bailey Latest Videos

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

Jax Thirio Bottoms: Encounter 1 – Jack Bailey

TwinkLoads 413
5 years ago Workout on the Balcony – Jax Thirio & Jack Bailey
34 min

Workout on the Balcony – Jax Thirio & Jack Bailey

FamilyDick 373
5 years ago A Virgin No More – Dale Savage & Jack Bailey
56 min

A Virgin No More – Dale Savage & Jack Bailey

DisruptiveFilms 723
5 years ago Bad Grades, Bad Boy – Jack Bailey & Brian Bonds
15 min

Bad Grades, Bad Boy – Jack Bailey & Brian Bonds

FamilyDick 8.9K
5 years ago My Stepbro’s Dildo – Justin Matthews & Jack Bailey
28 min

My Stepbro’s Dildo – Justin Matthews & Jack Bailey

NextDoorStudios 384
5 years ago Am I Qualified? – David Skylar & Jack Bailey
28 min

Am I Qualified? – David Skylar & Jack Bailey

NextDoorStudios 4.6K
5 years ago An Obedient Ordination – Jack Bailey & Johnny B
22 min

An Obedient Ordination – Jack Bailey & Johnny B

MissionaryBoys 122
5 years ago Twink Fuck Hole with Jack Bailey
25 min

Twink Fuck Hole with Jack Bailey

MaverickMen 404
5 years ago Stepdad Joins The Show – Brian Bonds & Jack Bailey
21 min

Stepdad Joins The Show – Brian Bonds & Jack Bailey

FamilyDick 510
5 years ago Jax Thirio Stacks Jack Bailey & Troye Jacobs
31 min

Jax Thirio Stacks Jack Bailey & Troye Jacobs

NextDoorStudios 297
5 years ago The Worthiness Review – Jack Bailey & Johnny B
26 min

The Worthiness Review – Jack Bailey & Johnny B

MissionaryBoys 134
5 years ago Incident #307: Collaborators Will Be Fucked – Jack Bailey
25 min

Incident #307: Collaborators Will Be Fucked – Jack Bailey

BoysHalfwayHouse 286
5 years ago Jack’s Muscle Daddy Gang Bang
26 min

Jack’s Muscle Daddy Gang Bang

RawFuckClub 555
5 years ago Hot Daddy Nights – Jack Bailey & Tristan Jaxx
20 min

Hot Daddy Nights – Jack Bailey & Tristan Jaxx

RawFuckClub 611
5 years ago Secret Sexcapades: Service Top – Johnny Ford & Jack Bailey
31 min

Secret Sexcapades: Service Top – Johnny Ford & Jack Bailey

NextDoorStudios 212
5 years ago Jack Bailey, Deepdicc & Ray Diesel
28 min

Jack Bailey, Deepdicc & Ray Diesel

DownlowBoys 394
5 years ago Incident 282: A Mouth Made For Sucking – Jack B
12 min

Incident 282: A Mouth Made For Sucking – Jack B

BoysHalfwayHouse 521
5 years ago Secret Sexcapades: Stepdad With Benefits – Roman Todd & Jack Bailey
37 min

Secret Sexcapades: Stepdad With Benefits – Roman Todd & Jack Bailey

NextDoorStudios 209
5 years ago Bored StepBros – Alex Meyer & Jack Bailey
21 min

Bored StepBros – Alex Meyer & Jack Bailey

BrotherCrush 3.5K
5 years ago Pretty Young Thang – Johnny Rapid, Alex Meyer & Jack Bailey
21 min

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

JohnnyRapid 165
5 years ago Jack Bailey & Blaine Porter – Lake Need
22 min

Jack Bailey & Blaine Porter – Lake Need

NakedSword 200
5 years ago Jax Thirio Pounds Jack Bailey
32 min

Jax Thirio Pounds Jack Bailey

NextDoorStudios 308
5 years ago Johnny Rapid & Jack Bailey – Lake Need
22 min

Johnny Rapid & Jack Bailey – Lake Need

NakedSword 142
5 years ago Getting My Stepbrother Wet – Jack Bailey & Daniel Hausser
19 min

Getting My Stepbrother Wet – Jack Bailey & Daniel Hausser

BrotherCrush 229