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Jack Bailey Porn Videos

751 videos
Jack Bailey

Jack Bailey in adorable, sweet-faced twink with a bright smile and an ass that can take quite a bit of punishment. So don't underestimate him! Jack Bailey filmed with Lucas Entertainment during the June 2022 production in Puerto Vallarta, Mexico!

Age: 29 years Born: 1997-10-29 Ethnicity: Caucasian Hair: Brunette Eyes: Blue Height: 178cm

Jack Bailey has 751 videos available on RawPornHub, mostly in gay, Bareback, Gay. The most watched scene has 1,161,814 views.

Spoiled Twink Seduces Older Handyman - Jack Bailey, Cliff Jensen - DisruptiveFilms 13 min HD PH
Spoiled Twink Seduces Older Handyman - Jack Bailey, Cliff Jensen - DisruptiveFilms
1,161,814 views
HETEROFLEXIBLE - INSANE ACCIDENTAL GANGBANG + BUKKAKE For Greedy Twink Tutor! INTERRACIAL FUCK FEST! 15 min HD PH
HETEROFLEXIBLE - INSANE ACCIDENTAL GANGBANG + BUKKAKE For Greedy Twink Tutor! INTERRACIAL FUCK FEST!
1,073,904 views
HETEROFLEXIBLE - Nerdy Twink Jack Bailey Is Hard Rough Gangbanged By The Football Team + CUM SHOWER 16 min HD PH
HETEROFLEXIBLE - Nerdy Twink Jack Bailey Is Hard Rough Gangbanged By The Football Team + CUM SHOWER
890,676 views
Innocent Teen Boy Gets His Perfect Round Butt Spanked For His Bad Grades By His Strict Step Father 14 min HD PH
Innocent Teen Boy Gets His Perfect Round Butt Spanked For His Bad Grades By His Strict Step Father
871,617 views
Teacher Reconnects With and Makes Love to Former Student - Greg McKeon, Jack Bailey - Disruptive 19 min HD PH
Teacher Reconnects With and Makes Love to Former Student - Greg McKeon, Jack Bailey - Disruptive
501,021 views
Little Stepbro Moves Into My Room - BrotherCrush 16 min HD PH
Little Stepbro Moves Into My Room - BrotherCrush
489,193 views
Gay Twink Jack Bailey Lets Daddy Fuck Deep Bareback 5 min HD PH
Gay Twink Jack Bailey Lets Daddy Fuck Deep Bareback
400,775 views
FamilyDick - Perv Stepdad Shares His Innocent Stepson With Horny Boss By The Pool For Promotion 16 min HD PH
FamilyDick - Perv Stepdad Shares His Innocent Stepson With Horny Boss By The Pool For Promotion
396,409 views
Curious Step Siblings Make Out Intensely And Play With Each Other’s Cocks 16 min HD PH
Curious Step Siblings Make Out Intensely And Play With Each Other’s Cocks
299,392 views
Twink Stepbrother Seduces His Step Sibling And Pounds His Tight Ass While Their Parents Are Away 16 min HD PH
Twink Stepbrother Seduces His Step Sibling And Pounds His Tight Ass While Their Parents Are Away
267,747 views
Sexy Stepfather Hires Twink Stepson To 'Work' At His Firm - David Skylar, Jack Bailey - NextDoorTwin 12 min HD PH
Sexy Stepfather Hires Twink Stepson To 'Work' At His Firm - David Skylar, Jack Bailey - NextDoorTwin
241,821 views
Cute Twink Gets Ass Plowed By Mechanic Fuck Buddy - NextDoorTaboo 12 min HD PH
Cute Twink Gets Ass Plowed By Mechanic Fuck Buddy - NextDoorTaboo
231,453 views
Delinquent Twink Jack Bailey Takes Older Creeps Dick Bareback POV 5 min HD PH
Delinquent Twink Jack Bailey Takes Older Creeps Dick Bareback POV
215,687 views
Bratty & Disrespectful Twink Taught Life Lessons From Hardened Mechanic - DisruptiveFilms 11 min HD PH
Bratty & Disrespectful Twink Taught Life Lessons From Hardened Mechanic - DisruptiveFilms
191,006 views
Flexible Twink Jack Bailey learns Yoga and gets Stretched Out RAW 5 min HD PH
Flexible Twink Jack Bailey learns Yoga and gets Stretched Out RAW
162,862 views
Super Hot Teens Jack Bailey & Masyn Thorne Meet For The First Time! 6 min HD PH
Super Hot Teens Jack Bailey & Masyn Thorne Meet For The First Time!
148,638 views
Jack Bailey Gay 4 Pay Threesome With Daddy Bareback 5 min HD PH
Jack Bailey Gay 4 Pay Threesome With Daddy Bareback
126,587 views
HungFuckers Jack Baily fucked hard by horse hung top Eddie Patrick 10 min HD PH
HungFuckers Jack Baily fucked hard by horse hung top Eddie Patrick
124,625 views
Gay 4 Pay Easy Bottom Jack Bailey Takes A Big Cock And Cums All Over Himself 6 min HD PH
Gay 4 Pay Easy Bottom Jack Bailey Takes A Big Cock And Cums All Over Himself
124,153 views
Pair of Twinks Jack Bailey and Jack Valor get Buttfucked by Colby Chambers and Mickey Knox BAREBACK! 5 min HD PH
Pair of Twinks Jack Bailey and Jack Valor get Buttfucked by Colby Chambers and Mickey Knox BAREBACK!
116,450 views
Bored Step Brothers Jesse Bolton & Jack Bailey Get Wild While Cleaning The Pool - BrotherCrush 16 min HD PH
Bored Step Brothers Jesse Bolton & Jack Bailey Get Wild While Cleaning The Pool - BrotherCrush
115,732 views
Gay 4 Pay Straight Boy Jack Bailey Is The Perfect Bottom 5 min HD PH
Gay 4 Pay Straight Boy Jack Bailey Is The Perfect Bottom
113,770 views
HungFuckers Cute horny slut Jack Bailey spitroasted by muscle DILFs 10 min HD PH
HungFuckers Cute horny slut Jack Bailey spitroasted by muscle DILFs
112,890 views
Cock Hungry Gay 4 Pay Teen Jack Bailey Fucked Deep By Big Dick Top 5 min HD PH
Cock Hungry Gay 4 Pay Teen Jack Bailey Fucked Deep By Big Dick Top
111,840 views
Creepy Twink Goes Too Far In Getting Stepdad's Attention - DisruptiveFilms 15 min HD PH
Creepy Twink Goes Too Far In Getting Stepdad's Attention - DisruptiveFilms
109,342 views
StepDILF Boss Fucks Twink Intern Stepson - David Skylar, Jack Bailey - NextDoorTwink 12 min HD PH
StepDILF Boss Fucks Twink Intern Stepson - David Skylar, Jack Bailey - NextDoorTwink
106,688 views
Barely Legal Twink Jack Bailey gets his ass WRECKED by Mickey Knox RAW 5 min HD PH
Barely Legal Twink Jack Bailey gets his ass WRECKED by Mickey Knox RAW
100,361 views
Mickey Knox Fucks Cock Hungry Bottom Jack Bailey RAW 4 min HD PH
Mickey Knox Fucks Cock Hungry Bottom Jack Bailey RAW
92,646 views
HungFuckers Eddie Patrick plows a big load into Jack Baileys hole 10 min HD PH
HungFuckers Eddie Patrick plows a big load into Jack Baileys hole
90,514 views
Jack Bailey Is Too Horny For His Str8 Twink Friend 5 min HD PH
Jack Bailey Is Too Horny For His Str8 Twink Friend
82,702 views
NextDoorTaboo - Secret Sexcapades Series Compilation FT Roman Todd, Jack Bailey N'More!! 21 min HD PH
NextDoorTaboo - Secret Sexcapades Series Compilation FT Roman Todd, Jack Bailey N'More!!
82,597 views
Detention Twink Gets A Fat Cock Wedged Up His Ass As Punishment 8 min HD PH
Detention Twink Gets A Fat Cock Wedged Up His Ass As Punishment
81,060 views
Horny Twink Threesome wt Muscle Hunk Roomie - Damien White, Jack Bailey, Trevor Harris - NextDoorTwi 13 min HD PH
Horny Twink Threesome wt Muscle Hunk Roomie - Damien White, Jack Bailey, Trevor Harris - NextDoorTwi
77,547 views
MenPov Intense POV Sex With Hung Jack Bailey 8 min HD PH
MenPov Intense POV Sex With Hung Jack Bailey
63,974 views
Twink Nympho Jack Bailey Brings His Friend Over For A Bareback Threesome With Daddy 5 min HD PH
Twink Nympho Jack Bailey Brings His Friend Over For A Bareback Threesome With Daddy
62,038 views
Jack Bailey gapes hole with a thick dildo 4 min HD PH
Jack Bailey gapes hole with a thick dildo
61,329 views