Jack Bailey Movies

  • 2023
    Split Me Open

    Split Me Open

    Split Me Open

    02023HD

    Big dick superstar Sean Xavier leads a stunning cast of hung studs ready to split open any bottom that crosses their path. Joining Sean are notoriousl...

    Split Me Open
  • 2023
    Lucas Men Extravaganza

    Lucas Men Extravaganza

    Lucas Men Extravaganza

    02023HD

    Hop in the sack with Kosta Viking, Babylon Prince, Harold Lopez, Brian Bonds, Santos, Jack Bailey, Bruno Galvez, Derek Kage, and Gustavo Cruz for the...

    Lucas Men Extravaganza
  • 2023
    Johnny Rapid: For the Fans Vol. 4

    Johnny Rapid: For the Fans Vol. 4

    Johnny Rapid: For the Fans Vol. 4

    02023HD

    He's one of gay porn's most-popular stars. He's always wanted to get more up-close-and-personal with his massive fanbase... and now he has his own lin...

    Johnny Rapid: For the Fans Vol. 4
  • 2023
    My Stepbrother, My Bitch

    My Stepbrother, My Bitch

    My Stepbrother, My Bitch

    02023HD

    Jack Bailey is catching up with stepbrother Jordan Starr when he finds out that Jordan is still a virgin. But when he offers to help Jordan lose his v...

    My Stepbrother, My Bitch
  • 2023
    After School

    After School

    After School

    02023HD

    Scott Finn, Jayden Marcos and Andrew Miller have all graduated from college and are celebrating for the weekend. When closeted Scott starts catching l...

    After School
  • 2023
    Brother Crush Vol. 21

    Brother Crush Vol. 21

    Brother Crush Vol. 21

    02023HD

    You won't believe how these naughty brothers fool around behind their parents' backs. You'll love watching older boys show the ropes to their innocent...

    Brother Crush Vol. 21
  • 2023
    Loser Has to Bottom

    Loser Has to Bottom

    Loser Has to Bottom

    02023HD

    It's Jack Bailey's first day at the new job his stepdad David Skylar got Jack at his company. Jack knows he's underqualified for the job, but it doesn...

    Loser Has to Bottom
  • 2023
    Like Old Times

    Like Old Times

    Like Old Times

    02023HD

    David Skylar is getting married and Alex Tanner thinks he's making a big mistake marrying his boring sister. Nonetheless, Alex decides to give David a...

    Like Old Times
  • 2023
    Ready to Hustle

    Ready to Hustle

    Ready to Hustle

    02023HD

    One of the most exciting things about being an old pervert who films hot young studs is having that sexy new shy guy walk through the door for the fir...

    Ready to Hustle
  • 2023
    My Step-Brother, My Bitch

    My Step-Brother, My Bitch

    My Step-Brother, My Bitch

    02023HD

    Jack Bailey is catching up with stepbrother Jordan Starr when he finds out that Jordan is still a virgin. But when he offers to help Jordan lose his v...

    My Step-Brother, My Bitch
  • 2023
    Breeding Season

    Breeding Season

    Breeding Season

    02023HD

    Seasons come and go, but at CockyBoys it's always Breeding Season. Watch and enjoy as these boys get lost in the pleasure of giving and receiving; tak...

    Breeding Season
  • 2023
    Washboard Worship

    Washboard Worship

    Washboard Worship

    02023HD

    Cody Viper has the shock of a lifetime when he finds out his college roommates Grey Gold and Des Irez are gay. But he's stuck with them for the rest o...

    Washboard Worship
  • 2021
    Secret Sexcapades

    Secret Sexcapades

    Secret Sexcapades

    02021HD

    Jack Bailey has it bad for Roman Todd, which is pretty bad considering Roman is Jack's stepfather. Jack wants more than a 'Stepdad With Benefits,' whi...

    Secret Sexcapades
  • 2023
    The Code

    The Code

    The Code

    02023HD

    When college morality officer George Meadows (Hans Berlin) catches wind that student Christian Grogan (Isaac Parker) has a fansite account where he se...

    The Code
  • 2023
    Dirty Move

    Dirty Move

    Dirty Move

    02023HD

    As best buds Tom Faulk and River Elliott sit on the couch sharing in a little boredom induced mutual masturbation session, they don't hear Tom's step-...

    Dirty Move
  • 2023
    Twinky Twinkle

    Twinky Twinkle

    Twinky Twinkle

    02023HD

    Tyler Wu takes a trip to NYC to meet up with sexy Justin Berry. Tyler tells us, 'The first thing about Justin that caught my eye was his fiery red hai...

    Twinky Twinkle
  • 2023
    Twinkology 101

    Twinkology 101

    Twinkology 101

    102023HD

    Evan Knoxx is loving life as a player for the Next Door Knobs. But when his teammate Nico Coopa suspects he's gay, Nico invites team captain Max Lorde...

    Twinkology 101
  • 2023
    Doctor Tapes 4

    Doctor Tapes 4

    Doctor Tapes 4

    52023HD

    There are some doctors that specialize in the care of making sure boys become healthy men and their treatment comes in many forms. Doctor Tapes is an...

    Doctor Tapes 4
  • 2023
    Rough Enough?

    Rough Enough?

    Rough Enough?

    02023HD

    There is something about Rough Sex that transforms these boys from sexy-boys-next-door into sex-crazed cum-sluts, whimpering with ecstasy as they are...

    Rough Enough?
  • 2023
    Open Up

    Open Up

    Open Up

    02023HD

    Is there a better feeling than the moment when a boy's wet mouth slides down a rock hard cock, or when a man's throbbing member slips into the soft sm...

    Open Up