All of Jack Bailey (70 videos)

• Loser has to Bottom (2023) | Full Movie
  23808

  02:17:00

  73%
• Troop Time Chapter 15 – After Camping | Jack Bailey, Marcus Rivers, Troye Jacobs & Scoutmaster Smith | Bareback
  8546

  00:30:58

  73%
• Virgin Stepbrother | Jack Bailey, Jordan Starr | Bareback
  34688

  00:33:19

  73%
• Chock-Full Of Jocks | Trent Marx, Amone Bane, Jack Bailey, Tony Genius, Michael Seraph & Dereck Defendi
  18359

  00:45:12

  73%
• Teaching My Grandson – Tape 3 – Hard Lessons | Jack Bailey & Lance Charger | Bareback
  15903

  00:17:00

  73%
• The Garden Boys | Jesse Bolton, Jack Bailey & Jax Thirio | Bareback
  45514

  00:33:07

  72%
• Inseam | Full Movie | 2022 | Chris Damned, Devin Franco, Jack Bailey, Jay Tee, Shane Cook, Adrian Hart, Austin Avery, Cole Connor
  63277

  02:36:38

  72%
• Jack Bailey & Sean Xavier | Bareback
  20802

  00:20:50

  72%
• Twinkology 101 | Dakota Payne, Jack Bailey, Carter DelRey, Trevor Harris | Bareback
  25935

  00:47:03

  72%
• Let’s Share A Bath | Jax Thirio, Jack Bailey & Max Lorde | Bareback
  12139

  00:28:14

  72%
• Stepdad Joins The Show | Jack Bailey & Brian Bonds | Bareback
  27659

  00:21:30

  71%
• Jack Bailey & Kane Fox | Bareback
  19096

  00:32:36

  71%
• Cannonball Contest | Jack Bailey & Taylor Reign | Bareback
  15462

  00:44:40

  71%
• Workout on the Balcony | Jack Bailey & Jax Thirio | Bareback
  25507

  00:34:12

  71%
• The Worthiness Review | Johnny B & Jack Bailey | Bareback
  14441

  00:25:45

  71%
• The Perfect Pool Day, Pt 2 | Isaac Parker, Jack Bailey, Derek Allen | Bareback
  17312

  00:36:17

  71%
• The Boy Cole Chapter 9 – The Master’s Grandson | Cole Blue, Jack Bailey & Lance Charger | Bareback
  12654

  00:20:13

  70%
• An Obedient Ordination | Johnny B & Jack Bailey | Bareback
  13459

  00:21:34

  70%
• Washboard Worship | Damien White, Jack Bailey, Trevor Harris | Bareback
  17823

  00:53:28

  70%
• I’ll Do Anything Else | Jack Bailey, Jesse Bolton | Bareback
  22445

  00:22:11

  70%
• Troop Time Chapter 12 – Boys Will Be Boys | Jack Bailey, Marcus Rivers & Legrand Wolf | Bareback
  16574

  00:24:29

  70%
• Authority Granted | Ashton Silvers , Jack Bailey | Bareback
  9002

  00:18:41

  70%
• Bad Grades, Bad Boy | Jack Bailey & Brian Bonds | Bareback
  11466

  00:14:42

  70%
• My Stepbro’s Dildo | Justin Matthews & Jack Bailey | Bareback
  25446

  00:28:07

  70%
• Remember When We Used To Do This | Max Lorde & Jack Bailey | Bareback
  11438

  00:31:13

  70%