1. Jack’s Playground

2003 · ★ 8.0

Jack, a trust fund child and aspiring music video director who happens to have a knack for persuadin…

2. Jack’s Playground 2

2003 · ★ 6.3

Jack, a trust fund child and aspiring music video director who happens to have a knack for persuadin…

3. Jack's Playground 3

2003 · ★ 6.3

Jack's Playground is a collection of Jack's personal videos, homemade in Santa Monica, California sh…

4. Jack’s Playground 4

2003 · ★ 5.5

Jack, a trust fund child and aspiring music video director who happens to have a knack for persuadin…

5. Jack's Playground 5

2003 · ★ 5.8

Jack's Playground is a collection of Jack's personal videos, homemade in Santa Monica, California sh…

6. Jack's Playground 6

2004 · ★ 5.7

Jack's Playground is a collection of Jack's personal videos, homemade in Santa Monica, California sh…

7. Jack's Playground 7

2004 · ★ 6.3

Jack's Playground is a collection of Jack's personal videos, homemade in Santa Monica, California sh…

8. Jack's Playground 8

2004 · ★ 7.0

Jack's Playground is a collection of Jack's personal videos, homemade in Santa Monica, California sh…

9. Jack's Playground 9

2004 · ★ 6.7

Jack's Playground is a collection of Jack's personal videos, homemade in Santa Monica, California sh…

10. Jack's Playground 10

2004 · ★ 7.5

Jack's Playground is a collection of Jack's personal videos, homemade in Santa Monica, California sh…

11. Jack's Playground 11

2004 · ★ 7.0

Jack's Playground is a collection of Jack's personal videos, homemade in Santa Monica, California sh…

12. Jack's Playground 12

2004 · ★ 7.0

Jack's Playground is a collection of Jack's personal videos, homemade in Santa Monica, California sh…

13. Jack's Playground 13

2004 · ★ 6.7

Jack's Playground is a collection of Jack's personal videos, homemade in Santa Monica, California sh…

14. Jack's Playground 14

2004 · ★ 8.4

Jack's Playground is a collection of Jack's personal videos, homemade in Santa Monica, California sh…

15. Jack's Playground 15

2004 · ★ 6.8

Jack's Playground is a collection of Jack's personal videos, homemade in Santa Monica, California sh…

16. Jack's Playground 16

2004 · ★ 6.5

Jack's Playground is a collection of Jack's personal videos, homemade in Santa Monica, California sh…

17. Jack's Playground 17

2004 · ★ 5.4

Jack's Playground is a collection of Jack's personal videos, homemade in Santa Monica, California sh…

18. Jack's Playground 18

2005 · ★ 6.0

Jack's Playground is a collection of Jack's personal videos, homemade in Santa Monica, California sh…

19. Jack's Playground 19

2005 · ★ 5.4

Jack's Playground is a collection of Jack's personal videos, homemade in Santa Monica, California sh…

20. Jack's Playground 20

2005 · ★ 7.3

Jack's Playground is a collection of Jack's personal videos, homemade in Santa Monica, California sh…

21. Jack's Playground 21

2005 · ★ 7.0

Sorry about Jack's 20, folks. I bitchslapped Jack to make sure that won't happen again. Montel Retu…

22. Jack's Playground 22

2005 · ★ 7.0

Help Give A Damn - Give To The Yummypie.com Telethon

23. Jack's Playground 23

2005 · ★ 6.7

"Cuttin 23 Of These Ain't Easy, Damnit!" Cousin Nick P., Ph.D., drops knowledge on what it's like t…

24. Jack's Playground 24

2005 · ★ 5.0

New Juicy Flavor! Longer Lasting Anal! Choc full o' fun and flavor!

25. Jack's Playground 25

2005 · ★ 6.0

Loads And Loads Of Spankin' Good Times! Watch Tera take the double Buda! See Rocki take it in the..…

26. Jack's Playground 26

2005 · ★ 6.0

It's Guaranteed Analicious!! Montel's back in da house! What's da assfuckathon?

27. Jack's Playground 27

2005 · ★ 6.0

Analizar Esto Maricon ... Did I just speak Spanish?

28. Jack's Playground 28

2005 · ★ 6.0

Jack's Playground is a collection of Jack's personal videos, homemade in Santa Monica, California sh…

29. Jack's Playground 29

2006 · ★ 6.0

Drop It Like Its Hot! Julia Ann's taking loads on her feet. Jack's Playground is a collection of Jac…

30. Jack's Playground 30

2006 · ★ 6.5

Jack's Playground 30 is packed full of the dirtiest chicks enjoying giving awe-inspiring blow jobs, …

31. Jack's Playground 31

2006 · ★ 6.3

"Jack's Playground 31," the superstar edition, stars the lovely Jana Cova in two delectable scenes, …

32. Jack's Playground 32

2006 · ★ 7.0

Jack's Playground 32 Adult DVD Description: "Jack's Playground 32, features Digital Playground's con…

33. Jack's Playground 33

2007 · ★ 9.0

Jack's Playground 33, features Digital Playground's one and only insatiable and sexy Devon. She's ea…

34. Jack's Playground 34

2007 · ★ 6.0

Exotic waves of molten cum erupt onto timid young flesh in this amazing exploitation of carnal vorac…

35. Jack's Playground 37

2007 · ★ 7.0

Jack is really busy casting for music videos and now he's landed Digital Playground's super fine con…

36. Jack's Playground 35

2007 · ★ 5.5

Jack is really busy casting for music videos and now he's landed Digital Playground's super fine con…

37. Jack's Playground 36

2007 · ★ 7.0

Jack is really busy casting for music videos and now he's landed Digital Playground's super fine con…

38. Jack's Playground 38

2008 · ★ 7.5

Jack is really busy casting for music videos and he's scored some super fine ass for volume 38. Digi…