Jack Drago self fisting
After taking the cucumber and the dildo, 2007 era Jack Drago had to try for the fist.
Category: 2000s
Pics and videos of Jack in his 20s in the 2000s
Jack Drago Oiled Jockstrap
By May 2007, I was finally starting to make some progress at bodybuilding and got together with Derek to shoot this set of oiled flex images.
Motel Sluts
Ricky Ricardo checks in to the Berkeley Motel and finds Jack Drago cruising for a barebacking in this 2005 film directed by Daddy Tiger and Bob Kurtz and shot on location in berkeley by Derek.
Shado
Back in August, 2008 I filmed a boy named Shado for my then website with Daddy Tiger… He jerked for the camera and I ate his cum. And delicious as the sex with Shado is, more precious to me is my video diary of the events.
Jack Drago and the Cucumber
Jack Drago sticks a cucumber up his ass and then eats it. Photos by Daddy Tiger, summer of 2006.
Jack Drago Mummified
Jack Drago mummified by Daddy Tiger in this hour long video from Black and Orange productions.
The Drago Dance
This was the video welcoming people to my website back in the day, kinda hypnotic, no? Filmed by Daddy Tiger and Jack Drago for Black and Orange productions, August 2007.
Macaulay Culkin
Former child star Macauley Culkin featured in The Face in 2002 in his Party Monster era.
You get me WET
Jack Drago and Bo Bently make love and do watersports in the shower in “Wet” filmed by Derek and Daddy Tiger in 2005 for the “Daddy Tiger’s Nasty Boys” collection.