Practicing Bondage as a teen
let me practice my incipient rope skills on him so I could develop into a dominant. He even let me stake him out in the desert and whip him with my brand new riding crop he bought me!
Category: 1990s
Teenage Jack Drago (legal Jan 1 1998)
Jack Gets Nipple Rings
AI enhanced images of me masturbating after having gotten my very first nipple rings back on April 7, 1999. Photos taken in Lake Tahoe by Dr. Bob.
19 Year Old Jack Drago in Bondage
19 year old me hadn’t picked the name Jack Drago yet. but he already had a tattoo and a dope habit. Here I am dropping my pants for a guy with an 8 ball of meth who promised to make porn of me but who wound up keeping me high all weekend…
Reservoir Nudes
Youngest legal nudes of Jack Drago outdoors, taken August 29, 1998, just before I got tied to the tree. AI Enhanced blow ups because the originals are tiny.
25th Anniversary of my first public bondage
For years I would have apologized for the tiny images but now we have the ability to AI upscale, so in honor of the 25th anniversary of my first public bondage pictures, the same old thing in a much more usable resolution.
Jack Drago Nude Beach fuck
jack Drago, 2002. You can tell it was a long time ago cuz I’m wearing a rubber.