Jack Drago by Era

Take a quick look at What’s new before you browse the most popular posts featuring Jack Drago by era.

  • Fisting like a Savage
    Fist Fucking like a savage in my Realtree camo pants and matching T-Shirt, February 5, 2025. Stay tuned after the gallery for part two.
  • Jack Drago in Jockstrap
    Modeling in my Jockstrap at my buddy’s place in San Francisco, February 5th, 2025.
  • Jockstrap Fisting
    Fisting my buddy in matching white jockstraps in San Francisco. Filmed February 7th, 2025 by Jack Drago.
  • Trash Pile Bareback
    After pissing in Slave JJ’s mouth and then making him blow me, it was finally time to raw dog him on the trash pile he built on my orders and plant my demon seed in his ass…
  • SF Nude Fisting
    As the sun faded on October 25th, we fisted again before Shadow Dancing in San Francisco. All videos taken by Jack Drago, look after gallery for bonus vid.
  • Trash Pile BJ from Slave JJ
    I had Slave JJ build a trash pile so that I could piss in his mouth and then he could blow me while kneeling on it.

1990s

Teenage Jack Drago (legal Jan 1 1998) in the 90s.

2000s

Pics and videos of Jack in his 20s in the 2000s

2010s

Jack Drago in his 30s in the 2010s

2020s

Jack Drago in his 40s in the 2020s, Pink hair era, baby!

Fetish

Fetish porn made by or featuring Jack Drago.

Video

Videos made by or featuring Jack Drago.

Hypnosis

Hypnosis memes and videos by Vast Country Hypnosis

Made by Jack Drago

Popular recent posts where Jack is credited as filmaker or photographer.

Satanic

Satanic writings, rituals, and hypnosis by Jack Drago

Popular Posts