Take a quick look at What’s new before you browse the most popular posts featuring Jack Drago by era.
- Posing For Bob, June 2026
Getting into my mesh outfit and posing for Bob Kurtz in it on my most recent visit. Photos and video taken by Bob Kurtz on June 13, 2026. - Singlet at Fist Fest
Modeling my wrestling singlet in the room at Parliament at Peach pals in February 2026. - Barebackin Wrecked Pussy
I found my husband happily bouncing on his huge butt plug; so I decided to fuck his ass right there while he was still wrecked. Enjoy seeing me play in my witchy pants? Watch me fisting his ass in this outfit. - Jacks New Jockstrap
Back in September of 2018 when I was still buff as hell, I gave away my old jockstrap to a slave and got this new one as tribute. - Tahoe City Jockstrap Fisting
Tahoe City was spectacular, but I spent most of my time fist fucking in a jockstrap. Photographed by Jack Drago May 21st, 2026 in Tahoe City, CA. - Uniform Breeding at Harveys
Rubber Pig came up to Tahoe on his annual hockey training conference in April of 2018, so I bred him in a full military uniform and took pictures on my cell phone.
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 Ritual
Satanic writings, rituals, and hypnosis by Jack Drago