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Category: Jack Drago

Images and video featuring site co-founder Jack Drago

  • Posted on September 5, 2024August 19, 2026
  • 2020s

Sounding JJ in the Hypno Sling

After I tied up Slave JJ in the hypno sling, I put on my Urethral Sounding Trainer hypnosis. Despite limitations in our prior session, this time JJ endured without complaint.

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  • Posted on September 2, 2024June 18, 2024
  • 2020s

Tying Slave JJ to the Sling

After tattooing my mark on his ass June 15th, 2024 of course I had to strap him down and express my ownership over Slave JJ with one more brainwashing session.

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  • Posted on August 30, 2024June 18, 2024
  • 2020s

Bating at Bobs Again

Regular as clockwork, I fly out to Berkley to visit Bob Kurtz and work on CR3 stuff and Bob wants to race me to ejaculation just to see how much I can shoot.

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  • Posted on August 29, 2024July 20, 2024
  • 2020s

GearUp Weekend 2024

Fisted 9x, pissed in front of 150 guys, raw dogged a stranger for 45min straight in front of a group of cigar smoking Leathermen. Barebacked on the front porch in full view, went naked hiking and got to see a live session from another hypnotist.

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  • Posted on August 27, 2024August 19, 2026
  • 2010s

Straight to the Bottom

Some guys just turn gay when their heterosexuality is shattered. Some go straight to the bottom.

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  • Posted on August 27, 2024June 18, 2024
  • 2020s

Leather Barebacking Slave JJ

After blowing me in my leathers, I had to plant my seed in Slave JJ’s ass. Check out the full gallery of this breeding session below.

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  • Posted on August 24, 2024August 19, 2026
  • 2020s

Tie Dye JO

I just can’t stop playing with myself with my sex drive as high as it is. It’s like I’m mesmerized by my own penis.

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  • Posted on August 21, 2024July 17, 2024
  • 2020s

JJ Brainwashed into Satanic Slavery

I use a straight jacket to restrain my slaves during brainwashing. Once the headphones were on, I proceeded to edge him through my Satanic Slavery video.

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  • Posted on August 18, 2024June 18, 2024
  • 1990s

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.

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  • Posted on August 15, 2024June 18, 2024
  • 2020s

Cock and Ball Torturing Slave JJ

I set up the sling, tied JJ’s hands and did some cock and ball torture on Slave JJ until he howled on his last night in Las Vegas on June 15th by first warming him up with a spoon then getting brutal with the ruler.

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