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Category: Jack Drago

Images and video featuring site co-founder Jack Drago

  • Posted on October 5, 2023September 20, 2023
  • 2010s

Jack Drago – Jay Evil FF 3 way

ay Evil and Jack Drago tag team Rubber Pig at Fist Fest 2019. This extended session was filmed by Kevin and directed by Jack Drago.

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  • Posted on October 5, 2023October 5, 2023
  • 2020s

DenvFist Handheld

My fisting buddy DenvFist came to visit August 28th and we had some fun in the hypno-sling.

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  • Posted on October 3, 2023September 28, 2023
  • 2000s

Ricky Shaves Jack on a blue tarp

Ricky Ricardo shaves off what’s left of Jack Drago’s pubes in May 2006. Photos by Bob Kurtz.

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  • Posted on October 2, 2023August 19, 2026
  • 2020s

Pumping my Dick to Hypnosis

After I finished the hypermale hypnosis file “Pump Away Manhood” I thought I might try it myself. Grab your pump and stare into the spiral with me…

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  • Posted on October 1, 2023August 19, 2026
  • 2010s

Locktober 2: Chastity Keys

There are few things more likely to hold a chastity slave’s attention than the keys to his chastity device, so enjoy this rapid hypnosis induction featuring my sub’s chastity keys.

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  • Posted on September 29, 2023July 26, 2023
  • 2000s

Bed Bondage series

Jack Drago gets tied up in bed by Daddy Tiger, April 21 2008.

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  • Posted on September 28, 2023August 19, 2026
  • 2020s

Handheld Handball

This video taken fully handheld at Virgin hotel on the day after the Beach Off session (August 4th, 2023) shows me getting creative trying to film with one hand and fist with the other.

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  • Posted on September 27, 2023July 17, 2024
  • 2010s

Milking Beast of Marbas

Watch me tie down Beast of Marbas in a cheap motel and milk his cock to satanic hypnosis in this rare footage of him I shot in September 2019 before he siliconed his cock and balls.

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  • Posted on September 25, 2023July 11, 2023
  • 2020s

Dore Alley 2021

Took Slave JJ to his first ever Dore Alley on September 25, 2021. Made him strip down and walked him on a leash through the streets in my leather kilt.

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  • Posted on September 23, 2023August 15, 2023
  • 2000s

Jack and Ricky in the Sling

After Jack Drago rode the sex swing, Ricky Ricardo wanted to join in.

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