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Gay Bondage PrisonerFollow as instructed leaving coat off on the floor by the locked box
Posted by Spida 09/08/2019 - 20:19
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Gay Bondage PrisonerI would certainly follow the directions - to the letter (ie. I'd read it 3-4 times before I began to be sure I got them right). Then patiently wait with my rock hard cock for the guard to arrive and inform me of my sentence. Nice start!
Posted by chillgguy 09/08/2019 - 16:12
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Gay Bondage PrisonerI would follow the directions completely and wait for the guard to come for me.
Posted by Bondagebuddy2 09/08/2019 - 07:03
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Jail Cell Gloryhole EdgingAs a sub this is a position I will find restrictive and very interesting:-) The total list of control plus the relentless polishing are big plus !
Posted by tomt 07/13/2019 - 18:33
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Gay Bondage Leashed Sub in Leather Chest HarnessVery hot leather, needs some around his cock
Posted by M m peal 07/05/2019 - 00:20
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Click on the pics below to enlarge them, and to animate any GIFs

Gay Sub Stretched on Rack Ass
  • Gay Sub Stretched on Rack Ass
  • Gay Sub Stretched on Rack Chastity
  • Gay Sub Stretched on Rack Chastity
  • Gay Sub Stretched on Rack
  • Gay Sub Stretched on Rack Chastity
  • Gay Sub Stretched on Rack Chastity

If you missed Part 1, you can find it here.

This boy had gotten his wish. His fantasy of being strapped to a rack and slowly stretched more and more  over time was being fulfilled. But did he bite off more than he could chew?

I had his hands cuffed and stretched up and out. I did the same with his feet. His body was being stretched in the shape of an X, and there was nothing he could do about it. But I built-in one more way to stretch a boy on this rack. Any ideas?

Yep, there’s a nice little rope hanging down from his tied balls. And there happens to be  an extra rope coming off of that bottom winch. So I hooked the two together to stretch another part of him…his balls! Now every time he hears a CLICK CLICK CLICK from the lower winch being cranked, not only will it stretch his feet apart, but it will also stretch his balls further down at the same time.

After doing this, I gave the lower winch a few cranks, just to make absolutely sure he felt what would happen with each crank of the lower winch now. He seemed surprised, never having thought I could come up with devices on the rack to stretch his arms, legs, AND balls. But I could tell that he secretly loved it, as I saw his cock throbbing and growing in the Jail House chastity cage that I had it locked in.

I walked over to him and whispered into his ear.

Me: “Hands, feet, balls, I’ve got them all strapped in now, boy. Every time you hear a click, either your arms or your legs AND balls will get stretched, yet another notch. Tightening you up even more than you are now. You’re mine, boy!”

Boy: “Yes Sir.”

Me: “Think you can handle it?”

Boy: “I think so Sir.”

Me: “If not, you could always break out of the restraints. Haha.”

He squirmed a bit, struggled, testing the restraints to no avail. There was nowhere he could go, nothing he could do about what was about to happen. He could fight it, but the rack ALWAYS wins!

Me: “This is a great position for an interrogation, boy.”


Me: “I want to hear all about how you jerk off. How you do it. What you think about while you’re jerking off. EVERYTHING!”


I went for the upper winch.


His arms were stretched even further than before.

Then the lower winch.


Now his feet were stretched pretty wide, and his balls were cranked a few notches lower.

Me: “What do you think about when you jerk off?”

Boy: “I think about being tied up.”

Back to the upper winch.


Me: “I want details, boy. You’re going to tell me all about it, don’t leave anything out, or else.”


I gave the winch one more crank to show him what would happen if I felt he was leaving any details out.

Boy: “I think about being tied up and tortured Sir. I think about being strapped to a rack and force stretched, Sir.”

Me: “Oh yeah boy? Like this?”


As I cranked the lower winch again, his feet were forcefully stretched wider apart, and his balls cranked lower at the same time.

Boy: “Yes Sir.”

Me (with my hand on the upper winch): “What else?”



His arms were now stretched almost to the max.

Boy: “I think about when you had me tied in a stress position with nipple clamps on and the Bumble Ball tied to the nipple clamps Sir.”

Me: “Oh yeah? When I asked you to list your favorites and least favorite/most suitable for punishment from what I’ve done with you in the past, you listed that one as one of the worst. But you actually liked it a lot, so much that you think about it when you jerk off?”



Boy: “Yes Sir.”

Me: “Wow, see what comes out in an interrogation boy, with the proper motivation to talk?”

Boy: “Yes Sir.”

Me: “Hmm, so you were secretly hoping I would punish you, and use similarly harsh punishment methods?”



He was forced to squat down a bit more, as his balls were pulled further toward the floor.

Boy: “Yes Sir.”

I could see his cock really throbbing in the chastity cage now, growing more and more until it hit the wall of the cock prison that it was locked in.

Me: “Your dick looks pretty excited there boy. Is it?”

Boy: “Yes Sir, it is.”

Me: “And do you want to cum?”

Boy: “Yes Sir, can I cum Sir?”

What else is in store for this boy, stretched to the max on the rack and desperate to cum? Should I unlock his dick and jerk him off as he so desperately desires? Or maybe get the vibrating wand out and take full advantage of his extreme horniness and inability to do anything about it? Maybe gag him? A few more cranks of the winches to make sure he has zero ability to squirm? (Hmm, speaking of that, is anybody wondering how ticklish this boy is?)

Doms: What would you do from here?

Subs: What would you want done to you in this predicament, whether that be more obvious, or what you’d be secretly hoping for?

Add your comments below with your thoughts on this to let us know.

And be sure to watch for Part 3 to see what happened next.


tomt on June 24, 2019 20:25

As a sub, it will be worst to have the chastity removed a ward put on it and then more question with consequences if I cum or don’t answers correctly or fast enough
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MotoMike on June 26, 2019 12:05

Now is the time for the wand attached with the rubber band, and then ... no cumming of course, but edging with more questions to get him to answer faster.
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Tyman13 on June 29, 2019 17:25

As a sub I would want the interrogation to keep going! I would want the cage to come off to be teased and maybe a plug to be entered so I was stuffed and really being tortured
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