If you missed the first 2 parts, you can find them here:

Part 1 

Part 2

Still strapped to the rack, stretched out nice and tight and looking hot as ever, there was nowhere to go. Well, nowhere but to get stretched even tighter. I now know he was secretly hoping that I would punish him more after conducting a little interrogation and finding out about his deepest, darkest, kinkiest secrets. But did he bite off more than he could chew? In this position, he was sure to find out.

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?”

Me: “Not yet, boy. Actually, I noticed you’re still squirming around a bit too much, as if the air is something going to stroke that cock that’s desperate for attention.”

CLICK…CLICK…CLICK…

I gave the upper winch a few more cranks. Then the lower winch, as he spread his feet a bit wider and bent his knees to crouch down even more. His balls were getting cranked down lower regardless. Whether or not he went with them was his choice. But he wisely chose to bend his knees a bit more and lower down with them.

CLICK…CLICK…CLICK…

Me: “There, that’s much better.”

Boy: [GROAN]

Me: “Does that dick want some attention, boy?”

Boy: “Yes Sir, very much so Sir.”

Me: “Ok boy, I’ll see if I can do something about that.”

I went and got the vibrating wand, a shoelace, and a thick rubber band. He was still wearing the Jail House chastity cage. I said I was going to give his cock some attention, but I said nothing about releasing his cock first. Plus, it would be so much easier to attach the vibrating wand using the slots between the steel on the chastity cage to hold the wand up. <grin>

Using the shoelace and rubber band, I secured the vibrating wand to the chastity cage. This also served as a nice weight hanging from his balls, since the wand does have a bit of weight to it.

He grinned for a second.

Boy: “I thought you were going to unlock my dick and jerk me off.”

Me: “All this talk about getting you off boy. I said I was going to see if I could do something about getting your dick some attention. I said nothing about getting you off. Actually, all this talk in general…needs to stop.”

With that, I grabbed an open-mouth gag and strapped it on him, locking it behind him. When he heard the ‘click’ of the padlock, he knew he was going to be gagged for a while. Gagged, and soon to be drooling, a nice side effect of the open-mouth gag.

I turned the vibrating wand on at a very slow intensity.

Boy: [GROOOAN]

I let him stew like that for a while, then I turned the vibrating wand up to a higher intensity.

Boy: “Ohhhhh…Mmmmmm…”

I saw some precum on his dick, actually I saw A LOT of pre-cum on his dick. I scooped some up with my finger and reached my finger inside the open-mouth gag that was forcing his mouth wide open.

Me: “Lick.”

He obediently licked the pre-cum off my finger.

Me: “If you’re going to have that much fun, enough to produce that much precum, you’ll need to clean up your mess, boy.”

Boy (still gagged): “Yeh hirr.”

I reached down and adjusted the wand so it was focused on the head of his dick through the cage, then turned the wand up higher. That REALLY got him moaning, desperate to cum. His dick grew so thick it looked like it was trying to bust out of the chastity cage. But we both knew there was no way his dick was going to escape the steel Jail House cage, no matter how badly he wanted to get rock hard and cum.

He was now breathing more heavily. It was as if I was watching a boy who was starting that rhythm that many boys get into when they’re about to cum, rocking back and forth, moving around in a specific pattern, all the signs that a boy is about to cum. Except that this boy had zero room to move, zero room to squirm even a little bit, and zero control of his caged dick. He was, however, pre-cumming A LOT, and I continued to scoop it up and bring it up to his mouth held wide open by the gag.

Me: “Lick.”

And he licked obediently once again. I noticed the gag was really starting to take its toll as the inevitable was starting to happen. He became a drooling mess, drooling uncontrollably, just adding to the humiliation of his predicament.

Me: “Wow boy, those armpits look pretty damn vulnerable like that!”

[silence]

Me: “Are you ticklish?”

[silence]

Me: “I asked you a question boy. Are you ticklish?”

[silence]

I could start to see a look of fear come over him.

Me: “We can do this two ways boy. You can either answer my question, honestly. Or I can get out the ABox and connect it to conductive rubber loops around your cock, then explore your body on my own. Of course that means if you ARE in fact ticklish, any time you make a sound, your cock gets it. Now I’ll ask you one last time boy. Are you ticklish?”

Doms: Should this hot boy’s exposed armpits be taken full advantage of? Or does he deserve a break (if he answers the question honestly)?

Subs: Just how vulnerable would you feel like this, stretched to the max, knowing there’s nowhere to go, no way to squirm away or protect any part of your body?

Add your thoughts in the comments below.  And watch for part 4 to see what happened next.