This boy has been visiting me for years. We tried chastity before, but it never worked out for very long. That being said, I knew that deep down he really wanted to be locked up. Some people take longer to get to know someone and build the trust required for something like chastity. Over the years, that trust grew more and more. He recently became very interested in being locked up again, and it was clear it was something he knew he needed.

I wasn’t sure if I wanted to try it again, since it hadn’t worked out in the past. But after a while of seeing, even feeling how bad he wanted it, I decided to give it another go. I locked him in a Jail House chastity cage. This device is pretty comfortable on most guys. It’s roomy enough so it’s not painful to wear long term, yet small enough to not allow him much pleasure. It’s a steel cage that’s secure enough to know your boy can’t just pry it open, yet discrete enough to wear under his clothes while only you and your chastity sub know it’s there. As an added bonus, there aren’t any pinch points like so many chastity cages have. You want your chastity sub to be turned on and trying to get hard in the cage, not turned off from getting pinched throughout the day. ;)

It had been over a month since he last got off. The day had come to tease his cock again, and consider letting him cum. But would I let him cum in the end? I’ll think about it while I tease the fuck out of his cock.  <grin>

I put him in locking leather wrist and ankle cuffs. I secured a leather hood on him and laid him on the bed spreadeagle on a towel, just in case I let him cum later. I tied ropes from the rings on each leather cuff to the corners of the bed, stretching him out nice and tight. I wanted to make sure there wasn’t much room for squirming away from what I had planned for him. Then I suspended a feather duster directly above his locked dick. I chose a feather duster with feathers that get the best ticklish/teasing reaction, for maximum effect. Then I setup an oscillating fan on a chair near the bed, aimed it right at the feather duster, and turned it on. It was great watching the fan blow the feather duster like a pendulum, with the center of gravity right over his locked cock. On every swing, the feather duster just barely grazed his locked cock through the bars of the jail that his dick was locked in.

Desperate for attention, he immediately began bucking a bit, trying to give his dick the attention it craved after a month of no attention at all. Of course, this would do nothing for him other than tease him even more since his dick was still imprisoned in the cage. But his mind wanted one thing and one thing only, to be allowed to cum as he so desperately needed.

After a while of watching him thrust his waist up and down since he could do nothing more, I decided to unlock his dick and remove the cage. But why stop the cock teasing treatment when it can be even more effective on his bare cock. Now it really started throbbing and pumping, after almost every sweep of the feathers hanging above him.

I continued this treatment for a while, taunting him, and asking him how badly he wanted to cum.

But should he be finished off, allowed to cum for the first time in over a month? Should he be teased with the far more intense vibrating wand? Or, should he be locked back in chastity, and for how much longer?

Add your comments below with your thoughts on what you think should happen.