The cocky jock was still cuffed spreadeagle on the bed, locked in a leather hood with the blindfold and mouth cover on. I hadn't put the removable gag in, yet. One hour and 5 minutes had past of the 2 hours that I told him he would be in this predicament.
Boy: "Come on, I can't take this anymore! My dick is rock hard and I need to cum sooooo bad, but it's just not enough. Just hold that wand under the head of my dick so I can cum already!"
Boy: "I need to cum so bad!"
Me: "You WHAT?"
Boy: "Sorry, I want to cum so bad."
Me: "And do you want to be locked in chastity for 2 weeks?"
Boy: "No, I don't."
Me: "Then deal with it. You have 55 minutes remaining like this."
Boy: "55 MORE minutes? But you see how hard my dick is. This isn't right!"
Me: "Oh it's not? Yeah, you're right. I should really do something about that."
I stopped the fan, the wand, and the 2 hour clock, then got some ice and used it on Jim's dick until it went down. Then I locked his dick in a Jail House chastity cage. I could hear the frustration in his "sigh" as he heard the padlock click.
Me: "There. I've taken care of that hard dick for you."
Boy: "That's not what I meant. I really wanted to cum, soo badly!"
Me: "Yeah, I don't think that's going to happen anytime soon, boy."
Boy: "Well at least that damn wand isn't keeping me right on the edge anymore."
Me: "You're right. Something else will keep you on the edge now."
I took the wand down, and replaced it with the feather duster that I had used previously. But now, it was going to tease his dick while it's locked in the chastity cage. I lowered it to the point that would ensure the feathers would sweep through the bars of the chastity cage.
Then turned the fan back on. I adjusted the hanging feather duster a bit to make sure it would tease the hell out of his dick AND balls. There was now a very minimal chance of him being able to get off since his big dick couldn't even grow to half it's size when hard.
I continued asking him every 15 minutes if he wanted to remain locked in chastity for the next 2 weeks. Each time I asked, he continued to say no. But the last time I asked him when he had 15 minutes remaining, he paused to think about it. Then he tried to negotiate.
Boy: "What if you let me leave unlocked, then I come back for another session next week?"
Me: "No, this isn't up for negotiation."
Boy: "Then how about you start my 2 week chastity sentence next week?"
Me: "No, I told you this isn't negotiable. You can either ask to remain in chastity for the next 2 weeks, or deal with the next 15 minutes. The choice is yours."
Boy: "My dick can't take much more of this. Please stop the relentless teasing!"
Me: "Are you asking to remain locked in chastity for the next 2 weeks, minimum?"
Boy: "I guess so."
Me: "Enjoy the next 15 minutes of endless teasing."
Boy: "Wait, what?"
Me: "I didn't hear a Yes Sir. I didn't hear you ask to remain locked in chastity for the next 2 weeks, minimum. So you get to deal with the next 15 minutes of relentless, locked, cock teasing."
Boy: "Sorry Sir. Please make it stop, and keep my dick locked."
Me: "For how long?"
Boy: "For 2 weeks Sir."
Me: "I don't know, you had your chance, and I didn't hear that the first time. Now I think you're going to have to go through another phase if you want this to stop now."
Boy: "Anything Sir, please, anything but this!"
Me: "Ok boy."
I stopped the fan and took the feather duster down, then moved him over to the bondage wall. I used a few quick release straps to secure him to the wall at his upper chest and one thigh. This severely restricted his movement so it wouldn't be too easy to get off. Then I secured two adjustable wand holders to the bondage wall and put one variable speed vibrating wand in each of them. I adjusted one so it was held up against the spot right between his balls and his ass, and the other at the side of his dick. After attaching a silicone masturbation sleeve to the end of the wand, I positioned it so it was slightly out of his reach. I wanted to make him work for this. I removed the chastity device.
Me: "Ok boy, at this point you're going to be relocked in chastity after this and remain locked for 2 weeks. Would you like an opportunity to reduce your 2 week chastity sentence?"
Boy: "Yes Sir."
Me: "I thought so. I know you're pretty horned up right now. It probably wouldn't take much constant stimulation of your cock to make you cum. Right boy?"
Boy: "Yes Sir. Please do that Sir. Please let me cum before locking my dick in chastity!"
Me: "Ok boy, I will."
Boy (sounding surprised and confused): "You will?"
Me: "Yes, boy, I will. You asked for it. I'm going to turn on the vibrating wand that's attached to the silicone masturbation sleeve that's right in front of your dick."
Boy: "Great! I can cum from those in like 30 seconds!"
Me: "I don't think you'll be saying great in a minute boy."
Boy (with a cocky attitude again): "Why the hell wouldn't I? I get to cum."
Me: "Yes, you can cum, but I don't know that you'll want to. You're going to fuck the silicone masturbation sleeve that's attached to the vibrating wand, non-stop. Every minute that you're fucking it good and continuously will take one day off of your chastity sentence, with a 3 day minimum sentence remaining. But if you cum, not only will you be locked in chastity for the full 2 weeks, but I will also take full advantage of your post-orgasm, extremely sensitive cock. Oh, and by the way, I'm also going to turn on a second vibrating wand that's positioned between your balls and ass. Both wands will be on full power."
Boy: "Oh come on!"
Boy: "Yes Sir."
I flipped the switch which turned both wands on at full intensity. He started half-heartedly fucking the vibrating masturbation sleeve knowing that if he put too much effort into it, he would cum. Then he would get post-orgasm torture, then locked up for at least 2 full weeks. I could tell he was trying hard to not let that happen.
About 5 minutes had passed since I turned the wands on.
Me: "Just so you know, you're at 0 days off of your chastity sentence."
Boy: "What? Why? It has to have been at least 10 minutes!"
Me: "It's been 5 minutes, and I haven't seen you fucking that masturbation sleeve good, like I told you was required. Your dick is barely touching it. Make it better, or stay locked for at least 2 weeks. Your choice."
He finally started picking up the pace a bit, thrusting his hips to slide his dick in and out of the silicone nubbed sleeve.
He continued this for a while, trying to impress me with his thrusting hips making sure his cock was kept right on the edge, without going too far and getting himself off. It was nice to see the look on his face getting more and more submissive the longer this went on. After 12 minutes, he did the worst thing he could've done. I saw a few drops of cum dripping out the other end of the silicone sleeve, and I immediately flipped the switch to make all stimulation stop, and effectively ruin his orgasm.
I waited for drop after drop of cum to drip down. There wasn't a lot since I had interrupted his orgasm, but I wanted to make sure it was done before I continued. As many guys know, a ruined orgasm provides none of the satisfation or a normal orgasm, it makes the guy want to cum A LOT more than he did before, and it still makes his dick about 20x more sensitive.
Me: "Now it's time to pay the price for cumming without permission."
I flipped the switch again to turn both vibrating wands back on.