Jim had finally cum. The moment he was desperately waiting for all along. But, is it better to cum without permission, or not to cum at all? He was about to find out.
As soon as I saw the first drop of cum, I immediately flipped a switch to turn everything off. The wand aimed at that incredibly effective spot between his balls and his ass, OFF. The wand that was magnifying the effects of the silicone masturbation sleeve, OFF. Every bit of pleasure that he was feeling stopped INSTANTLY. Some guys are familiar with this feeling, known as a ruined orgasm. Those who don't know what a ruined is will never forget it once they experience it. It brings a guy absolutely none of the pleasure of getting off, with all the post-orgasm sensitivity. And as an added bonus, the guy will then want to get off about 20 times more than he did before the ruined orgasm. If only Jim would've been a good boy and not gotten off until I told him it was ok to do so. He'll learn.
I locked his hands behind his back using Darby style handcuffs. I wanted to send the message that he wasn't going anywhere until he was punished for cumming without permission, and these cuffs are pretty heavy and inescapable even if you have the key in your hands.
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. He immediately pulled back until his dick came out of the masturbation sleeve. I forced it right back on, securely so it wouldn't come off again until I wanted it to.
I let the wand do it's worst. The wand alone, used in the right way and at the right time (such as immediately after an orgasm) can be plenty of punishment on its own. After a ruined orgasm, it's even worse. He continued to squirm and try to shake it off, but it was no use. It wasn't going anywhere.
I asked him if he had anything to say about what he did wrong. He was silent.
Me: "Ok, the wand stays on. Actually, I think I'll turn it up."
I increased the intensity of the wand, then he really started squealing.
Boy: "I'm sorry Sir! I shouldn't have cum without your permission!"
Me: "No, you shouldn't have, boy. But it's too late now. You had your chance."
I grabbed an open-mouth gag and strapped it on him, locking it behind his head. Now all I heard was moans, but I could almost make out the begging and pleading through the muffled moans.
Me: "This will continue for 30 minutes, boy."
Boy: "Whaaaa mmmpffff!"
Me: "Haha, deal with it. You wanted attention for your cock all along. Now you've got more than you can handle."
About 10 minutes later, his moans got pretty loud. Then I noticed a drop of cum dripping out of the masturbation sleeve, and I immediately flipped the switch to stop everything once again.
Me: "Looks like you got off again boy. You didn't actually think you were going to get any pleasure from a second attempt, did ya boy?"
I waited about 2 minutes to be sure he was done, then instantly turned everything back on. Both wands, the one magnifying the effects of the mastrubation sleeve, and the one persistently teasing his ass, started up again. I cranked up the intensity a bit higher this time.
Me: "That's what ya get boy. Only 20 more minutes of this remaning."
Boy (still gagged): "Kwennny ninnuts??"
Me: "Yep. Hope it was worth getting off, twice! Now you're even more sensitive than after the first time. Haha."
For the next 20 minutes, the boy formerly known as the cocky jock was a babbling, begging mess, through the thick muffling gag of course.
I finally flipped the switch which put an end to his hyper-sensitive cock's punishment, and I removed the masturbation sleeve and both wands. I walked away to get something, and it seemed like he wondered why I wasn't releasing him.
Me: "Did you forget about your 2 week chastity sentence? You didn't hold back from cumming, so you didn't earn any time off of that."
I grabbed a Jail House chastity cage and locked it on his dick.
Me: "This should prevent you from getting any pleasure out of this thing for the next 2 weeks."
Now that I had his dick locked up, I released him from his predicament and removed the gag.
Boy: "Come on! I need to cum, I mean I want to cum so bad!"
Me: "You just did, twice."
Boy: "Yeah but I don't feel like I got off. I'm actually A LOT more horny now than I was before I got off."
Me: "Yep, that was the plan. It's called a ruined orgasm. That's what you get for letting yourself cum against my orders."
Boy: "But you have to let me jerk off before you send me home locked in this cage!"
Me: "I what??"
Boy: "I mean...I'm sooo horny."
Me: "Not as much as you're going to be now. For the next 2 weeks, here's what you're going to do every day:
If any of these rules aren't adhered to, there will be hell to pay.
Me: "I suggest you quit while you're ahead, or at least not as far behind as you could be."
Boy: "Yes Sir."