The Underwear Game
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First you'll need to convince him to play. It shouldn't be difficult, he's always horny and the idea of something a little different will get him hard. Then you'll need to find the perfect pair of underwear to put him in, I'd suggest a pair of soft cotton boxer briefs. I'm terribly biased, but just think of how they'll come down those muscular thighs of his. The underwear should be white no matter which style you choose, because I know he leaks a lot when he gets riled up and it'll be a delight to see all those wet-spots form as you tease him.
Now in order to play the game properly, you'll have to convince him not to touch himself. If he touches himself the game is over. The point is restraint. You could tie him up, but it's almost hotter if you don't. Let him war with his desire to get a hand on that massive cock of his. Again, it's hotter if he has to struggle with himself.
If you want to really get him going you might want to get a buttplug inside him, sandwiched neatly between his tight hole and the soft cotton underwear. Make him sit on it and he'll keep himself entertained. As the action ramps up, he'll start riding that thing like it's his ticket to heaven. I don't need to tell you how amazing his cock looks pressed up against his boxer briefs, straining against the fabric, trying to spring out. But we both know that's not going to happen, not for a long while at least. He'll start humping his underwear, it's inevitable. He'll leverage himself on the chair, use his feet and thighs to rock himself forward and slide his dick across the front of his underwear. It'll also work the buttplug inside him, making him taut with pleasure and causing the first beads of precum to seep into his the front of his undies. If you aren't hard yet, you sure as hell will be now.
Now this will be fun to watch, but make sure you don't let it go to far. It's not the easiest thing to cum in this position, but it's been known to happen. If he starts to get too into it, stop him. He'll beg, of course. He'll tell you how badly he wants to cum. How it's been days since he's shot his load. He'll tell you to look at how hard his cock is. You should look at it. That means it's working, that means he likes this game even though he's begging for it to be over.
You should start working his nipples. He's sensitive to that. However loud he was moaning before, it'll double. Be gentle with one and rough with the other then switch. Use your fingers for a while and then your mouth once those nipples get nice and hard. By now his begging will start to become background noise. Let it wash over you. He's horny and young and he wants to cum so bad. He'll swear that he'll cum right in his underwear if you keep on doing that to his nipples, but it's unlikely. And if he does, well that would be hot too, wouldn't it?
Now feel free to give his cock some attention. Trace the outline of it with your fingers. Jerk it off a little through his underwear. Squeeze it from the base and let out any precum that's trapped inside. Enjoy it. This is what you're working for, this moment when he's so rigid and aching and totally under your control.
You're the kind of guy who likes to suck cock. Maybe you think I don't know, but I do. So lick the head of his cock. No, don't take his dick of out his underwear, just lick it through the cotton. He'll try to get your mouth around it, but he's not in charge. Hold it with your hand if you want to and suck it or just lick it, it doesn't matter, there's no wrong way. If it feels right then do it.
At this point you’ll enter do or die territory. His begging will deteriorate into moans and incoherent fragments of sentences. His gyrating will become erratic as he approaches his breaking point. Now is the moment where you have to make a decision. How does it end?
You can whip out your own hard-on at this point and jerk off in front of him while he watches. You could whisper filthy things into his ear and then shoot your load all over his chest, or you could bend down a little further and unload right over his nice white underwear. Assuming you choose the second option, which you probably know is what I'd suggest, you can just leave the rest to him. Let him rock on that buttplug up his ass and hump his cum soaked underwear. Considering how turned on he is, he shouldn't have any trouble getting close, but you might want to help by sucking his nipples. A little nipple play and he should be primed to hump a hot load of cum right into his underwear, right up through the cotton, making a huge wet-spot for you.
Before you let him clean up, just admire the scene a little. Just take in his demolished underwear and listen to his panting. Smell the fresh spunk and sweat and musk. Maybe you'll peel the underwear off of him and keep them as a souvenir so that later, some lonely night you can find them and sniff them and add a fresh load to them.
Now tell me, doesn’t that sound fun?