Queen of Everything

First off, it's two weeks of daily masturbation with orgasm denial. He'd be instructed to get himself as close as possible without cumming - three times daily. There's a point to this, I promise. The idea is to increase sensitivity & build up a good head of tension. Just regular ol' chastity can work, but it's far more effective with daily edging. Regular chastity might take a month or more to reach peak sensitivity. I'm too impatient for that, lol.

The daily edging is always accompanied by gentle stretching. A plug or a dildo that's just slightly larger than what he's used to. Once he stops feeling the stretch, move up to something bigger. And yes, I do mean that in the middle of a session. The constant slight burn helps to keep a boy from cumming by accident. (Honestly, the stretching isn't strictly necessary to get a hands-free orgasm. I just like the idea of a boy getting fucked up the ass by something bigger than him & cumming everywhere because of it.)

So fast forward two weeks. I'd prefer to do the Main Event on a Saturday so that we can just go ahead & make an afternoon of it. I'd start by stripping him down & kissing him - paying special attention to the neck & underside of the jaw. A naughty boy might have to have his hands tied behind his back, but a good boy could keep his hands on my breasts instead. I'd probably leave a couple of little love bites on the dear boy's neck - I'm terrible about that. Anway, I'd eventually move on, leaving a trail of kisses down to his definitely-hard-by-now nipples. The really excellent thing about the two weeks of edging & denial is that Everything becomes more sensitive. Even boys who don't usually get a lot out of having their nipples sucked can hardly stand it. So I'd do that for a while, & use the opportunity to get the boy laid out on his back. (A bit uncomfortable if his hands are tied behind him, but that's his fault, isn't it?)

Once he's on his back, a good boy just needs to bring his knees up, maybe wrap his legs around my waist. A naughty boy would have to be further restrained, of course. A good, sturdy spreader bar fastened just above the knees should do the trick. I don't particularly like strapons for the first time around. I prefer a hand-held vibrator with a realistic shape. Having it in hand gives me better control, I find. The vibration isn't always necessary, but quite useful for stubborn cases. The first thing I do with the vibe is slowly thrust it as deep as it will go. If my boy's been stretching himself like he was told, the toy should go all the way. If it doesn't, or if he tenses up too much, then a good spanking may be required to get things back on track. Once the vibe's in good & deep, I like to leave it still for a few minutes. Give the boy some time to relax, build some more tension. If he's very good, I might let him suck on my nipples in the interim. Then, once he's just about gotten used to having something in his ass, I start moving. Slow strokes, at first. It's all about finding the angle which best hits his prostate. Sometimes this can take a while, but it's worth taking the time to figure out properly. If you just start banging away, sure, you're going to hit the mark sometimes...But anything worth doing is worth doing correctly, & an anal orgasm comes from prostate stimulation. Once I've found the right spot, I'll concentrate on that, & slowly build up some speed. The real key here is to use the edge of the head to sortof gently scrape across the prostate with each thrust. I like to thrust in hard & pull out more slowly. By now, his cock is probably hard, bouncing uselessly on his belly. I love the sight of it.

Eventually, I may have to turn the vibrating motor on. If that's the case, I'll press it hard against the prostate, & then thrust more shallowly. With all this lead up, there's basically no way that can fail to elicit an orgasm. It doesn't always result in proper ejaculation, though. Sometimes you'll get a dry orgasm instead. That's always surprising for the boy, but I'm not deterred. I'll just keep at it until I get what I'm after. Depending on my mood, I might not even stop then. Overstimulation is such a cute look, & a vibe up the ass is a great way to achieve it.