I've been wanting to fuck a boy with a strap-on for as long as I knew about boys and strap-ons. It's been a long time coming but I'm glad I waited for the right boy, the right moment and the right bit of kit. I remember telling Dandy that I wanted the first time to be "special" and I remember grinning as I said it, with images of coyly strewn roses and soft lighting. I liked the idea of taking him out for dinner, wining and dining him before taking him home and having my wicked way.
That wasn't how it eventually played out, it was more spur of the moment than that (perhaps I am becoming more spontaneous?) but perhaps surprise made up for lack of anticipation. The evening began with him working on his service techniques - massage, rimming, finger-related dalliances. The kind of attention where I can just lie back and enjoy myself, feeling pampered and cared for, exactly how I want to be treated. After a while I realised that I wasn't going to orgasm and got a little restless, so stripped him and placed him, hands on head, at the end of the bed for a brief inspection. I check him out. Long slow looks. No words, but amused smiles at the winces and twitches that come when I flick and press my fingers around his cock. Easy target.
I lead him onto the bed and start playing with his arse, it's a natural movement by now, to hold one arm around his shoulders and neck and the other inside him, feeling him squirm and open up to me. And moan, of course, those delicate little moans and whimpers that make me want to push him further and further, just to see how he'll react. After a while I get up and fetch the strap-on and a blindfold. Starting slow, as I promised in an email a long time ago: it's important to keep promises, whether they are nice or nasty. I used the dildo as an insertable first, to warm him up a little before attaching the straps. The dildo was already half inside him as I put the strap-on on, but once I'd gotten in place I pressed deep into him, watching his mouth open, his back arch up. I wrapped my arms around him and felt him. Actually felt him. Similar to girl-fucking, the strap-on was absolutely an extension of myself, a way of pushing into him and I got wet very quickly. But more than that, I got direct pleasure not just from his pleasure, the feelings I was giving to him but by the act of taking him, of owning him. Of making him mine.
As I fucked, he responded and did so in a way that was almost helpless, writhing beneath me and unable to articulate anything beyond curling fingers into the pillows, or gasp semi-coherent "thank yous". The gratitude added to the moment, as did knowing that the sensation which I could not feel but knew well enough from personal experience, had a certain intensity that was not-quite-pleasure. I moved him into a couple of different positions - flat down, on all fours, on his side and he complied just as one would expect from a toy. Each time he did so, it made me smile at his keen desire to be taken and used, at what he was offering up and the sensitivity of the experience. To hold someone tight whilst at the same time teetering on the edge of hurting them was very personally intense - I felt a deep, strong compassion for him and a desire to look after and protect him at the same time as make him break down and cry. Then dry his tears.
Then do it again.
5 weeks ago