I discovered the activity I now know as “sounding” in the art cupboard at school when I was fifteen. If I had the reputation of being a little faggot, Keeler had the reputation of being the dirtiest fucker known to man. He wasn’t gay, per se. I’m not in touch with him now but I’d take a guess he’s at least bisexual, though hypersexual might be more accurate. Or omnisexual. Anything was game, except other boys of course – at least not openly. There were rumours about farm animals, about his own dog, and he boasted about fucking certain large fruit, holes in trees, in the golf course. He’d have put his cock in a wasps’ nest. He probably has done.
One day after school I caught him in the art cupboard with a paintbrush sticking out of his cock. He was wanking away, pumping methodically, lubed up with some other art supply. He gave me a wink. I just stood and watched. The brush handle rose and fell with each pump, which made sense, but then continued to do so when took his hand off his cock as he approached orgasm. This was some kind of magic, I thought. It was only later that I grasped the physiology of urethral muscles, after I’d shot a paintbrush out of my own cock, as I watched Keeler do, followed by a gush of watery cum.
This wasn’t the first time I’d caught Keeler wanking in the art cupboard; it had already become something of a routine, and usually I didn’t just stand and watch. I’d wondered why he’d taken the position of art room monitor then realised he got to stay after school and had access to whatever he wanted from the cupboard. But why would he want anything from the art cupboard? Well, it was a cornucopia of joy for the imaginative masturbator. Thick gloopy paint, clay, putty, the delicious aroma of turpentine and glue…
Once I’d happened upon his routine, and he was happy for me to join him, I’d usually wank alongside him or sometimes suck him off. Almost always he came in my face, which was my fetish rather than his, but he really got into it. He said his cum looked good on my face, which I took as a compliment.
The first time I got a paintbrush down my cock was also the first time I got him to touch my cock.
“I can’t get it to go in,” I protested.
He told me to wait until I had enough precum. But even then I pretended it just wouldn’t go.
“You’re going to have to help me.”
He told me to hold my cock firmly as he gently pushed the handle down my slit. At the first sign of pressure I faux-winced and took my hands away. He told me not to be a baby, grasped my hand and put it back on my cock. As soon as he did, I grasped his hand and held it within my own, tight at the base of my cock. He knew my game, but I wasn’t going to miss this chance to have his hands on me.
I didn’t count on retaliation though; he forced the handle down harshly and I drew in breath. It was a shock, an entirely new sensation. I was amazed my urethra gave so much to the force and width. But it did.
I refused to release his hand from my cock, and thrust repeatedly in his grasp. His response was to push the brush down further, right down so it was entirely inside my cock. Judging by the surprise on his face I don’t think he’d ever managed that himself. I came pretty much right away, and shot the brush hard against his chest. He shielded himself from my cum, catching most of it in his hands, which he then wiped roughly over my face.
From then on we incorporated this paintbrushing (as we called it) into our masturbation routine, and, not to be beaten he got a brush right inside him our very next session. I held my thumb over his slit so it wouldn’t come out, then pumped him to orgasm, releasing the brush like a bottle rocket.
Our after-school ritual could have lasted until the end of Year 11, had we not been caught by Mr Miller, the art teacher. He was a student teacher, early twenties and straight in every sense of the word. He talked about his church a lot. I think he thought he’d found the devil when he caught sight of us, pumping our cocks with paintbrushes sticking out of them.
We were barred from art monitor duty from then on. It didn’t matter; I’d learned the ropes and there were plenty of tools that could stand in for a paintbrush.
I took to sucking on my paintbrush handle in Mr Miller’s classes, and staring him out whenever he spoke to me.
On his last day as a student teacher, before he moved to a permanent job at another school, he took me aside and told me I was going to hell. He told me I needed to mend my ways or my soul would forever be in peril.
I told him I fantasised about him when I masturbated (this wasn’t a lie – he was beautiful). I told him I’d love to stick a paintbrush down his cock.
I put my hand down my trousers and told him to do it again, harder.
I’d love him to know what I’ve been up to since then.
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