(this is an essay I’m thinking of submitting to the Portland Mercury Sexy Essay Contest)
High school – those two words bring up a riot of bright memories. High school sex? A darker subset. Angst, disappointment, longing, Jesus Christ, bondage, milkshakes, and lesbian awakenings.
I had strange luck with the ladies. The ones I got were amazing, special, beautiful, wonderful – but thin on the ground, so I tended towards clingy and unsure, and sought the unsure to cling to. And that’s how I found Sara. Sara Rainbow. Tall, heavy breasted, long faced, outcast. Unconventional looks, my mother would say. Horse faced my friends would snicker. But I set to work on making her mine, and soon enough – she was.
And that’s how we ended up in my bedroom, stripped to the waist, those enormous delightful breasts playing across my pasty chest, the crotches of our blue jeans locked in a frictive crush. And that’s when it happened.
I should explain – Sara Rainbow was a late bloomer. She hadn’t figured out masturbation, knew almost nothing of the sexual anatomy, much less of the act itself. After an early makeout session, she called to ask me if I had soaked my pants, because it had gone all the way into her panties, and I didn’t have the heart to explain. She was so clueless, in fact…
Making her sexy face, and dry humping in earnest, she came down full force on my tented penis – It first shuddered, and then buckled painfully, causing an audible pop of gristle. I stared, open mouthed at the ceiling, a cry caught in my throat, eyes tearing up. And as my brain flashed the days that would come, the bruise, imagined the lump of scar tissue that still gives a gentle kink, she looked at me through heavy eyes and mouthed. – “Did you come?”