Where it happened: Under a bridge
I was 17, and had just gone out on a date with my current boyfriend. We were both horny teenagers, and given that both of us still lived with our parents, and neither of us had a car to go somewhere else, we’d started fooling around in semi-public areas; a grope here, a deep, french kiss there… By the time we had finished our dinner -sushi- we had worked each other into a frenzy of hormones and lust…
Luckily, there was a seldom-used creek bed nearby, which we decided to “explore” in for a place to make out and maybe give each other head, or jerk each other off… As it turns out, while exploring, we found a nice, large bridge that cars in the downtown area used to pass from one side of town to the other. Looking up, we could see graffiti, but no walkways, one barely-visible balcony above, but very little in the way of visibility. I asked him if he wanted to… You know, do /it/. He looked back at me cockeyed for a moment before smiling. Horny again at the very mention of sex, we dove against each other, kissing, hands roaming over each others’ bodies, my hard cock grinding against his through our pants.
He stood with his back against one of the bridge’s walls, and unzipped himself. Even in retrospect, and no longer a virgin, I’m still surprised at how well we managed; he was pretty large, and the only lube we had was a sample packet from a local LGBTQ Awareness booth. I quickly dropped my pants to my knees and moved my back against him, letting his teeth nibble over my neck and ear. We opened the small container of lube up, spread it mostly over his length (pretty big, at around 8″, and thick as a roll of silver dollars), and pushed the rest into my ass with a single finger.
Finally ready, I bent forward a bit and he took his substantial cock in hand to point at my tight ass. I pushed myself back against him slowly, nervous and horny as could be. Slowly, I felt the slippery head of dick push past the tight ring of my hole, and I gasped at how thick it felt. It hurt, but I wanted to keep going so bad that I just stood absolutely still for a moment, getting used to the painful stretch. Slowly, I pushed myself back against him again, sinking another inch or so in. I backed away for a moment, letting the lube ease the motion, before pushing against him again, taking his big cock deeper into me.
Five or six thrusts back against him, my breathing was shallow and tired, my own six-inch cock bobbing and throbbing in the air as I’d taken as much of his cock into me as I could- just a couple inches left, he said. Now was his turn. His hands took me by the shoulder and hip, holding me up so that he could push his cock into my ass slowly. I asked him to go faster; I was so horny that all I wanted was him to fuck me hard and fast with his big dick. He picked up his pace quickly, and I could soon feel his hips slapping against my ass with each thrust, feeling his cock dig into me wonderfully. My own hands played carefully with my own member, careful not to make myself cum until he was closer, and spreading one of my asscheeks wide, hoping to take his wonderful, hung dick deeper into me.
Barely a minute passed with him humping against me, our breathing short and careful, not making any noise to make sure that nobody could hear us, before I heard him grunt that he was close. I breathed back that I was too. He asked me what he should do, and I responded the only way that I wanted; “Cum inside me.” His thrusts got less regular, but deeper and harder, grinding his pubes against my ass until I finally heard him let out a breathy moan. My own hand was a blur on my cock, jerking myself off while my anus was speared by his thickness, and as I felt him swell up, I felt myself go over the edge. I breathed back to him, almost choking with my inability to speak, that I was cumming too. He held my ass tightly against his waist as he rode out his orgasm, filling my hole even further with his spunk, as my jizz shot onto the rocks underfoot. An eternity passed in moments, and he collapsed against the wall behind him, pulling me with him. He gripped my hand with his and held me tight in a warm embrace as we both smiled and giggled in the warmth of our afterglow. Finally, he pulled his now-limp cock from my ass, and I moved off of him, feeling tender, but wonderfully sated, with his cum slowly beginning to drip down my thighs.