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  • Getting fucked on the trail

    • It was a year before my first anal experience and I had come to the realization that I was gay or at least bisexual. I was 18 at the time and had just given my first blowjob to an older man while jogging in the park. Since then Id taken to cruising the local parks that had all the tale-tell signs of cruising. They were somewhat empty, out of the way, occasional condom wrappers and tissues on the ground and had a few guys hanging out in the parking lot.

    Since giving my first blowjob, I had given about 6 more in the following year. They were all older men, at least 25 years my senior, and I assume most if not all were married. The experiences were normally the same. The older guys would want to fulfill their fantasies of being with a younger boy and couldn't wait to have me service them, normally in the front seat of their cars. In the end, I always wanted to be fucked by one of these guys, but most of the encounters were quick blow-n-go's. I wouldn't even get a chance to open up the car door to spit before they'd be starting up the engine to leave.

    Eventually I had a free weekend morning and decided to check out a new park that seemed perfect for action. It wasn't long before the older guys were checking me out but none of them seem interested in leaving the parking lot. It was too open for my tastes and I feared being that out in the public.

    I walked by a small trail when I noticed that someone was following me from the parking lot. I found a secluded opening among some trees and waited to see who it was. He was in his early 50's, graying hair, glasses and was wearing a preppy shirt and jeans. If I remembered right, he was sitting in a white Volvo station wagon when I last saw him and everything screamed that he was a married man on the prowl.

    I stood next to the tree acting as though I was checking out the view. He walked up next to me and made some small talk about the weather. I could tell he was all excited by the bulge in his pants.

    "So you like to come out here often?" he said.

    I shyly replied "sometimes". Try to do my best submissive porn star pose.

    "You want some action?"

    I barely said yes when he pulled out his cock through his fly. It was long, but average girth. It had that soft skin look to it that I love to suck on. I knelt down in front of him and slowly licked the tip of his dick, paying close attention to underneath the head. I slowly took more and more of him into my mouth each time and made sure to look up and make eye contact. I ran my hands up his sides and for some reason he grabbed my hands, interlocking our fingers, and began thrusting his hips into my face.

    I needed to take a quick break and decided to pull off with a popping noise that all the porn stars did. I leaned back and asked him how I was. He just moaned, "Mmmm great, but I'd really love to fuck you instead."

    At first I was stunned because I didn't expect it from him. But the longer I was with him the more aggressive he was becoming. I didn't have a condom and wasn't sure how to answer. Until now, all my blowjobs were bare, which I realize how stupid that is. What I was about to do was even more stupid and it was the one and only time I've been barebacked. "Hell yeah" was all I could get out.

    I tried to act tough, as though I was an old pro at letting another guy shove his cock in my ass, but honestly I was scared. I should have had a condom, but my teenage horniness got the better of me. I pulled down my pants and leaned against a tree. I spit in my hand and began lubing up his cock as though I was some nasty whore.

    To this day I don't know why, I guess nerves, but I squeaked out "please be gentle, I've never done this before I was hoping he'd make passionate love to me among the trees, living out some daddy-son fantasy. It was more like I was some nasty teen whore in a porn about to be fucked hard and when she was about to start crying, fucked even harder. Needless to say he just chuckled at me as though I was joking.

    He dropped his pants and I remember looking down at my feet, seeing his pants on the ground thinking, "this is it, this is what you've wanted." I heard him spit once more on his hand and rub it on his cock. He grasped my hip with one hand and directed his cock with the other. I used carrots and candles to this point but this was the real thing and it hurt. I could feel his head starting to push into my rectum and started to pull away.

    "Oww oww.take it slow" was all I could say.

    To keep me from moving too far away he grabbed both hips and started to slowly but steadily push himself into me. My ass felt like it was on fire as it stretched to fit his dick. For a few minutes he was gentle, applying constant pressure until his cock popped through my asshole.

    I moaned loud but it was from pain not pleasure. Once he was inside he kept pushing until he buried his full length inside me. He started sliding his cock in and out of my ass, with a steady hard trust.

    "Oh shit, oh shit, oh shit" was all I could say as this total stranger was taking my virginity along a park trail. With me crying out he began pushing harder. I could tell he was taking out all his sexual frustration on me, that he couldn't with his wife.

    I reached back with both hands to slow him down and keep him from going too deep, but he just held my hands like he did earlier. I realized that for the first time, I wasn't in control of the situation and that I couldn't stop it if I wanted to. I was so horny at this point thinking of myself as some cock starved nympho in porn, but scared how it would end.

    He started fucking me harder and harder, with each thrust pushing me past my comfort zone. By now, my shoulder was against the tree and taking the full brunt of his weight being slammed into me. My ass was a bunch of numb burning nerves by this stage, but I could feel him deep inside me.

    "Who's your daddy?" he moaned. When I didn't reply quickly he slammed himself deep inside me and kept it there while pulling my hands back. "Who is your daddy? he said again.

    "You are, daddy"

    "Oh yeah? You like being daddy's slut?"

    "Arrgghhhh yes daddy" was all I could say.

    He began fucking me so hard I thought I would scream. His hands slid to my hips allowing me to hold onto the tree. He was going to come but where? I worried about the lack of a condom and cursed myself for not bringing one. His hands grabbed my hips tighter and I could feel his cock starting to twitching inside me, ready to explode.

    "Can Daddy come?" Before I could even plead with him to pull out, he gave one more deep thrust and let loose inside me. He was buried balls deep inside me and I could feel his cock pump his cum inside me for a minute or two. For good measure he continued fucking me for a few minutes to milk everything out of himself and into me. He pulled out, rubbing his cock against my ass to clean himself off.

    "Wow, you fuck like a champ. That was one hell of a tight ass." He pulled up his pants and took out a cigarette. "I hope to see you around again. You sure were great kid." He patted me on my shoulder and left.

    I stood there in shock. It's what I always wanted but not sure what to think. I was scared by the lack of a condom, but horny none the same. I stood there and started to jerk myself off to finish the job and left.

    On the drive home, the whole fucking replayed in my head, as I clenched my ass cheeks tight to keep his cum from dripping into my underwear.


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