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JamieLong
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Blog Entries posted by JamieLong
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There's park that was by my house in the suburbs that I had jogged by a couple times, but never really went into, and I ended up meeting a 19 year old bottom there one night. We had been chatting on Grindr for a while (he lived less than a mile away) but he was flaky as fuck and never really wanted to meet up. One night as I hit him up he said let's meet up, and told me about the trails that this little park has. I agreed to meet him and put on sweats, no underwear of course, a hoodie, and running shoes (best hookup outfit). and walked out to meet him. It was a cloudy night, slightly chilly, and when I got to the park I walked in a little bit and let my eyes adjust. There was just enough light to see the trail, so I started walking into the park some more. I got to a fork where the trail started a loop around the park when I saw him walking toward me. He was quite cute, taller than me, and a few extra pounds. He had sweat on as well and a light jacket. We exchanged hellos and started walking along a trail until we came to a log that had been cut into a bench. We stood there kissing for a bit and with him groping my cock through my sweats and I had my hands inside his sweats grabbing his ass. He unzipped my hoodie and kissed his way down my chest, dropped my sweats and starting sucking my cock. I grabbed onto his hair and worked his head on my cock for a few minutes, occasionally pulling his head off and leaning down to kiss him. He was a completely submissive bottom boy. After a bit he stood up, turned around and asked me to fuck him. I was happy to oblige so I got a packet of lube out of my pocket and lubed both of us up and sank my cock into his ass. I bottomed out and he moaned in pleasure as I started to slowly fuck him. After a couple minutes he got his phone out and wanted me to film him getting fucked. I hated to use the light on the phone because it destroyed my night vision, but it was hot knowing he'd be jacking off to my cock plowing his ass later. After a few minutes of filming my cock sliding in and out his ass his phone stopped recording because of a low battery. I handed it back to him, grabbed on to his shoulders and started fucking him faster and faster until I started shooting in him. I stopped balls deep inside him and just let my balls drain into him. He turned back to me and asked if I had cum in him. I told him yes and he just pulled off of me and pulled his pants up. We kissed and hugged and went out separate ways. I hope my cum was dripping down his leg as he walked back home.
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I met another guy on Grindr while I was out in downtown Portland one night. I don't know what it is, but I went through this period in my late thirties where guys aged 18-22 were thirsty for me. This guy was 20, so he couldn't meet me at a bar, so I went down to Riverplace, on the Willamette river, where his apartment was. I was dressed for going out, and he was in a hoodie and sweats. He was shorter than me, but built like a jock. I had a condom and lube with me, but I usually don't tell people about the condom unless they ask. We started kissing eventually we made our way down to a sort of secluded spot on the river's edge. I got his cock out and started sucking it til he was moaning in pleasure. It was about average length, but had a good girth. I got a packet of lube out of my jacket and lubed up his cock and my hole. I turned around and lined his cock up with my hole and slid it in bare. He only fucked me for a couple minutes, but he shot a huge load in me. I zipped up my pants, we hugged and I drove home with this kids college load in me. When I got to the toilet I was impressed at how much he shot up me.
I got a little paranoid the next day and went down to the spot to make sure there weren't any cameras around. It was definitely one of the riskiest places I've had sex.
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Turns out I've had sex in public quite a bit. I'll share a couple more here.
At my old place out in the suburbs, there was a paved trail that went back behind the houses and along a greenway that ran along the freeway. There was some light coming through from the freeway, but at night, it was quite dark. One night a cute 18 year old twink messaged me from less than 1000 ft away. He was visiting his sister and was looking for some fun in the new city. After chatting a bit, he wanted to meet up, but somewhere outside. I told him about the trail and he thought it was perfect. I threw on some sweats and a hoodie and went out to meet him. He walked up to me and he was hella cute in person. He had a few extra pounds, but that has never bothered me. He was a bottom, and wanted to get fucked, but he wanted to be safe, so I had brought a condom and lube. We started kissing right away and after a bit he couldn't keep his mouth off of my cock and started giving me an expert blowjob. After a few minutes he asked if I had brought a condom, and I got it out and he slid it on me. He pushed his sweatpants down and got on his hands knees, and I started pushing into his hole, which was quite tight. I only had slid in a couple strokes when the condom broke. I pulled out and told him what happened, and he asked if I had another, which I didn't. I took off the broken condom and just started rubbing my cock in the crack of his ass as I reached around to jerk him off. He was moaning in pleasure and turned his back to me and we made out for a little bit. Then he said to just put it in, so I happily lined up my cock and slid back in, his tight hole gripping my cock. Here I was, 39 years old, bareback fucking a 18 year old twink out where anyone could walk along. It was so fucking hot. He shot his load after a couple minutes all over the ground in front of him, and then turned around so I could jack off into his mouth. We hooked up one more time before he left, in my bed that time, and unfortunately with a condom.
I used to meet another guy there as well. He was 25, short, and a total top, and mostly I just sucked him off, but he fucked me there a couple times, with a condom though. I couldn't get him to fuck me bare which was a shame because he shot nice loads. Normally I don't swallow loads, but I always did for him. I loved going to meet him wearing a jock strap under my sweats so I could just pull my sweats down and sit on his cock. We almost got caught one time because I saw a guy walking along there which was weird at 2 am, but we were out there, so, to each their own I guess.
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I love business trips. All all-expense paid to go fuck guys in another part of the world. This time I was sent to Denver for ten days. The first night I was there I went out to a couple bars, chatted with a few guys but no one really caught my eye. The clubs eventually closed down and I was looking around the parking lot of the last bar I was at, watching my prospects dwindle rapidly, when I saw a cute little twink sitting in his car. He was probably around twenty-two. I walked up to his car and said hi because he had the window down. He looked up at me and he was crying. I asked if he was okay and he said yes, and not to worry about it. I asked what he was up to the rest of the night and he told me he was going over to a friend's house for some drinks. He asked if I wanted to come along so I jumped into the car with him and off he went.
We got to his friend's house and he introduced me to everyone and got me a drink. They were watching Queer as Folk, and I told them about the British one and how I thought it was way better. The twink I had arrived with snuggled up to me while we were watching. At one point, he turned and kissed me. The rest of the guys got up shortly after that and went outside to smoke. We kissed for a while longer, then he took me up to his friend's bedroom. He wasted no time getting my clothes off and I quickly stripped his off of his lithe frame. His body was on the smaller side, tight and compact, with his tiny abs perfectly defined, but his cock was anything but small. About seven and a half inches and pretty thick. I sucked it for a little bit before he pushed me down on the bed.
He sucked my cock for a bit then started licking my balls and down towards my hole. Up to this point I had never been rimmed before, so I was a little nervous about him going down there. Also, I wasn't bottoming much at the time, it just hurt me too much, and besides, I wanted to fuck his little body senseless. He finally got to my hole and I was floored. It felt amazing! I can't believe I had missed out on it for this long. He shoved my legs up to my chest and went to town on my hole, working his tongue inside and making me writhe with delight. After about five minutes he stopped and got up and got some lube from the biggest bottle of lube I've ever seen and greased himself up. He got my legs up on his shoulders and lined himself up. Almost as an after-thought he asked me if I wanted him to put on a condom. I shook my head no, and he pressed the head of his cock to my hole. Spent a minute working it up into my hole, letting me get used to it. Once he managed to get his cock into the hilt, he slid back out and started fucking me slowly.
It was a magnificent fuck. For almost forty-five minutes he drove his cock into me. Before him I was never able to last more than fifteen minutes as a bottom. He had me on my back, face-down, doggy, and on my side. Finally his friend interrupted us because he wanted to go to bed. We got dressed and went back to my hotel. As soon as we got in the door we took our clothes off. He got on the bed on his hands and knees and told me to fuck him. I got out some lube, and smeared some on my six and a half inch cock and sank into him. I fucked him doggy-style for about ten minutes, then flipped him on his back to finish off. I slamming my cock into him, and jerking his cock when he told me not to come in him. I was disappointed but agreed. I jerked his cock until he came, and just as I was about to unload I pulled out and shot on his stomach. We got up and went to the bathroom to shower, and then he got dressed and left. I should've got his number but didn't. I could've fucked him a few more times. Business trips are fun.
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I hadn't seen Jack in several months. We used to hang out at clubs, but never did anything beyond making out. Apparently he had moved out of the city, but was back visiting family and friends. We had a couple drinks and caught up. We started talking about the last time we were making out and he asked me if I wanted to do anything. I said of course, so we left the bar and headed for a nearby park. It was after midnight by the time we got there. There were a couple trails that had a reputation for being cruisy, and we passed a couple guys that checked us out. We stopped on the trail and started making out. Another guy came along and passed by us, then stopped a little ways away, sat down, and watched us. I didn't really want an audience so we walked back down the trail. We got off the trail and went a little ways into the woods so no one could see us.
We started making out again and rubbing each other through our pants. We both unzipped each other and took turns sucking the other. After I sucked him for a bit he stood me up and turned me around. He started kissing my neck and ears. He slid my trousers down and and put his cock up against the crack of my ass and started sliding up and down it, his pre-cum making it slick. He kept sliding his cock further down my crack until he was pressing the head against my hole. He was oozing so much pre-cum that it lubed up my hole and he was able to slide his dick right in. No talk of condoms, he just started fucking me. He wasn't that big, about five and a half inches, but he knew how to work it. He bent me forward, grabbed my hips and fucked me for almost ten minutes, me jacking my cock the whole time. I shot first, my cum spraying out into the darkness. I asked him if he was close because it was starting to hurt, and he said yes and about thirty seconds later he pulled out and shot his load down on the ground. I didn't mind him pulling out at the time because I was still paranoid about STDs, but now I always want a guy to shoot in me.
We pulled our clothes back on and I dropped him off back at the bar where his friend was waiting for him. Never did see him again.
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