JamieLong

I like wearing a jock when I'm bottoming. Otherwise naked.

Anyone have a favorite hookup outfit? I like a t-shirt or a hoodie, shorts or sweats, no underwear unless I'm bottoming in which case I wear a jock strap, and slip on shoes. I love being able to strip off in a couple seconds and be ready to fuck. I have a sleeveless hoodie that I love wearing when it's nice out; it shows of my arms nicely. I have a couple kilts as well, but I've only hooked up once when I was wearing one. I really want to get fucked while wearing one.

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.

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.

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.

It's been a couple of weeks since my last load. It was at Hawk's PDX, which is usually hit and miss unless it's CumUnion, but a cute guy in his mid twenties on Grindr had on his profile that he was there and taking cock, so I went. After checking in and stripping down I went around to find him. He was on one of the raised platforms there just jerking his cock alone, so I went up to him and we started kissing immediately. After a little bit he sucked me off for a while and then handed me a condom which kind of bummed me out, but I put it on and started fucking him doggy-style. After a while he pulled away and turned around and started kissing me some more. Another slender guy, maybe late twenties, walked up and started rubbing the guy's chest. I moved out of the way and they started making out as well. The new guy started lining his cock up with the cute guy's hole until he was stopped and given a condom. I could tell that he was disappointed like I was, but he put it on anyway and fucked the bottom until the bottom jerked himself off onto his chest. After that the bottom got up and went to the shsowers. The new guy hadn't got off yet, so I leaned close to him and whispered that he could fuck me bareback if he wanted. He nodded in agreement, took the condom off, and I got on all fours in front of him and he slid a nice 6 inch bare cock into my ass and started fucking away. As he was fucking me I leaned back to him and told him to make sure to cum in my ass. He smiled and nodded. 5 minutes later my hole was filled with a strangers cum, and I was a happy boy.

A while back I found this 21 year old twink on Grindr who had a profile pic of him in cut off jean shorts. I messaged him and we chatted back and forth a bit and he agreed to meet me so I drove to pick him up. When he came out of his house he was wearing the same short as in the picture because I had commented on how sexy they were. He got in and I drove him back to my place. Fortunately it was late at night because I was a bit nervous about anyone seeing us, because in that outfit, it was pretty obvious what we were up to. We got into my house and into my bedroom, and we chatted a bit before we started kissing. He had on a short sleeve flannel (I love slowly unbuttoning those off of a guy) that I got off of him, and I pulled the short shorts off him revealing a cute little jock strap that barely contained a thick 7 inch cock. I got undressed and he started to suck me off for a bit until I flipped him over and started rimming out his tight little hole. I got him nice and wet and lubed up my cock and sank it balls deep into him, bare of course. I fucked him for about 10 minutes and he jerked himself to orgasm and shot a sizable load on my bed. His cock went soft and we cuddled a bit chatting and kissing, and he got hard again. Now everything about him screamed total bottom, but I can't pass up the chance to get a great cock in my hole. I asked if I could ride it and he agreed, so I lubed him up and slid down on his bare 7 inch cock. He proceeded to fuck me as well as any top, flipping me face down or on my back, whatever he wanted. My legs were up on his shoulders when he shot his second load deep inside my ass. I hadn't cum once yet so he pulled out and then flipped over on his back and put his feet up in the air exposing his hole to me. He told me I could fuck him til I came. I put his legs on my shoulders and sank back into him and started fucking, and he got hard AGAIN. I went about 5 minutes more fucking him and told him I was cumming and shot my load into him just as he had a third orgasm. We cleaned up and I drove him back to his place before the sun came. I absolutely love it when a guy has more than one orgasm in a session.

I went to the CumUnion in Portland at Hawk's last year. Had a decent time. Wandered around a bit checking things out. A younger bearded guy took me into an alcove and we started making out. He was there with his boyfriend. I was a little disappointed when he gave me a condom, but I still went along with it and fucked him for about twenty minutes 'til he shot his load. After walking around a bit more, I was in the glory hole tunnel when a guy walked through and stopped in front of me and started fondling my cock. He got me hard then turned around and backed his ass onto my cock. I fucked him there for about ten minutes while a few other guys watched. We moved to the slings and he got into one and I fucked him for another 10 minutes until I unloaded in his ass. I left him in the sling and I went to shower. Hawk's was fun but I prefer Steam.

I met Dave at the bars. We hit it off immediately and spent the night talking, until the bar finally shut down. We left and decided to go to a new bathhouse that had just opened down the street. We got checked in and got a shared room. We stripped off, making out briefly, and then went out to explore. We got in the hot tub for a bit and chatted with some guys. Had a nice chat but decided to get out and roam a bit more. The club was nice but plain so we headed back to the room where we made out, I sucked his nine inch cock and he sucked my six and a half incher. He was a total twink but turned out to be a top. I totally had him pegged as a bottom. He proceeded to fuck me bare in a couple different positions and ended up shooting his load deep in my ass. We met up again another night and ended up going to another bathhouse and he fucked me in the hallway. The club was pretty empty and no one really bothered us much. He cock felt great in my ass, I've always felt more comfortable taking larger cocks than smaller ones. He always gave a good fucking and ended up shooting another load up me. The next time we met he came over to my apartment just before I had to go to work. We were standing in my living room and made out for a little bit. He turned me around and put his hand down my pants, grabbing my hardening cock. He jerked me for a little bit then undid my trousers and pushed them and my underwear to the floor. He pushed his down freeing his massive nine incher and started sliding it up and down my crack while kissing my neck. He spit on his hand and slicked up his hard cock and put it back against my crack. He slid down and came back up and hit my hole. He pressed slowly against me and popped in me bareback. He fucked me for a couple minutes while I jerked my cock. He thrust in deep and shot a load in my ass while I shot a load across the carpet in front of me. I didn't see him for a couple years until I ran into him again at the bar. He came up to me and told me he was HIV poz. I asked him if he would still fuck me if he wore a condom. He said sure, but we didn't really have a place to go. He grabbed a condom and took me to an apartment building he used to live in. There was a door to one of the stairwells that didn't close all the way so we pulled it open and went to the top where there was a landing and a ladder to the roof. We could look over the wall and see down the stairwell. It was about three am, and Dave stripped down naked. I was a bit nervous about it because while it was unlikely anyone would come up to where we were at, it was still a possibility. I still got naked and he sucked me and rimmed me. He stood me up naked against the low wall looking down the stairs so I could see anyone that came out of the door on the floor below. He rolled the condom on and proceeded to slide all nine inches of his tool into my ass. He fucked me from behind while standing up for about ten minutes, then he dropped me to the ground on my back, putting my legs up on his shoulders and slammed his cock in and out of my hole. He kept at it, kissing me and sliding his rubber-covered cock in and out for another fifteen minutes before he flipped me over on my hands and knees to fuck me doggy style. Before he entered me again I heard a pop that I didn't really pay much attention to. I was pretty drunk and when I reached back to guide his dick into my ass I still felt the condom. He fucked me for a little while more and then I decided to turn around and lay on my back again. As I was guiding his cock back into me I realized only the base of the condom was intact. He had been fucking me bare for the last few minutes! The moment I had that realization I almost had a spontaneous orgasm. He slid half covered dick back into me and I started to jerk my cock. It only took me about thirty seconds to shoot a load all over my chest. I told him to pull out after I came because his cock was starting to hurt my ass. He pulled out, took the broken condom off and jacked his load onto my chest as well. He never said anything about the broken condom. I realized he broke open the condom while he was repositioning me. I guess he was used to fucking me bare. I was so turned on when I noticed the broken condom, I wouldn't have cared if he seeded me with his poz load. I saw him again a few years later on the local light rail. He was checking me out, but I couldn't tell if he recognized me but he was definitely cruising me. I had to get to a class, but I should have gone after him for one more fuck and one more load in my ass.

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.

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.

(Names and places have been changed 'cause I'm shy, but this is a true story) For a while, Bailey’s was the club to go to. Fridays and Saturdays were gay nights, and it was mostly straight on the week nights. Every once in a while they would have a foam party. They would put a low wall around the dance floor and fill up the space with foam. I was working swing shift at the time, so I usually missed those Saturday night foam parties. One night however, I got off early and got to Bailey’s around midnight. There wasn’t much of a line in the front foyer, so I was a little concerned it might not be busy inside. I walked into the club and my fears weren’t justified, The club was pretty busy. There was a walled off space on the dance floor, maybe twenty-five feet by twenty, about four feet high, just filled with foam. Everybody inside was wearing speedos, board shorts, or underwear. Some guys were walking around the outside of the foam area, foam still covering their legs. I got a drink from the bar. I was way too nervous to take off my clothes so I just stood on the wall drinking my drink and checking for any hotties in the foam pit. There were a couple of really cute guys I made eye contact with. One of them beckoned me over and I just shook my head a little bit and held up my drink, letting him know I wanted to finish it first. I finished my drink and then one more then I decided to take the plunge. Walking over to the coat check, I removed my coat, shirt, trousers, and socks and put them in the paper bag they provided and handed them over to the attendant. I kept on my New Balance trainers and my black Calvin Klein boxer briefs. I tucked a twenty dollar bill into my waistband and walked back into the club. I walked up to the bar and got another drink and downed it and then went into the foam pit. I caught my breath a bit as I went into the foam. It came up over my navel and was colder than I was expecting. I found an open spot and started dancing. It was quite liberating. I could have dropped my boxer briefs and no one would have known, the foam was so thick, which was probably the point. I danced for a little bit and was catching the eye of a hot muscle boy. He was slightly taller than me (I’m 5'10") with a bodybuilders frame, probably 23 or 24 years old, and I could just see as he shifted he was wearing a skimpy speedo. He smiled at me and I smiled back. I turned away as I was dancing and when I turned back he was gone. I went out of the pit to look for him but I didn’t see him anywhere, so I went to the bar and got another drink, and then a bottled water to chase it down with so I didn’t get too drunk. I finished my drink and went back onto the foam-filled dance floor. I was dancing for a little bit when someone bumped into me. It was the hot muscle boy! I smiled at him and he smiled back at me. He leaned in and asked me my name, I answered, and he then introduced himself as Paul. He put his arm around me and drew me close as were dancing. We started grinding our crotches together and I instantly got hard, my 6.5" cock pointing down the leg of my boxer briefs. Paul smiled at me and brushed his hand over it. I put my hand on the back of his head and pulled him close. Our lips met, and we kissed. I opened my mouth wider and he responded in kind, and our tongues met in a short but passionate French kiss. He pulled away and turned around, grinding his ass back onto my cock. I reached down and pulled my cock up so it was sticking out of the waistband of my Calvin Klein boxer briefs. We danced that way for a couple minutes and then I felt a pair of hands on either side of my waist. I looked over my shoulder and into the eyes of a really cute early twenties twink. I put my hands back and ran them down the sides of his body. It felt like he was wearing a pair of cotton briefs. My hand brushed along the front of his briefs and I could feel the hard outline of a 7" cock stretching along the waist band of his briefs. I looked back at him again and he smiled at me. He kissed me, our tongues dueling, and ground his crotch up against my ass, sandwiching me between this cute twink and Paul, the hot muscle boy in front of me. We danced that way for a few minutes more, with the twink’s hands on my waist, and mine wrapped around Paul. Then I felt the twink’s hands slide down into the waistband of my boxer briefs and then pushed them down to my thighs, exposing my cock and ass to the cool foam. I felt him shift behind me, then he nestled his cock in my crack, grinding up and down. He kept sliding his cock up and down my crack, slowly getting lower and lower, until it slipped down and pressed against my hole. At least thirty other people were dancing around us and this twink has the head of his cock up against my hole, ready to fuck me, and I was ready to let him. I felt him push and I relaxed my hole, letting the head of his bare cock slide inside of me. I moaned and leaned my head back on his shoulder. He started kissing and licking my ear as his cock pulled back slightly and then sank further up my hole. As we danced to the music he used the motion to slide further up my ass until I felt him bottom out. Then, timed to the music, he started long strokes in and out of my hole. Paul meanwhile, was still dancing with his back to me, grinding his Speedo covered ass on my now naked cock. He reached back and felt down my body. He could tell my underwear was gone and he squeezed my hard cock. He grabbed my hands from around his waist and put them down the front of his Speedos. His cock was kinda small, not much over five inches, and not too thick. Not bad, I thought. I can work with this. He ground his ass harder on my cock, and then I slid his Speedo down over his ass. My cock slipped right into his crack like it belonged there. Paul shifted forward, letting my cock slip lower until I felt it line up with his rosebud. This hot muscle boy then backed on to my cock as the twink behind me shoved his cock forward into my ass. The head of my cock popped through Paul’s ring, his sphincter gripping me like a vise. The foam was providing a little lubrication, but not enough to sink farther in his hole, so I pulled out, gathered up some more foam and slathered it on my rock hard cock, and slid it back inside.It went in easier this time, but it still took almost a full minute to work my cock all the way into his ass. Once I bottomed out, it was easy to pull back out and get a rhythm going. There I was, on a crowded dance floor, house music blaring, foam up to the middle of my torso, with a twink’s bare cock sliding in and out of my ass, my bare cock buried deep in the ass of the hot muscle boy in front of me, and no one paying any attention to us. (I’m sure a few were doing the same thing.) We managed to get a rhythm going where the twink behind me buried his cock deep in my ass as I pulled out of Paul’s ass. We kept fucking right in the middle of the dance floor for a little over five minutes in time with our dancing, when the twink behind me whispered in my ear, “Can I cum inside you?” I just nodded and smiled at him over my shoulder. He gave me a quick kiss on the lips and started fucking me faster, gave a few quick thrusts and sank balls deep into my ass. I knew he was blowing his load in my ass. He kept his cock deep in me as we swayed to the music, and then he slowly pulled out. He pulled up his briefs, kissed me on the neck, and walked off. This boy had fucked me bareback on the dance floor of a crowded club, shot a load inside me, and I hadn’t said a word to him. I continued to fuck Paul for a couple more minutes when he pulled his ass off my cock and told me to follow him. He pulled up his Speedo and I pulled up my boxer briefs, trying to make my raging hard on as inconspicuous as possible. He led me into the bathrooms and into an empty stall. I closed the door behind us as Paul pulled down his Speedo again, bending over the toilet. “Get in me,” he ordered. I stepped up behind him, pulled my boxer briefs down, spat in my hand and lubed myself, grabbed his waist and lined my bare cock up with his hole and sank back in with ease. I started rapidly sliding in and out of his now loosened ass, sinking balls deep each time. Paul started jerking himself off. “Let me know when you’re gonna cum,” he instructed. I kept fucking his ass for another minute and then said, “I’m gonna blow.” He started furiously wanking his cock as I felt my orgasm rising. I started long slow strokes as I unloaded shot after shot of cum deep into his muscular ass. I sank balls deep one last time as Paul shot his load into the toilet, ropes of cum splashing into the bowl. I withdrew from Paul's ass, and he then pulled up his Speedo as I pulled up my boxer briefs. We made out for a little bit. “Any chance I could get a ride home?” he asked. “Of course,” I replied. We left the bathroom, went to the clothes check and dressed. I drove him to his apartment, dropped him off, and went home. We exchanged info, but I didn’t see him again, mostly because he moved away shortly after that. Nor did I ever see the twink who had fucked me. But I am now a big fan of foam parties.