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JamieLong

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Blog Entries posted by JamieLong

  1. JamieLong

    Fucking a Stripper

    By JamieLong,


    BB
    In Oregon, strippers can be as young as 18 to work in bars. I was watching a cute one one night, he was short, maybe 5’2” maybe 105lbs. He kept making eye contact with me and I tipped him a couple times. At the end of the night as the bar was closing I left and saw him standing out on the street in a t-shirt, short shorts and sandals.
    “Good show” I told him.
    “You liked it?” He asked.
    “Made me wanna take you home,” I replied.
    “So take me home daddy,” he said coyly.
    We walked back to my apartment and as soon as we got inside he stripped down to just a skimpy little jock strap and went to sit on my couch. I stripped down to my boxer briefs and went over and started kissing him. He wrapped his legs around me and started thrusting his ass against me. I kissed my way down his front and over his jock covered cock until I got to his tiny little hole. I pushed his legs back to his shoulders and started eating him out, my tongue going deeper and deeper into his hole.
    “That feels so good daddy,” he moaned.
    “Gonna feel even better when my cock is in there,” I told him.
    “You can only fuck me if you carry me into your bedroom,” he said.
    He was so small it wasn’t a problem. I picked him up and carried him into my room and put him down on my bed. I rolled him over until he was face down and went back to rimming him. After a few moments I got the lube from my bedside table and lubed myself up. As I started pushing my bare cock into him he started moaning.
    “Fuck that feels amazing!” He exclaimed.
    “That’s because I’m in you bareback,” I told him.
    “You are?” he asked. “Are you going to breed me?”
    “Do you want me to?” I asked him.
    “Fuck yes,” he said as I started to pump in and out of him. He kept telling me to fuck him harder. For almost 5 minutes I fucked him senseless, finally shooting my load deep into his tiny ass. I pulled out of him and rolled over on my back. He cuddled up on me and as we were kissing, I could feel my load dripping out of him onto my stomach.
    In the morning, as soon as he woke up he spooned up to me and slid my cock in him again and I fucked another load into him.
  2. JamieLong

    Tricked by a Twink

    By JamieLong,


    BB
    I had met a cute 18 year old twink at an all ages club and after exchanging a few calls, we finally agreed to meet up at my apartment. I was expecting more of a date, but he had other ideas, which was fine by me, because I really wanted to fuck this little twink. I was mostly topping at the time, and although I had fucked bareback before, I was using condoms pretty regularly. We went out to get food and afterwards came back to my place. He looked around a little bit and started putting the moves on me.
    He leaned in for a kiss and it turned out he was a great kisser. After we made out for a few minutes on the couch he put my legs on his shoulders and started grinding his crotch against my ass. We both still had clothes on at this point. He said “I’m gonna fuck you.”
    “I usually top,” I said.
    “Too bad,” he replied. I told him I didn’t have any condoms and he looked disappointed.
    “We should still get naked though,” he said to me.
    “Well of course,” I replied.
    We went into my bedroom and got undressed as fast as we could. We 69ed briefly and then he turned back around and started kissing me again, getting in between my legs again. I could feel his cock grinding against me, every once in a while it bumped up against my hole. He stopped grinding with it pressing against my hole and I wasn’t letting it in.
    “Damn I want to fuck you,” he said. I told him sorry, then he asked if he could dry hump me. I agreed and rolled over on my stomach. I felt him lay on top of me, nestling his 6 inch cock in my ass cheeks. He slowly started doing long strokes across my asshole and in my ass crack. Every once in a while his cock would go down and rub against my ball sack, and every so often the head would push against my hole, but I would move slightly so it kept sliding up my crack.
    “You have any lube?” he asked. I got it out of the bedside table and he lubed up his cock and started humping me again. He started kissing my ear which I love, and it caused me to arch my ass up just slightly just as his cock was pushing against my hole. I felt the bare head go in. “Oops sorry,” he said as he pulled out and started sliding his cock along my crack again. This happened a couple more times over the next few minutes, him apologizing each time it “accidentally” slipped in. Meanwhile my cock was getting so fucking hard as this twink kept teasing my hole, I decided to do something about it. The next time I felt it hit my hole and started to push through, I thrust my hips up at him, causing his bare cock to sink all the way in my ass. I heard him moan with pleasure.
    “Want me to pull out,” he asked? I told him to just go for it. Without another word he pulled back and started thrusting his unsheathed cock balls deep in my ass. His cock had good width and felt amazing in my ass.
    “Told you I’d fuck you,” he said. He started thrusting his bare cock in and out of my ass. I knew I should ask him to stop until we could get a condom, but I was just so turned on by this beautiful twink and his assertive attitude.
    After fucking me like that for a solid 10 minute he flipped me over on my back and slid his naked cock in me again. In between kisses he told me he was going to cum soon. I started jerking faster and a minute later he asked me where I wanted him to shoot.
    “Just cum in me,” I told him.
    “Good, cause I just did,” he said. I was so fucking turned on my that I shot my load immediately all up my chest and across my face.
    “I knew you’d be a bareback bitch,” he said. Of course I was. His cock stayed in me until he went soft, and we cuddled for the rest of the night.
  3. JamieLong

    Condom to Bareback

    By JamieLong,


    BB
    I’ve known my friend Chris for quite a few years. We see each other out at the bars a lot, and we hook up occasionally. He’s usually pretty religious about wearing a condom. One night I saw him on Grindr and hit him up asking if he wanted to meet up. He was hungry so he picked me up and we went to a food cart so he could eat. Afterwards we drove up to a park overlooking the city and parked just outside the locked gate. We made out for a little bit and he sucked me for a while. We got out and went to the center part of the park and he sucked me some more as I was sitting on a little brick wall, totally out in the open, but there was no one around and it was the middle of the night.
    He suddenly turned me around, pulled my pants down to my knees and started rimming me. After a minute he stopped and asked if he could fuck me. I said yes and heard him open a condom wrapper. I was a little disappointed but wasn’t gonna say no to any kind of dick. The condom was lubed but we didn’t have any other lube, so he used spit to lube up the condom more and also my ass. His cock is 5 and a half inches, and he managed to get it in, although it was a little difficult.
    He fucked me from behind for about 5 minutes. I was leaning against the way enjoying it when he said he was close. I suddenly said “I want you to breed me.”
     He stopped and asked “really?”
    “Yeah,” I said, so he pulled out and pulled the condom off. He spit on his hand and rubbed it onto his now bare cock. He put the head against my hole and teased it for a little bit.
    “You want this bare cock don’t you,” he asked.
    “Fuck yeah.” I replied.
    “I had no idea you were such a cum slut.” he told me.
    “Well you always wanted to wear a condom,” I said.
    “I’m only going to breed you from now on,” he said and sank his bare cock into my ass. He started thrusting and said “fuck, I’m not going to last long without a condom.”
    “I don’t care,” I said, “just come in me.
    “Oh fuck,” I heard him say and felt him go balls deep and he held is cock there as his load spilled into me.
    He slowly pulled out and asked if I wanted to cum in him.
    “Fuck yeah.” I said, spinning him around and pushing his jeans below his ass. I spit on my hand and coated my cock and thrust up against him. He resisted for a couple seconds, but my bare cock eventually slid through his sphincter. I didn’t want him to change his mind so I fucked him quickly and a couple minutes later I told him I was cumming.
    “Do it in me,” he said so I kept thrusting as my load shot out and I seeded him for the first time. Definitely wasn’t the last though.
  4. JamieLong
    I had been to several bathhouses before, Club Portland, Steam Portland, but always with someone I knew or was hooking up with that night. I had even fucked bareback at bathhouses, and been fucked bareback, but always with people I went there with. We would either get a room so we could be private or go off into a corner and fuck, and if someone wanted to join I would just wave them off.
    The first time I went alone I was prepared to use a condom. Steam Portland has them everywhere. I got a room so I could hide out if I got overwhelmed. I had brought my own packets of lube because I knew the condoms would be there. I wandered around the club for about 15 minutes checking out guys, watching some guys fuck in the steam room and get sucked off in the hallway. A cute guy in his late 20s cruised me as he was walking down the hallway. I started after him and saw him go into the glory hole booths. From the other side I saw is hand on the hole so I walked up to it, took my towel off and put my cock in the hole. I wasn’t hard yet, but I immediately felt a hand on it and I started to chub up. As soon as I was totally hard I felt a mouth wrap around my cock. Someone I hadn’t even spoken to was sucking me off and it felt amazing. After a few minutes he stopped and a moment later I saw him walk around. I grabbed my towel and went over to him. He asked if I had a room and I said yes and started leading him back there, my towel over my shoulder and my hard cock leading the way. Normally I stayed pretty covered up but I was suddenly feeling bold.
    After I closed the door to my room, we started making out. I took off his towel and started jerking him off with one hand and grabbing his ass with the another. After we kissed for a few minutes he asked me if I was neg, I told him yes and he pushed me back onto the bed. He sucked me for a little bit and asked if I had any lube. I got it from right beside the condoms and gave it to him. He opened it up and and spread some on my cock. He put some in his ass and then straddled me pointing my dick up towards his hole. Then this stranger whose name I didn’t even know slid his ass down onto my bare cock until he bottomed out. He leaned forward and kissed me while starting to rock up and down on my cock. After about 30 seconds I took over and started thrusting my hips up, driving my naked cock as deep as I could in him. If he wanted it bare, I was gonna give it to him.
    After about 5 minutes of him riding me he got off me and told me he wanted it from behind. He bent over the bed and I stood up behind him. I bent over and rimmed him for a few moments before guiding my bare cock back into his ass. I buried it balls deep before pulling back out to just the tip and thrust back in again. He started jerking off and I knew it wouldn’t be long before I shot my load. I fucked him for about a minute more before I told him I was about to cum. He didn’t say anything so I kept going until I felt my orgasm build. “Fuck I’m gonna cum in you,” I told him. He started furiously jerking his cock as I felt my load shoot into his ass. I stopped thrusting deep in him as the last of my load emptied into his hole and I heard him moan and he shot his load onto the bed.
    I slowly pulled out of him and watched as my load dribbled out his ass and onto the floor. He turned around and we kissed some more and he left to go shower. Never did get his name. I showered as well and went back to my room and got dressed and went home.
  5. JamieLong
    I've known my fuck buddy James for years. We met at a party I had at my downtown apartment. We hit it off, and he ended up being the last one at the party. We were talking in the kitchen as it was the farthest room from the bedroom where my boyfriend had gone to sleep. James and I were both leaning against the counter when we reached the inevitable lull in the conversation. At the same time we both leaned in and started kissing. He's a short Hispanic dude, wiry but muscular frame, and you'd think he was a total bottom just by looking at him, but I found out he was actually a total top. We kissed for a few minutes and he started groping my ass so I grabbed his cock through his trousers. He was huge. Right about 8 inches and girthy, with a wide bulbous head. Holy fuck I thought to myself, I need to get fucked by this cock.
    Alas, it wasn't to be that night, but James did turn me around up against the cabinets, sliding my trousers and underwear down just below my ass. While he stroked my cock, his slid up and down my ass crack, every once in a while he'd let the wide head push up against my hole, but he wouldn't go inside. It felt so big it seemed like it would never fit. He ended up just dry-humping my crack until he shot his load over my back and I shot mine on the countertop.
    We kept in touch for the next couple years, and the first time he fucked me was about 6 months after my breakup. He insisted on wearing a condom, which I was kind of bummed out about, but still totally cool with. I respect people's choices in that area. It took a while to take his cock at first and it felt like he was splitting me open, but eventually I got used to it and the sex was always good. Usually he'd pull out, take the condom off and cum on me. We hooked up a couple of times a year for years, him always using a condom.
    Then a couple years ago I was sitting on top of him with his massive condom covered cock buried in my ass and we were chatting a bit while I got used to his cock splitting me open. He asked me if I had any kinks and I told him not really. I mean I like fucking while wearing only sneakers, and I love wearing a jock strap while bottoming, but I don't really consider those kinks. Then I mentioned that I really like getting fucked bareback and having a guy cum in me, but can never really find the right guy I want to do it. Suddenly he lifted me off his cock and rolled me onto my back. I watched as he pulled the condom off his cock and he went up between my legs, and for the first time, I watched his massive cock sink bareback into my hole.
    I didn't think it was possible but my cock got even harder and I started furiously masturbating as his muscular ass drove his bare cock in and out of my hole. This went on only for a couple minutes until he told me he wouldn't last long fucking me bareback. I told him I didn't care as long as he shot his load inside me. About 20 seconds later he let out a moan and told me he was cumming. As he was thrusting his load deep in my ass my own load started spewing so hard it hit me in my face. He laughed in shock and licked a bit off my face as his cock kept slowly moving back and forth in my cummy hole.
    Finally he pulled out and his cum spilled out of my gaping hole. I left satisfied. The next time we had sex was memorable as well. I was on my hands and knees wearing only a jock strap as he ate out my hole. Then with no talk of condoms, he just lubed up his cock and sank it bare into my hole and fucked another load into me. We haven't used condoms since.
  6. JamieLong

    DPed By Married Couple

    By JamieLong,


    BB
    I had met Evan and Eric through my ex-boyfriend when we were still together and always thought they were really cute. About a year after my breakup I ran into them one snowy day at one of the local gay bars. Snow days are kinda rare, and the city was pretty much shut down. We made it to last call and started walking back home. I made a joke about them stopping at mine to warm up since it was on the way, and to my surprise they agreed. While we were at my place chatting someone brought up sharing body heat and I said we should probably try that. They both agreed and we all went to my bedroom and got naked. I was pleasantly surprised to see they both had cut 7 inch cocks. Since I was new to them, they both focused on me, Eric was kissing me while Evan sucked on my 6 inch cock.
    I mentioned it had been a while since my last three way, so we all tried to figure out what to do, and ending up in a circle suck, Eric was sucking me, I was sucking Evan, and Evan was sucking Eric. We played with each others cocks like that for about 10 minutes until Evan asked if we wanted to switch it up. I said I would love to be fucking one of them while getting fucked by the other. Evan said I could fuck him, so Eric would be fucking me. I asked them if they wanted to use condoms, as I was cool using them or not. They whispered to each other for a moment, then they both agreed not to use condoms. I was ecstatic.
    I got out the lube and lubed up my cock and Evan's ass. He was on his back as I slid my bare cock into his ass. Eric let me fuck his husband for a minute while he lubed up his cock. Then he fingered some lube into my ass. I held still in Evan while Eric fed his 7 inch cock bareback into my hole. It took us a minute to get into a good rhythm but we found it worked best with Eric holding still while I fucked Evan. Just the motion of me fucking Evan made me fuck myself onto Eric's cock. We carried on like that for a few minutes until Evan asked if he could fuck me. I eagerly agreed, so Eric was on his back with me in between his legs with Evan's bare cock pleasuring my hole. Being in the middle I was in heaven.
    We fucked like rabbits for about 5 minutes more when Evan pulled out of my ass and said he wanted to try something. He told me to sit on Eric's cock, so I eased my bare cock out of Eric's hole and positioned my ass above Eric's uncovered cock and slowly sank down on it. I leaned forward to kiss Eric and as I did, I felt a new pressure at my hole. Evan was gonna fuck me at the same time as his husband! I was so horny and excited for my first double penetration so I relaxed as much as I could and let Evan slowly shove his cock in my already full ass. It was a little awkward but they managed a couple minutes of fucking me. There I was, my ass stretched more than it ever had been by two bare cocks. It was intense!
    I could tell they were getting tired but I was determined to get both of their loads, so I suggested they spit roast me. They both pulled out of me and I got on my hands and knees and Eric got behind me and slid his bare 7 incher back in my hole. Just before I took Evan's cock in my mouth I told them I wanted them both to breed me. Eric wasted no time driving his cock into my ass as I sucked his husband's cock. After a couple minutes I heard Eric say he was gonna cum and felt him thrust deep into my ass and collapse on my back. After a moment Eric pulled out and Evan wasted no time jamming his cock into my cum-filled hole. He fucked me for another 5 minutes and then whispered in my ear that he was about to breed me. Do it I told him. He kept thrusting in and out of my ass as he orgasmed and we both collapsed on the bed.
    Evan pulled out of me and I rolled over and started jerking my cock. Evan asked if I wanted to breed him and I readily agreed. He put his legs up on my shoulders and I sank my bare cock into his ass. I was so horny from the sex that night that I barely lasted a minute before my own load was blasted deep in his ass. I pulled out and got a towel and we all cleaned up and cuddled for a bit before they got dressed and went home.
    So far that's been my only double penetration, but I'd be down to try it again.
  7. JamieLong
    I work up earlier than usual one morning before work. I was feeling horny so I got on Grindr and spent a while looking for someone to fuck me. I ended up finding a muscular Latino guy with what looked like a big cock about 30 minutes before I had to leave for work., I finished cleaning out and showering and went to his place which was conveniently on the way to my work. He met me at the door wearing sweatpants and a t-shirt. His English wasn't too great, but he led me through to his room. By this time I only had about 15 minutes before I had to get to work so we didn't waste any time starting to kiss.
    He grabbed my ass and started squeezing as I felt his cock through his sweat pants. It was at least as big as it looked in the photos, had to be over 8 inches with a narrow head tapering to a wide base. He unbuttoned my trousers and slipped his had into my underwear and started rubbing my hole with his finger. I reached into his sweat pants and began slowly jerking his cock. I was short on time so I undressed completely and so did he. He turned me around and bent me over his bed.
    He spread my cheeks apart and started rimming me. I was in heaven, but on a time crunch, so I told him to fuck me. I heard him rustle around and then felt the lubed up head of his cock at my hole. We hadn't talked about condoms, but he obviously wasn't wearing one, which was alright by me. I felt the head push past my sphincter and he sank in about halfway before pulling out just to the head of his cock. He did this a couple more times, going deeper into my hole until he was finally balls deep in me. His bare cock felt amazing in my hole.
    He fucked me from behind for about 5 minutes and then flipped me over onto my back and pushed me further up the bed. He spread my legs apart and thrust his uncovered cock back into my hole. He drove in and out of my hole as I wrapped my legs around his muscular body. I jerked my cock furiously and only after a couple minutes of him fucking me on my back I shot my load all over my stomach and chest. He kept thrusting his bare cock in and out of my hole while I just relaxed and enjoyed it. Finally, he thrust his cock as far as he could in my ass and I knew he was cumming inside me. He paused for a moment with his cock buried to the hilt in my hole before he pulled out and cleaned his cock off with a towel. He tossed it to me and I wiped my cum off myself and wiped the lube from my ass and got dressed and went to work.
    His load stayed in my ass all day.
  8. JamieLong

    Finally Breeding the Ex

    By JamieLong,


    Breeding
    MY first dating experience was when I was 19 and I dated this guy Ken for about 3 months before he dumped me for another guy. I don't really count him as a boyfriend since we were only dating a few months, but I still call him my ex. Or first date started in the middle of the night. He picked me up and we drove around, parked for a bit and made out for a while. Then we went back to his place and fooled around. We only kissed and sucked each other, but he was the first guy to actually let me shoot my load in his mouth and then he swallowed it.
    We didn't really share much except a good sex life, but when we fucked, it was with condoms. I almost always fucked him. He was the one to take my ass cherry. I really wanted to get fucked, and he was willing, so one day we were at his place and he broke my cherry with his condom covered cock. It got cut kinda short because he noticed I was bleeding. I was kinda freaked out and it put me off bottoming for a while, but eventually I got to the point where I was totally versatile several years later.
    I ran into him about 10 year later at Pride and we talked a bit and caught up. He was being really flirty and said something about hooking up. I told him I was down so we ended up going back to my place which was only a short walk away. At my place we wasted no time kissing and getting naked. It felt amazing to have my cock in his mouth again. He sucked me for quite a while, then asked if I wanted to fuck him. I said yes and asked if he wanted me to use a condom, and he said it was okay if I wanted to fuck him bareback. I lubed up my cock and started pushing it into his hole. It was like fucking him for the first time.
    I slowly slid my bare cock in and out of his hole, building up speed. I put his legs up on my shoulders and started driving my cock deep in his ass. He moaned in pleasure, not even jerking himself off. I only lasted a couple minutes before I sank my bare cock deep in his ass and finally shot my load inside him. He kinda giggled and said wow, that was awesome. He hadn't cum yet, so I asked him if he wanted to shoot a load in me as well. He said yes, so I lubed his cock up and then straddled him and sat down on his 5 and half inch cock bareback. I rode him up and down for a minute before letting him take over, thrusting his bare cock into me. He only lasted about a minute before he said he was gonna shoot. He thrust a few more times as his load filled my ass.
    As I kissed him I pulled off his cock, and I felt his load dribble out of my ass onto his stomach. There was no blood this time, only semen.
  9. JamieLong

    An Unexpected Breeding

    By JamieLong,


    Breeding
    In my early twenties I was quite the slut. I usually topped, and didn't mind if guys wanted to use condoms. I still don't even though I prefer bareback. I met this guy Tony at a bar one night and ended up going back to his place. We made out on his bed for a while, and before we even got our clothes off I could tell he was going to try to fuck me. At that point I wasn't bottoming much, mainly because there were just so many bottoms in town, and also my first experience bottoming wasn't that great so I was a little gun shy. One thing that helps is a guys attitude. He's gotta be assertive when he's fucking me, not aggressive, just assertive. That really turns me on, and it's exactly how Tony was acting.
    We got our clothes off and started 69ing. He had a great body and 6 inch cock similar to mine. We sucked each other off for at least 10 minutes. He wasn't just sucking my cock, he was licking all around my ball sack and taint which I love, and I returned the favor. He finally flipped back around and spread my legs as he started kissing me again. I could feel his cock just under my testicles poking my taint and occasionally my hole. I was kind of clenching because I wasn't expecting to be fucked that night. He sat up and reached into his night stand for a condom and lube. Mind you, at no point did he ask to fuck me, he just expected it and I was just so turned on by that.
    He got the condom on and lubed up himself and my hole. He put my legs up in his shoulders and put the head of his cock at my hole. I was kinda clenching, and just couldn't relax at first, but he kept pushing and eventually sank his whole condom covered cock into my ass. Once he bottomed out I started loosening up and started to enjoy him slowly thrusting in and out. He went slow at first like he could sense my initial unease. I just stared at his awesome body as he pumped his cock in and out of my hole. After a few minutes he pulled out and flipped me over onto my hands and knees, and entered my doggie style. I absolutely love that position, it makes me feel submissive. He started fucking me faster in this position, and after a few minutes ended up driving my whole body flat against the bed, his body covering mine while he drove his cock in my hole. Suddenly he stopped and pulled out.
    "The condom broke," he said. He got off me to pull the broken condom off and throw it away. I rolled over onto my back thinking we'd just have to jerk off. He came back, got the lube and lubed up his bare dick and mine, and I started jerking. He climbed up between my legs and spread them apart while working the lube on his cock. He put his left hand on the back of my head and started kissing me, and with this right, I felt him line up his bare cock with my hole. Again, without asking, he just sank his cock into my ass, only this time, it was bareback. I was kinda in shock, but also so horny I just let him start thrusting his cock in my hole again. We kept kissing as he was fucking me, and I was furiously jerking my cock because I was so horny.
    After about 5 minutes of getting bare fucked by this guy I met a few hours before, he told me he was getting close. He started kind of slowing down and doing shallower thrusts, and it seemed like he was about to pull out to cum.I don't know what came over me, but I wrapped my legs around his body and squeezed him into me. I started spewing my load across my stomach.
    "Oh fuck I'm coming," he said, and thrust his bare cock balls deep in my ass as he unloaded in me. He collapsed on top of me and we kissed some more as his cock softened and slipped out of my hole. After a minute I could feel part of his load seep out of my hole and down my crack. I fucking loved that feeling.
     
  10. JamieLong
    The first time my cock was ever in a guys ass bareback was only for a few seconds when I was 20. I had gone home with an 18-year-old twink and after we were naked I was lying on this couch and he straddled my cock and lowered himself on to my bare cock. (No lube, it was pretty impressive.) I was, of course, paranoid about STDs so I asked him for a condom. Still ended up being a great fuck but I do regret asking for that condom. The next time was about a year later with the guy who would become my boyfriend. The first time we had anal sex we had been jerking off with lube and then he just sat down on my cock and started to ride me. I ended up shooting my first bareback load in him that night.
    A couple years later, we had never used condoms when I was fucking him. We had great sex with simultaneous orgasms and I always shot my load in him. He mostly bottomed. We occasionally had 3-ways but they were always with condoms. My boyfriend had a great slender, yet muscular body, and guys were always after him. One night we got chatting with this muscle stud and ended up going back to his hotel with him. We all got hot and heavy and started making out and stripping and we found out this stud had a massive 9 inch cock. The stud asked us which of us usually fucked the other and when we told him he wanted to see me fuck my bf. My bf wasn't really feeling it from me because I could tell he wanted this stud to fuck his brains out and let the guy know. My bf asked if the stud had condoms but he didn't, so my bf asked for his hotel keycard so he could go pick up some condoms so this hot muscle stud could fuck him. The stud looked around but for whatever reason couldn't find the keycard in the pile of all our clothes on the floor of the hotel room. Having failed at that, we all started jerking and sucking and making out.
    At one point, i was laying on my back and my bf was laying face down with hot muscle stud laying on top of him. I was making out with him as he was jerking me off and grinding his cock against my boyfriend's ass crack. At one point both the muscle stud and my bf became kinda still. I had a hunch and reached between the muscle studs legs to feel his cock.
    All 9 inches were buried bareback balls deep in my boyfriend's ass. I almost had a spontaneous orgasm.
    Normally my bf insisted on condoms with other guys, but this muscle stud was fucking hot. I knew what was happening but I whispered to my bf "is he in you?" My bf said "fuck it" and flipped the muscle stud over on his back and sat down on his cock again. He rode him for a couple minutes while jerking off and eventually shot his load on muscle stud's stomach. He got off the stud and I scooped up my boyfriend's load, smeared it on the stud's cock and sat my own ass down on his huge cock. I whispered in his ear to breed me and he said okay. It only took me a couple a minutes to blow one of the biggest loads of my life over this guys stomach, and a few moments later I felt him sigh as he unloaded deep in my ass. We got dressed a few minutes later and went home. When I took my underwear off to go to bed I could see where a bit of his cum had leaked out of my ass.
    Every guy we fucked was bareback after that.
  11. JamieLong
    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.
  12. JamieLong

    Taking My First BB Load

    By JamieLong,


    Taking First Load
    I had already taken a cock bareback, but the guy pulled out before he came. I had been fucked a couple times before that by guys wearing condoms, and it was fine, but it didn't really do much for me. I got off, but it wasn't anything to write home about.
    The first time a guy actually came in me was the first time I really got the appeal of bottoming. I was 21 at the time and we met on an AOL chat room (late 90s, lol) and I agreed to meet him at his place. He was a fit twink just a little taller than me. We had coffee and chatted for a while in his bedroom and eventually moved on to kissing. He stripped of my clothes and went down on me for a bit and then I turned around and started stripping him off. As I slid his underwear off I realized his cock had to be close to 8 inches long. It wasn't what I would call too thick but it had a nice girth to it. I sucked him for a little bit and then he pulled me up to make out some more, rubbing our cocks together.
    I sat up on his legs and started stroking his cock and he did the same with mine. After a minute or so he asked me if I wanted some lube and I said yes. He added some lube to our hands and we went back to slowly stroking each other. After another couple minutes he pulled me down to kiss him, and I had to scoot up his body so my ass was just over his crotch. I had to reach behind me to keep stroking his cock. It was basically at my ass crack so I started rubbing the head of his cock on my crack while stroking the base and his balls. I kept kissing him as he started slowly thrusting his cock up and down my ass crack. His cock got progressively lower and lower down my crack until he was thrusting against my hole. I couldn't help relax my hole just enough for the tip to start pushing through with each thrust. I knew I should've asked him for a condom but I was just so fucking horny I let the tip of his cock keep poking a little deeper into my hole.
    Finally, as he was thrusting up I sat back just enough for the head of his cock to slip past my sphincter. It didn't hurt, I just had a full feeling in my ass. He stopped thrusting, I guess he wasn't sure if he should keep going with out a condom, but I just slowly lowered my ass onto the rest of his cock. I bottomed out on his cock and then just started to ride him. His cock was rubbing my prostate in just the right way, and I felt an orgasm building. I had stopped jerking myself off and was just riding him. After a couple of minutes he said he was about to come and I told him to do it, and he started moaning as he thrust his load deep in my ass. I kept riding him, and about 30 seconds later, without even touching my cock, I had my first hands-free orgasm and I shot my load all over his stomach. After I finished his cock felt massive in me and started to get a bit uncomfortable so I slowly lifted myself off of him, and a bit of his load leaked out of my ass onto him.
    I didn't bottom for a while after that as I had started dating a guy that was mostly a bottom.
  13. JamieLong

    I Got Stealthed

    By JamieLong,


    BB
    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.
  14. JamieLong

    Sex in Public pt. 5

    By JamieLong,

    Managed another park hookup while I was house-sitting for some friends out in the suburbs last week. I was feeling really horny, but mainly wanted someone to dump a load in my ass. It was getting pretty late and I was getting ready to go to bed when a 26 year old messaged me on Grindr. Turns out he was a guy I had hooked up with before. He always insisted on using a condom with me, but the last time we hooked up, he tried to fuck me bare, but I wasn't cleaned out or feeling it. Tonight I was definitely feeling it, and I was determined to take his load. Instead of coming over to where I was staying, he suggested a park about a half mile away. I agreed and set off to meet him. It was a nice warm night, so I was just dressed in a T-shirt, shorts, jock strap, and running shoes. We arrived at the entrance of the park at the same time and proceeded to walk down the trail deeper into the park. The moon wasn't out so it was dark, so he took his phone out and used to the light to show the way. I typically like to let my eyes adjust to the dark, but to each their own. We went about a hundred feet in just so we could be seen from the street and started making out. 
    As we were kissing I started undoing his pants and slid them down to his ankles. I took his cock into my mouth and sucked him off for a little bit, but this guy comes really quick so I wanted to make sure it was in my ass. I stood up and kissed him again and told him I wanted him to dump his load in me. I turned around and pulled my shorts down, leaving my jock strap on. He got out a packet of lube and lubed up his cock. He's only average sized but I didn't care. He put the head of his cock to my hole and pushed through. he slowly slid in and out for a few seconds, then started going fast, bottoming out his cock in my ass. It only took a minute before I heard him grunt and say I'm cumming. He pulled out and pulled his pants up and I pulled my shorts up. We said good bye and I walked back to my friends place with cum dripping down my leg. 
  15. JamieLong
    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.
  16. JamieLong
    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.
  17. JamieLong
    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.
     
  18. JamieLong

    Denver Trip

    By JamieLong,

    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.
  19. JamieLong
    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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