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I met Adam online and we ended up going out on a date. He was 20 and I was 22 at the time. It went really well and we went back to my place and got naked. He had a beautiful uncut 7 inch cock that I loved to suck. We sixty-nined for a bit and then he rolled a condom onto my cock and rode it until we both came. We met up a half dozen more times, a couple times we sucked each other off, and the other times, I would fuck him, but always with a condom. I didn't see him for while after that. After he turned 21, I ran into him at one of the gay bars. We chatted and hit it off again, and ended up going to the nearby sex club. The place was empty except for the attendant, so we had the run of the place. I bought a little tube of lube and grabbed one of the free condoms they had all over. We went to a little raised padded area after we got undressed and proceeded to make out, rubbing our cocks together. I spun him around so we could sixty-nine, and I deep-throated him, almost causing him to cum. He wanted me to fuck him, so I dutifully put on a condom, since he had always insisted on me wearing one. I put his legs on my shoulders, and with my cock covered and lubed, slid inside him and fucked him for a few minutes. After a bit, he wanted to take a break, so I pulled out of him. We lay next to each other and he pulled the condom off me and threw it into a nearby trash can. He asked me if I ever bottomed, and I told him I did occasionally, but it was pretty rare at the time. He got me up on my knees and pushed me against a wall. He wrapped his arms around me, his right hand started slowly jerking my cock. "I guess the bottom is going to become the top tonight," he said. "Okay," was all I said. He nestled his cock in my crack and slowly started rubbing it up and down. The he drew away to grab the lube. He lubed up his fingers and slowly started putting one finger, then two into my ass. I was moaning in please as he was doing it. He removed his fingers and put the head of his cock at my hole and and started to push in. The head of his cock pushed past my sphincter, and then he pulled it back out. He missed on the next thrust, so I reached back to guide his cock in. I was a little drunk and not really paying attention, but I realized he wasn't wearing a condom. "You're not wearing a condom," I told him. "Don't worry, I'll pull out before I cum," he said, thrusting his cock back into my hole. This time he shoved all 7 inches balls deep into my hole. He pulled back and started fucking me with a nice rhythm. I was so turned on by having his cock in me bareback. I knew it was risky and that I should have him put on a condom, but my horniness took over and I let him continue to fuck me bare. He fucked me for a solid 5 minutes, we were both moaning our pleasure. "You don't have to," I told him. "What?" he asked. "Pull out." "Pull out before I cum?" he asked. "Yeah," I said. He continued thrusting his raw cock in me. "Are you sure? I'm pretty close, but I can still pull out," he said. "You don't need to," I said. "I should probably pull out," he said as he started picking up the pace of his fucking. "Don't," I said. He kept thrusting, his dick kept hitting my prostate just right. "Last chance, I'm about to cum, you sure you don't want me to pull out?" he asked. "Just fucking cum in me please!" I said. "Fuck yeah, here it comes!" he said, and thrust his cock in my 3 more times then sank it deep in my ass. I felt his cock twitch as his load emptied into my hole. A few strokes of my cock were all it took for me to shoot my own load all over the wall in front of me. He pulled out and I spooned him, my still hard cock nestled in his ass crack. "Always nice to turn the tables on a top," he teased. "Don't get too many ideas," I said, and he moaned in pleasure as I pushed my bare cock into his ass for the first time. 20 minutes later, my second load went deep in his ass.

Most guys will fuck bareback. Even if they say they don't, they usually will. I hooked up with a guy I had met out at the bars a few times and ended up going over to his place. We kissed for a while on his bed and things started to get hot and heavy. I stripped him and revealed a nice 6 inch cock with a slight upward curve to it. I sucked him off for a bit until he started kissing me again, then took off all my clothes and started going down on me. After sucking me for a bit he started licking my balls and going lower. He hooked his arms under my legs and lifted my ass off of the bed. I felt his tongue connect with my hole. As he started rimming me I realized there was a pretty good chance he wanted to fuck me. After rimming me for a bit, he started kissing his way up my body, his crotch moving closer to mine until I felt his cock hit the bottom of my ball sac. As we made out, his cock kept probing until it finally touched my hole and I moaned. "Can I fuck you?" He asked me. "Yeah, you have a condom?" I asked. I wanted his bare cock in me, but I love condom to bareback action, so I wanted to tease him. "Yeah, I think so," he said. He leaned over to his bedside table and got some lube and rummaged through the drawer. "Fuck, I though I had one," he said. "Damn," I said, "I really wanted to get you off with my ass." "There might still be a way to do that," he said. "How so?" I replied. He turned me face down and started pouring lube into my crack. "What are you doing?" I asked. "Put your legs close together," he said. I did what he said, and then he laid on my back, nestling his cock in my crack, stroking it up and down, brushing against my hole. He drew back his cock, now wet with lube, past my hole, and thrust down in between my legs along my taint. "Imitation hole," he said, making me laugh. For a few minutes, he fucked his cock in between my legs. It felt pretty good rubbing along my taint. Every once in a while, he would draw up and rub his cock along my crack before plunging down in between my legs again. I figured it was only a matter of time before he tried putting it in my hole, but he seemed content with what he was doing. I started squeezing my legs together harder, and he seemed to like that. At one point he drew up nearly all the way and I clenched my ass, which put my hole int the path of his cock. I felt it connect and I squeezed my legs together as hard as I could. He chuckled and pushed his cock back down. This time it made contact with my hole. He felt the resistance and pushed slightly harder, causing his naked cock to slide balls deep in my hole. He continued pistoning his cock up and down, but this time, he was full on fucking my ass. He fucked me for another few minutes and then announced he was about to cum. I told him to do it and he groaned and thrust deep, emptying his balls into my ass. He collapsed on my back and I relaxed my legs, moving them apart a little bit. He felt the movement and pushed up a bit, looking down toward his cock. "Wait, am I inside you?" He asked. "Yeah," I said. "When did that happen?" "Just the right time to catch your load," I said. "That's fucking hot," he said, collapsing down on my back. His softening cock popped out a few minutes later. He had me over a few weeks later and within 5 minutes of walking in the door, I had his load dripping out of my ass.

There used to be an all-ages club in Portland, and from time to time I'd go there after the bars closed to sober up and dance (they had the best music). One Saturday night I ended up there and was dancing for about 30 minutes when this teen started dancing with me. He was really cute and well-built, not too muscular but he was quite fit. We talked for a while and he asked me where I lived. I told him I only lived about a half a mile away and he asked me if I wanted to get out of there. I agreed and we walked back to my place. While we were chatting he told me he was into older guys because he thought the sex was better. That definitely got my cock tenting my pants as we were walking along. We got to my place and I asked if he wanted anything. He said no, so I led him to my bedroom. I pulled him down onto the bed on top of me and started kissing him. He was a really good kisser. I quickly stripped his clothes off and turned him face down and admired his bubble butt as I stripped off my clothes. I dove straight for his hole and started rimming him. He moaned and asked if I was going to fuck him. I told him that was the plan. He asked me if I bareback, and I said only if he wanted me to. He said yes, and he wanted me to breed him. I couldn't believe this teen was talking like that, but I was ready, willing, and able to fulfill his wishes. I continued to rim him as he loosened up, and I could work my tongue inside his tasty hole. I grabbed some lube out of my bedside table and put some on my cock and his hole. I laid down on his back with my lubed-up bare cock nestling in his crack. I started kissing his ear and sliding my cock up and down his ass crack. He moaned and started writhing below me, trying to get his hole to line up with my cock. Finally as I pulled back I felt my cock head nestle up against his hole. I slowly pressed forward and felt the tip of my cock open his willing hole. He moaned even louder as my raw cock slid all the way inside him. "Is this what you wanted?" I whispered. "An older guy's cock in you bare?" "Fuck yes," he said. "Breed me daddy!" I slowly pulled out until the tip of my cock was barely in him and slid back in again. I started fucking him slowly, building up speed. I could tell by the way he was moaning and wriggling under me that he was a total bottom. I fucked him for a solid ten minutes when he said he was getting close. "Without touching yourself?" I asked. He told me he could cum hands-free, and that was something I definitely wanted to see. I pulled out of his tight ass and flipped him over onto his back. I started kissing him as I sank back into hole. I managed to fuck him for about 5 minutes more when his moans reach a fever pitch and he said he was gonna cum. I pushed myself up on my arms and he begged me to fuck him harder. I thrust my raw cock back and forth in his boy cunt, his moans getting louder. He moved his hand toward his cock and I grabbed both his arms and pinned them over his head as I continued to fuck him. His eyes rolled back into his head and sure enough, without him or me touching his cock, it started spurting up his stomach and across his chest. The sight sent me over the edge and I shot a huge load in his teen ass. I collapsed onto him and kissed him. Told you, he said, and we both laughed. I told him I had done that once, and he said he does it all the time. I cleaned him up and we cuddled up and fell asleep together. In the morning, I made him breakfast, and afterward, I bent him over my couch and fucked him until we both came again, me in his ass, and him all over my couch. It was hella hot.

I messaged a cute 19 year old with a great bubble butt on Grindr one night, and after chatting for about an hour or so, we agreed to meet up. We didn’t specifically mention having sex, but I was pretty sure it was going to happen. We lived kinda far from each other so we arranged to meet up halfway at a park near where he used to go to high school. I got there and I saw him on a path by the baseball diamond, he was even cuter than his pictures. It was a warm night and we were both wearing just shorts and t-shirts. He took me along the path to a bench that was secluded by trees so it was pretty dark, and no one could really see us unless they were really close. We talked for about 5 minutes before we started kissing. He sat on my lap and ground his ass against my crotch as we kissed. I knew I was going to fuck this twink’s ass. He slid off me and knelt on the ground and pulled my cock out of my shorts and started sucking it, it felt perfect. After about 5 minutes he turned around, pulled his shorts down, showing me a jock strap on his perfect bubble butt. He bent over so I could see his hole. Still sitting on the bench I started rimming him. I stuck my tongue as far as it could go in his ass and I could tell he had cleaned out well. This boy wanted to be fucked. “You want this ass?” he asked. “Fuck yeah,” I said. “You have a condom?” My heart sank. I usually don’t have a condom because most guys are willing to bareback these days. “No," I said. He sat back down on my lap still facing away from me. My cock was nestled in his crack and was still wet from his blowjob. He slowly started rubbing his crack on my cock. He kept getting a little higher until the bare head of my cock nestled against his hole which was still wet from my rim job. “Fuck I need that cock,” he said and started slowly sliding down my naked dick. He sighed as he bottomed out and started riding me. He bounced on my cock for a couple minutes, then got off me and knelt on the bench, holding on to the back rest and jutting his ass out. I rimmed him some more until he said fuck me til you cum. I sank my cock back into him and asked him if it was alright to cum inside him. He said yes, I want your load. I fucked him slowly for 10 minutes and then felt my orgasm coming. “Fuck I’m gonna cum in you,” I said. He moaned as I emptied my balls into his willing ass. I slowly pulled out and spread his ass cheeks apart so I could watch my load dribble out of his ass onto the ground. The next time we met up at the park he was lubed up and ready to go and I just sank my bare cock into him. No mention of condoms.

I had only fucked one guy bareback and was looking for another guy that would let me breed him. It was fine with my boyfriend, but I wanted to try it with other guys. I had briefly been inside one other guy before my boyfriend, but I quickly made him put on a condom (now I regret that). I loved emptying my balls deep in my boyfriend and wanted to feel what it was like with someone else. I had been talking to a guy online for a few months. He was from Seattle and I had met him in some chat room. I asked him how he felt about barebacking, and he said he loved it when a guy dropped a load in him, so needless to say, I was excited to meet him. He ended up visiting Portland and was staying downtown, so we arranged to meet one evening. I went to his hotel and knocked on the door. He was my height with a great toned body, brown hair and eyes, and really cute. I was pretty nervous but he invited me in and we sat down with some beers. He was sitting on the bed and I was sitting in a chair close by. We chatted for a while and by the second beer, he invited me over to sit on the bed. After all, we both knew what we were there for. We quickly started kissing and our clothes came off really fast. I got him on his back and he wrapped his legs around me and my crotch was grinding against his. I wasn’t even trying to fuck him yet, but my bare cock just happened to line up with his hole and he used his legs to pull me into him. He must have pre-lubed his ass because my unsheathed cock just slid right into him. He felt amazing. He told me I could fuck him as hard as I wanted but he was actually a really sweet guy and I wanted to savor the experience. For about 10 minutes I slowly slid my bare cock in and out of his tight hole while our tongues wrestled. He was an amazing kisser. I started picking up the pace knowing that I would shoot soon. After a few minutes he whispered “give me that load!” I felt it building and started kissing him again and jerking him off. I sped up my thrusting and a few moments later I told him I was going to cum. One of the best orgasms of my life came over me and as I was thrusting I felt at least 8 pumps of cum coat his asshole. Just as I had finished shooting he started moaning as his orgasm started from my hand job. His load shot all over his chest. I kissed him as I slowly pulled out. We got in the shower together to wash off, and he showed me as my load ran down his leg. One of my hottest fucks ever.

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.

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.

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.