JamieLong

I met Jayden out at the bars as with most of my hookups. He was a blond twink about 6’1” with a bubble butt and great dick sucking lips. Excellent kisser as well. I took him home one night from the bars and he ended up fucking me doggy style with his 6 inch cock. I was in my trying to use a condom phase so I had him wrap it up. He didn’t seem to mind. After I jerked myself off while he was fucking me, I took the condom off him and sucked him off. He shot a nice load in my mouth that I let dribble out and down my face. I was definitely looking forward to another hookup, but didn’t get to see him for a few months. I saw him out randomly on the street downtown and we made plans for me to come over to his place. Just before I was supposed to go to his place I texted him to confirm his address and asked him if he had condoms. He said he did so I quickly headed over to his place. He was in a town house that only had a garage on the bottom floor with a small foyer and a staircase going up to the main house. I rang the doorbell and a few moments later he pulled me inside and started French kissing me with his beautiful lips. He quickly started stripping my clothes off and I took off his t-shirt and pushed his shorts down to the floor. We were both completely naked in a few seconds. He sucked my cock for a minute and then I returned the favor. I was down on my knees sucking him when he pushed me down so I was laying on my back on the floor, with my head on the first step of the staircase. He lifted my legs up and started rimming me. I was in heaven, his tongue felt amazing. “You have a condom?” I asked him. “Yes,” he said, barely stopping from his rim job. “Where is it?” I asked. “Upstairs in my bedroom,” he replied. “You want to go up there?” I asked. “No.” He said, continuing to rim me, occasionally licking my ball sack. “You’re not gonna fuck me?” I asked him. “I am.” He said. Then he spit on his hand and lubed up his bare cock with it. He put the head of it at my wet hole and started pushing in. “We should probably use a condom,” I said. “I’ll stop if you want me to,” he replied as the head of his raw cock pushed past my sphincter. I Of course I was too horny to stop him and let him slide balls deep into me. We started passionately kissing and he started jack-hammering my hole. I could tell he wasn’t going to last long. Sure enough, a few minutes later he started moaning into our kiss and started to pull away. I wrapped my legs around his back and grabbed his head with one hand to keep our kiss going and jerking my cock with the other. His moans reached a fever pitch and he thrust deep in me. I could feel him flexing his cock as he bred me. I came a moment later, shooting a load up onto my chest. A moment later he pulled his cock out, his seed spilling out on the floor below my ass. He got up and went into his garage to get a towel from his laundry area. He cleaned up his load from the floor and wiped us off. “I’ve wanted to fuck a load into you since I met you,” he told me. “Looks like most of it came out,” I said. “Guess I’ll have to try again,” he said. The next time we made it up to his bed and his load stayed inside me.

I met Matt on Craigslist, back when they still had the personals section. He advertised as a vers bottom, and when I saw pics of his body and cock I knew I had to meet up with him. He had a massive 8.5" cock. I told him I usually topped at that point, so he was looking forward to hook up as well. He told me he was poz, but undetectable, but I could fuck him bareback if I wanted. I told him I prefer to use a condom (in those days) and he was cool with that and he had some available. He was also in a open relationship, but was playing separately. We agreed to meet up one Saturday afternoon. I got to his place and he was every bit as cute as his picture. About 6 foot 1 and a nice defined body with rather thick legs. We exchanged pleasantries and quickly got down to business, stripping off our clothes and getting on his bed. He was a great kisser, but I wanted a chance to suck on his massive cock, so we got into a 69 position and went down on each other. His cock was amazing. Even though I was mostly topping at the time, I definitely thought about bottoming for him. Eventually he wanted me to fuck him, so he gave me a condom and lubed his ass up as well as my cock. It was a great fuck with him on his back. I came in the condom, and he he shot a load all over his stomach, chest, and even his face. We had exchanged numbers and agreed to hookup again a few weeks later. Same thing as last time, making out, 69ing, Me fucking him on his back with a condom. This time though, about 5 minutes into fucking him I felt the condom snap as I thrust into him. I pulled out and looked down, seeing the condom gathered at the base of my 6 inch cock. I told him the condom broke and asked if he had another one. He said no, but I could keep fucking him if I wanted. I wasn't sure, but horniness overtook me and I plunged back into his ass bareback, eventually shooting my load deep in his ass, with him again shooting his massive load all over his chest and face. We didn't talk for a couple years until I was going through old text messages and I saw some from him. "Hey, what's up stranger?" I sent him. "Oh hey" he replied a few minutes later. "Crazy I was just thinking about texting you the other day." “Oh really?” I said. “Yeah, kinda disappointed I never got to fuck you,” he replied. “lol, no way, I was totally disappointed I never got to ride that cock of yours,” I told him. “Wanna?” He asked. I told him hell yeah, and would definitely be up for fucking him again as well. We got caught up, he told me he was single and had moved from a house to a condo on the east side. We arranged for me to come to his place in a couple days. The day of I showered and made sure I was cleaned out. I got there and we hugged and went to sit on his couch. He had a really cool townhouse style condo. He got me a glass of wine and we talked a while. At one point we both put our glasses down and leaned in and started making out. He was an incredible kisser and we did that for about 5 minutes. He broke off the kiss and said he’ll be right back and went upstairs to his bathroom. I figured he was cleaning out and getting ready for me to fuck him. We hadn’t talked about condoms at all, so I wasn’t sure if we were going to use them or not. I was kind of excited at the thought of barebacking with a poz undetectable guy again, after all u = u. I got up after a minute and went over to his dining room table, which was bar height, and had a couple art books on it. I leaned on the table and started looking through one of the books. I heard him come down the stairs and then he came up behind me and slid his arm around me. I saw him put a bottle of lube on the table beside me. He started kissing the back of my neck and nibbling on my ears. I instantly got hard. I leaned back and turned my head so we could kiss a bit more. As we were doing that he started undoing my belt and jeans, pushing them and my underwear down to the floor. I stepped out of them and kicked them aside. He broke off our kiss and kinda pushed me up against the table. I heard him take off all his clothes and then he lifted my shirt off me, leaving me totally naked except for my socks. He kissed down my back until he got to my ass crack. He licked down my crack, spreading my cheeks apart until he found my hole with his tongue. My cock was rock hard, knowing I was going to get fucked. I had told him before coming over I might not be up for getting fucked, as at that time it really depended on my mood as I was mostly topping. He was cool with that, but with his tongue buried in my ass, I was more than ready. Up to this point, we still hadn’t talked about condoms, and my heart was pounding at the thought of him sliding his bare cock into me. I felt him stand up behind me and he leaned into me, his cock standing straight up in between my ass crack and his stomach. He started slowly sliding up and down along my crack, which I felt get a little slimy with his precum. He grabbed the bottle of lube and stepped away from me a bit. I felt a couple lubed fingers play with my ass, getting it ready for his 8.5 inch cut cock. A few seconds later I felt his lubed up bare cock head press up against my hole. My cock was so hard, and I was sure if I jerked it even a little I would explode immediately. He pressed forward and I relaxed, letting my ass expand as his unsheathed tool slowly made its way into me. He asked if I was okay and I nodded. He continued sliding all the way until I felt his pubes up against my ass. There was a little pain, but not much. My ass just felt really full. He slowly started pulling out as I leaned my head back on his shoulder. He pulled out to just the head and slid back into his pubes, slowly settling into a rhythm of long dicking me. He started with both hands on my chest, but after a minute sawing his dick in and out of me, he he put an arm around my chest and another on my cock and slowly started jerking me with his still lubed hand. I was in heaven. His cock stroked my prostate and his hand kept working my dick. There was a clock in my eye line and I watched the minutes tick by as I was barebacked by this poz undetectable stud. I could see a faint reflection of him fucking me in one of his paintings, glimpsing his 8.5 inch cock as he pulled nearly out of me each time. After a full 10 minutes of fucking me tip to base with his bare cock, I felt him start to shorten his thrusts and speed up a bit. “I’m getting close, do you want me to pull out?” he asked. I shook my head no. “Breed me.” He thrusting picked up pace even more, both hands going back to my hips to help jam his naked cock into me. I started jerking myself off and after only about 15-20 seconds, I felt the most amazing orgasm come over me, and I shot a huge load under his table and all over his hardwood floor. “I’m cumming,” he moaned as he switched to quick, short thrusts in and out of my ass, finally bottoming out as his raw cock finally stopped pumping its load in me. He put his head on my shoulder for a few moments. “Look between your legs,” he told me as he started pulling out his cock. I felt the tip of his bare monster cock leave my hole and a few moments later a stream of his white cum leaked out of my ass forming a puddle on the floor. “Holy fuck,” I said. “I actually didn’t think you were going to fuck me bareback.” “That’s okay, right?” He asked, concern in his voice. “That’s the best!” I exclaimed. He went to get a towel and wiped off his dick and my ass and cleaned the cum off the floor. We cuddled naked on the couch and finished our wine.

I went to Steam Portland one night looking to get fucked. I had gone a couple time before looking to bottom, but either struck out or ending up topping. I had cleaned out and lubed up with a dildo at my place before heading out. When I got to Steam it was moderately busy. I went to the steam room for a bit just to hang out, but no one caught my eye. After a bit I got up and made a circuit. I saw someone was at one of the glory holes, so I went up and opened my towel up and put my cock through. A moment later a mouth wrapped around my dick and started sucking me. I got hard pretty quick and after a few minutes, wrapped my towel around myself and started wandering around again. I made my way back to the steam room and was sitting there for a bit when a cute twink came in and went slowly by me. He made eye contact and I nodded at him. He came up to me and asked if I wanted to fuck him. I said sure, even though I was looking to bottom. He got on his knees up on one of the platforms and I got behind him. He grabbed my dick and guided it to his hole. He didn’t say anything about a condom, so the moment my cock hit his hole I pushed forward. He was lubed up enough I sank balls deep right away. His ass felt amazing. I fucked him for about 5 minutes then he pulled his ass off my raw cock and went out of the steam room. After a few minutes I went out to the showers and had a quick rinse. I walked back up towards the front to check out the sling area. The twink I was just fucking was in the sling getting dicked by an older guy. I watched him for a bit and let him suck my cock while he got fucked. After a minute of that, I pulled out of his mouth and went to the tunnel and cell block area. I was almost out of the cell block area when a fit mid-twenties guy came in the opposite direction. He stared at me hard as we passed each other, so I went into a semi-hidden alcove with a raised platform and sat down. He followed me and stood in front of me and opened his towel, revealing a 6.5-7 inch cut cock. I leaned forward and started sucking him off, opening my towel and starting to jerk myself off. After a few minutes he pushed my onto my back and took my cock into his mouth while playing with my balls and teasing at my hole with his fingers. All of a sudden he lifted my legs up and started rimming me, driving his tongue deep in my hole. I knew he was getting me ready for his dick. He stood up and lined his cock up with my hole, never asking for permission, just expecting it. Now I had been fucked bareback before by people I had just met, but it had always been guys from Grindr or people I talked to at bars. I at least knew their names. We hadn’t even spoken as he spit into his hand and rubbed it on his cock, lining it up with my ready hole. He slowly pushed the raw head of his dick forward, splitting my hole open, and I could feel my cock getting harder. He put my feet on his shoulders and sank his cock in so his pubes were against my ass. Then he started to pull out… And thrust back in again. He started fucking me with his bare cock with purpose. This was a man on a mission to breed a stranger, and I was his lucky conquest. After a couple minutes he let my legs down and I wrapped them around him, urging him on. He leaned forward and started kissing me, our tongues dueling. A few minutes more, his raw cock thrusting in and out of me, he whispered “where do you want it?” I told him shoot in me and after another minute his thrusting slowed down and he put both hands on my chest and pressed down as he shot his load deep inside me. He bottomed out in me and I could feel his cock twitching. Then he pulled out, grabbed his towel and walked off, leaving me with the first anonymous load I ever got at a bathhouse. I got up, threw my towel over my shoulder and as I was walking out, the twink I was fucking before was laying on his back on the padded bench. He smiled at me and I got between his legs. I pushed them toward his chest and lined my bare cock up with his hole. I could see cum seeping out of his hole as I started to sink into him. I made out with him for a few minutes until I could feel my orgasm building. I asked him if I could cum in him and he said yes. As I was about to cum I could feel the load in my ass start to leak out of my ass and down my leg. That sent me over the edge and I flooded the twink with my own load. I pulled out, thanked him, and went to go shower and go home, a very satisfied boy.

"We still on for happy hour?" A text message from a number I didn't know. Sort of made sense because I was just waking up late one Sunday morning, not having much recollection of my night out the night before. I was curious, so instead of a normal reply like "who's this?" I agreed to meet and gave a location of a favorite bar and a time, making sure I arrived a half hour early so the person would see me and join me. I'm clever like that! 30 minutes passed and a cute, tall, slender guy walked in that I vaguely recognized. He came up and hugged me and we exchanged pleasantries for a bit. The he called me out for not remembering him. He was a confident, assertive guy, I really liked that. He told me his name was Jacob, and that we chatted the night before, but I was pretty drunk. We had a laugh and he was a good sport about it. We had some food and a couple of drinks and he invited me back to his place, which was a short walk away. When we got to his place we sat on his couch with a couple beers and chatted a bit more. Since he was an assertive guy, he made the first move going in for a kiss. He was a great kisser and I was content to make out with him for a while. Things started getting hot and heavy and we stripped the clothes off of each other. He had a really nice 6 inch cock, not too thick, nice mushroom head, easy to fit in the mouth. We sixty-nined on his couch for a while, me sucking on his cock while he alternated between my cock, my balls, and my ass. I could tell he wanted to fuck me, so I asked if he had a condom, because I was still in my I should probably wear one phase. He said no, and I said damn. We both sat up on the couch and I put my arm around him and we started jerking off as we kissed. After a bit he offered me some lube, and lubed himself up as well. After a few minutes, he got off the couch and went in between my legs, pulling me forward so my ass was just hanging off of the couch. He sucked me for a little bit while continuing to jerk himself off. At one point he lifted my legs up and rimmed me for a few minutes, getting my hole loose and wet. He put my legs back down and licked his way up my body until he was kissing me again. His left hand was slowly jerking my cock while I could feel his right hand jerking his. The way he was positioned I could feel his hand bumping up against my ass as he jerked off. He stopped jerking and held his fist against my ass, and started thrusting his cock through his hand. As it went through his fist it pressed up against my hole. Every few strokes his cock head spread my hole a little more. His cock was well lubed and my ass was loose from his rim job. I wanted to say something, but his hand felt great on my cock, his tongue was deep in my mouth, and his raw cock was slowly pressing deeper into me. Suddenly I felt the mushroom head of his cock slip past my sphincter. I let out an involuntary moan. Just as quickly it was back out, him thrusting like he hadn't just penetrated me. A couple more times it slipped easily in, just past the head of his cock. I was so turned on. I knew I should tell him to stop, but I was at that stage of horniness where sex takes over. He abruptly stopped thrusting, the head of his bare cock just starting to spread my hole open. He placed his left hand on the back of my head, and with his right he slowly jerked my cock. He stared directly into my eyes as I felt him start to push his cock bareback into me until his pubes pressed against my ass. "Sorry, it just slipped in," he said, smiling down at me. "Accidents happen," I replied. He slowly started to fuck me. "Want me to pull out?" He asked. I shook my head no and he started speeding up. He felt amazing in me, his cock managed to hit my prostate just right. After a few minutes, he flipped me over so I was doggy-style, my knees on the floor and my upper body on the couch. He sank his raw cock back into me and grabbed on to my shoulders and started fucking me again. He was the perfect top, not aggressive, but assertive, like he deserved to be fucking me bareback, but he wanted me to enjoy it to. He fucked me that way for almost 10 minutes. "Can I cum in you?" He asked. I figured he'd been fucking me raw for so long it wouldn't matter, so I told him yes. He pulled out, flipped me onto my back again, and thrust back inside me. I started furiously jerking my cock as he fucked me faster and faster. Moments later my orgasm hit and I started shooting cum up past my shoulder. He suddenly kissed me and thrust deep and held there. We made out for a bit, and then he slowly started to pull out, leaving his load deep in me. He drew me up on to the couch and spooned me with his softening cock nestled in my ass crack.

For most of my sexual life I mostly topped, but started to branch out more into bottoming. One day I was looking on Grindr and saw a guy I had attempted to hook up with a couple of times. He was really cute, but mostly ignored me when I had tried to message him before. I sent him a message that afternoon, and he actually responded. He said he was looking for a quickie, and asked if I was down to bottom (I had vers in my profile.) I said yes, and he gave me directions to his place. He was about a 20 minute walk from my apartment, so I put on a t-shirt, shorts with no underwear, and shoes, and headed to his place. When I arrived he opened the door and I stepped in. He had a really cute face, and he was a bit heavy set wearing a t-shirt and some basketball shorts. We started making out just inside the door in his foyer. He cupped my ass cheeks and was massaging them as our tongues wrestled. I started massaging his cock through his shorts. We kissed for about a minute and then he pushed me down toward his cock. I pulled his cock out, it was about 6 and a half inches, tapered, with a really wide base. I started sucking him and he told me to get it nice and wet. I slobbered on his cock for about a minute before he stood me up and turned me around, pushing me against the wall. He drew my shorts down over my ass cheeks, and I let them fall the the floor, kicking them away. We hadn't talked about condoms, but when he spit into his hand, I realized he wasn't going to use one. He put the head of his cock at my hole and pushed it in. It was fine at first but when he pushed all the way in it felt like he was splitting me apart. He grabbed my hair with one hand and put his other on the small of my back and started vigorously fucking me. I knew I couldn't keep up that pace for long. He used long strokes the whole time, pulling out to almost the tip of his cockhead before sinking back in balls deep. He only lasted about 2 minutes before he told me he was about to nut. He went balls deep again and I could feel his cock twitching as he unloaded in me. About 5 minutes after I had walked in the door, he pulled his cock out of me, his cum spilling out of my gaping hole on the floor of his foyer. I pulled my shorts on, gave him a quick kiss, and left. The whole way home I could feel his cum in my ass crack.

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 had gone to Steam just before midnight on a Friday night. It wasn't that busy and I spent the next 90 minutes cruising around, no one interested or catching my eye so I decided to call it a night. So it wasn't a total bust I checked Grindr when I got to my car and found a message from a headless torso that just said "bb?" I responded "pic?" and he sent a grainy photo I assumed was a few years old. He was really cute so I figured why not, his stats looked good, and I wanted to fuck. He gave me his address and it turned out to be really close to Steam, so I got to his place in a couple minutes. I saw him come down the stairs in a bathrobe and he was better looking than the photo. He opened the door for me an I followed him up the stairs to his apartment. As soon as he got inside he took off his bathrobe and sat down on his couch. He had been completely naked underneath and sported an impressive cock at least 8 inches long. "You okay fucking a cummy hole? I've already taken a load," he asked. I told him yes and immediately took off all my clothes. I went over and stood in front of him and he took my cock in this mouth and started sucking. He blew me for a couple of minutes before I had to go down on his monster cock. It felt so good in my hands and mouth I knew I'd have to get it in my ass as well. I flipped him over so he was doggy style on the couch and started rimming him. I could taste lube and a little bit of cum on his used hole. After rimming him for a minute I couldn't wait any longer so I stood up, spit on my hand and used that to lube my cock. I lined up with his hole and slid easily inside and went balls deep. He moaned as I started sliding in and out of his cummy hole. I fucked him from behind for almost 5 minutes, grabbing on to his hair and shoulders to make sure my raw cock bottomed out each time. He looked over his shoulder and asked me if I bottomed. I told him I did and he pulled off my cock and sat down on the couch. As he lubed up his cock I straddled him on the couch. I positioned the head of his cock at my hole and started sliding down. I had cleaned out for Steam and lubed up a bit, but his cock still felt like it was splitting me open. After working my ass on the head of his cock for about 30 seconds I slid down the rest of his 8 inch bare shaft. I kissed him as I started riding his cock. He felt absolutely huge in me and I knew I wasn't going to be able to be fucked for long. Fortunately a minute later he told me he was about to cum. I told him to shoot inside and a few seconds later i could see cum leaking out of my ass onto his pubes. I started jerking off but he said no, nut in my ass. I lifted myself off him and lifted his legs to my shoulders and plunged my hard raw dick back into his hole. I fucked him for a couple minutes more until I could feel my orgasm building. I told him I was about to cum and he told me to fill him up. I shoved my cock as far up his hole as I could as I started unloading in him. I kissed him and told him I love flip-fucking. After I pulled out of him we showered together and I got his number from him. We hooked up a couple more times after that, exchanging loads each time.

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 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 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 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.

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.

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.

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.

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.

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.

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.

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.

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.

Finally went to Buckman Field in PDX a couple weeks ago. Walked around a little bit, checking things out. Saw a cutie standing alone so I walked away from the track a bit. He followed me and we started making out. Asked if he was a top or bottom and he said top, so I lubed his cock up with spit and turned around. He fed his cock into my ass and fucked me with a nice 7 inch cock. Dropped his load and left. I walked around a bit more, then was hit up by a guy waving his cock at me. I wasn’t really into him but figured what the hell and started sucking him. I got bored sucking real quick and just got on my hands and knees. He stuck it in and fucked me for about 5 minutes and dumped a load in me. I’m thinking about heading to Steam this weekend because I’ve been bottoming more lately and I just want to take a bunch of loads.

I was house-sitting for a friend a couple weeks ago and naturally got quite horny, so I downloaded Grindr just to see if there was anyone in the area. I had previously deleted Grindr since I wasn't having any luck, but this time I was messaged by a 20 year old twink about a mile away. We chatted for a little bit, he mentioned he was going to a friends place alter and was just killing time, so I invited him over. I wasn't explicitly looking for sex, but was horny nonetheless. He agreed and pulled into the driveway about 15 minutes later. He was hella cute, thin, slightly shorter than me. We sat on the deck and chatted for about 20 minutes. There was a pause in the conversation and he said, "so what are you thinking?" I said "I'm thinking I want to kiss you." He said "I think we can make that happen," so we kissed and made out for a few minutes on the deck. I grabbed his hand and took him inside to the bedroom. I put him down on the bed and stripped off his clothes, and took mine off. He had a nice cock, and a fantastic bubble butt. We rolled around on the bed kissing for a little bit. I kissed my way down his body and took his cock into my mouth and sucked him off for a few minutes until he pulled me off so he could get at my cock. He sucked me for a few minutes, licking around my balls as well, until I pulled him back up to kiss him some more. I flipped him over face down and licked my way down to his ass crack, pulling apart his cheeks to get at his hole. I rimmed him for a couple of minutes, getting his hole nice and wet, and then I asked if I could fuck him. He said yes and turned over onto his back. I had a condom nearby if he wanted it, but I just started spitting on my cock to lube it up. I lined up my cock to his hole and slowly eased in. He took it like I pro. I leaned in and kissed him as I started to move in and out of his ass. I fucked him like that for a few minutes, then had him get on all fours so I could fuck him doggy style. I held on to his hip, occasionally grabbing onto his hair as I fucked him faster and faster. I was getting close so I flipped him over and slid my bare cock back into his ass as he started jerking himself off. I asked if I could cum in him and he said yes, so I slammed my cock in and out of his ass until I started flooding his ass with my cum. I started slowing down and just then he shot his load all over his stomach. We cuddled for a little bit, then he had to leave to go to his friends, my load in his guts.

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.