jbucktown

I couldn't tell what I should do. I knew I could never fuck bareback again. It was dangerous. It was wrong. People would judge me and think I was a whore and I'd never get a boyfriend if people knew because they would talk about me barebacking with guys. So, I was a "good boy." I tried hard not to hook up because I was picky, but also because I didn't want people to think any of that stuff. I didn't mess around with anyone for a few weeks. I still went out with my friends and got drunk and danced, but I was a "good boy." One night I was out dancing and I met this hot guy. Shorter than me, tight body. Probably 5'8" and just ripped - Ripped Boy. I was into him and we danced and drank and he wanted to hook up, but his friend was from out of town and single and he didn't want to hook up if his friend didn't. I thought, he is such a nice guy. I said, "Give me a second." I grabbed this cute guy and pulled him into our dancing group. I kissed him and asked his name, turns out he's a Navy Boy. I told him our dilemma and he agrees to go dance with the friend and they hit it off. Next thing I know, Navy Boy is back over to me and says, "I just felt that guy's cock and it's huge. I bottomed last night and I'm still sore. I'm not sure I should go home with him." I am so accommodating and sweet and really want to get fucked by the Ripped Boy that I say, "It's no big deal. Let's all go to Ripped Boy's place and hang out and see what happens." Navy Boy agrees. As we leave the bar I see Navy Guy is really sexy and that Ripped Boy's friend is attractive but not in Navy Boy's league. I was nervous that they wouldn't hook up and Ripped Boy and I would then not hook up. LOL. We all pile in Ripped Boy's car and his friend and Navy Boy are in the backseat. I see the friend open Navy Boy's zipper as they make out. Ripped Boy stops to get gas, Navy Boy runs inside for cigarettes and the friend says we should get condoms. Ripped Boy agrees and then Navy Boy comes back with some beer and cigarettes and Ripped Boy says let's get some booze too. So we all get in the car and hit this late night store and I run in and get some vodka. Back out and in the car. Now the Navy Boy has his shirt off in the back seat and Ripped Boy says, "You got my friend a total hottie. Thanks." Off to the house. We get inside and Ripped Boy and I go to the kitchen, make out, he plays with my ass as I make the drinks. Spilling some when he plays with my crack through my jeans. We get back to the living room and Navy Boy is in his briefs making out hard with the friend. Ripped Boy says, "No fair. You should get naked too." He grabs at my jeans as I hand the guys their drinks and put ours down. I let him undo my jeans and I am in my boxers and I take off my t shirt. I straddle Ripped Boy's lap just like Navy Boy was to his friend and make out with him. It's getting really hot and I am hard as fuck. Navy Boy and I kiss some too. Navy Boy asks loudly, "Hey, you're a bottom right?" I said yes. Ripped boy slips his hands into my boxers and rubs my asshole some. Navy Boy has finished his drink and into the kitchen we go so I can make him another one. He slips my boxers down and rubs his cock on my ass. He says, "You have a hot ass. Can I fuck you?" I said, "Sure, but I'm with Ripped Boy tonight." Navy Boy grabs some salad oil off the kitchen counter and rubs some on my crack and hole. He fingers me and says, "Please." At this point the other guys come in and the friend says, "I bet we all fuck College Boy (me) tonight." Ripped Boy walks over to me and takes the salad oil and says "Does this feel good?" I laughed and said, "Sorta." He kisses me and lubes up Navy Boys cock with the salad oil and says, "Fuck College Boy." I spread my legs and kiss Ripped Boy, not thinking of anything but how turned on I was. Next thing I know, Navy Boy's cock is slipping inside me. I moaned and then the friend kisses me and Navy Boy is resting his cock in my ass. I'm making out with Ripped Boy and the friend as Navy Boy starts to go to town on my ass. Navy Boy and the friend start kissing and the friend takes off his clothes and Ripped Boy bends me over more to suck his cock. I'm sucking his cock and Ripped Boy says to his friend, "I told you we didn't need them." I have no idea what they are talking about. I'm sucking cock and getting fucked. I'm in heaven. After a few minutes, Navy Boy tightens up and says, "I'm gonna cum." Now I realize, Navy Boy who got his ass wrecked last night by some random dude is in me bareback. I can't do anything much because he started cumming in my ass as I am still sucking cock and realizing we never used a condom. I take his load and then Navy Boy pulls out and he and the friend grab their drinks and head back to the living room. Ripped Boy is fingering my ass now as we share a drink. I am so shocked that I just let another random guy bareback me. I turned to Ripped Boy and say, "OMG! That was so slutty. I didn't know we weren't using a condom." Ripped Boy takes my hand and leads me to his bedroom. He sits me on his bed and I can feel Navy Boy's cum in my ass. He climbs on top of me and we are making out so hard. My cock is so hard because I had a load in my ass and was with this hot guy. He spreads my legs and says ur ass is still so slick from the oil and Navy Boy's cum. Blushing I say, "I'm sorry about that. I didn't know." Ripped Boy turns me over and rubs his cock on my ass crack. He says, "Do you need more lube?" I said, "No. I think I'm good." He slicks his cock up with the oil on my ass and slides his bare cock in me. I said, "Fuck that's hot." He said, "My cock in you feels really good." He fucked me good for about 10-15 minutes. Then he said, "I'm going to cum in your ass." I said, "Do it. I want your load." I took his load and he slipped out of my ass. He slapped my ass and said, "You are a hot fuck." Ripped Boy and I made out some more and fell asleep. I woke up with him fucking me early in the morning. After a while on my side, I turned on my back and spread my legs for him. I noticed his friend watching us from the doorway and stroking his cock. Ripped Boy came in my ass again and fell asleep. I got up to go to the bathroom and I came out and saw the friend on the couch in the living room stroking his cock. I asked where Navy Boy was and he said, "He went back home." I said, "Navy Boy was hot." He thanked me for hooking them up and said I was hot too. I walked over to the couch as we talked. He had a 9" cock. I said, "You have a big cock man." He said, "Too bad Navy Boy didn't want to get fucked. You looked like you like getting fucked by Navy Boy and Ripped Boy." I blushed and said, "I did." I asked me if there was lube in the bathroom and I said yes and went to get it for him. I came back and squirted some on his cock and rubbed it all over his cock. He pulled me on top of him and we kissed and I straddled him. He said, "You like cock don't you? Why don't you sit on mine." I got shy and said, "We don't have a condom." He said, "You haven't used one yet tonight." He was right. I was a cum dump for two guys already that night. I gave in and he pushed his cock against my hole as I leaned back down on it. He said, "Ride my raw cock bitch." I did. I rode him and made out with him until he was close and he said, "Take my load slut." I sat down on his cock and felt him explode in me. He just kept coming. I was so turned on I came on his chest. He loved it. I eased off him and cum for three different guys slipped out of my ass and down my thighs. I was so turned on and so scared of what I had just done. Not just one guy, I had let three different guys bareback my ass in one night and I had taken their cum. I went back to bed with Ripped Boy and fell back asleep. We got up and he drove me back to my apartment. I found out on the ride that he had a boyfriend. I was kind of shocked and said, "But you just fucked me bareback and came in my ass twice. How can you have a boyfriend?" He said that I was so hot he had to have me. I blushed and we exchanged numbers and he said, "Can I see you again when my boyfriend is out of town?" I said, "Yes." I got out of the car and he called out, "College Boy, come back." I walked back the few steps and he kissed me hard and asked if I'd let his friend fuck me too. I said yes. He said, "You're so hot," and he drove away. I went upstairs to my apartment and said I swore I'd never see him again because he was a cheater. I also swore that I'd be better about using condoms. I had to be, right? No guy wants to be boyfriends with a slut, right? I said, never again to both barebacking and seeing Ripped Boy. I did see Ripped Boy again a few times, but I made him wear condoms. He said he understood. We stopped fucking when his boyfriend figured out he was fucking me. I might have kept my promise about making Ripped Boy use condoms, but I did get barebacked again. But, that is another story.

Moderator's Note: The first couple of pages of this story don't have chasing in them. It only starts near the end. I've been lurking on here for a while and decided to post about my experiences slowly progressing from a safe sex only guy to a bareback slut. I don't know how many of these stories I'll post, but if y'all like them, I'll post more. I grew up in the late 80s/early 90s in New York. In my brain back then, everyone who was gay died. I tried hard to hide my sexuality. When I would lapse and mess around with a guy, it was only oral and making out. I never swallowed cum and always felt guilty afterward. Eventually Aaron, a neighbor boy, and I started trying to fuck. It hurt and we stopped most times, until one night in a not yet developed part of his subdivision he fucked me. It was safe that time and every time he fucked me after. I'd always feel guilty after Aaron and I messed around, but we always did it again until I graduated from high school. After that, we only saw each other when I was home from college. Aaron is another story. My freshman year, I didn't really fool around with guys much. I joined a fraternity, dated girls, drank and partied. In was my sophomore year when I met my first boyfriend. He was a medical student, 4 years older than me, at 23. He always topped me and he always used protection. I was also not really satisfied with our sex, but I was in love. That is, until we broke up about a year after we started dating. It was my junior year and I moved out of the fraternity house spring semester because I was tired of having a roommate. I moved in with a straight guy and finally had my own room. I hooked up with a bunch of guys and was learning to top as well as bottom. I was having a blast. I was still all about using condoms every time I fucked back then. I was very serious about only playing safe. Then I turned 21 and my friends and I started going to the gay bars to dance and drink. It's here that I should say I was 6'2", blonde, blue eyes, 185 lbs with a 30" waist and a 7.5"cut cock. I became really popular at the bars, not that I thought anything of it. I would hookup with guys and still always used protection, but the more I drank the more likely I was to get fucked that night by a guy I had just met - white, black, latino, asian, didn't matter as long as they were young and hot. One night, I was dancing on the box in jeans and a pretty tight fraternity t-shirt and this guy got on the box with me and we started grinding. We kissed and went to get a drink. We ran into friends and I learned this guy's name was Matt. We had a few drinks, danced some more, and I could feel his dick getting hard as he was grinding my ass. He said let's have another drink and talk. We went off and talked and drank some more and he turned out to be a really cool guy. Unfortunately, he wasn't a local. He was in town for work and staying with a friend for the weekend. After a while, he kissed me and his hand slipped into my pants and grabbed my ass. We made out at the bar like that for a while and then he pushed me into a darker corner and slipped his hand down the back of my pants and underwear and rubbed my hole. I moaned and I kissed him hard and asked if he wanted to get out of there. We left and went back to his friend's place a few blocks away. He had me naked as soon as we were in the door. I didn't even know if his friend was home, but I was naked and sucking Matt's cock in the living room of this apartment. He was hard and I was getting his cock wet as fuck. I wanted to make him feel good more than anything in that moment. He took his shirt off and then as he got the rest of his clothes off he told me to turn around. I got on all 4s and he ate my ass. No one had ever done that before. I was in heaven. I was moaning and pushing my ass back on Matt's tongue. He ate my ass for about 10 minutes and then he turned me over and we made out and I could taste myself on him. It was so hot. I wrapped my legs around his waist and we must've made out for 20 minutes or more. It felt like forever and I was so into it. The whole time his cock was rubbing in my ass crack and poking at my hole. I knew we should stop and get a condom but I was so turned on and I figured we wouldn't fuck yet. His cock felt so good on my ass that a spread my legs more and just then his cock slipped in my ass about halfway. I was shocked and so was he. We hadn't used any lube and he wasn't trying to penetrate me yet, but there was his cock in my ass bareback. It felt so good. I grabbed his ass and as he looked into my eyes questioningly, I said, "Don't stop. Fuck me." He started to rock his bare cock in and out of my ass. I loved it. No cock had ever felt this good in my ass, On the floor on this random guy's friend's apartment, I was getting barebacked and I loved it. I thought about stopping but I didn't want to. I knew it was dangerous, but it felt so great that I just kept kissing him and saying "Fuck Me." It didn't take long before I felt him getting close to cumming. He started tensing up and I slid my hands down his back and grabbed his ass hard. He looked at me as said, "I'm going to cum in your ass." I said, "Do it. Cum in me." and I pulled him into me as he shot his cum in my ass. I'd never felt anything like it. It felt so good that I came right after he shot his load in me. He said, "Wow that was so hot.' and he slipped his cock out of my ass. He said, let's take a shower and we did. In the shower he said, "I never thought you'd take get fucked bareback. You seem like such a good boy." I told him that was my first time bareback and he got hard immediately. He asked if I wanted his bare cock in me again. I just leaned against the shower wall and spread my legs. He lined up his cock and for the second time ever, I let a cock in me without a condom. He fucked me there until the water got cold and then we went out to the couch in the living room. He slid his bare cock in me again fucked me on the couch on the living room eight next to my jeans where I knew I had a condom in the pocket. I didn't want the condom though. I just was his bare cock. I was on all 4s and he was behind me. He was getting close again and I was jerking my cock. It's then that he said, "Tell me you want my cum." I heard a noise, but was so into getting fucked that I just said loudly, "Cum in my ass." He blew his load into my ass. I was so turned on that I was in a haze. I had just let a dude cum in me again and I loved it. After a few seconds, we looked up and there was his friend who had just seen me getting fucked and heard me begging for cum. He smiled and said, "Glad you're having fun Matt." I was so embarrassed. Matt was too, but less so than me. Matt and I slept together that night for a bit, but I couldn't sleep knowing what I'd just done and been seen doing. I left Matt my phone number and left for my own apartment. I was really freaked out, but that night and for almost a month I jerked off remembering Matt fucking me bareback and cumming in my ass. I told myself I wouldn't fuck again without condoms, but part of me knew that wasn't true.