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Tell me about your wildest hookup experience

Been reading this thread for years and finally going to share the wildest thing I've ever done.

So I was living in a relatively small town with basically the closest gay person being in a town that was around 30 minutes away. I always saw him on Craigslist posting about needing head and wanting to date people, it's still like that so I think he just uses the dating line to pull in gullible guys. I was actually pretty excited because one day I saw a post that had his same stats and he would be going to an adult store that had holes in the stall. I knew he wouldn't get any action there and that he would be horny on his way home and I would finally get to meet him.

I ended up meeting him in another small town between me and the adult store, it was pretty dark and we arranged to meet at a gas station just to meet each other. So he pulls up and turns out it is not the guy I was thinking of, which actually disappointed me. We talked a little bit then I got in his car and we drove to a baseball field that was relatively close and in a park. He didn't really say much when I tried to make small talk but when we got to the dugout he immediately unzipped his pants and pulled his dick out. This dick was basically perfect, like literally 8 inches and just the perfect size. I sucked his dick for a little while then he grabbed my bulge and just started rubbing it. I unzipped my pants and he just went at it sucking like he couldn't get enough, turns out he may have been married and had kids at home so he didn't get out much. Eventually he pulled out some lube and told me that he wanted to be fucked. I stuck my dick in for a few seconds and we notice a car driving through the park and heading towards us so we quickly pulled our pants up, didn't even have time to zip them. It ended up being a cop checking why people were in the park and he said since we were there and my pants were unzipped he knew exactly what we were doing but hadn't seen anything so he couldn't do anything, he also asked me about 10 times if I was really 22 since he said I looked like I should be at home in bed for school the next day. We got the talking about not doing that there and to leave and not come back.

The guy I was with was kind of freaked but the second we got in his car he just told me to follow him after he dropped me off. We ended up driving outside of town and going down a few side roads until we knew no one would come by. Right when we parked he got out really fast and was basically racing over to suck on my dick some more. After a few minutes of that the lube reappeared and I had him pushed up against the back of his car and fucked him for about 30 minutes. He kept alternating between me fucking him and turning around to suck my dick, always asking where I wanted to blow at. I hadn't been with many people and was still plenty freaked out about the cop so I ended up not getting off, he seemed a little disappointed but he blew all over his back bumper which was pretty hot. He did remark that we were going to have a fun summer but sadly I never saw him again, I think he was just looking for a quick fuck and found it. I also never saw him post again so it's possible that he moved quickly or he may have just been with someone and felt guilty enough to not do it again.
 
Re: tell me about your wildest hookup experience

I suck my bosses cock
 
Uhm.. Wish my two male-male hookups (so far :o) were a one lovemaking session instead.
The first one was more passionate and intense between me and a guy my age, while the second one was more about physical action with a more mature hottie. They both were good, but left me wishing for a more exciting third one. :rolleyes:
 
My wildest one is probably pretty tame to most people, but it was wild to me since it happened close to when I was first out. For a couple of months, I had been talking to this Latino bear and he was interested, but we could never manage to hook up. He's got gorgeous green eyes, a great beard and is just cute in wholesome way. One time I texted him and asked him if he was good in bed, to which he replied "why don't you find out?". I went to meet up with him and he was with a designated driver, since he had a few drinks. He was tipsy, but not drunk enough to just sleep with anyone. We got back to his place and he started kissing me in this hungry way. Our clothes came off and he actually picked me up and laid me on his bed. Granted, he is a bottom and I'm a top, yet he was quite aggressive for a bottom. He started kissing my neck and the feel of his beard was driving me wild. He put condom on me and started to ride me, I didn't even put in that much work. He rimmed me too and it was amazing, because that was the first time I had that done to me.

Even after I came, took a shower and got dressed, he pulled my dick out and just started sucking it so good. Then I plowed him from behind. Haven't had a chance to get with him again, but definitely would like to.
 
When I was in my teens and early 20 me and this guy use to cruise town. I use to suck him off while we drove.
 
It was in a mall department store men's room. There was this young very hot looking Latino in one of the stalls. Had to be between 19 to mid 20's. He was so good looking. He had one hand hanging down in his lap that blocked my view of his cock. All of a sudden he looked up and realized is was peeking at him. I couldn't resist and asked "Can I see it"?

He was a bit surprised, but moved his hand and let me see. It was at least 8 inches, and cut. Most likely he was born here in the US since he was cut. Then I really got up my nerve and asked him if I could touch it. He opened the stall door and I reached down and felt up his beautiful dick. Then he looked up at me and said "suck it for me".

I dropped to my knees so fast it would make your head spin! I sucked him and he grabbed my head from the back and slowly fucked my mouth. His dick felt very warm inside my mouth. My hands roamed under his tee shirt as I felt his warm body all over. I then rubbed his crotch with my hands and sniffed them to get his sent on me. What a hot man! He lifted his shirt so I could tease his nipples as I sucked him. At one point I pulled his dick out of my mouth briefly so that I could kiss the head of it. That made him smile.

Unfortunately right after I put it back in we were caught by the store manager. Luckily we didn't get in trouble. He just stood there holding the men's room door wide open. Didn't say a word, just held the door open, which we understood meant get out and don't come back.

I never saw that guy ever again, but to this day I can remember how warm his dick felt in my mouth and how unbelievably handsome he was. No one has ever come close to turning me on the way he did.
 
Well it isn't as hot as that ^ but I went to a guys place and he said his friend wanted to join in so I was ok w/e. Then his friend had someone come over, so one was being fucked by one, whist sucking another and i was rimming the fucker at the same time, before the next guy fucked the guy i would eat out the bottoms wide hole... very hot time.
 
My hottest? So many....but...On a family trip to the mid east... (where they hate/kill gays especially bottoms) I shared a room with my brother. (I bottom for my brother, which, sadly, is taboo even in the friendliest of US states/cities) Before bed our first night there, we got a kick out of discussing their laws and ours. "It's not like it will change anything we're about to do," he said as he began dropping his shorts and pulled out his cock, which I immediately and instinctively took into my mouth.

I felt in insane rush passing through me as I considered the dire consequences of " being caught." Our family was in the rooms next to ours, completely oblivious to the forbidden activities we were both enjoying! "You're slurpping is too loud... shhh...we need to be very quiet," whispered my brother as I sucked his cock. I tried to keep quiet , but it was not easy to keep quiet while I was being rewarded with the taste and feeling of his precum in my mouth.

"Turn around and get that towel pillow. You gotta keep quiet while I fuck you in the ass and we don't want to make a mess." I quietly laid there in ecstacy, my ass in the air while my brother generously rimmed me. There's no going back at this point, I am HIS. My brother cruelly teases my hole with the head of his cock..I look back at him begging for it with my eyes, and then I feel him begin to push in. I gasp as I feel my asshole stretching and put my face on the pillow, careful to be quiet while my brother's big cock enters me.

He fucks me slowly at first, going balls deep, holding it there for a moment each time, and then picks up tempo. I tightly squeezed around his cock, cherishing the forbidden, illegal act. I moan face down into the pillow, continuing to squeeze his cock while a massive orgasm begins building inside me while my brother fucks me harder and deeper. I didn't know how I'd stay quiet, nor did I care-- my brother's grunting signaled he was getting close to orgasm, too.

I wanted him to make him cum his brains out. I look back and beg "cum inside me," while reaching back to rub his balls. A few more thrusts and I erupt in a massive orgasm all over my brother's cock, which seemed to be going deeper and deeper inside me. He grabs me, holds me tight, thrusts his cock balls-deep inside me and begins pumping me full of sperm. It was such a hot and sexy feeling, knowing I made my brother feel that way, I gave him an orgasm, AND I had his cum inside of me which I'd be feeling for the next several hours in addition to the stretched/fucked/owned feeling.

I laid in bed in total ecstacy afterwards, enjoying the feeling of my asshole being freshly fucked/stretched and full of my brother's cum. It makes me feel so "owned." "We gotta do this EVERY NIGHT we're here" my brother told me. I agreed. (and we did) I laid there with my ass in the air for a little while and then went to sleep. I slept so perfectly well. I always do after a proper fucking.
 
Re: tell me about your wildest hookup experience

hothrd said:
The wildest hookup happened with a marine guy that was back in the country for two weeks. He was sexually deprived so he wanted to do it. We couldn't find anywhere to do it as all the hotels and all seemed to be full. Because of this, we ended up going to the office building at work. We went up to the tenth floor and went at it for 3 hours overlooking the city on a clear saturday late night sky. I felt to ashamed afterwards for weeks, but now I think it was awesome to be fucked while overlooking the downtown skyline. And it was true that he was deprived of sex, I felt like he needed to onload all his sexual energy on me, and he did, gave me a night i will never forget.
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sounds hot I hooked up with guy who worked at navy exchange while I was in the navy his hookup was to show me how to get fucked laying on my back since I never got fucked that way. god he was horny and fucked me three times without pulling out wow was I full of come
 
I don't have many stories to choose from, so I'll take my first experience..

I met this 63 year old on this web site(like Okcupid, but local in my country and just for gays) when I was 21. I wasn't and I am not gay - more like bicurious. He was the typical "trucker", as I would describe him. Beard, hairy, short hair, big belly. We decided to meet up on this empty parking lot, and we did. I was beyond horny. We drove to a disclosed part of the city with lots of fabrics and such, not a soul in sight. He wanted me to take off my clothes - which I did, nervously. Totally naked in his car, he put my hand on his cock and I felt my heartbeats beat out of my chest. I felt his cock for a while before he took off his pants, and I became even more horny when I saw his cock. Somewhat short, but wide, hairy and uncut. "Perfect" I thought to myself, before I began sucking on his erect cock. It felt fucking good. I didn't really know what I was doing, but judging from his sounds, I guess I did something right. After a few minutes I felt something wet encircle my asshole, damn it felt nice. He had sucked on his finger and he was beginning to finger fuck me. Awesome. But after about 30 minutes I had to give in, he reeked of nicotine. I stopped, put on my clothes and left.

Afterwards I have regretted my decision over and over again. And the thoughts of it has given me many orgasms. I really wished he would cum or fuck me.
 
That guy was just an awful human being, and I've met a lot of people like him. The ability to be anonymous is really making us worse.
 
For my 25th birthday, I went home with guy and he told me that he would pick up guys for his cousin. I thought it was hot so I decided to go. We went to his house and I specifically asked them if they were real cousins and they showed me their IDs and indeed they shared the same last name. They kinda looked alike so I told them that whatever they did, I would do so let's just say that I did it all that night!
 
I’ll share one of mine. I was hanging out with some friends and the guy I was dating at the time. We were in my friends huge family room watching a movie. It was dark I was laying on the couch with my guy with a blanket over us. My friends were seated on the other couch and floor watching the movie. My guy kept pushing his ass up against my crotch getting me hard. We both had shorts on. I manage to get his and mine undone and slid down. Next thing you know I’m sliding in him trying to keep him somewhat quiet as I fuck him. Thankfully the movie was loud and my friends were not paying any attention to us.
 
My first MM encounter was in my late 40s, only a few years ago. With one exception, all of my MM encounters have been in gay saunas or via web site hookups. I've been to gay bars a few times, but never managed to connect. But then there was this one time when ...

I was on a work trip a few years ago in Japan, where being gay is legal tho gay men tend to be very discrete. I don't speak Japanese and I stood out somewhat as a tall-ish GL white guy, a silver dad type. So here I am on a subway on the last train of the night nearing the last station, which is a short walk from my hotel. I'm sitting there, minding my own business when I notice some other guy is eyeing me. He's Asian, but not Japanese (maybe Malay?), good looking, 30-something, dressed like he works in an office. I catch him looking at me, and return his stare. He looks away, so I look away, but then I look back, and he looks back too. I look at him hard as if to say "Yes, I'm glad you like me. I like you too." I think other people on the train might have noticed us looking at each other, but WTF it's not like I'm ever going to meet any of them again, right?

The last stop arrives and we get up. I get off first, but stop on the platform to "check my cell phone". He slowly ambles up beside me. We look at each other. He tries speaking to me, but I don't speak Japanese or Malay and he doesn't speak English. He says "no money". I'm confused. Is he a hustler? He's dressed business casual, and looks like he's on his way home after work. I said "no money". After a while, I decide he thinks I'm a hustler (LOL) and he wants to be sure I'm not asking for money. OK who really knows, but after we both say "no money" again to each other, I point to my hotel and ask "hotel?". He nods. We enter my hotel, and he follows me to my room. I pretend I don't know him inside the hotel as there were other people from my work staying there too. But we make it to my room. I pull him inside. We drop our things. I kiss him aggressively, which he loves. We start to strip off our clothes, and I push him into the bathroom. Soon we're both naked and showering. I suck his cock for a bit under the spray -- it's uncut and a good size. He loves it. Then he goes down on his knees and sucks me. It's amazing, knee buckling hot. He stands up and turns around, grinds his ass (which is very clean, I can attend) against me. I want to take him there, but safety first, so I grind a bit more. We turn off the water and dry each other off, caressing and attentive. I hang up the towels, and pull him onto the bedroom. I push him over onto his stomach on the bed. I grab a condom, put it on, lube up my cock, and start to penetrate him. He loves it and is in ecstasy as I push harder and harder, slowly, into his fine ass. Eventually, I'm all the way in and I stop to enjoy the moment. Here I am, balls deep inside some much younger good looking Asian guy, and we managed to hook up just by looking at each other. Amazing. I fucked him slowly, then harder and harder making him buck hard. I feel my orgasm building, and I warn him that I'm going to cum (maybe he understands "cum"?). He keeps going to I do too, and I release a big load into him. Wow. I stay inside him a bit while my orgasm finishes, then I pull out, take off the condom and toss it in the garbage, and lay down beside him. He cuddles into my arms for a bit. I realize he hasn't cum yet, tho, so I start to stroke him clear designs on his cock. He lays on his back on the bed and I start to suck on him, giving lots of attention to his lovely mushroom head, licking the shaft, sucking on his balls, and rimming him just a little (normally I don't rim, but I knew he was clean). I went back to sucking his cock, and he whimpered more and more. He gave me warning that he was getting close (not in words, so much, but the meaning was clear). Eventually, he started to spurt. I looked up into his eyes, and swallowed every drop. I kept his cock in my mouth until he was totally done cumming, and swallowed again. Then I crawled up and gave him a long, wet French kiss. After a little more making out, he got up, dressed, and left. I flew home the next morning.

This encounter is 100% true. I love that I managed to pick up some younger dude without being able to talk to him, that he picked me out as a GL western silver dad type, which clearly floated his boat, and I enjoyed being the top / alpha for all of our encounter. It's never come close to happening again.
 
It was around Christmas 3 years ago. A close friend was having a big Christmas party for all his friends and coworkers. I knew or had previously met everyone there, so I wasn't expecting a "hook-up". That was until I saw one of my good friend's coworkers, we'll call him "Steve". As I said, I had previously met him and had the biggest crush. He was tall, thin and a bit of a nerd (my type of guy).

Anyway, we had mingled in passing throughout the evening but I had also caught him staring a few times. The longer the night went on, the more alcohol was consumed, the more I caught him. It felt like this went on for days, then I got the courage to say something to him. You know, liquid courage. I found him in the crowd, and whispered in his ear as I passed him. "Meet me in the garage". Not sure why I said garage, I guess I was trying to be unconventional.

I went to the garage and waited, and waited and waited. This time it felt like weeks. I was just about to give up, when the door suddenly opened. There he was, just staring at me. Before I could say "I thought you weren't going to come", he lunged at me. Our lips locked together tightly and my hands drifted to his belt. His cock was free and ready for the taking. It was glorious! Everything that I'd hoped it would be. About eight inches long, cut and pretty thick. I dropped to my knees and engulfed it almost uncontrollably. Steve's hands were running through my hair as I blew his mind. Suddenly and without word, he pulled me to my feet.

"Take off your pants" he said. I didn't even hesitate, I quickly dropped my pants and stepped out of them. He grabbed my right leg, lifted it as he kissed me again. I leaned back against my friend's car as he took his other hand, spit on it and rubbed it on my exposed ass. He repeated that a couple of times before I felt him pushing inside of me. It took my breath away. He just stared at me as he lifted my other leg and pushed it all the way in. I wrapped my arms around him and he began thrusting.

It was pure ecstasy. He kissed me passionately and said in a breathy whisper "I'm going to cum". All I could muster was a moan and a nod. His pace quickened alongside my pulse followed by grunting. A few quick thrusts later, he unloaded an immense amount of cum deep inside me. I was exhausted from the sheer passion of it. Steve then carefully put me down, pulled his pants up and gave me one last long kiss before walking back inside.

When I finally returned to the party, Steve was nowhere to be found. I caught up to my friend and asked "Hey, where did Steve go? I haven't seen him in a while". My friend looked at me oddly and said "His wife called him and told him to come home. She's such a bitch!"
 
novastar said:
My hottest? So many....but...On a family trip to the mid east... (where they hate/kill gays especially bottoms) I shared a room with my brother. (I bottom for my brother, which, sadly, is taboo even in the friendliest of US states/cities) Before bed our first night there, we got a kick out of discussing their laws and ours. "It's not like it will change anything we're about to do," he said as he began dropping his shorts and pulled out his cock, which I immediately and instinctively took into my mouth.

I felt in insane rush passing through me as I considered the dire consequences of " being caught." Our family was in the rooms next to ours, completely oblivious to the forbidden activities we were both enjoying! "You're slurpping is too loud... shhh...we need to be very quiet," whispered my brother as I sucked his cock. I tried to keep quiet , but it was not easy to keep quiet while I was being rewarded with the taste and feeling of his precum in my mouth.

"Turn around and get that towel pillow. You gotta keep quiet while I fuck you in the ass and we don't want to make a mess." I quietly laid there in ecstacy, my ass in the air while my brother generously rimmed me. There's no going back at this point, I am HIS. My brother cruelly teases my hole with the head of his cock..I look back at him begging for it with my eyes, and then I feel him begin to push in. I gasp as I feel my asshole stretching and put my face on the pillow, careful to be quiet while my brother's big cock enters me.

He fucks me slowly at first, going balls deep, holding it there for a moment each time, and then picks up tempo. I tightly squeezed around his cock, cherishing the forbidden, illegal act. I moan face down into the pillow, continuing to squeeze his cock while a massive orgasm begins building inside me while my brother fucks me harder and deeper. I didn't know how I'd stay quiet, nor did I care-- my brother's grunting signaled he was getting close to orgasm, too.

I wanted him to make him cum his brains out. I look back and beg "cum inside me," while reaching back to rub his balls. A few more thrusts and I erupt in a massive orgasm all over my brother's cock, which seemed to be going deeper and deeper inside me. He grabs me, holds me tight, thrusts his cock balls-deep inside me and begins pumping me full of sperm. It was such a hot and sexy feeling, knowing I made my brother feel that way, I gave him an orgasm, AND I had his cum inside of me which I'd be feeling for the next several hours in addition to the stretched/fucked/owned feeling.

I laid in bed in total ecstacy afterwards, enjoying the feeling of my asshole being freshly fucked/stretched and full of my brother's cum. It makes me feel so "owned." "We gotta do this EVERY NIGHT we're here" my brother told me. I agreed. (and we did) I laid there with my ass in the air for a little while and then went to sleep. I slept so perfectly well. I always do after a proper fucking.
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So fucking hot!!!!
 
My boyfriend and I started having bareback sex pretty recently, it was kind of by accident. We were both lying on the couch and very horny, me on top of him and wearing my favorite jockstrap, so I began rubbing my ass against is cock (the feeling of a dick on my ass turns me on as fuck) and then he started pushing. Suddenly, without any lube or saliva or even fingering my ass, his dick started slipping inside my hole until it was completely in. In that moment we looked each other in the eyes, somewhat scared (bareback was new to us both) but extremely aroused, so we decided to continue and I started riding his rock hard cock up and down, slowly first, but then faster and faster; I had never felt his dick inside me in such an intense way before.

Soon we were in the missionary position and he was fucking me hardest than ever, looking me in the eyes with a very serious, fierce and masculine look, like he knows he is completely in control, he owns me and I'll do anything just to feel his dick inside me for one more second, making me go one step further down the path of becoming a total bottom. Sadly, that time he didn't cum inside me but he shot the biggest load over my face, completely covering it with his cum. We both agreed that it was the best sex any of us has had so far.

Since then I've been fantasizing with him filling me with his cum and it dripping from my hole while he keeps pounding me for a while. We've actually talked about it and we're very eager to do it but we haven't had the occasion yet. Needless to say, we never let our cum get wasted and we always come in our mouths and then kiss passionately; we love how every time it has a slight different flavor.
 
This just happened, and I'm still sort of in awe. Made a profile here cuz I felt I just had to share the experience.

I'm into gloryholes (private ones, not ones in adult book stores or dirty bathrooms and whatnot). I found one recently on Doublist that was nearby and tried it out. Guy on the other end was pretty good, visited a few times in the past, but tonight was a whole other ball game.

It helped, I'm sure, that I had edged myself the night before in preparation. And, I think, that I had worked my arms (biceps, triceps, and forearms) very intensely that day, so much so that they are still sore even now (a feeling I love). But this was some next level stuff.

I'm a multi-cummer. I usually only cum once, but sometimes when I'm really horny or the sex is really good, I can cum more than once. Usually, this means I cum 2-3 times in a session. My record is 4. Or, I should say, WAS 4.

I got to this hole already pretty horny. I'd been looking forward to it all day. When I got there, I did all I could to keep from cumming quickly, and I held out for a decent amount of time, but of course the dam eventually broke. The guy on the other end knew I was a multi-cummer, so after I finished he paused for a bit, but then kept sucking. Before long I was cumming again...but my balls still felt full, and I was still horny as hell. This time I started slowly moving back and forth myself, inching my cock out then back into his mouth, until that, too, made me cum. At three loads I expected to hit my limit...but I didn't. I still felt a need to breed his throat. I started humping that mouth harder now, hilting with each thrust. This guy has a magic throat, velvety and warm, pulsing against my cock, and he appears to have no gag reflex, so he just let me face fuck him. I came again, but still no cooldown. He nursed my cock, having not let it out of his mouth this whole time. One of my legs was numb, but I leaned against the doorframe to compensate and started fucking that throat again, eventually blowing a fifth load down it.

At that point the exertion finally caught up with me. I told him I'd need to sit down for a bit to get the feeling back in my legs, and he offered me to come sit on the couch on the other side of the gloryhole. So I did, still naked, and we got to talking a little. He was playing with my cock and balls, and running a hand over my pecs every now and again, and eventually that got me hard again. He blew me on the couch, and I came for a sixth time, but I'm honestly not even sure anything came out that time. I'd literally cum myself dry.

I'm so lucky to have found this cocksucker, definitely going to be feeding him again in the future. I really want to get him to film it so I can watch him suck my cock, but not sure he'll be down with that. If I do (and with his permission ofc) I'll probably post the footage online somewhere. Cuz goddamn, I don't think I've ever seen a gloryhole video where a guy cums more than three times in one go...I felt like a goddamn stud horse lol.
 
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