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Tell me about your wildest hookup experience

I have several that I equate to the wildest experiences I've had, and I'll share a few here if that's okay.

A buddy and I when seniors in high school wound up doing some hot things together. We knew we couldn't do anything at either of our houses, so at school we were walking down the corridor near the end of the day, and were talking about how we still really wanted to play. So he suggested the two of us stay late at school and catch the late bus home, and we could figure something else out. After the bell, the two of us sought out a private storage area of the high school where we knew no one ever was. It was this large stairwell that circled around the back part of the auditorium and went above the top floor toward the roof. It became the area where objects were placed and left for a long time. We had the place to ourselves. This was my first fully grown, mutually consented, person to person sexual encounter, and it was with another guy. I dropped my jeans, and he dropped his pair of white painter’s pants (popular back then). He was huge compared to me, but I realized that he didn’t seem to care about that. He loved my cock and aggressively sucked me. It felt good, right, and natural. It was so hot to be looking down and watching his male head bobbing in and out as he sucked, to see his male hair moving to his actions, and his male lips tightly wrapped around the shaft of my dick, soaking me up good.* It was heaven to me.

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I had to have his as well. So I switched the action and took his large dick in my mouth. The heat, the texture on my lips and tongue, the taste, the scent of his thick bush of dirty blonde pubic hair, the pressure against the inside walls of my cheeks and the soft but significant pounding on the back of my throat… It was the perfect cocktail of combined sensations. I was a fully and firmly established cock lover. I didn’t want to be anything else. We finished ourselves off by jacking our loads into a single 3 inch wide pool of warm white cum that we shot onto one of the steps, and left it there. Our melded deposit of boy batter just waiting for the next person to discover. I often think back and wonder what that pool of cum looked like over time, and if anyone ever found it. That was hot.

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I dated this girl for the first time and over the evening we found out that we were both bi. When I took her home she hook me up with her gay brother. It was weird having sex with her brother while she watched and masturbated,
 
It had been a while since I sucked a guy off, so I posted an ad on craigslist for a blow & Go at the mall. A 25 year old guy with a 10 inch cock responded. He was going to be at the mall with his girlfriend, and would love to get sucked off.

We emailed back and forth, I had him meet me in the men's room of a store that has small rooms as stalls, not the typical dividing panels.

Since we had only exchanged descriptions, not pics, I told him to go to the handicapped stall, close the door, but not lock it, and have his cock out, and msg he was there.

I walked in the stall, I could tell he was nervous. I locked the stall door, took his cock from his hand and dropped to my knees. It took him a minute to relax and get fully hard, but in almost no time he shot his load in my mouth. I swallowed and left.

I thought I would have felt awkward or guilty after, but I didn't.
 
The day i had two big cocks at the same time in one in my ass the other down my throat they kept switching then i sucked both of them off till they filled my mouth up with their delicious loads of CUM.
 
Very sexy, lean, handsome young black guy came onto me in the steam room. He actually had lube and condoms tucked into a towel and wanted to fuck me. I told him it's too busy for that, too many guys coming in and out of the steam room. However, saw him a few months later, early on a weekend morning. No one was around. He sat next to me and we started fooling around. Again, he pulled out the condoms and lube. Well, it was quiet enough that morning. :sex:
 
That is so hot. Wish I could join you for a threesome. (I would get tested too to enjoy the full bareback experience.) :) [Meant this as reply to Zabien.]
 
meeting two strange men in glory hole and ended up going to the motel room and letting them both fuck methen i swallowed them both
 
A friend of mine want to have a 3some with her and her boyfriend. Almost from the when we started taking our clothes off her bf totally ignored her and focused completely on me.
It was flattering, but so obviously hurtful to my friend even during.
To me, very wild.
 
I met a stranger in a bathroom stall on campus and I sucked him off under the stall. We moved to a lecture hall for more room and he made me take everything off. I gave him a long slow blowjob. It was really thrilling but I don't think anyone saw us :( He exploded on my face then I spent good time swirling his cum all of my face with his cock. I ended up walking home glazed still :)
Ooh and it was recorded :)
 
In the cuddly cabin of a friends boat, they brought a guy to meet me, lots of alcohol later on a dare he fucked me in the cabin as my friend as his bf listened.
 
In back room of a men's clothing store with salesman. It was almost in the dressing room but need lube.
 
wildest hookup experience that I ever did is quick fuck in living room while there is mom beside the room (kitchen). Mommy so busy with her cooking that didn't realize her son was fucking with his buddy. hahaha
 
Two nights ago after work i was feeling so damn horny for some cock ,my mind was set on taking a big cock down my throat and or deep in my ass i went home to shower and shave im comepletly hairless .once i got to the porn shop i went straight to the back ,it's a big shop and the boothes are big with long benches soi i put $ in the machine n got ass naked i took out my lube and put some condoms on the bench then i unlocked the door.after about five mins a latino man walked in the first i asked him was do you have a big cock if not don't waste my time he asked is 7' inches big enough ,i didn't say a word i reached for his zipper pulled his pants down and his cock hung between his legs limped i moaned and said oh yeah just what i wanted i told him to get naked and lay down on the bench,then i got between his legs grabbed his cock n started to stroke it .
To be cont....
 
Last year at the start of my last semester of college, a couple buddies took me to a gay bar in the city. I had just broken up with my fiance and I was in a really bad place emotionally. While we were dancing I noticed my Criminal Law professor in the crowd. I had only first met the man that week, but I knew for sure it was him. We made awkward eye contact a few times and then slowly made our way to each other on the dance floor. We danced for about a half hour while he whispered funny comments in my ear. It was the first time I'd laughed in so long.

Eventually, Ben whispered to me, "Would it be inappropriate of me to ask if you wanna get the hell out of here with me?" I laughed. "Very," I responded. "Let's go." I told my buddies I'd meet up with them later and then found myself walking around the city with Ben. The cold January night air had my teeth chattering, but I was too distracted by Ben's chiseled jawline and manly laugh to really notice. At some point during the conversation I had started rambling on and on about how I could never be a city guy, when Ben grabbed me and pushed me into the alley against a brick building, hard. He put his hands on my face and pulled me in for one of the most romantic kisses I'd ever experienced. "The Holiday Inn is just down the block. We could get a room there. Please, let me love you." At this point, he had given my crotch a squeeze and kissed me hard again, and I couldn't have said no if somebody paid me.

Once we got into our room, it didn't take long for the clothes to come off. Ben started sucking me in a way I'd never been sucked. There was something violent yet gentle about his technique, and I was moaning louder than I ever had in my life. When I warned him I was close to cumming, he stopped and rolled me over, giving my ass a gentle smack. Then he pushed me apart and started rimming me from behind. I gasped - this was something foreign to me as my ex refused to do that while we were together. It was considered taboo for us. As Ben probed me with his tongue, I felt something in me come alive - waves of pleasure rocking my nervous system, and I couldn't believe this was happening with a professor.

Ben must've been able to read my mind, because just as I felt an orgasm starting to build, he pulled his tongue out of me and rolled me over on my back again. "I want to look in your eyes." I couldn't believe how romantic this was for a one-night stand. He reached down off the bed into his jeans pocket and produced a condom while I laughed inside my head about the fact that he brought condoms with him to the club. He slid one on and was soon inside me. I could tell he was trying to be gentle, but I had just had a rough break-up, and I needed somebody to take it out on me. Soon my hands were on his ass, driving him into me while attempting to pick up the pace. He caught on to what I was doing and really let me have it. I couldn't stop myself - an intense orgasm rocked my body as I shook on the bed underneath him.

Typically, I was used to my ex pulling out after my orgasm, so I expected the same with Ben. I was surprised, however, when Ben's thrusting didn't stop. It was uncomfortable for me at first, but soon I started to feel that familiar pleasure and before I knew it I was screaming out moans of ecstasy again. I had four orgasms like that before Ben allowed himself to have even one. He is twelve years older than me, but it sure as hell didn't show. After that night, the two of us started seeing each other casually but ended up breaking things off after graduation, agreeing to be friends. I haven't seen him since, but boy do I think about the incredible sex we'd have every time I need a visual to get myself going.
 
That is one hot story! Sadly, my professor offered no such extra curricular benefits!
 
That is one hot story! Sadly, my professor offered no such extra curricular benefits!

I was crazy about him! He was easily the best sex I've ever had - so far. I don't think a day went by where I'd see him and he didn't end up on top of me somehow, lol. The hottest part about all of it was when we'd make eye contact in the classroom and he'd try not to smile. I'd get so hard watching him up in the front of the room lecturing about Law while all I could think about is the hot sex we'd had just two hours before. It's a shame things didn't work out with that stud!
 
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.
 
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