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Tell me about your wildest hookup experience

That has to be one of the wildest moments ever posted here. Phew!
 
Mine was actually in a spa sauna at the four seasons in London. There was an extremely good looking British man who kept staring at me but we never got very close. He was in the dry sauna and he was obviously playing with himself and staring at me. We were the only ones there at the time. I was in a hot tub and I made it obvious that I was watching him.

I went into the wet sauna and he soon walked in also. I was sitting back with my eyes closed and when I open them he was hard as a rock and he was playing with himself. I asked him if he needed some help and he just kind of stuttered. I explained to him that I had never done something like this before and had only been with two other men in my life and that was a long time ago.

He then asked me if I had a room at the hotel or if I wanted to come up to his room. I explained to him that I only had a few minutes and that my wife, yes a woman, was on the women’s side. And then I asked him again if he needed some help and he kind of covered up himself with his towel.

Again I told him I only had a few minutes and if he needed some help and he just stuttered again. But his cock was hard and he couldn’t or didn’t hide it.

Something came up for me and I got down on my knees, pulled his towel off of him and put his cock in my mouth. It is been along time since I had a cock in my mouth, actually years, and to be honest with you I sucked his cock just like I wanted my cock sucked. He was maybe 6 to 6 1/2 inches hard and not real thick and I was able to take all of him into my mouth and down my throat. God he tasted incredible and he felt even more incredible in my mouth. I slowly move my head up and down and he put his hands on my head and moved me on his cock almost fucking my mouth.

This went on for almost 2 minutes and he continued to push my head down so that my nose was buried and his pubes. Before I knew it he was on was pushing me away and told me he was about to cum. And I was not about to stop sucking him. He pushed my head down again and then tried to pull my head back up but I still had half of his cock in my mouth as he started cumming. And while I have almost no experience he obviously was a big cummer.

It was amazing feeling his cock twitching as he kept shooting into my mouth and when he stopped I pulled my head up and showed him his cum in my mouth and then I close my mouth and swallowed every drop. However, a little bit of his cum had dripped out and he took his fingers and scooped it up and told me to clean them. He was not a shy man now that he had been several minutes earlier. He actually seemed very dominant.

And when I got up he turned me around and pulled me over his lap and told me I was a very very bad boy and proceeded to start spanking me which really shocked me. Especially since we were in a hotels spa. And anyone could walk in at any time. After spanking me for over a minute he took two fingers and pushed them all the way in my ass and when me did I came immediately all over his leg.

He again told me that I was a very very bad boy and told me to get up and clean him up. And again I got down on my knees and licked up all of my cum. He then stood up wrapped his towel around him and walked out. I kind of kneeled there in disbelief that I had done what I had done and left the sauna and went to get dressed. He was finishing getting dressed and there were a few men there.

As he was leaving he said very loudly to me so that everyone could hear, thanks for the blowjob and swallowing. I must have turned 50 shades of red which match the color of my ass cheeks which was visible to everyone. My back was to him and as he left he gave my ass two very hard swats. And again everybody just looked at me and a couple of the man started laughing. God it was so humiliating it’s such a turn on.

I only wish I had been alone because I would have followed him to his room and let him do whatever the hell he wanted to do.
 
I was on a gay hookup site I was married to my ex wife at the time. Then I bumped into an ad for my eldest son's friend. I was about 46 he was about 28. I never replied. I didn’t want him to know I was bisexual. Well a few weeks later I answered a Craig’s list ad and this guy and I started chatting. We exchanged a few pics but no headshots. Then about a week later I’m back on the hookup site and my son's friend messaged me. He told me he placed the cl ad and knew it was me. We started chatting and eventually hooked up several times. It was a little strange since I knew him since he was 10. But we connected and it was some great sex. We talk from time to time. Our fling only lasted a summer. But, it was nice him telling me he always had a crush on me and thought about me when he masturbated as a teen. And yes the sex was good.
 
My wildest was actually a few months ago. My current friend (Sleep with other men) and I hooked up with a current partner he had. Sexy as hell and huge dick. However, that friend of his was busy and heading to another guys house he had just met. Well, he invited us. Anyway bla bla bla,.. after about an hour we started playing around. I was in a room with 3 other sexy men. My ass was getting really loose cause it knew what was going to happen. Two started sucking dicks, and another pulled off my pants. Instead of sucking my dick he turned me over and started licking my ass. He ate me out for a few minutes then I asked "What are you waiting for" (Or something like that) My friend told him to go we both fucked other guys. It went in pretty easy. My ass was ready. He was great. His dick was good size, but he knew how to do it. My ass start dripping it was so good. It was so good I said "Dont pull out" Huge load busted in me. My night wasn't over. Another guy came over pounded my ass and busted one. The third guy came over and his dick was f**king huge. Probably #2 on my ass's list. Then he busted (They were already hard). My friend came over and turned me on my back to fuck me like the bitch I am. He busted after about 2mins.

After we were done, I had got busted in 6 times by 3 guys.
 
I have a story! I was at my mom's apartments, watching my little sisters while she was at work. Well, my step-dad gets back to the apartments, so I'm free to leave at that point, but I decided to stick around and spend some more time with them. Me and my sisters get in the apartment pool and start horsing around. A few hours later, this black man (in his early 20's. I'm also in my early 20's) walks in and gets in the pool. He was very attractive. Tall, skinny, muscular, and hairy. He had some swim trunks and a tank top on.

Me and him get to chatting while my sisters play, and we don't even realize when they get out and go inside. Once we had the pool all to ourselves, he asked if I wanted to wrestle. I said yes.

I'm not particularly good at wrestling, but honestly, I just wanted him to touch me. And I could tell by the suggestive tone, he wanted a little more than just wrestling too.

So we waded out to the center of the pool, and went at it. At first, his advances were very subtle. Brushing against my crotch, or briefly grabbing my ass. But then they got obvious, and we both got hard.

When he would grab me, he would grind against me. Or he would shove my face into his armpit, or even hold me underwater against his crotch. Sometimes he would use his feet to rub my boner through my swimming trunks.

Eventually I hinted that I wanted to get out and go take care of things. We walked back to his apartment, and went into his bedroom. He proceeded to throw me down on the bed, and stripped his wet trunks and top. He was like 8" hard.

He climbed on top of me, and pulled my head against his balls, and told me to suck on them, which I did happily. He tasted great. And his musk was intoxicating, surpassing the chlorine. Then he had me suck him off, and made me deep throat him, and he came down my throat.

He pulled off my trunks and proceeded give me a footjob, which was a new experience for me. I hadn't cum in a while, so when I did, it was all over both of us. He had me lick us clean, and then he fucked me in the shower.

I left after that and we haven't seen each other since. But I expect that if we do, it's bound to be a fun time. My family also didn't question where I had been. Just worked out as a crazy kinky wrestling experience.
 
Definitely getting sucked off at 3am in my car by someone on Grindr I had never met before I screamed and couldn't stay still for 10 minutes as he worked me and thought I was gonna black out when I finally exploded as I had the most mind blowing orgasm ever shooting down his throat I was feeling dizzy and shaking as I struggled to drive home lol
 
It was with this guy working in a pharmacy. We were chatting for a week or two, agreeing to meet each other again (we already met before that). Suddenly, he went to the seaside for another week. A whole week I was so hard, couldn't sleep much, waiting for him to come back.

When he came back, we agreed to meet at the pharmacy when he was on shift. I went there, he took me back in the storage and undressed me fully. I felt very rutty. I immediatelly sank on my knees and took his penis in my mouth. I sucked it impatiently. I even deepthroated him quickly a few times, which I rarely do, as I gag a lot. He ejaculated in my mouth and I ate it.

He then went back to the front to check if there were any customers. When he came back, I sucked him more. He saw I wanted more of his cum and jerked his dick rapidly. When he was about to cum again, he told me to suck it. I ate him cum again. If I did not ejaculate as well, I suppose we could go on like this until he was drained.
 
I'm american, and once I was in a japanese gay bar, and sucked off 5 japanese twink boys in the bathroom stall (at different times)...and fucked one.(!) I was such a slut back then...
 
Not my wildest, but one of the most surprising times: thick dad bod straight guy showed up to fix my jacuzzi. He was probably mid 50's, shorter, thick strong build, big grey moustache. He gave off biker vibes. Really laid-back cool guy- as he worked we chatted a bit. It was obvious that my man and I are together...he started in with the comments, slowly at first. "you two married?" "Ah, that's cool, I dig it." "Yeah, I messed around with a guy back in college. had a good time with my buddy but hadn't done that sort of thing since then"

And on, as these things go...he kept working, we kept chatting.. he smoked pot and I said I've got a bowl packed, if you want"....he said that my house was his last stop and his girlfriend wasn't home tonight, so he had some time to kill. When he finished, we smoked a bit and kicked back. His hand was down on my crotch, my boyfriend’s hand was on his crotch...the three of us kissing....clothes getting torn off...moved to the bedroom.

The dude must've been holding a lot back, because I never saw a straight guy as hungry for dick as he was. He couldn't get his mouth on our dicks any faster. going back and forth, he looked like a kid in a candy story. Ended up getting him on all fours, my boyfriend's cock in his mouth and my face down on his ass, eating his butt out.

the minute my tongue touched his hole, he quivered and let out a moan. Very reactive to his ass being touched. I love that.

I started to really work his hole over; working the outside nerve endings, rubbing my goatee across it, and getting my tongue deep up in his ass while holding his ass cheeks open wide. He really loved sucking on a dick and getting that ass played with. damn, gives me a boner just remembering how much he was getting into it.

I was playing with his dick as I was eating his ass and he was reacting so loud and pushing back on to my face.

Now, I'm a pretty big guy, so I'm not going to go shoving my cock into some straight ass that hasn't had anything in it for years....and I can tell, there's been nothing in it - maybe a finger or two. But he was tight. There was no way I was going in there without a lot of work....so work is what I started out to do! ;)

He choked on my dick a bit.. sucked me as much as he could...then laid down on his back legs up in the air.

My boyfriend put his dick back in his mouth and fucked his face. I had eased my index finger into his ass and found his prostrate...His hole started to relax and open; his legs went even higher and his moans more frantic. I kept vibrating his hole and rubbing his prostrate, my boyfriend face fucking him as he was jerking himself off. He blew his load.

From the intensity of his orgasm, we all blew our loads. I felt his hole tighten up, his prostrate get hard and then he started blowing his load all over his hairy chest.

We all shot our loads over his chest. He fucking covered him in jizz.

He left with the biggest smile....he was all, "damn, that was better than I remember"
He called us a few month later. He came back over one more time, installed a light in the jacuzzi for free. :)

well, not exactly free....

I knew if I could work his hole over one more time, I would have him ready to get it fucked by my cock. He was really into his ass being played with and I knew he'd love a dick going in it. I knew I would be able to get him to take my dick on the next one, but he ended up texting us to say he was moving pretty far across the country to another state.

Damn. Hopefully that girlfriend is playing with his ass.

I always seem to have luck with straight guys. lol. Ate one guys ass out all night while he edged. Got another that loves to have an annual 'bonding weekend with the bros', where he gets to test the waters on things in a safe zone. Started out as a 'can I measure it?' to 'I wanna feel it in my ass' in about 5-7 years. lol. New he loves to get nailed by us. He loves having sensual intimate sex with smooth women, but once a year needs a sweaty testosterone animalistic fuck session with his hairy buddies. That was over years though, unlike the jacuzzi tech.
 
Back when craigslist was going good I posted ads quite a bit as a bottom looking for nsa sex. I had this one older white guy that was coming to my area answered and called my cell said he was on the way, and I talked him into my house. it was before noon and in don’t usually do anything during the day as a have neighbors and non sex friends that visit since I am retired and love company.

As he drove up I walked to his truck as we chatted. he was really horny, so I told him to come on inside the house. I had him undress as I got on my knees to get a good view of his cock. wow, it was so thick and close to 8 inches. it stood straight out as I rubbed my face all over it smelling it and getting his precum on me. he got weak so I had him lie down and I got my mouth on it and began sucking, kind of teasing as I could tell he was enjoying my sucking, I never touched it with my hand, just his balls. I couldn’t stand it any longer and asked," you want some pussy baby?" as he rolled over to undress I stood beside the bed and sat down to offer him my pussy.

I said, " Can you get to it like this baby?“ He got up to me and I lubed him up. he went in filling my pussy up, it was awesome. he got on the bottom and kept bumping , filling me up. his gigantic cock was awesome, felt so good even though I never got hard. I started playing with his nips as he had asked. he kept begging me to let him cum in me, but I had said in the beginning I wanted him to pull out so I could suck him off. as he pulled it out and started stroking I got on my knees and opened my mouth, his cum shot was awesome. then I cleaned him up with my tongue. as it was a nsa fuck he walked to the sink to clean up. I stood in the door and could not keep my eyes off his beautiful cock, he may have been on the blue pill as he stayed firm and thick almost straight out. well, he had pet allergy I didn’t know about, and he said he could not come back, dang. I loved it! I masturbate thinking about his cock often. Mmm
 
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Back when craigslist was going good I posted ads quite a bit as a bottom looking for nsa sex. I had this one older white guy that was coming to my area answered and called my cell said he was on the way, and I talked him into my house. it was before noon and in don’t usually do anything during the day as a have neighbors and non sex friends that visit since I am retired and love company.

As he drove up I walked to his truck as we chatted. he was really horny, so I told him to come on inside the house. I had him undress as I got on my knees to get a good view of his cock. wow, it was so thick and close to 8 inches. it stood straight out as I rubbed my face all over it smelling it and getting his precum on me. he got weak so I had him lie down and I got my mouth on it and began sucking, kind of teasing as I could tell he was enjoying my sucking, I never touched it with my hand, just his balls. I couldn’t stand it any longer and asked," you want some pussy baby?" as he rolled over to undress I stood beside the bed and sat down to offer him my pussy.

I said, " Can you get to it like this baby?“ He got up to me and I lubed him up. he went in filling my pussy up, it was awesome. he got on the bottom and kept bumping , filling me up. his gigantic cock was awesome, felt so good even though I never got hard. I started playing with his nips as he had asked. he kept begging me to let him cum in me, but I had said in the beginning I wanted him to pull out so I could suck him off. as he pulled it out and started stroking I got on my knees and opened my mouth, his cum shot was awesome. then I cleaned him up with my tongue. as it was a nsa fuck he walked to the sink to clean up. I stood in the door and could not keep my eyes off his beautiful cock, he may have been on the blue pill as he stayed firm and thick almost straight out. well, he had pet allergy I didn’t know about, and he said he could not come back, dang. I loved it! I masturbate thinking about his cock often. Mmm

MMMMm, made me soooo damn horny reading it.*|*
 
when i was in my early 20’s i started to discover my attraction to older men.

I found a guy on grindr who was much older than me, grey and white hair, hairy chest, small beer belly and a short white beard. He sent me pictures of his leather sling and said he was into younger twinky guys like me. I told him i’d love to be put in the sling!

I went to his house, when i arrived i stripped down to my leather harness and leather zip up jock. Put on my collar and leather boots.

He led me to his sex room where he had a massage table and a sling. He put me in the sling, with my head hanging off the back. He came around behind me and i started sucking him like my life depended on it. He was grunting and groaning and fucking my face.
He then took his cock out of my mouth and had me suck and lick his hairy balls, then stuck his cock back down my throat and facefucked me until he blew his big warm load down my throat!

When i was done draining his cum, he came back around in front of me, lubed up my cock and stroked me until i shot my cum all over myself!
Afterwards he helped me out of the sling, helped undress me and then we had a shower together to clean up and chatted and got to know each other.

He kissed me goodbye and i left.

We repeated this a few times over the next year or so before we lost touch. I’d love to do it again!

You can see pictures in my show yourself off thread of me in his sling!
 
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New York, New Year’s Eve, my regular boy pussy was with his family out in CT, I had been to a party at a club on the West side, walking home through the area just north of Times Sq I found myself walking by this cute couple, after a few blocks we talked, they were from Ireland on Holiday, they were looking for a place to get some food, it’s like 1:30 in the morning. They are young and super cute fit lads!

I tell them about a 24 hour pizza place near my apartment, they are pretty drunk so I tell them to follow me. We all get pizza, I say my apartment is a few blocks away, do they want to go there, I have drinks to wash down the pizza. So we all go to my apartment, before anyone has 2 sips of their drink we are all making out and stripping.

We all climb into my bed, the guy who is the bottom in their relationship says the only rule is I’m not allowed to fuck is boyfriend who is the top; this rule will be broken!

We do everything you can imagine, multiple times, we kissed, rimmed, fucked and sucked until our dicks, lips and boy holes were raw. Yes, after going deep with my tongue, I topped the top and he loved it!

At about 6am, they say shit, we gotta get back to our hotel and get ready for a flight back to Ireland and off they went.

After sleeping several hours I woke up and found my Dick felt like a cab had run over it, it was raw from so much action and needing a little time off in the new year to heal! Definitely one of the hottest sessions of my life.
 
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