Most unexpected sexual encounter

[lapdog2001]

i was 18 on holiday in croatia on a nudist beach

And ......

 

[witoutit]

I just remember one time meeting a distant friend's cute younger gf at the bar one night who was out with "the girls", and when I went outside for a break from the crowded noisy smokey clatter, she was right behind me. Sitting on a step out on the side of the building she nearly sat on my lap. Talking, she began rubbing my inner thigh, and before I knew it we were deep kissing. She left that bar with me later and before I'd gotten out of the parking lot she had my dick out and was sucking it! I drove outside of town to a secluded area and parked. I layed her across the front seat and fucked the hell out of that little honey before I dropped her off at home, and her bf was still up pacing the floor. They broke up shortly after that.

 

[wronskjan]

Some time ago I had date with girl from erotic dates website. She was short girls (about 150 cm height) with BBW body type and huge F Cup boobs. We were in the pub, talking, and się started to touching my cock throug the jeans (It was expected). Then she said something like "I need to see this fat cock" and sneak under table, unzip my jeans and suck me to end and swallow. That was unexpected. Leter we end at her place and done a lot of stuff. That nice I had my first anal experience.

 

[Fortheloveofmen18]

Some time ago I had date with girl from erotic dates website. She was short girls (about 150 cm height) with BBW body type and huge F Cup boobs. We were in the pub, talking, and się started to touching my cock throug the jeans (It was expected). Then she said something like "I need to see this fat cock" and sneak under table, unzip my jeans and suck me to end and swallow. That was unexpected. Leter we end at her place and done a lot of stuff. That nice I had my first anal experience.

Hot!

 

[9038421]

Revenge nightclub Brighton, wanked a guy off on corner and he cum all over my jeans. Took him home and fucked him.

 

[marty220]

This happened last year before covid. I was at my friends house for a birthday party. Tons of people were invited; her coworkers, friends outside of work, and old high school friends. I wasn’t out at the time or looking to hookup with anyone so I was just expecting to have a drunk night with all my close friends. One friend from high school who is a year older than me showed up. He’s out and I haven’t talked to him in years, probably since we graduated high school. Anyways around midnight he randomly came up to me and started flirting, touching my ass, holding my hand, whispering things into my ear. I didn’t know what to do and I just thought “he’s drunk so let me go along with it”. An hour or so passes by and the people he came with are starting to say goodbye. As they’re saying goodbye he comes up to me and tells me to go with him upstairs to the restroom. At this point the alcohol was speaking for me and it had been years since I had any action so of course I agreed and followed him up. We started making out with each other, like aggressive, drunk, tongue, touching, everything. In the middle he asks me if I want to suck his dick. Before he can even finish I’m squatting on the floor taking his dick into my mouth. He was huge and thick. Completely took me by surprise cause I would’ve never thought he was packing like that. It was unbelievably hot. I would go from sucking his dick to making out again and on a loop for about 10 mins. Last thing I remember was him stroking himself about to cum and I was so drunk I don’t remember if I swallowed or he didn’t finish. There was no mess in the restroom so I genuinely don’t know. I haven’t talked to him since but we have a lot of mutual friends so who knows if it will happen again. I wouldn’t mind sucking him again at all.

 

[Howu1ikeit]

Dance floor with people dancing around us

 

[ZuhayrKhan27]

My first year in College, I met an older man who was in his 40s and very hot. He had a huge collection of sexy underwear. Being my first year in College, I didn't have a car so he would pick me up. We lived 5 minute drive away from each other. Once in his apartment, he would turn on porn, and start sucking my cock, licking my balls, and rimming my ass while I played with his junk in his hot undies. Eventually the undies would come off and I would play with his cock. He would take my load in his mouth and then drive me back home. This continued for almost a year or two. Anyhow, one Friday afternoon, I was able to borrow my cousin's car to run some errands and decided to stop by his place to see if he was home and we can mess around. I knocked on the door and some other guy opened the door wearing nothing but white boxers. You can tell he was sleeping on the couch and had woken up to the knock on the door. He told me he was the nephew and his uncle was at work. He invited me inside so I took my chances and came inside. We sat talking for a bit and one thing led to another and we ended up messing around. It was hot. Like his uncle, he was smooth and had a nice thick cock with big balls.

We're you over 18?

 

[ZuhayrKhan27]

This happened last year before covid. I was at my friends house for a birthday party. Tons of people were invited; her coworkers, friends outside of work, and old high school friends. I wasn’t out at the time or looking to hookup with anyone so I was just expecting to have a drunk night with all my close friends. One friend from high school who is a year older than me showed up. He’s out and I haven’t talked to him in years, probably since we graduated high school. Anyways around midnight he randomly came up to me and started flirting, touching my ass, holding my hand, whispering things into my ear. I didn’t know what to do and I just thought “he’s drunk so let me go along with it”. An hour or so passes by and the people he came with are starting to say goodbye. As they’re saying goodbye he comes up to me and tells me to go with him upstairs to the restroom. At this point the alcohol was speaking for me and it had been years since I had any action so of course I agreed and followed him up. We started making out with each other, like aggressive, drunk, tongue, touching, everything. In the middle he asks me if I want to suck his dick. Before he can even finish I’m squatting on the floor taking his dick into my mouth. He was huge and thick. Completely took me by surprise cause I would’ve never thought he was packing like that. It was unbelievably hot. I would go from sucking his dick to making out again and on a loop for about 10 mins. Last thing I remember was him stroking himself about to cum and I was so drunk I don’t remember if I swallowed or he didn’t finish. There was no mess in the restroom so I genuinely don’t know. I haven’t talked to him since but we have a lot of mutual friends so who knows if it will happen again. I wouldn’t mind sucking him again at all.

Nice

 

[ZuhayrKhan27]

I was standing in line outside in the dark, waiting to get into a movie. I was with my gf and wearing a black muscle shirt and skintight black leather jeans. A young dude joined the line behind me and all of a sudden he pressed himself against the tight leather of my ass and his hand reached around and started stroking the bugle of my cock. I could feel him getting hard as he pressed against me. Cindy saw what was happening and started laughing, and the kid pulled away.
Later in the lobby I had a good look at him and saw he was a young dude who sometimes came into the sex shop where I worked.
He was in a tank shirt and wearing French stretch jeans that looked as though they'd been painted on. Cindy saw my interest and whispered "3 way?" in my ear. I didn't think so — there was something too obsessive about him, even though I was wondering what it would be like to fuck him. He followed me into the men's room and said I this was not a good time and told him I was only interested in dudes who were bi. I left him in the washroom looking at himself in the mirror while he adjusted his cock. That was the last time I saw him.

Nice

 

[ZuhayrKhan27]

This was super hot, and being from Los Angeles I know it's true because of the way you described that particular elevator in that particular hotel lol.

Haha great

 

[ZuhayrKhan27]

I played on my college tennis team. I remember that the team was invited to the home of one of the sponsors. She lived in a very big home in Winnetka, IL.

The team and I were in our whites. For each of us, there was a middle aged woman, who took an interest in us. The one lead me upstairs to show me the rest of the house. She led me into one of the rooms, and, closed the door.

Before knew what she was doing, my shirt was off and my shorts were around my ankles. i was still wearing my jockstrap, although she had that off quickly. I was instantly hard. We fucked for the longest time.

It's nice to read heterosexual encounters of men mostly interested in men. It's refreshing to read

 

[ZuhayrKhan27]

This past weekend I was invited to go on a motorcycle ride with three other guys. I new one of them, but had never met the other three. All four of us are bookish types and the motorcycles were a Moto Guzzi, a Triumph, a Laverda and a BMW. The ride took us on a circuitous route to a restaurant in a small country town, then to a spot by a nearby small lake. It was a great ride!

The ride to the restaurant was sedate and nice, through beautiful country that winds back and forth along a highway that ought to be called a laneway in spots. We stopped at the restaurant to eat and talk and found a good table close to the back of the restaurant that also had the benefit of a great view of the mountains. During lunch it became clear that the two men I didn't know were a couple. They were both articulate, nice guys who had been together as a couple for several years. The conversation throughout lunch was light and interesting, just as I like it, and, after the tipping the server, we all paid our own share and left.

The lake is close by and accessed after going up over a rather substantial hill, through a series of sharp bends and by entering an area managed by the state. We rode down close to the edge of the lake and we all dismounted and sat together by the lake shore. The talk was light as it had been in the restaurant and I did not think much about any of it. One of the men excused himself so he could use one of those forestry-maintained restrooms. The guy who invited me got up and followed, heading to the restroom. The man who was left looked at me and, out of the blue, half asked and half stated, "You know we're gay? Right?" I told him I had figured they were as they did nothing to hide it. He followed that with, "Did Mac say anything to you about our routine when we go for a ride together?" I repeated to him that I was told the ride would be a ride to a restaurant, down to the lake, and back over the mountain to town again. He asked, "Did he say anything about where we go after the ride?" I told him, honestly, that he didn't. He was quiet for a while, but finally said, "We usually go back to our place (referring to his and his partner's home) or Mac's and spend some time there." All I could come up with was, "Oh... Okay..."

About this time Mac and the other guy returned from their visit to the restroom. The guy I had waited with, Eric, asked Mac, "Did you say anything about what we do after a ride to [me]?" Mac responded, "No, I wasn't sure if I should... I was nervous about it..."

From there I learned that these three men ride together regularly and always finish the ride at one or the other of their homes and "play." Mac apologized and said he thought I might be bi or gay and had gotten shy about approaching me about it. I told him he was half right and said, "I'll let you off the hook... I'm bi..."

At Eric's house it did not take long for the four of us to be sitting around naked and talking. Four middle-aged guys together, butt naked and getting set to get up close and personal. The day ended at almost midnight on Saturday night. I was still hard from the little blue pill as was Mac. Eric and his partner wanted to go to bed and that left Mac and me to go our separate ways. Outside, standing by the motorcycles, Mac asked me if I wanted to go to his place and I told him I did. I followed him back to his place and we went right in and right to the bedroom, we had sex and slept until almost nine on Sunday morning. Mac got a call from Eric's partner, James, who asked if we had slept together to which he said yes we had. Mac invited James and Eric to come over for lunch and the day was spent with all four of us united in sex play.

The whole thing was totally unexpected, and I have seen Mac every day since then.

Wow a foursome orgy

 

[ZuhayrKhan27]

Enjoyed

Thumbs up

 

[ZuhayrKhan27]

I took a cruise in the South Pacific lots of years ago. I had gone on the cruise to meet females and have fun. I met plenty of females and got nowhere. It was frustrating. One night, after leaving a dance where I got precisely nowhere with anyone, I headed back to my cabin. I had a cabin to myself. The passageways on the ship were quite narrow and I was just about to unlock my cabin door when a guy walking towards me asked, "No luck for you either?" I was surprised at that and he explained that he had seen me sitting alone at the dance and saw me leave, he, apparently, had been sitting close by and was having the same issue as me. He would ask single women if they wanted to dance and was knocked back every time. Exactly the same issue I had.

So... When I left, he decided to leave as well, not with the intention of talking to me, but to go back to his cabin and go to bed. He went one way, I went the other, and it turned out we both had cabins off the same passage. His was a shared cabin, mine was a single occupancy cabin with a queen bed and a view of the ocean. We talked for a few minutes and I unlocked my cabin door when he said he was going to have to go to bed frustrated and sharing with three other guys he didn't know so unable to fix his frustration. I got what he meant and said I was glad I had a cabin to myself. The conversation went on and we talked about the women at the dance and seeing some of them leave with other guys. I ended up asking him if he wanted to come in so we would not be crowding the passageway. Numerous people had to get by us as we talked. One woman said "Take it into your cabin guys!"

The two of us went into my cabin and he surprised me by telling me he wasn't gay. I reminded him I hadn't asked and told him I was not gay either. I did not tell him I was bi for fear he would think I was trying to trap him. We sat in the chairs in the cabin and talked about home, jobs, and a thousand other things. Eventually he asked, "What do you think gay guys do? Do you think they just play with each other or something?" It was obvious he was curious about having sex with another guy and I told him what men do together. He asked, "Have you ever done it with another guy?" I told him I had. He asked if I had enjoyed it and I told him that I really liked it. He asked how I knew which guys would want to do it with other men, and I told him about places to meet, accidental meetings, and other ways men hook up. He asked if I had ever had another man's cock in my mouth and I told him I had. At this point he admitted he had always wondered about what it would be like, so I asked if he wanted to find out.

The next few minutes were really awkward. He sat there silently, then asked what we would do, how we would go about it. I told we would simply undress and go to bed and see what happened from there. He said, simply, "Okay..." and stood up. I could see his erection through his pants easily. I could also see that he was leaking a little pre-seminal fluid through his pants, so I knew whatever we did, it wouldn't take long.

We both undressed facing away from each other. I turned around in time to see his pants coming off and saw he was not wearing any underwear. His bottom was white and round and firm. I was half-erect and looking forward to seeing him turn around. When he did I was pleased to see he was around 8 inches in length and hard as stone. He stared at my groin like he had never seen another man's penis before. I went to the bed and pulled the covers back. He just stood there not moving. He only moved once I got on the bed. He slowly walked over to the bed and sat on the edge. I asked if he was okay and he said he was worried that he would cum too quickly. I told him it didn't matter and that I understood. He turned and lay down on the bed. He was rigid with nervousness, so I took the lead and started stroking his penis. I could tell he was likely to cum very fast, so went down on him, taking him into my mouth very slowly. I did not even get all the way down his shaft before he came.

After he came, things got very awkward. He had no idea what to do with himself and I let him off the hook by telling him he could leave if he was uncomfortable, that I would be okay if he did. He apologized for coming so quickly and I told him it was no big deal, so long as he felt better. A minute later he was gone out of the room.

That night I went to sleep after relieving my own little problem and worried about what could come of it.

The next morning I went to breakfast in the dining room and saw him there. He smiled and said hello as I walked past and I said hello back to him and went to my table to eat. At about eleven am I met him again on deck. He thanked me for putting him out of his misery the night before and said he had to wait for the other people in his room to leave before he could masturbate thinking about the night before. He asked if I had felt alright about it and I told him I thought he was wanting round #2. We ended up back in my cabin and - this time - having a long session with a lot of oral sex, a lot of body exploration, and finishing up better than either of us expected.

The cruise was a two week deal with a lot of island stops along the way. We had sex eight or nine times before the cruise ended and it turned out he like m/m sex as much as I do.

Was a great cruise with even better sex!

Hot story. The first session when he came in your mouth, did you swallow the milk?

 

[SpruceMoose]

One of my female friends told a male friend that I was bi, and he had also recently come out as bi. I had always thought he was hot so I was excited by the prospects. We messaged and sent some pictures for a bit, but he said that he couldn't hang out that day cause he had stuff to do.
A bit later on he messaged and said "hey actually do want to hang out today?". We ended up meeting at a trail close by to my house. At first we were just hiking but on the way to the spot I had planned, he stopped and said "I'm too excited, I gotta feel that monster" and he grabbed my dick through my shorts and started rubbing it.
We were both basically rock hard at this point but I said we're almost there.
Further down the trail there was a little Hidden Side trail that went to an overlook with a bench. We put down a blanket and then I pummelled that ass. For a surprise hookup it's still to this day is one of my best lays. Couldn't believe how much he came from getting fucked, it was like a fountain.

 

[MilfBanger78]

Hmmm i have a few

My niece's best friend. (Niece is only 4 yrs younger than me since my sis was from moms first marriage) Chick had a crush on me from a VERY young age, wont put a number on it in accordance with the rules lol. Anyways fast forward 10 yrs, she finds me on facebook and i wind up fucking the shit out of her on n off for yrs

A gym buddy that I had talked to about where to buy cheap protein powder etc. Exchanged emails. Chatting on yahoo. Started swapping porn links. He gets on cam one day and hes naked lol. and HUNG. Wound up doing a lotta 3somes with him.

Married co-owner of the pool store near me. Hot MILF in her 40s, was a slow day we wound up talking and flirting a bit. Slipped her my number didnt expect much to come of it. Texted me like 5 mins later, we were fucking the next day, turned out to be a total nympho. I still see her, even funnier her teen son works there now too lol

But probably my top one, was when i was like 21, had a lawn/hauling biz. Wound up doing a lawn right down the street. Older biker guy on disability and a wife in her 40s. She would flirt so bad. I played it off cuz the hubby was a cool guy. Finally one day she messaged me and pretty much told me they were swingers lol. So yeah the 3 of us wound up having fun on n off.

 

[Tight_End_SC]

Mine was in a casino with an employee on duty there (TRUE STORY)! This happened in the middle of the day so the place really was not as busy as maybe it would have been later on. The dude worked in one of the offices so he was dressed in nice pants with a shirt and tie. HOT ass on that fucker too by the way. It was his amazing bulge that captured my attention at first though... one of those 'HOLY FUCK' moments when you just have to check it out, but I really was not gawking. When our eyes locked we both just sorta smiled and I of course spoke and said hello. He wished me good luck on the machine I was playing then proceeded to pass by and continue on his way to where he was heading.

A few minutes later I noticed him again. He was near but not right next to me so I felt that it would be OK to focus on him a bit more, which I did. His bulge and that bubble butt, the beard, fuck... the amazing hot man was just too much for me not to notice. He came back over to area where I was playing slots and at that time I stopped playing the machine I was on and headed over to where he was. Yes, I realize they have cameras all over these places and I was not going to do anything stupid but I started to play a machine closer to where he was. He was chatting with some of the floor servers, I was playing the slot machine very close to them, and he kept looking at me. We were cruising each other for sure.

I will not drag the story out too much but the cat and mouse game continued for a while longer. I left and went to the 5 dollar slot area where even fewer people were and the next thing I know he is heading that way. His zipper is half way down but not in a way that would allow anybody to see his boxers. Now this really happened guys (2003 or maybe 2004). He comes up to me and just starts making small talk. I mention to him that his pants are not zipped up. His response to me was something like "I figured you may like that".

At this point in my life, I knew to not let the opportunity go so I knew to go for it. I asked him to follow me... I knew there was a handicap bathroom where you could go in and LOCK (twist deadbolt type of lock on the door) in the very private restroom. We went inside, I locked the door and the next thing you know his pants and my pants were down. Yea, I know this was very risky but again, I went for it. He leaned back against the sink and I proceeded to give this man the best head I could. I think he lasted less than 5 minutes before he fed me his hot load. He said for me to wait a few minutes in there, he gave me a kiss and a hug, washed up and left. It all just happened so fast that I was just reeling from the experience. I waited, then left and never saw that man again.

Looking back at this, I would never do something like that today. The risk is just too high.

 

[gohara]

I have had a few encounters with Uber drivers. One was an Uber eats delivery driver. He was picking up a Wawa sub for me. I messaged him and asked if he could grab me a couple of things inside the gas station that I couldn’t get on Uber eats. He agreed and delivered my food and other items. I text him after he left and said thank you again. He responded with “if you’re a top, you can really thank me” so I told him to come back up. I fucked this dude all over my living room, my balcony, my bedroom, the kitchen. Then had him leave and I went about my business.

 

[tippindascalez]

I have had a few encounters with Uber drivers. One was an Uber eats delivery driver. He was picking up a Wawa sub for me. I messaged him and asked if he could grab me a couple of things inside the gas station that I couldn’t get on Uber eats. He agreed and delivered my food and other items. I text him after he left and said thank you again. He responded with “if you’re a top, you can really thank me” so I told him to come back up. I fucked this dude all over my living room, my balcony, my bedroom, the kitchen. Then had him leave and I went about my business.

I would love to have a hot Uber driver...mine have not been hotties, that's for sure!