Most unexpected sexual encounter

[Essexboy8714]

Hey all,

Something I've always thought about myself, what's your most unexpected sexual encounter you've had, e.g (with someone you never expected it to happen with but it did?)

For example mine is with an old school friends sister...

We saw eachother now and then over the years as I was friends with her brother,always though she was hot but that was it,one night we bumped into eachother on a night out in a bar,got talking,ended up kissing and swapping numbers,over a few days we spoke more,and ended up meeting up and ended up in bed together,this went on for a good year on and off,

What's yours?

 

[Goose_Eggs]

I was 24 in grad school, would have been late 80s. I was working the summer for a guy who owned a landscape company, who happened to be a horn-dog of a fuckbuddy. Because I spoke a bit of Spanish and he was short of help, he asked me to manage a small crew on a 3-4 day job. By the fourth day I was down to just two guys, one of whom was about 45 and spoke good English (Tony), the other about 35 and not so much English (Manny), both really nice but the one with broken English was very appreciative of the job as he'd been having problems and wanted to move back to Texas. Tony was very average middle age and thick in the middle, Manny was much better shape, had done more physical labor and stripped to the waist everyday to work. By the last day at lunch we'd gotten pretty chummy, I knew all about their families, where they were from, personal lives, girlfriends, wives and ex-wives, etc.

At the end of the day, I offered to buy them a beer for their hard work all week. They didn't want to go to a bar but let me buy them a 12-pack. I offered to drop them at their place, a long-term motel where they were living, they invited me to have a cerveza as thanks for the ride. We were probably on #3, sitting on plastic chairs in the parking lot when the Manny (the Spanish speaking guy) has the other one ask me in English if I knew that Rob (the owner) was gay. Rob was pretty openly gay, but not wanting to appear too knowledgeable on the matter I said I "thought me might be". Tony (the English speaking guy), said "oh yea, he has grande pinga" and they both laughed. Clearly I knew, as we had been off/on fuckbuddies for about a year, but I just stayed neutral. So then Manny asks Tony to ask me in English if I like guys or girls, as he looks at me with a very kind expression and says "its ok, no problem", sort of like it was ok for me to tell them. I just grinned a bit, and said I hadn't had a girlfriend for a couple years, I take whatever I can get. We all laughed, Manny says "panocha, culo, verga, todo Bueno, you like all -- that's good my friend". and laughs again.

Well by now I'm getting toasted and should be outta there, but being 24 I have no good sense. The guys are getting pretty loaded also, Tony whining about his wife in Mexico that the sends money to, Manny carrying on about how much he appreciated me giving him a chance this week, he really needed the money. Then Manny gets kinda serious talking to Tony, sort of pushing him to just translate and tell/ask me something. Now Tony speaks a bit of broken English, and it wasn't that hard for me to communicate with him, but he told me early on he was more confident that he would be accurate if Tony translated. So Tony gets a bit sheepish, says, "Manny is very grateful you letting him work and be good friend, if today you feel like the dick you can, uh, uh, his." as he sort of does a Michael Jackson crotch grab so I get the picture. I look over and Tony has a very serious look on his face, nodding yes. I'm a little shocked, and I guess it showed because Manny starts talking very fast to Tony, who translates, "he says its ok, he has a gay brother and his friends have sucked it, he has a very big dick and guys like it, even it in the ass if you want." I said, "your ex-wife...….?" , and Tony says "its ok, don't worry". I'm still trying to soak this all in and not look so shocked I scare them off, Manny gets up while nodding yes, kind of wide-eyed, and steps inside his motel room about 6 feet and opens his pants to show me how big his cock is, maybe thinking I don't believe it. Well I'd been watching their crotches for several days (cuz its what I do), and I'd never have guessed there was that much in there, it was definitely large and he just stood there rubbing his fingers through his thick black bush. I was rubbing my cock thru my pants as Tony walked up behind me, almost like he knew what I was thinking, says "go have a quick rinse if you want" pointing to the bathroom. I gave my ass and crotch a quick scrub and as I came out of the bathroom the door opened to the parking lot and in walks Manny in nothing but a towel, he had showered next door in Tony's room. Tony never came back or participated but we did have about an hour of really hot sex. He never kissed or sucked my cock, but he jacked me like a big dog, chewed and played with my nipples while I sucked his cock, he eventually grabbed a hold of my asscheek and says "yes?". I instinctively turned around as he rolled a condom on and handed me a jar of Albolene (clearly he was prepared to do this), so I could lube my ass. Turned out he wanted me to lube his cock and guide it in while he just stood here, it wasn't fitting real well, so he laid on the bed and pointed for me to sit on it. After another try or two, he jumped up and went thru a pile of laundry and pulled out what looked like (and smelled like) an old bottle of poppers. Well that was enough to do the trick, it was in and he started pumping, I was running my hands through his chest hair and I guess he could tell I liked it because he says "you cum?" as he points to his furry tits. I was young and didn't have the control I do now, I shot all over his chest in a few minutes, he jacked more on my cock and rubbed the goo into his matted hair. I've always had a taste for hairy guys, and this one made me so hot I never lost my boner after cumming, lol. As he was still fiddling with and pulling on my cock he says "mmmm, duro…….mas?" I thought, I don't be able to walk tomorrow, but what the hell, and as I reached back realized he'd gone to 1/2 hard. So I get off him, pull the rubber off and get ready to suck it some more, when he flips over to all 4s offering me his totally hairy ass. I'm not usually much of an ass eater, but this was so hot and hairy and I thought he might like it, but he made clear that was what we were fucking, no ass eating. I got rubbered up and he put a glob of Albolene on my cock and said something in Spanish that I didn't get. He reach back and held my cock in a death grip and said "slow!". I was in much better control having cum once already, I fucked him long and slow, then faster and rougher, for close to 30 minutes. He never got fully hard again, but jacked himself a little and I stroked him while I pumped away trying to figure out what would make it good for him. He seemed to like it best on all 4s, which was hot for me because I could look at his very hairy asscheeks and it was while pumping away and reaching down and feeling his 1/2 hard big dangling all heavy that I came a second time.

Guess this thread didn’t really call for so much detail, but it was not only “unexpected” but very memorable for me as it is still wank fodder 25+ years later, lol. Also this experience really set my taste for spontaneous stroking with another horney dude.

 

[Oztrich]

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!

 

[MisterB]

I was 20, in my first apartment with two other gay roomies. The complex had 300 or so 2- and 3-level garden apartments, sprawled over several acres, and was already about 15 years old when we moved in. Things were starting to need repair/replacement. Like our apartment's central A/C.

Each of us had telephoned the office to get the A/C repaired over a few weeks; each repair would get it going for a few days and then crap out again. Clearly time for a new unit. Nope. They can fix it they say. So...the roomies, without me knowing, hatched a plot.

The office was open on Saturday. The sent me over in person rather than let me telephone them. It was really hot. I had on a pair of short shorts (they were the style then!) and a t-shirt. I approached the counter, and saw the complex owner was there that day. 35ish, blonde surfer dudish, married, kids. Pictures of them on the office wall.

I was surprised he decided to help me himself. I told him about the A/C problem and the several failed repair attempts. He said he'd need to take a look himself before a new unit could be authorized, which was unlikely. He had me hop into his bright yellow Corvette and we motored over to my building. Normal make talk kinda conversation.

When we walked through my front door, he said, wow, you are right, it's really hot in here. He said he needed to check all the rooms; I assured him it was the same temperature throughout. He insisted. We walked the apartment; last room we checked was the master BR, which was mine at that time.

That's when the questions start. How soon did I want the A/C fixed? I replied something like I think it needs to be replaced, because your maintenance guys can't seem to get a lasting fix. He said he can have a new unit installed Monday. Wow, I remember thinking to myself. This has worked out well.

Next question. You got any porn magazines? Say what? So I tell him I do and does he want to borrow some? No, let me look at them now he says. Finally my "lightbulb" starts to go on. So I tell him that I do but they are guys with guys. No problem he says. Next thing I know he's on my bed, magazines spread out in front of him, he's got his dick in his hand (still wearing his clothes) and says to me "Get naked if you want your A/C installed Monday".

My new A/C was installed Monday morning. We never had another problem with any maintenance issues while we lived there. Totally most unexpected sexual encounter. Boy, I was so naive...

 

[Jarizzi]

I was living with a female roommate, an ex-gf actually. One of her male friends went to the Catholic high school in our town. He would stop by our apartment every so often to say hi to her. He was crazy hot but I just assumed he was straight as an arrow. I had so many fantasies involving him, though.

One day I was home alone drinking and he stopped by looking for her. I told him she wasn’t around but he saw that I was half-drunk, I offered him a beer and he said he’d just stick around and hang until she got back. We were watching a movie and he started talking about this picture I had hanging on my wall, a pic of two guys making out. He asked if I was bi and I admitted that I was. Then he blew me out of the water by confessing that he was bi too! I still kept my cool though because I was a few years older than him. Didn’t think he’d have any interest in me.

Somehow he saw my stash of porn movies in my room and convinced me to put one on. It was a straight porn and I figured he was just a repressed Catholic dude who didn’t have access to porno. While we were watching it, he asked me if I thought the guy in the porno had a big dick. I said ‘hell yeah it’s pretty big.’ Then he suddenly whipped out his erect cock and asked me if I thought that HE had a big one. I was shocked at his brazenness and told him his dick was big (and it WAS HUGE btw).

Then he just asked me point blank ‘Do you wanna suck it?’ I couldn’t believe this was happening, that he was just coming on to me like this. Of course I didn’t hesitate to jump up on the bed with him and suck his amazing cock. He sucked me a little too. I ended up blowing him until he shot a huge load (which didn’t take long). After that night, he would stop by to see me and I’d suck him off every time. He seemed really nervous about our experiences together but he always initiated everything. Sometimes he’d blow me too but overall our sexual encounters were about me getting him off orally.

That started a sexual relationship that was on and off for many years. We eventually had full sex and did just about everything together. Looking back, I can’t believe it all happened. He was just this straight stud who I would have never thought would be into guys at all.

 

[auncut10in]

Our printer had run out of ink, so I told my partner I would pick some up at Office Depot on my morning bike ride. I went into the store, found the ink and went straight to the check out. It had a small line, but nothing too bad. There was a couple in front of me that I figured out were probably gay. There I was standing behind them in my red biking shorts. One of them glances down and does a double take. He looks up and I just smile. Then he turns back around and with his hands behind him backs slowly into me until he was close enough to give my dick a big squeeze. So random, and totally unexpected encounter. And this is with other people behind me.

While they are paying for their purchase, the guy asks where the restrooms are. The clerk points them out, he turns to me and smiles. Yeah I got the message. I pay for my ink and for some reason have to use the bathroom as well. I walk in, and as soon as they see who it is, they both reach out and start rubbing my dick. Of course I get instantly hard. For the next few minutes they take turns sucking me off until I shoot my load in one of their mouths. I stuff my softening dick back in my biking shorts and continue on my ride.

Office Depot? Wasn't expecting that.

 

[xguy311]

One time I was on the subway coming home in New York. I looked across the way and this beefy Puerto Rican guy...nice thick frame, but defined, great arms in a tank top and shorter shorts was sitting there. He was so hot. I looked over and we briefly made eye contact and then I looked back across the way. We did this a few more times. As my stop was coming we finally made direct, full on eye contact and he opened his eyes WIDE in an expression of "you're into me?!?" Which was funny coz he was in better shape than I was!

I went to get off at my stop and he got out too! As we went down the stairs he very obviously looked back at me several times. He went to the right at the stairs to exit and my apartment was to the left. I went to the left and down the stairs and then thought "oh man I gotta see if he's interested." I made my way back to the street that would be near the exit he took. As I turned the corner there he was waiting. I went over and said "hi" and he said "I only live a few blocks from here." I told him I was game.


We walked to his apartment as I slipped off my wedding ring quietly in my pocket. I was married, though we were open, but I didn't want that to stop him from playing. We got to his place and he had this cute big friendly dog waiting. He told her to calm down and took me into his bedroom. We immediately stripped and he sucked my cock good. Great full lips and he took it all like a champ. I was dived into his thick full latin ass. It was delicious. Then to my delight he wound up turning around on all fours and grabbed a bottle of lube. I started pumping away. He was very vocal and so I joined him in the moaning and grunting and slapping his ass with my balls and my hand. Finally I couldn't take it anymore and released a hot huge load deep in his hole.

We got dressed and as I put on my pants my ring fell out. He looked at it and said "oh I hope that's not yours" with a wink. I just smirked. We opened the door to his room and to my shock as we did so this lean, cute, somewhat hairy guy walked out of the room across the hall from his. "Oh this is my room mate" he introduced me. After my shock I just thought "damn why didn't we include him"...he had to have heard us fucking as we made TONS of noise. It was great. We had a few repeat plays after as he walked me down with his dog and gave me his number. Good times! And totally unexpected.

 

[RowanB]

Someone I used to work with. Straight & married but even so still hooked up with a few of the girls at the office. Hot guy, very muscular.

Anyway, we went to another city to visit a client and took the train back to London together at the end of the day. When we got to London he wanted to go for a drink, so we did and then had quite a few.... I was always hot for him, but he's straight so I would never make a move.

To my surprise, he turned the conversation to dick & asked me if I shave. Said that I like it clean and he said that he keeps himself clean too. Few minutes later he "wanted to show me"and get my opinion..... Lol. We hooked up that night and now, a year later, we're still hooking up regularly.

 

[long_uncut]

It wasn't anything so unusual I suppose, but I didn't expect it to happen when it did or the way it did. I had chatted for quite a long period of time with a guy and thought he was someone I would like to get to know better. We arranged to meet for breakfast at a local fast food place for a face to face visit. We talked an hour or so about various things and about our sexual interests. I am a heavy precummer and when we got up to leave the restaurant my shorts were wet and as we were standing beside our cars I felt comfortable mentioning to him, "Look what you have caused." By then I also had a raging hard-on. He took one look and suggested we go to his shop. We did and he sucked me off there. That was three years ago and we continue to be good friends, sharing an intimate relationship as well as other friend activities.

 

[indyfrat79]

Last year I stayed at an all inclusive hotel in Playa del Carmen. I went to the restroom by the pool one day and was taking a leak at the urinal. One of the maintenance guys also came into the restroom and stood at the urinal next to me. He was early 30s, nice stubble, appeared to be hairy, nice soccer build. We made eye contact briefly and I could tell that he was staring at me. I looked over and saw his big uncut dick, looked at him, and smiled as well. He told me to follow him. I said ok and did. He quietly snuck me into the maintenance room on the back side of the pool restrooms. He immediately began feeling me up. He wasn't into kissing and pointed at his wedding ring. I smiled and went along with it. I could feel his growing cock and got on my knees. He began fucking my face and came within 3-4 minutes. It was a huge load for me to swallow. He wouldn't suck my dick but told me to spit on his hand so he could use some of his cum to jerk me off. I too came quickly and shot my load on the floor. He pointed me to the door and I took my seat back near the pool with hubby, telling him only that I had to run up to the room for a minute. I didn't see my friend again but wondered how many guests have had that beautiful uncut dick in their mouth.

 

[CockMySuck]

I have a story that's happening in real-time.

I have a friend (we'll call him Josh) I've known for the last 5+ years. Josh and I met as coworkers shortly after college and have been friends since. While there was always some flirtation between us, he has been a serial dater of women and I've assumed straight. He's been in relationships (again, with women) most of the time I've known him, including up until recently.

I mentioned flirtation. The whole time we were friends, Josh has made flirty comments. About me being cute, or sexy, or having a nice butt... other joking sexual comments that I'd just brush off, because I've known straight guys to do that kind of playing, joking, fishing for compliments, etc. I don't ever make much of it... Well, Josh didn't ever come onto me but, little did he know, I was always open to hooking up with him; maybe he picked up on it a little, but I don't think he really knew. A few years into our friendship, just because of some of his flaky behavior, our friendship dwindled and, even when it picked back up, I had him at arm's length knowing he might flake out again – not responding to texts, cancelling plans, etc.

Right before the pandemic, Josh and I saw each other in-person at an event and caught up briefly. After that, it wasn't really until later in the year that we began texting each other. He texted me "Miss you" and things picked up. We met up at a park one day with other friends, and it was pretty uneventful. After the fact, the flirty messages between my friend and I started.

The texting was playful, but I was so hard each time. It started with him mentioning that, next time we hang out, it would just be the two of us, and that sparked my interest. Then, we were talking about his kind of sexy quarantine beard and whether I liked it or not; I joking offered to get beard oil (which he hadn't heard of) and help massage it, which I know made an eyebrow raise for him. So simple but, after that, every time he flirted with me, it turned me on and it was happening over text. One late night in particular, he texted me something innocent and it escalated into a joking conversation about us cuddling. He made a joke about him being hard with a winky face... The next day, he texted to apologize for being so forward. I told him that that was tame and I would take whatever I could get.

Shortly after that, one day I texted him after seeing he received the vaccine, which I'd also just received. I texted him that I was excited for him, and he texted me back (again, seemingly jokingly) that he couldn't wait for a time when we could safely make out. I responded with something direct about being open to making out with him, and left it in his court to read that as a joke or an invitation. A week later, one late weekend night we were each in bed texting, and the texts with Josh, my former coworker and former best friend who I believed was straight, turned very sexual. I think I made some joke about helping him learn to swallow (he mentioned spilling his drink) and that led him to wonder about when I'd teach him how.

Ultimately, Josh told me that he was hard, and then that he's wanted to suck my dick for a while – which blew my mind! It would be one thing if he just wanted me to suck his dick, He told me about how, when we saw each other at the park mid-pandemic, that he was thinking of cancelling other plans to invite me over to his place to try to hook up. I suggested we snapchat because we were both alone, hard in bed. Shortly after, we began trading really hot dick pics and cum shot/jerk off videos. It was amazing the first time I saw his dick because, honestly, I'd wanted to see it for most of the time we'd known each other – especially with what a stud he was with women, seeing one or more at a time. It's wild to now have that closure and to know that we're going to meet up soon, where I'm going to blow him, he's going to blow me, and maybe we'll do more, He was saying he regrets not doing all of this together sooner.

It's only been a short while so we're planning to meet up soon. I'm sure I'll keep you all updated, but just wanted to share this mostly unexpected thing that's only now come up with a long-time friend.

 

[slimgurl]

Gas station eye contact ... true story from about 6 years ago. I was getting gas at a station not too far from my place. After putting the nozzle in my car, I notice a young guy totally checking me out at another pump. I smile, of course. He was no doubt attractive. He smiles and does not look away. He filled his tank before I did and then walks over. BOLD! Which I appreciate. He was just shy of 6-0 tall, white but with olive tone, dark hair, lean body. Had on sexy jeans and a black t-shirt. His eyes check me out, but not in a perverted way. It was classy and sexy at the same time. I was just out for some errands and only had not short jean cut-offs and a white halter top, no bra. Nips were visible. There was immediate magnetism, and to be honest, it had been quite a while since I'd done anything w a guy. We did some small talk. It became obvious we were both open to more. He asked for my number, and I have it to him. Literally an hour later, which I had spent wondering if I should have been more assertive, he calls me. "You wanna hang out." I can't believe I did it, but gave him address. He was over in 15 minutes, and I had his cock in my mouth within five minutes of him being in the door. He was not crazy long but had impressive girth that challenged my mouth. He was a good fuck, great energy, and I found out he was 21. Yikes! We met a few times after that for sex before going our separate ways. So, when you get gas, look around and see

 

[Maksim]

This was two years agoa before I met my boyfriend.

I do LARP (Live Action Role Play), where you dress up in fantasy costumes and go into the wilderness to act out crazy stories and battle with foam weapons. It's very nerdy and incredibly fun.

My character is a fire wizard. It was sunset and he was in the woods searching for magic artefacts. During my search I caught sight of another group of players from an opposing faction. Now we all immerse ourselves in this game pretty seriously so we are not really thinking about sex all that much while we're there. And we weren't this time either.

Anyway, I am captured and tied up. While this large group of about fifteen people wander off to hunt down more people, three soldiers are left behind to guard me and another prisoner. For men and one woman.

Our characters start talking pretty bitterly to each other and I convince one of my captors to untie me and challenge me to a fist fight. So I get untied and we mock a fight.

The thing is, it turns into a wrestling match on the ground, and it's not sexy at all. It's clumsy because I'm in a cloak and he's covered in green body paint which is starting to come off. We both tire and start pinning each other to the ground. I don't know when it happened, but I realised soon enough that I was rock hard and my fuck was digging into his side, but I just ignore it and we continue roleplaying. A minute later, and I feel his hard cock pressing into me too. And fuck it's huge, like at least 8 inches.

I don't think the other three have caught on to our arousal at this point. And we haven't broken character. In fact I think it was the fact that we were in character that we could be so bold. Anyway, the violence subsides a little, and we are now half wrestling half grinding in the middle of the woods. I think at this point two of the onlookers figure out that we are getting excited and find a discreet reason to leave. The third, another guy, just stays. Nobody breaks character.

Clothes are start to come off and we are now both shirtless, and I can kinda see where this is going, except I don't want to have sex with a guy in front of another guy, in a public space. But this is where it gets really surprising for me. The third guy intervenes in our fight to break it up.

He's the guy who I peel the clothes off. Lean body with a hint of a six pack, and a decent cock but not nearly as big as the other.

We are all really confused at this point. We are in character and nobody wants to break it because it's a nice mask to hide behind in terms of accountability. I'm the first to nove and I put the third guy's dock in my mouth while the guy I originally fought with is jerking off.

Luckily enough its twilight and densely wooded, so as long as we're quiet, we shouldn't get caught. The encounter is oral between us all. Small with no advance warning and no lube and no condoms is a no go. But lasts a good 20 minutes I'd say. There's no kissing... It didn't feel tender enough an occasion. I still remember cumming on the second guy's enormous cock. He was jerking off while I came on top of him so I shot onto his forearm as well.

What weirds me out most is that our characters just resumed their business right afterwards. We are all three still friends but we don't have any sexual tension when we hang out. It kinda fizzled out as quickly as it came.

 

[hotbtminla]

This was a couple years ago but I still remember it pretty vividly, in large part because it was so unexpected. A close friend of mine was dating this girl who is a painter and lives in the Arts District in downtown LA, specifically in a sort of commune type set-up - loft apartments that also serve as workspace and gallery space for artists in what used to be industrial buildings. This particular one is like 3 buildings with a large shared common courtyard (more like a court-park, it was big) and everybody knows each other and they're all artists (i.e. 1/3 truly talented artists, 1/3 weirdos, 1/3 insufferable posers lol). You get the drill.

Her birthday coincided with a big community art showing so there was this big ass party. My friend asked me a 2 other friends to go, and even though it's not my scene I was like fuck it, it's something different and at the very least I'd get some comedic stories out of it.

While I am quite proudly and confidently what one would call "easy" I had zero expectations I'd get laid that night. I wasn't going to the party to find someone to hook up with, I was hanging out with my friends and I'm not really one to vanish or bail on people simply because someone wags their cock at me.

I know I looked good that night. Specifically recall that a couple days before I got the single best haircut of my life (every hair on my head is in a different cowlick so I remember a good haircut like other guys remember baseball stats). I was in a black t-shirt and had been working out a lot, had great shoes on - I looked good and was feeling confident, but again, hooking up was furthest from my mind. I wasn't trying to be sexy or charming (I'm told I tend to be both in general, but the point is I wasn't being flirty with anybody).

The party was fun but just as weird and oddly cold as I expected, but still it was fun to be able to talk to people who have wildly different day to day lives from me. Not long after we got there I was sipping a drink, surveying the huge loft and the crowd, and I saw this guy who was, quite frankly, one of the sexiest guys I've ever seen in my life. He was about my age (early to mid 30s at the time), shorter than me (I'm 6'1) thin but more in a wiry way than skinny. Mediterranean or Hispanic complexion, longish curly/wavy hair, and handsome in an offbeat kind of way. What drew my attention initially was that he laughed at something really loud and he had one of those charming, full bodied laughs. When I saw him I was immediately transfixed - he had that casual ease about him that was super sexy (in retrospect BDE but that wasn't a thing yet). His shirt was unbuttoned just enough to show he's got chest hair, and the way he moved, even when standing still, just screamed sex.

Then he glanced over in my direction and we made eye contact. I realized I was openly staring at him and got kind of bashful. He smiled at me and then went back to talking to his friends.

This routine went on for the next 90 minutes or so. I'd be somewhere talking to people, or getting a drink, or out in the courtyard, I'd look around nonchalantly and BAM we'd make eye contact from a distance, he'd smile at me, and then we'd go back to talking to whoever. The flirting was fun, but I didn't even know if he was gay, bi, or just a horny dude (or potentially a dude who enjoys winding guys up). And also I was. Not. There. To hook. Up. Plus I was a bit intimidated by him. I mean, I felt good about myself that night but was so bowled over by how completely hot he was that I was like "yeah no that isn't happening."

I can't recall how I wound up in the hallway of the loft - I know wasn't leaving yet, but was probably looking to take a leak (this was like one giant party across several lofts so numerous bathrooms were being shared). But I'm walking down the hallway of this industrial building and I hear "hey! hey bud!"

I turn around there is Hottie McHotterson trotting down the hall. He was like "you're not leaving are you?" and I was like "well soon but was just getting some air" and he was like "good because you weren't going to leave until I got to meet you." We introduced each other (I will call him Tony here) and he put his arm around me and said he would get some air with me. I recall being slightly dazed while this was happening.

Tony wasted zero time. In fact he kind of took it from 0 to 60 like an Italian sports car. He kept leaning in and talking quietly, but saying stuff like noticing I couldn't stop checking him out, that made him feel good, that he likes when cute guys make him feel good, that I was the cutest guy at the party, etc. YES I KNOW it sounds like he was laying it on thick, because he was, but also I think everything was expedited by the dozen or so eyeball fuckings we gave each other up to that point. Meanwhile I was being (in retrospect) absurdly bashful, I'd never had a guy this sexy talk to me like that in this setting. Which made him smile even more and say shit like "don't be shy bud, I loved knowing you couldn't get enough of me, and obviously want my bod." And he'd make me say it out loud.

Then he told me to kiss him. And I did. Butterflies galore. Then he quietly said "I've got a really big cock" and nodded while holding eye contact with me. I stammered something like "um" and he just smiled and said he did, and he asked if I like big cocks, made me say it out loud, etc. He asked if I wanted to see it and I was like "HERE?" I mean, we were in the hallway, not the middle of the party, but still there were people everywhere. He kissed me again and grabbed my ass, which pushed me into him, and I could feel it. I moaned or groaned or otherwise made a sound that said it all. He took me by the hand and led me up a couple floors to the top of the stairwell, where it would open to the roof but it was locked. We made out some more than he unbuckled his pants and opened them and said something like "there you go bud" and said I could feel it or see it or do whatever I wanted with it, and that it was my cock tonight.

He was, if anything, being modest when he said he had a big cock. It was magnificent: long, thick, uncut, and his balls were big too. Easily one of the Top 5 cocks ever in my presence, and on a guy who is shorter than me and wiry, so it looked even more like a whopper. And that's when "Mr. I'm Not Hooking Up Tonight" blew Tony at the top of the stairwell. More like I made love to cock with my mouth. The whole time he was talking dirty too, encouraging me to enjoy his cock. I had his shirt unbuttoned and was massaging his hairy pecs and stomach, tweaking his nipples, sucking the hell out of his cock. When he said he was close I just looked up into his eyes and kept sucking, and he smiled and nodded and shot in mouth. I swallowed every drop like it was my favorite meal.

Then we went back to the party and rejoined our respective friends. Continued to make eye contact. When it was pretty late and my friends were getting ready to leave and calling Uber etc, Tony tapped me on the arm and said "let's have a drink before you go." So I made some excuse about getting my own ride, and followed Tony over to his loft, during which he explained he didn't have any wine or booze, but that he was recharged and ready to fuck my hole, and that he wanted to find out how many times I could make him cum. I left about 36 hours later lol.

 

[ohiorod]

My most unexpected sexual encounter was several years ago when I was traveling in southern West Virginia. The desk clerk at the hotel was unusually friendly and even went to the extreme of telling me that he got off work at 7:00 in case I needed anything.

My gaydar was definitely off that day and I did not pick up on it. Once I got to my room, he called and asked if everything was okay. That didn’t surprise me since it has happened before, but usually in larger hotels in big cities. Still no gaydar!

At 7:05, he knocks on my door and asked if I needed anything. Now, that set off the alarms! So I did say that I was having trouble with the tv since so many channels, and especially cnn and msnbc were showing a no signal message. He kind of pushed his way into the room and checked out and fixed the tv. Once more asking if I needed anything else. This time, I played along and asked “like what ?” He offered a personal massage and that turned into him being a very talented bottom. He said he had his eye on my bulge from the time I walked into the hotel. He snuck out a side door when he left as he said he could be fired for going to a guest room off duty. We had about an hour together and I would have gone longer, but it was 8:15 and I hadn’t had dinner yet. I did enjoy his hungry hole though and he had a great bubble butt.

I never stayed at that hotel again due to the quality of the mattress. I didn’t sleep well that night and I had to do a four presentation for social workers the next day with minimal sleep. But every time I pass that hotel when I am in that city, I remember that very unexpected sexual encounter .

 

[4552511]

So I bought a house and was getting my things together. Decided to hire a pool guy who could help me maintain the pool and a gardener since my house and the surrounding was over 2700 sq ft. My pool guy I never saw but knew the job was being done as he preferred to come when I was at work, but my gardener Alfonso (changed his name) came on my day off which was Momdays. He was tough rough looking mexican kinda guy. Spoke minimal English but did a great job and was always grateful. One morning he complemented my physic and asked me how often I go to to the gym (in broken English). Him being married with kids didn't think any of it and I responded 5 times a week. Started noticing after that day, that anytime he saw me, he would hug me full on hug where his dick would touch my dick. His was soft so I thought it was just coincidental. On one occassion, I came downstairs and wanted to show him a patch of dead grass I needed him to take care of. He asked me to lead the way. However most of my downstairs are reflective windows so I caught him checking out my ass as I walked ahead of him. Still thought it was coincidental, so the the next time I would see him, it was time for some good gym shorts and tank top to show off my chest, butt and legs.
The next Monday came along, he rang the door bell, opened the door wearing my workout tank top and shorts as if I was about to head to the gym. He stopped in his track but quickly collected himself upon me opening the door. Greeted me with the full on hug, calling me Amigo and told me I looked good (in broken English and a deep tone). He then told me he needed to show me something wrong with the sprinkler timer by the garage. Since it needed a flashlight to see what he was showing me, I had to step closer. He stepped closer and he was pointed his flashlight to show me what he was talking about, he pulled me into him. He was burly, in his mid to late 30's, broad shoulders, big rough hands, wide body and a goatee and moustache that screamed man that loved his beer and women Hahahaha. As he pulled me closer showing me what was wrong, he ground his dick into mine e subtly. I asked him to show me again and I did the same thing to him. He proceeded to show me and then cupped my ass. I closed my eyes and then he whispered "I want fuck you Amigo". Without saying much, I took him by the hand and led him upstairs where we undressed, gave he pushed my head down. Gave him a blow job and he had to stop me before he came. Asked me if I had a condom, i quickly reached over to my nightstand and got out my lube and condom. He was 6.5 inches but not really thick so it was good since the last time I was with a guy was like 4 years past and last time I was fucked was 7 years past. I asked him how he wanted me, and he motioned to me to get on my back. He put on the condom, I lubed my ass and he went in. He kissed me as he lay ontop of me, cupped my ass and started pumping away. He started to bite on my neck as he fucked me sending me to heaven. He didn't last long as he kept saying "you tight Bro , you tight". Then he had one final thrust and convulsed ontop of me before kissing my neck and my lips, thanking me. He held onto the condom as he pulled out of me, then pulled it off him and showed me his spunk in it saying this could get me pregnant. We both laughed. He obviously wanted to let me know he still liked women. He asked me to jerk off which I did while he watched and got dressed. I got a wish cloth cleaned myself and put on gym clothes wherein he pulled me closed immediately, gave me a deep kiss, grabbed my ass in such a way my feet was off the ground(he was strong). Put me up against the wall and said, I fuck you again next week? I said of course. He gave me his number and asked me not to send him and sex messages but to say I needed my tree trimmed or grass treated. Yeah never expected my gardener to bang the shit out of me. Hahahaha

 

[Oztrich]

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.

 

[Heavyballs34]

Mike

This is a true recount of an unexpected encounter which resulted in a true friendship. I have changed his name, however everything else is as it happened. Please excuse the 'length', ahem...

I've had a few 'unexpected' encounters, but one that always brings a smile to my face was around 6 years ago, and which, incidentally is in running as biggest dick I have encountered, but I'll come onto that. It involves a guy who has since passed away and I'll always treasure the memory of us and our friendship.

Around springtime 6 years ago I'd just moved into a new apartment and over the course of the next few weeks, met and got to know my new neighbours. One of them was an older guy, Mike, late 60s (later confirmed as 68yo), lived on his own. He was what you would describe as a 'rough diamond', you could tell by the way he spoke and his appearance that he had certainly lived a life. That's not to be unkind, that's just the way he was. He'd sometimes stopped to speak, he was friendly enough but you got the impression that you wouldn't want to get on the wrong side of him.

Anyway Spring turned to Summer and I had settled into my new apartment. I had a rare weekday off and it was warm out so after gym and a few chores I decided to relax in the communal back yard with some beers. I changed into some jogger shorts and a t-shirt and went out back. I always free-ball in shorts in summer and today was no exception, love the feeling of my cock and balls hanging loose and always show a good bulge in the jogger shorts

So I put some beers into a cooler and headed down into back yard. On the way down I bumped into Mike and said I was headed out back for some beer in Sun and he was welcome to join me. He thanked me and said he'd join me after he done some chores, I replied in the affirmative and headed out.

Around half hour later Mike appeared carrying some beers and sat down at the table next to me. He was wearing some longer knee-length shorts and a wife beater. It was the first time I'd actually seen him show any body, and I was pleasantly surprised. He was much shorter than I, barely above 5' tall (actually 5'2"), but had a lean muscled body that a guy half his age would kill for. You could tell he obviously kept himself in shape when he was younger through manual work and at 68yo had the body to show for it. We sat and shoot the shit over the beers and I found out more about him. He had been a coal miner (hence the body) and worked at a builders merchant when the mine had closed down. He had been married around 22yo, no kids, and his wife had unfortunately died 10 years back and he'd been living on his own ever since. I commiserated with him and he acknowledged and said he would always love her. I told him I’d not long broken up with my ex-boyfriend and was just content enjoying single life. There was momentarily shock on his face the he grinned and said there’s nothing new under the sun, your only young once lad, swigging back the beer.

Conversation turned to the apartment block and how I enjoyed the area. I said it seemed a nice area and the neighbours are pretty friendly so so far so good! He laughed and cheered my beer. He then asked me if I heard the woman in the apartment between our apartments, (she is quite the screamer!)

I burst out laughing and said 'Mate, you can't fail to hear her, although I give as good as I get!" (I am pretty vocal!) He hollered with laughter and said he hadn't heard me. He proceeded to tell me that he'd had a drunken one-nighter with our loud neighbour the year before but that was all it was as he 'broke her' as he put it. It was my turn to burst out laughing, ‘Mate, your like the gable-end of a £5 note, there’s nothing of you, and she’s a big lass!’ He laughed back saying that he was hung like a horse. I laughed it off saying ‘Yeah right mate, whatever!’ There was silence and he then got serious and said ‘come into my apartment and I’ll show you’ and then got up and headed inside. The beers obviously had an effect on both of us as I followed him a few seconds later. I followed him into his apartment and closed the door behind me.

He then stood in middle of his hallway and asked me if I was ready. I was still laughing and said sure, show me what you’ve got! He dropped his shorts and I realised why they were knee length! Hanging limp between his lean legs was thick 6” dick. That’s big soft, but on his short stature it looked freakishly huge! I was gobsmacked and then I remembered myself and went ‘Fucking hell mate you weren’t joking, no wonder you broke her!’ He laughed and said ‘that’s nothing, watch!’ He picked up a ruler with one hand and he proceeded to jerk it a few times with the other until it was a 3/4 hard at nearly 10”. He said at his age that’s all he can usually manage, but rock hard it’s nearer 11"!

He then asked me if I was enjoying the show and nodded to my shorts, which were now tented out and getting soaked with pre. I hadn’t even realised I was rock hard myself! Mike then said ‘Go for it lad. We both need it!’

I didn’t need telling twice. I got on my knees and throated that huge hog of his like my life depended on it. It was the biggest I’d taken in a while and I gagged a couple of times but kept on going. Mike just kept a hold of my head and groaned. After a few minutes of worshipping his horse cock he let out a guttural moan which grew louder and he started pumping what felt like a gallon of cum down my throat. His dick then went limp and I had to physically catch him as he fell back. Once we caught out breath he gasped it had been a while. He then got all serious and started getting dressed, telling me no one can know and keep it between us. I gently reassured him and he told me I was a good lad and said we’d do this again.

Over time we got into a routine, he’d leave a pair of shoes outside his apartment door and that was my signal to come on in and drain his huge hog of a dick. I still marvelled at it’s size as it just looked obscene on his short 5’2” stature! He reciprocated a few times but he was just as happy to sit back and let me take care of him. We became good friends and I helped him out around his apartment with tasks he couldn’t do anymore. As time went on he opened up more about his past. He’d had some man-on-man experience when he was in his teens, but in the late 1950s early 1960s it just wasn’t accepted. When he met his future wife he put it out of his mind and never strayed all the time they were married. As he got older the ‘fun’ subsided but I always called in for a catch-up and looked out for him. Last summer he took ill and was confined to hospital. I was due to go on holiday and called into the Hospital to see him. He was in good spirits, and we talked about life in general, but you could tell he was fading. When visiting was over, he grabbed my arm and looked into my eyes and thanked me for my friendship. I held his hands and told him it had been a pleasure and left.

I had a phone call from the hospital the day before I was due to come home telling me he had passed. I will never forget him.

 

[absolutjock]

Last month I was in San Jose for a week on business. Decided to get on Tinder. Took me a couple days but found a hot betty serious about meeting up and just getting down (too many people on Tinder looking for dates now, right?).

She met me at my hotel bar. Smoking hot. Probably 5 - 8 years my senior but everything was holding up real nice.. including some perfectly upgraded tits.

We went up to my room. She immediately goes for my pants. I pull off my shirt. She pulls down my boxer briefs and my swollen cock flops out. She gasps. She says, "Yes. Yes. Yes. My husband will love this." I'm all, "You're married?"

She says, "Yes, but he knows I'm here." I'm like, "Really?" "Yes. He loves seeing me enjoy a nice, young, big cock."

I'm speechless.

"He'd love to see your cock. Can I show him?" She pulls out her phone. "Siri, Facetime with Greg."

He answers without saying anything.

She says, "Honey, look what I found." And she proceeds to measure my cock for him against her face.

"God, that's perfect," he says. "Suck that monster for me baby."

I still can't believe what's going on, but I don't stop it. She holds the camera out selfie style and starts to suck me off for her husband.

I hear him say, "Ask him to hold the camera."

Without hesitating, I take the phone from her hands. She pulls off her dress, takes off her bra and then really starts chugging my cock hard.

At this point, while I am holding the camera for Greg POV style so he can watch her suck me off, I'm watching Greg. It was slightly disturbing at first, but then he just keep commenting on what awesome abs I have. What a beautiful cock I have. He kept saying "You like how my wife sucks your big cock?" It frankly became a real turn on.

We proceeded to fuck for two hours while passing the phone back and forth so Greg could watch us from different positions, and at times, tell us what to do to each other.

It was seriously one of the hottest nights, and I've had a few.

It never occurred to me that Facetime cuckolding was thing, but now, I'm kinda on the look out for more couples who are into that sorta thing.

 

[candy1990]

I was in my early 20s and living with my friend at her dad's place, he was late 40s, he was friendly, handsome and recently divorced. I'd taken a Friday off and i guess he wasn't aware of this as i caught him completely naked on his way to the washroom when i got up that morning, we both froze and i couldn't help but check him out i mean he had a nice body for an older guy and he was soft but it looked big i was just staring at it until he put his hand over it and apologized saying his didn't realize i was still home at which point i retreated to my room. Later that day he approached me and apologized again, i told him it was fine then said something about him having a nice body for an older guy, we continued talking but i couldn't help but notice the bulge in the front of his sweats and after a few glances he caught on and with a bit of a laugh asked if i wanted a closer look, i was embarrassed that he caught me but i said yes and he actually pulled it out, i was pretty horny and went with it and he fucked me right there on the kitchen counter. We continued fucking for the next six months or so until i moved.