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?

 

[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.

 

[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.

 

[622675]

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

Great story.

Reminds me a of an old saying.

 

[notN2pussy]

Years ago, a friend I had talked to on CL for a few days finally agreed to meet, at my place, evening. I opened the door and a friends' dad was just walking up to my door! We were both shocked, but he got to his knees pretty quick

 

[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...

 

[EllieP]

Well, this brought up some wonderful old memories. We worked together for a couple of years. We flirted like crazy, but both of us knew not to screw up a relationship with an office romance. But it would get so heated in the office that some days I would be crazy with lust when I'd get home. One day he told me he got a job offer he couldn't refuse. My heart sank. It was for an agency three blocks away!

Lunches were never the same.

 

[Chrysippus]

It started when the all-female crew from Venus landed in my back yard... One of them got quite vexed when she caught me staring at her breasts, which were in two rows of three. But they all loved the trampoline! Hooah!

 

[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.

 

[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!

 

[sangheili90]

Not that long ago I was out grocery shopping and after checking out at the register I was stopped by one of the employees there when I was walking out the door. He said to me that there was an "older woman" who wanted to give me her card and that she wanted me to text her sometime. I took the card, having no idea who the woman was or what she really looked like, he described her to me and I recalled seeing someone who matched her description but I didn't actually meet her.

Anyway, I got home and decided to text her, as I didn't see what harm could come of it and it would prove to be an interesting experience. She replied relatively quickly, we texted back and forth a bit and we decide to meet up at her place later that night. I spoke to her briefly over the phone just before I got to her house, but I was pretty anxious about the whole thing.

I arrive to her door and I see a woman who is substantially older than I am, my initial impression was that she was 60+. She lived in a small town house with tons of other homes around so I didn't feel all that unsafe. She invited me in, as she was still getting ready, so I sat down on her couch as I waited. To say the least I was very shocked about the whole thing, as I really wasn't expecting her to be that much older, but I wasn't going to bail out on her at that point, as that would have in my opinion been extremely rude. We hop in my car and we spend a bit of time together that evening, just talking. I actually did like her on a personal level but the massive age difference and the manner of which I met her made it a bit awkward at first.

We arrive back at her place and she invites me in to hang out more with her, which was fine as I did actually enjoy her company. She made a comment about the cowboy boots I had on and mentioned to me that she owned almost 20 of them. I asked her to show me some of them so she lead me to her bedroom where she had her wardrobe. I sat on the foot of the bed as she was showing me some of her boots and I knew that this was going to lead to something more.

After she was done showing me her boots there was what felt like a long silence and I could feel the tension and anticipation. I initiated by saying "I know this is forward but would you like to have sex?". She thought about it for a couple seconds, mentioned that she liked my approach and then said she would love to.

I started taking my clothes off and she complimented my body as I went down to just underwear. I took off my boxers and when she saw my cock she instantly got on her knees and wrapped her lips around the tip of my cock. She was only able to work with about half of it but she tried to deep throat it to no avail, she later mentioned it was a bit too much. I sort of felt like fucking her but not knowing anything about this woman I decided not to go through with it, so I let her finish me off orally. She swallowed all of my cum and I got dressed.

I hung out with her for a bit longer after that, as I didn't want to just leave awkwardly, before I ended up leaving.

After that she would text me pages every single day, due to wanting more of my cock. She sent me a text saying that she wanted to try to deep throat it, as she saw it as a challenge due to it's size. I did go over one more time for a bj but she became increasingly problematic with the texting over the subsequent days,so wanting to avoid leading her on I mentioned to her I wasn't interested in anything more sexually from her.

 

[rope9839]

Not long after I was out of college, at a company Christmas party, one of the senior managers invited me back to his room to fuck his wife. It was out of nowhere. Crazy situation.

 

[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

 

[Redheadchi]

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

Such a hot story, I'm going to keep my eye out now

 

[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.

 

[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.

 

[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 .

 

[halcyondays]

Lots from which to choose but one of the most unexpected happened the summer I graduated from college. Home visiting my folks in suburbia I was browsing alone in a local bookstore on a hot afternoon when in walked a middle aged woman I recognized instantly.

She had lived across the street and few doors down when I was a kid. When I was in junior high I had a fall and broke my wrist. My parents were both at work so she drove me to the emergency room. A couple years later she and her family moved to another neighborhood in the same burb.

I wasn't sure she recognized me over a decade later in the bookstore, but she came right up to me and began an enthusiastic conversation about some book or author she loved. We chatted amiably. She became quite flirtatious touching my forearm several times. I finally asked her if she remembered who I was. She said oh yes everyone knows you... you remember me don't you? We lived on the same street? She had. Yes Mrs. W, I said. You drove me to the hospital when I broke my arm. I didn't think you'd recognize me.

Our conversation moved to the cafe next door were we sipped cold drinks. Her toes slipped out of sandals and played footsies with my ankle and shin. When I suggested we go somewhere private she agreed immediately. In the hotel room her clothes came off quickly. We banged all over the bed. She cried out her O's over the hum of the a/c.

She had always been an attractive blond with impeccable hair and makeup even as harried mom of two preschoolers. When I first saw her in the bookstore I realized she had upped her game. Her baby bump was gone. Her big tits were highlighted in a tight scoop top. Her natural blond had tan and peroxide highlights. She had become a disciple of Jane Fonda's workout tapes.

During one interlude while her hand held my balls and my long cock rested against her forearm she said, you have a reputation for this.

For what? I said.

For this, she said, squeezing my balls a little and moving her forearm against my cock.

Who knows? I asked.

Everyone, she said.

 

[IntactMale]

I went to a office holiday party with one of my coworkers. There was an open bar and everyone was getting drunk. My coworker was going to give me a ride home but he ended up getting drunk and getting sick and had to stay the night in the hotel next to the place where the party was being held which left me with no ride home. I mentioned this to a group of coworkers while we were standing outside as some people were smoking when a female coworker who was a couple of years younger than me offered me a ride home which I of course accepted. In retrospect we were both drunk and we shouldn't have driven at all.

When we got to my place she asked if she could come in for awhile to sober up, which I of course said she could. I was oblivious to what seems really apparent now so I was really surprised when we shut my apartment door and she immediately grabbed my cock, pulled it out and started giving me a vigorous blowjob. A couple minutes later and we were fucking on my couch. We spent the rest of the night drinking and fucking. It was the most sex I had ever had in such a short period of time. We eventually went to sleep and both woke up with terrible hangovers.

Things got really awkward after that. She started talking about how much she liked me, and honestly the feeling was not mutual. Since she was a coworker I had to walk on eggshells to get out of the drunken mistake I had made and it was a couple of months later before I could get myself out of that situation.

 

[Mickey1234]

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.

Really great story, man. And beautifully told.