What was your most surprising or unexpected sexual encounter?
I think mine was with my insurance agent, a very proper and straight seeming man, who came to my place for an interview.
I had just come back from the beach, and my suit and towel were on the sofa and as I cleared them away, he said a couple things and asked if I ever went to the nude beach, and that he was a nudist. At the mention I blushed and got hard. A couple of exchanges later he was telling me he liked to look at the cocks and then did I want to strip. He had a kind of power, and five minutes after he walked in the door we were having sex.

When I was pretty young I use to suck a friend who was my age a lot. I'd do it for him but he didn't do it for me. I'd usually do it for him at his house when his mom was away. One afternoon he called me and told me to come over as his mom was gone for the day. I went over just expecting it to be me and him. When I got to his house my friend's older cousin was there too. He was about 4 yrs older than us. My friend had told his cousin what I did for him and he told me his cousin wanted me to do it for him. I was really nervous and embarressed that he had told him. I told my friend I didn't really want to do it for him. My friend insisted. I was very sub to my friend so I agreed. He made me take all my clothes off and suck his cousin while he sat on the couch in the den. My friend watched. The older boy had a grown up looking uncut penis. I'd never seen or even heard about ones like that. He gave me my first mouthful of cum too. My friend hadn't started squirting yet. It really surprized me and he held my head down on his penis until he finished. I choked and gagged and spit it out in my hand when he let me up. It was all unexpected for sure.

I think that one of my unexpected encounters was when I was at the gym early one morning several years ago. After my workout, I was sitting in the sauna with two other guys, both about my age. One was just sitting calmly; the other was playing with a sponge, squeezing water out of it onto himself. He was making the whole thing look really erotic, and I was hardening up. I could tell that the guy was really horny; but I didn't think anything would happen in there, or that he'd carry things any further, especially with the other guy sitting there watching. I was wrong. The guy put his sponge down and came over and sat on the bench in front of me. Before I knew it, he turned around and had my dick in his mouth. He gave me some of the best head I've ever had. The other guy just sat there like nothing unusual was going on, while the first one sucked me and swallowed my load. Have to love those kind of surprises.

once, my ex and i were at a party and decided to go off into one of the bedrooms for a much needed quickie. we went into the room and were seriously going at it on the bed. we hadnt realized that we left the door unlocked, and a friend of his wandered into the room. we didnt know he was there, until we heard a noise in the corner and looked and saw this dude standing off in the corner, whacking like there was no tomorrow. no, we didnt stop, we gave him a show. no, he didnt join in, but having him standing in that corner jacking off was the hottest situation i have ever encountered. when he decided to cum, it wasnt but a few seconds, and we were both cumming like crazy too. i guess thats where my cum spewing fetish got started..............

my most unexpected time happened less than 2 weeks. I was staying in my friend bills flat. bill is str8 by the way. one night when bill was playing xbox with a very good looking also str8 friend of his I went out for a drink and to try and find a willing guy. at 2 am I had given up and heade bach to the flat rather drunk. when I got back bill was passed out druk on the sofa and his friend was still playing games. after 10 minutes in my room there was a knock on the door and in came bills friend he was very drunk and swaying all over but I noticed he was rubbing a huge bulge in his jeans. I didnt say a word I yanked down his jeans and his boxers in one revealing a great looking cock it must have been nearly 8 inches long with a thick heavy foreskin. after sucking him to full attention I slipped a condom oven it and spent a good 10 minutes bouncing up and down on his tool before he reached a screaming orgasom. it was some of the best sex I have ever had

Most unexpected....was 28 or so and chatting with a guy on gay.com. Met at his house and was incredibly surprised to find out he was my dentist. Even more unexpected is the 10" of cut meat dangling between his legs. Was an odd hookup for me as he claimed her was versatile and after doing some oral and j/o, he wanted nothing more than to top me. I told him he'd have to ride me before I even thought about that monster going in me. Details aren't important but let's just say I left his house with a pussy full of his cum. Intense to be taken but the pain my ass lasted for days....very unexpected.

that's cool.

My most recent "most unexpected" happened just over a month ago. I logged into "Squirt" one morning to find a message "Phone me" and a number, from someone literally half my age who appeared to live within walking distance.

I called the number and, as we live in the same village, we arranged to meet later that morning.

Surprise!! surprise!! when I opened the door to our local policeman - in mufti of course . Great body , great kisser .

A doctor in New York, with his practice high up in an office building, told me, "Get undressed. Take everything off-- including your socks, and lie on the examining table. I'll be back in a few minutes" I thought this strange, since I had a respiratory problem. But I did as he ordered. He came back, spent maybe ten seconds examining my feet (I suppose as a justification for telling me to take my socks off) then gave a lot of time to examining and handling my cock and balls. I got a hard on, of course, and without a word or a smile or a glance at me he started sucking me off.

He was about forty, in good shape, with rimless glasses, very professional and businesslike. He gave me a slow, thorough, intense blow job-- the kind I like best-- sucked the last drops of cum out of my softening cock and swallowed them, and wrote me a prescription. It took care of the respiratory problem. I thought he might skip the fee. But as I left his secretary in the outer office told me what I owed and I paid it.

this sounds very hot

Wow! That is a hot story. Me? I'd want to be the friend in the corner!

Most unexpected for me was when I posted an ad on craigslist while traveling. I got a reply and found that were both in the same hotel. He came to my room and I was already naked. We hadn't traded pictures, but had described ourselves. He told me he had a 9" cock, which I always discount because most guys aren't honest about their cock size, but when he took off his pants, I could see the huge bulge. The he pulled down his underwear and his cock was bigger limp than I was hard. It was uncut, very thick and heavy too. I started playing with it and he got hard. It only got a bit bigger, but it was huge. I'd guess bigger than 9". I could barely get the head in my mouth.

We played with each other a bit, and I couldn't stop sucking his massive cock. He was a little shy and not very aggressive, so it turned into me having him lay back and let me suck his beautiful cock.He started to moan and said he was going to cum. I worked his dick as best as I could and he started cumming, and cumming, and cumming....I couldn't swallow fast enough so i backed off and watched the thick stream of cum ran down his shaft. I then grabbed my cock and shot my load all over his hairy balls.

He cleaned up, quickly got dressed and left saying nothing more than "thanks". I emailed him several times and never got a reply back.

To this day, his cock was the most perfect specimen I've ever seen in person. I wish I'd have taken a picture of it.

Years ago a couple friends and I used to go fishing near Yellowstone for a long week, in June, in one guy's small motorhome. It was a long trip from home in the Bay Area, and we usually stopped in an RV park in Winnemucca on the way home. One evening there, one of the guys and I decided to go try out the nice big hot tub near the pool. Sitting in the hot water was great, and I could feel a water inlet massaging my back. Being horny as hell after the long week, I 'sneakily' moved around like I was watching the folks in the pool, and maneuvered so the inlet was shooting the water onto my soon-to-be hard cock. Felt like heaven, and I was in ecstacy....I knew it wouldn't take long. I thought I was hiding what I was doing, but Bill surprised me by saying "makes the cock feel good, doesn't it?" Shocked the hell out of me and I turned quickly to look at him. He was sitting with bubbling water up to his shoulders, and said "come over here...there's an outlet on the edge of the seat that feels pretty good." I slowly waded over toward him, and he told me where to sit, which was basically right next to him. He was right, there was a strong water inlet, that was kind of pulsing some, from the pump I guess. Smiling he looked at me and said, "slide your suit down and let it hit you right behind the nuts...feels incredible!" He was right, and soon I was moaning as quietly as I could. Suddenly I felt Bill reach and hold my cock, slowly stroking it....and he told me to play with his, too. So we sat there slowly jerking each other off, and it didn't take long for both of us to cum. I must have been looking at him funny, because he said "Tom will be happy to hear about this....he and I have been playing with each other for a long time and were hoping you could join us!" That was the start of a great evening, and the next day we took turns driving so the other 2 could play some.

My most unexpected was on a greyhound bus on my way back from the MEPS station when I was joining the navy. I was 17 and this older guy was sitting next me. I had noticed he was overly friendly with his touching while talking to me. Not sure what I was thinking but he kept trying to draw my attention to his boner in his pants. He had mentioned that I could touch it if I wanted to, I turned him down but did anyway a short while later. He ended up pulling it out and I played with him between people walking past to the head in the back.

A few years ago I was cycling to a farmer’s market in t0wn. It was a warm Saturday summer’s day and I needed to pee. I stopped off at a multi storey car-park. I chained my bike up and went into the toilets there. Not exactly a cruising type of toilet. I had no expectation of anything and besides did not have much time.
There was a lad at the urinal and I could see he was stroking his cock. He looked young and I was a bit concerned it might be a set-up, either a mugging or something involving a police sting, but then I thought it unlikely they would do it in a car park toilet. He caught me looking at him and dropped his gaze to his cock then looked at me again. I knew he wanted me to play with him
Even so I intended to walk away as I was in a hurry. But as I washed my hands I was thinking he would probably cum lots being young and I was sure his cock would taste nice. My urges got the better of me and I thought no harm in giving him a quick wank. I began to wank him and noticed he was trembling with excitement. I so wanted to watch him shoot his load but I also wanted to suck him too and taste his cum. I got to my knees. He was wearing white briefs. His cock was beautiful. About 7” and quite thick for a young lad. It smelled so fresh. I eased his foreskin back to see a lovely pink head with a dewdrop of pre-cum. His pubic hair was soft and dark. I cupped and kissed his tight balls, ran my tongue up the length of his shift and licked the pre-cum from his cock, savouring the taste. Just as I was about to take him in mouth he groaned, his cock started to jerk and he spurted a stream of hot cum onto my face.
I quickly got my mouth round his cock and swallowed as much of his cum as I could. And there was plenty. I squeezed his balls gently to get it all out. I licked the all the cum from his cock head. After gently kissing his beautiful young cock I tucked it back into his briefs.
I said I had to go but would be happy to suck him properly same time next day. I did go back but he never showed.
For me what had been a routine piss turned out be the most satisfying bj I have ever given.
I hope he enjoyed it.