Most unexpected sexual encounter

[1454612]

After my wife and I separated ,I stayed a month with a bandmate that I hired to work for the shop I was . He wasn't very skilled at anything. The boss paid him a small wage and I was training him to help me. I was paying him extra if he helped with my commission jobs.
He had a new baby and they were tight on funds. I knew his gf very well ,so it worked well until I knew my next move. I wasn't there much and paid WELL.
I needed relief and didn't want to disrespect by jacking in common area where I could be seen by his gf. She had seen before ,but he was not aware and he was pretty insecure. I wouldn't use the bathroom in the child's room. Just felt creepy. SO, I got my portable dvd player and was sitting at the table on the secluded patio where they smoked. It was late and she was crashed.
He came out to smoke upon hearing me. I was dressed but had porn queued . He wanted to borrow it and I told him I was needing it. He pushed and I said " watch it here" and told him" Im not gonna mess with ya". I stood and dropped my pants, and he said" Damn, you pack heat" . A lil snicker and I thought no more of it. After a few mins I noticed that he wasn't watching the porn. He was watching me. He got embarrassed when I noticed ,and I told him that it was no big deal. I told him he was very welcome to look all he wanted. I didn't go into great detail ,but I told him that I have jacked with buds before . He said " Wow, really?" I said " yeah, it is nice that you want to look ,and I like jacking off with friends" I turned my chair towards him so he had a better view. He said" Damn, that is a really big cock, bro" I said " thanks" He said " No, thank you".
He was very curious about the jacking and asked if we had certain rules. I said" Show respect and enjoy yourself together. He asked" has anyone ever touched your dick when you jacked with them". I said" of course". His jaw dropped and before he said a word I asked" Do you want to touch my cock?"
He got wide eyed and asked" are you being serious?" I said" If you want to I want you to". He said" I don't want to seem like I am totally gay ,but big dicks are my secret fetish and this is a basically a fantasy for me". He grabbed my cock and it was about half erect. He said" Damn, this is so hot". He stroked me and put both hands on it. His cock was standing straight up,and it had a little oozing out. He got me pretty hard and I rubbed it against his cock. His jumped and he moaned.
I held mine against his and jacked us both.
He leaned back and said " Ohhh fuck" and the cum shot once then oozed. It spurted and flowed over my hand and down our dicks. I stood up and rabbit jacked my cock and came on his still hard dick.
He got embarrassed after he came and it was a little awkward. The next day he went to play golf out of town with his dad.
I was laying in the sun with headphones. His girl took the kid to his mom's and I didn't know she was back. She sat by me and said" I got up to get a drink and saw you two out the kitchen window".
I was unsure what to say. She said" He really needs someone to help him with his sexual identity issue". I asked her" what do you mean?" She informed me that her pc was acting up and discovered that he was looking at naked men and some gay videos. She said" he has a couple vhs tapes under the sofa. She told me she asked him if he had been with any guys. He said " no, just porn ,and that he was just comparing and was kind of curious,but wasn't no fag". She said " it is ok if that turns you on,just don't go behind my back". I told her what we did and how it came to be. She said" I am glad it was your and that he didn't go to some truck stop or craigslist's". She told me that he is very insecure and thinks he is too small. She said she tells him he is plenty for her,but he doesn't believe her. I told her he was obsessed with mine ,and kept telling me it was huge. She said" It is". She told me that she saw it hard last night, and thought" omg".
I was wearing a pair of white Jockey Life bikini briefs as I tanned. The sweat and oil had them pretty transparent. I went for my tshirt to cover myself ,because I didn't have a towel. She said" it's ok,Im not bothered at all. You can wear that all day". When my hand touched my dick I realized that it was sunburned.
Pretty bad too. She laughed a little at first,but when she realized that it was as bad as it was she got concerned. I went to the shade and sat. She asked" how bad is it?"
I said" I don't know, but it hurts".
She said" Well look". I pulled my underwear down and it was pink with a red stripe of bad burn. She said " Ohhh no".
She went in and got her Noxema.
She asked" have you used this before?" I said " no". She said" I am going to put this on. don't freak".
She gently coated my dick with it ,and commented how her hand wouldn't go all the way around it. She said" I will go to Walgreens for aloe burn gel". I waited nude for her. She got back and put it in freezer to cool for a bit. When she put it on it was cold and I flinched. She said" ooops, did I hurt ya or is it just cold?" I said" very cold". She filled her hands and warmed it a little ,but the cool was soothing. She put a few coats on and it started to plump me up a bit. She said" Keep that thing under control...and giggled " It got half hard in her hand, and she said" you do have a really big dick". "Does this hurt?"
she asked. I said" no, it feels good".
She filled her hand again and stroked me. I got fully hard and she kept on. She got a little faster,and I came on my chest. She said" I didn't do anything he didn't. Then winked. The next few days I healed.
The next weekend I got a suite at the casino. She confronted him and had him come to play with me. She told him that he needed to work out every curiosity that he had to see how he really felt about things. She got it started. She said" I am gonna take a long hot bath,and you two have fun.
We jacked and sucked. She joined. She taught him how to deep throat. He came in my mouth. I came in both of theirs. It was a good time, but his jealousy ended up costing the friendship. Well, for a few years anyway... He calls occasionally to play if I am up for his company.

 

[Goose_Eggs]

guess I was over the 1000 character limit ……. here is rest

Four beers and all that hot water I was dead, never even heard Daniel come to bed. With the four beers though I had to get up once to piss in the night and woke really early needing to piss again. Between a regular morning woody and not having beat off for a couple days now I had a 3/4 chubby, thought I'd hurry to bathroom before Daniel was awake. I stumbled on one of his shoes and looked over to see him laying there looking right at me, sun just coming up so plenty light to see, as I turned for the door. One of those long pisses that seem to go on forever, finally got down to about 1/4 chubby and headed back to bed. Daniel was laying on his side wide awake, so I said, "all that beer last night, makes ya piss like a race horse" as I walked back in. "yea, horse is what I was thinking too (laughs), man I remember you sporting a big one, but I'd have sworn you were circumcised". "Huh?" I said as I laid back down in bed. "Remember that time after playing gold at the country club, walking into each other in the showers?" he says laughing again. "yea, that was a long time ago". "but your dick hasn't shrunk any since then" he says with another laugh, "but I sure don't remember you being uncut, guess my memory may be first thing to go (chuckle). "Oh, no, you're right, I AM circumcised. I started noticing it about 12-13 years ago, thought my dick was shrinking, lol, doc says just saggy dick skin just like saggy butt …. Basically wearing it out from years of abuse, lol." He looks directly at me and says, "if that were the case mine would have fallen off my now! (big laugh), ain't so much humping going on but I'm still jerking the gerkin every day to keep sane." "Yea, I saw that yesterday," I said. He just laughed, said, "yup, I'm clearly a morning guy, body gets used to it and demands attention, kind of like a puppy wagging its tail same time each day to be fed," as he rolled over I could clearly see a boner under the covers. "you looked like a morning fella too when you just got up (he winked)". I said "yea, they do kind of have a mind of their own, don't they? ……. guess I'll go make some coffee give you some privacy (I winked and grinned back). "Oh you know I'm not a shy one (chuckle), go ahead and rub one out over there too if you got the urge, hell its only natural. Be kind of like being back in school …… you know John (the future father in law) said last night it was like being in a frat house here, lol, so I guess an old fashioned circle jerk wouldn't be out of place". My dick was getting hard, and it was pretty apparent under the thin covers. Looking right at me he said, "in totally cool with it, no sucking or ass play, you know, just beating off like we did as kids," as he pushed the covers down past his bush and held onto his cock. I didn't say any more, just
started rubbing my dick. We never moved from our beds, just watched each other and jacked off. He came before I did, then sat up watching me rubbing cum into his chest hair. I started thinking I needed to hurry and cum so things wouldn't be awkward, so I started beating hard and fast causing my balls slap loudly from side to side, and the only thing he said was "damn buddy, wake the neighbors". I shot all over my chest laying there a bit exhausted, he got up and walked by me toward the bathroom saying, "right way to start the day, I'll make some coffee".

When I came into the kitchen, the others were up also. We fixed a big breakfast and all went skiing again that day. Neither of us said anything about it, and he was not one bit different in attitude or behavior, just typical Daniel. That night we all went out to dinner, got home late and straight to bed as we had to leave pretty early next day for the city. In the morning we were all having coffee/breakfast, Daniel said he still had packing to do headed toward bedroom, he called back toward the kitchen for me to check and make sure I didn't leave anything in closet or dresser. I put everything in the dishwasher then went to get my suitcase, Daniel was sitting on the edge of the bed, pants around his ankles, cock dangling off edge of bed and him wiping the cum dribbling down his chest, he looked up, "you just missed the show" he grinned, "but there's always tomorrow morning".

We got back to the city, had lunch and a few hours of "did you have fun, what did you do?" with the women, then everyone started going their separate ways, I flew home that evening.

Like I said, it wasn't really "sex", but it was certainly unexpected! I've always found Daniel an attractive man, though not really attracted to him, but there has always been something sexy about his casualness with nudity, talk, and now I know masturbation as well. I didn't get the sense of any gay or bi tendencies, I think he is just another major peter beater, lol. I've always teased about him always camping and hiking with his buddies, now I have no doubt what's going on out there.


​

 

[JonSomebody]

I've had several unexpected sexual encounters in my life..but I will share this one...There was this very hot "straight" guy that had moved into the building that I lived in at the time and he was known throughout the neighborhood as a "ladies man". Every night..I would go jogging at the baseball park that was nearby and I would always see him and many times with different women on his arm. He always made a point to speak to me which I thought nothing of until one night he stopped me coming into the building's front lobby.

He started a conversation with me by introducing himself properly and asked me my name as well. As he went into his conversation...he mentioned that one of his ladies had asked about me and wanted to know if I was seeing anyone. I told him that I was not interested and he went on to say..."she's hot" and I responded with "yes...she is..but I'm not interested because I'm gay". He smiled and said no judgment and thanks for your honesty...However, not too long afterwards...I started to notice how he would appear out of nowhere during my daily run and wanted to talk to me.

One night..I was coming into the building and he stopped me and then invited me to come visit him some time to have a drink or talk with him. Although I never did get around to doing so...I did not need to...he came to visit me instead. I can tell by his demeanor that he had been either drinking or high and in my head ...I was thinking how hot he was and his body in those tight jeans and t-shirt looked amazing but I never thought that things would go as far they were about to.

Okay..so let me speed this story up...a few days later...he saw me coming down the street and asked me to come with him into his apartment..(he was talking to me from his living room window)..since we both stayed on the main level...I stopped and knocked on his door...he invited me in and offered me something to drink. He got to talking as usual and then he went on to tell me about how he had gotten into a fight a few years prior and he got cut with a knife by the guy he was fighting with.

While he was telling me about this fight...he preceded to take off all of his clothes and stood before butt ass naked in order to show me this untraceable slash towards his lower abdomen. At this moment...it did not take me long to figure out what was going on or what he was trying to do. Like I've mentioned earlier...his body and cock was amazing...and he took my hand to guide me to feel this unnoticed stab wound but he also ran my hand across his chest as well. This is when I noticed he was getting aroused and he pulled me in closer to his body and started kissing me.

He then started whispering dirty talk in my ear while he had my hand stroking his rock hard cock. We started kissing again as his hand went down my pants to grab my then rock hard cock as well....He then told me that what's about to happen has to stay between me and him and he went on to say that he had been watching me for awhile very closely and knew from my demeanor that I would be the one that he could trust with his secret.

The evening turned out to be incredible and afterwards...he asked me to lay with him for awhile. My head was spinning because I could not believe what had just happened. Now...not thinking it was going to happen again...it was not long for me to find out that I was wrong about that...we had sex a lot and things went to another level one night when he bent over the chair in the living room and asked to fuck him...I fucked him in every room of his condo...he was amazing and I love his loud moans and dirty talk. He was a hot freak and as he said..."Fuck my pussy stud!!"...

This arrangement went on for quite some time..things did take a turn because although he was still dating women...he did not like for me to go out with other men and would get very jealous to say the least...this created a problem between us and he gave me an ultimatum..which was a huge mistake...I stopped seeing him and not too long after that...he got engaged to one of his ladies and moved away...I never saw him again...

 

[OctoGun]

A lot of hot stories in here. Here’s one of mine that springs to mind.

I was staying at a very well known hipster hotel in downtown LA. I got lost going from my room to the elevator. The guy who refreshes and refills the bar could see I was lost, so he walked me to the elevator.

I pressed the button and waited. For whatever reason the elevator was taking forever. Out of the corner of my eye I noticed the hotel staff guy was still stood at the entrance to a room, just messing with stuff on his cart. I turned and looked, and he was staring at me.

he was good looking, latino, shaved head, muscular, looked like a real tough guy. So, I continued waiting. Elevator still hadn’t arrived, I turned to look at him again and he was still staring. Then he sort of gestured his head down at my bulge. That was enough of a signal to me. I walked past him, back to my room and left the door on latch.

20 seconds later he knocked and walked in. He got on his knees and sucked me off. After that encounter he came and sucked my dick every day of my stay (we nearly got caught once when the cleaner came at the same time). Bonus was I got free bar refills too.

 

[StareDecisis333]

Don't know if this can be properly categorized as sexual encounter.. so forgive me if it isn't

So this happened a few years back.. I have this friend, he's a college wrestler and I believe also did compete in nationals division, and then there's me taking up a law degree.. so bookish type of a guy..
we agreed to meet at a local university library.. because I promised a day with him for missing out on his birthday a week prior.

So I was trying to look for a book on some decided court cases. and my friend just lazily follow me bored as fck.
then while I was reading the table of contents...
he suddenly just randomly stood behind me..
He was taller than me by the way.. a good few inches
and then out of nowhere he spoke and said "why do you always smell so good?"
his words didn't actually register in my mind.. so I didn't understood or heard what it was..
So he leaned closer down to my nape... so close, I can feel he intentionally breathed heavily so I can sense the warm breath.. and said it again.. "Why do you always smell good?"
and I'm like.. "Dude, you're ass alright?" and turned around confused. He said.. "Why can't Jen smell like you?" and then grin very seductively.
I broke the ice and responded.. Is everything okay with Jen? or she killing you again (Jen is his gf who's so toxic)
then He just put his right arm around me and said.. "I'll always have you with me right man?". and without warning he bit me on the neck and started sucking on my neck skin.. and gave me the most visible painful HICKEY OF MY LIFE. And fuck me.. I just stood there.. I let it happen. and he wasn't satisfied with that, he made it so sloppy too.. his drool was a lot.. it made my collar wet.

had to put on my emergency hoodie and zip it up tight to hide the hickey.. and he was just smiling and laughing like an asshole that day.. and what weirder I felt no sense of danger from it... and from time to time he brings up that hickey story for fun.

 

[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

 

[stretch8888]

I've always been a bit oblivious so there have been a good number of unexpected sexual encounters but i had one yesterday that came right out of no where.

Friend of mine I've known for about six years, average height, petite body, small perky tits and a great ass, blonde hair blue eyes, very cute and shy, I've made a few advances but never got anywhere. She starts texting yesterday saying she was in town visiting family for Easter and was wondering if she could swing by for a break from her family. She came over and we were catching up over a few beers, i get up to grab us another and when i return out of no where she asks "You wanna have sex?" certainly caught me off guard as i didn't have a response and she just smiled as i looked at her, then she tells me the guy shes kind of seeing has been away at work for almost a month so she hasn't had sex in a while and with her family is stressing her out all weekend she was kind of hoping I'd be interested in some friends with benefits action, she didn't have to ask twice and we made our way to the bedroom, practically ripped each others clothes off, given her typically shy quiet personality i was a bit shocked, i don't think she was expecting me to be so big but she didn't waste any time getting it in her mouth, she had skills but i was eager to get inside her so i yanked her up and she was fucking tight but she took it, from there on it was just some hot sweaty straight up fucking, finally got her on her back and was giving her every thing i had, pulling out didn't even cross my mind until I'd unloaded inside her, i apologized for not pulling out but she didn't mind, we laid there for a few minutes before she noticed i was still pretty hard, checked the time and said we could go again if i wanted, she gave me a quick suck then climbed back on and we fucked one more time before she had to head to another family dinner.

 

[AlteredEgo]

My online dating profile is really, really silly. Over the top ridiculous. I think it's very funny, and only someone who gets and enjoys my jokes is really up to the task of hanging out with me. Every few years I dust it off, update some of it, and make it public for a little while. Some of the people I meet that way are destined for friendship. Maybe we really enjoy each other's company, but just have no mutual desire to bang. I've actually been friends for about as long as OKCupid has existed with one such dude, for example. We don't even flirt with each other anymore, but we keep up with each other's lives. If he needed something I had, I would take care of it. Vice versa. That sort of thing.

Anyway, I made such a friend. More recently, about a year and a half ago. We are goody in the same ways, and we just clicked instantly. Around him, I laugh so hard I can't see or breathe. Funniest dude I ever met. We have heaps of silly fun. I was surprised when I picked up on a hint that he was sexually interested, and realized he'd been subtly dropping hints for ages. I really thought he didn't find me attractive. Turns out, he just didn't think I could ever find him attractive, and there was a bit of a preemptive rejection. I'm glad we figured it out. Now he's more fun than ever, and it's easily the best sex I have ever had.

 

[cedarizzo]

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.

This reminds me about an encounter I had with a guy when I first came out. I was still living in the small conservative town where I had grown up. But I had a few gay friends and 3 or 4 times a week we would travel an hour to a bigger town that had a gay bar. I didn't have a car at the time, so I relied on my friends for rides to the bigger town. We knew a lot of people in the bigger town, so quite often we would go to after hour parties and would end up spending the night at different friend's houses.

One summer night, a friend was moving to Chicago and they had a big going away party. The guy that gave me a ride to the party had planned on spending the night with his boyfriend. So I had made plans to spend the night at the house where the going away party was being held. It was a great night. Had a blast at the party. A majority of the people went to the going away party. It was a hot balmy night. I remember when the party was going strong it was getting warm inside the house. I went out to the front porch and the breeze felt great. There was already a group on the porch when I noticed a cute guy I had seen at the bar a few times. He was around my age (early 20's at the time), about 6 foot tall and around 150/160 in weight. He had short blond hair and the most amazing green eyes. And when I had seen him smile, he had the cutest dimples. The few times I had seen him at the bar, he was always hanging around the same people and they were always dancing or hanging out right next to the dance floor.

So when I was checking him out, he looked over towards me and got that cute smile with the dimple. Being a bit tipsy, I got up from where I was sitting and walked over towards him. I smiled and introduced myself. He told me his name (which for the life of me I don't remember). There wasn't any place to sit near him, so I motioned out to the front lawn and asked if he wanted to go sit out there and talk. He got up and said sure. We sat on the front lawn for a few hours as we chatted. The only time we got up was to refresh our drinks or to piss. Each time we went back to the front yard to sit down, and we would sit closer to each other. By the end of the night, we were sitting next to each other with our legs and arms touching. I felt really good and tipsy, I reached over and held his hand while we talked. He didn't pull away and leaned his body against mine.

While we were talking, I learned he was from a small town about 45 minutes away (in the opposite direction from me) and the people I had seen him with at the bar were his friends from the same small town he was from. They always car pooled together to the bar and usually they would leave the bar together. (That is why I hadn't seen him at any of the other after hour parties.) He said he was an artist and he did have that artist type of personality. He was cute and I had a great time chatting with him. But the party was winding down and I knew I would be passing out soon. I asked him where his friends were (since they usually car pooled together) and he told me that he went out with his friends but they left without him. He already had a ride home, but they wouldn't be able to pick him up until later in the morning. I told him I was spending the night at the house and he was welcome to share the bed with me. On the way upstairs to the bedroom, we said good nights to everybody. We got into the room and discovered it was a twin size bed. He got a smile on his face and said he was game if I was. I just smiled and said definitely! I started taking my clothes off when he asked how I slept. I told him I slept naked usually. I could keep some clothes on but it was warm and I wouldn't be able to sleep. He agreed that it was too warm to sleep in clothing. He said he was going to strip down to his underwear (which he had already done.) I laughed and said that would be fine but I was going commando that night. So with that, he took off his underwear and was completely naked. His dick was about 6" and not erect but getting bigger. That just made my dick start getting hard. I got in bed and scooted over to one side to give him some room. He got in bed and we pulled the sheet up.I was on my side, and he was laying on his back. I draped my arm over his body and felt his abs and chest. He had a nice hairy chest and I loved running my fingers through the hair. His hand was by his side, right next to my dick. I felt his hand reach up and start stroking my dick. I moved my hand down and grabbed his dick which by now had grown to full 8" size. We started making out while we played with each other's dicks. He was a great kisser and we were really getting into it. He got up and moved my body so I was laying on my back. He got on top of me and we started making out again. He moved down my body and stopped when he reached my dick. He sucked my dick for about 10 minutes before he started to push my legs up and started to rim me (that was a first for me!) He started to kiss me again, which I didn't know what to think about that after he had just rimmed me, but he was such a great kisser that I didn't mind it. While he was kissing me, I felt the head of his dick hitting my hole, I reached down and grabbed his legs and pulled him in, with that, he stopped kissing me, spit on his dick and pushed his dick into me. He felt so amazing as he went in and I was really getting into it. He took it slow at first, and it wasn't until he was all the way in that he slowly started to pull it back out. I put a pillow over my head because I realized I was moaning loudly. He held it with just the head of his dick inside me. I reached for his legs again and pulled him all the way in. When I felt his balls slap against me, I let go of his legs and he started to fuck me. We were making out again while he was busy fucking me. I knew I was getting close and told him I was really close. He stopped kissing me and began fucking me even harder. He was pounding my ass hard. And then I saw his eyes roll back in his head. With that, his rhythm stopped, he held his dick deep inside and I could feel it pulsing. That sent me over the edge and I started to shoot my load all over my chest. He collapsed on top of me and we were both short of breath and covered in sweat. After a few minutes, I got up and found a towel for us to wipe up with. We both fell asleep in each other's arms. The sun shining through the window woke me up about 8am. He was still asleep and I tried my best to get out of bed without waking him up. I almost made it out of bed when he pulled me back down and started kissing me. He looked at his watch and realized his ride would be there soon. We exchanged numbers and said our goodbyes.

I later found out we had been a little bit loud last night, everybody heard us having sex. We talked on the phone a few times, we would meet at the bar on weekends. But I didn't have a car at the time and his van wasn't reliable. A few months later, he moved out west to start a new job. I never saw or talked to him again. It was a very unexpected but fun encounter.

 

[Oralgami15]

I was in my early 20's and three of us (me, another guy and a girl) rented a house that was far enough away from the beach to be affordable but close enough to get there as often as we wanted. Two college students had been living in the finished basement but when the school year ended in May, they left. We placed an ad looking for someone to rent the basement and two girls from Boston came down looking for a weekend place near the beach. They were a little older, had decent jobs and were a bit more "experienced" than we were.

One Saturday, probably their second weekend in the house, "Judy" and I were the only ones home. It was raining and thus Judy wasn't going to the beach. We started drinking beers and smoking and just trying to get better acquainted. My roommates played backgammon a lot and I asked if she played. She said she was pretty good in college and I invited her to play. Pretty soon we were playing strip backgammon. I was kicking her ass at first and when she had to take off either her shirt or pants she didn't hesitate to pull off her shirt revealing a sexy little lacy black bra. I was getting turned on and started making some high risk moves hoping to quickly see what she was wearing under her jeans. However, my bold moves proved foolish and I found myself left with only my tighty-whities on as we began the game I had to win. I lost. I had been to nude beaches many times before, and had my share of girls. This was different. She looked at me with a look of pure delight and she was not going to let me off the hook. "C'mon, stand up, take 'em off and let me see what you've got". I did what I had to do and dropped them and I never felt so naked before as I watched her eyes study my body. "turn around so I can see your ass". After being thoroughly inspected, she stood up and grabbed my dick and said "let's go downstairs" and lead me by my dick down the stairs and to her bed.

 

[nailz]

During a really bad storm/power outage with my yoga teacher. I said eww, I don't want to go out in that, and asked him if I could hang around the studio until it stopped.
So we sat around a bunch of candles just talking about silly stuff and eating chips and drinking vodka-OJs and totally out of the blue he asks "Want to fuck?" (So much for romance )
I thought about it for a bit and just said OK, why not..

Don't judge: it's just sex, and it's a great way to pass the time

 

[HorseHung40's]

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

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

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

 

[pradelicious]

I was in a taxi with my best friend after a night out in town celebrating my birthday that day. It was a weeknight so my friend had to go home early to sleep and the clubs were not really happening since most people had to work the next day except for me who took the next day off. I was seated in the front because my friend wanted to have a quick lie down and sleep at the back after a long day for him.
After dropping my tired friend home at his place, the cab driver, a very nice mannered and clean looking guy in his 30s broke the ice with me and asked me about my night. I just explained that it had been my birthday dinner and it was rather unfestive as it was a Tuesday. He chuckled and said that I was still young and there were going to be better birthdays.
I asked about him and he said he'd been married for 5 years, no kids and he drives the cab on top of having his own business. Then I realized that the guy was rather hot looking because when we were chatting earlier I had not turn to look at him. I told him that it was sweet of him to try and cheer me up. He asked me if I had a girlfriend and I said "no". He asked me "why not" in a chuffed kind of way. I hesitated for a while and said that I was not attracted to girls. Then it became awkwardly silent. He turned on the radio to some A/C station. Michael Bolton played.
We reached the street that was adjacent to my house. It was 12.40 am. He stopped the car at the side of the street. I was puzzled.
He then asked: " your house must be on the next street?" . I confirmed it. He took a few minutes to continue but then said "so, what kind of things do you do to another guy?"
I told him, " I don't know, but I like to suck dicks I guess..." He looked ahead into the quiet night throught the windscreen. Most of the neighborhood was dark except for the street lights.
Then he turned to me and asked " do you want to suck mine?"
I thought ; hell why not, it was my 24th birthday, I was single, the guy was very polite and cute...

So I unzipped his jeans, by this point our seatbelts were off and he was hard. He let me take control and seemed inexperienced to that kind of behavior. 8 inches, cut, smells of clean musk, well groomed from what I saw in the soft lighting. I reclined his seat and went to town.
He was so into it, arms both up and his eyes closed, I made sure each testicle and inch of his penis felt my 24 year old tongue while my hands caressed his inner thigh, flat tummy and chest. He was quite a moaner. About half an hour later, while my tongue was on his frenulum, he got up and held my head and politely told me that he was going to shoot his load. Before he could finish his sentence, a very hard hitting load shot up and hit his car windscreen, my nostril, then subsequent jizz shot him in his eyes and clothes. It was pretty intense.
Then he profusely apologized and told me 1. He hadn't cum in more than a week because his wife has her period.
2. I was his first gay experience.

I reassured him it was fine, then he asked me if he could make it up to me by taking him home where " I can do whatever I want to him". I thought about it for a second then I lied saying I had to work in the morning. He gave me his number, I pretended that my neighbor's house 4 doors down was mine.
I never called him, because I did not want a regular fling with a married man.

 

[bravesoldier]

I've told this one before but truly, it was quite unexpected. Rather, how everything in the meet unfolded and where. Quite a few years ago I chatted with a guy through some avenue, don't quite remember where. We were about an hour apart and he was horny as fuck to suck cock and swallow a load. He said if I'd meet him halfway he could pull off leaving his job to make it happen. That was the first thing, the guy actually left his job for a quick suck meet. We met in a small town around halfway for both of us. He knew of, get this, a cemetery we could meet at. It was that day I realized cemeteries are not places that are deserted. People visit them regularly, lol. We get there and his initial stare was amazing, I never forgot it. We stood and talked for just a minute, him describing what he would do if someone were to ride through and see us in an out of the way place. So, pretty quick after the instructions he quickly led me to what he called an enclave in the growth behind the cemetery. I felt like a kid playing in the woods again, lol. As quick as we got deep enough inside the growth, this guy, probably in his late 30's, dressed in office attire quickly dropped to his knees and furiously began sucking my cock. He worked me good moaning and really getting into it. It wasn't long before I was began to feel cum rising from my nutsack into my urethra. I told him I was about cum and he said to really give it to him. Then came the point of no return and I pumped my load straight in his mouth while listening to him moan tasting it and wanting more. When he got my last drop and sucked me clean I dropped to my knees for him. As I remember he had to jack himself off but that was cool as sometimes that happens. He then said he was on a serious time constraint as to get back to his job. So.. just that quick we ducked into the bushes, he drained me and we walked back out. Where we came out of the overgrowth was kind of behind the cemetery and sure enough when we emerged from the woods someone was driving through. That's when he carried out his plans to divert suspicion of cock sucking in the woods. He began pointing at a couple of things so the people driving through would think we had something to do with the cemetery, perhaps a burial boundary line or something.

As quick as the car was gone we got back to ours, said goodbye and left. Driving home I'm on instant replay.. This guy left his job, drove at least half an hour, got on his knees in the woods behind a cemetery to get a guy's load in his belly.

The last thing I remembered before he drove off was him speaking of having a piece of gum handy to take the smell of sperm off of his breath. Very memorable encounter.

 

[massi23ita]

This was totally unexpected... I was at airport and my flight got delayed so I decided to have a look on the terminal shops. While I was walking around I met eyes with a guy: no words needed, he goes to the nearest toilet and I follow him. I found him waiting for me in a cubicle, we closed inside e I had one of the greatest bj of my life.

 

[HOU_HEADHUNTER]

Recent experience with a married guy who only had a picture of his beautiful cock as his profile picture. He hit me up first. Of course I'd seen his profile many times because he's in my area so his profile comes up next to mine often. He introduced himself and told me he was happily married and he was interested in meeting someone close for regular encounters. He told me he and his wife enjoyed kink and his wife encouraged him to reach out to me to see if I'd be interested in coming to their house and giving him a blowjob while she watched. He clearly stated that she wasn't interested in anything more and she would only be a set of eyes as it gets her off seeing gay guys sucking him off. This was a new experience for me and I had to think about it but figured what the heck. I took a chance and went to their house we chatted had some drinks and went straight to work. They told me they got turned down a lot by gay guys because of his wife being present. I told them I was hesitant at first but after they explained their unique fetish I felt it was cool and decided to do it. I sucked him off while he was reclined in a chair while his wife sat over to the side playing with her clit and nipples. His eyes were glued to her playing with herself and occasionally he'd allow himself to look down at me going to work. I noticed his eyes rolling back from time to time and that really got his wife going. Didn't take very long before he was gripping the side of the chair and his body was getting rigid. He yelped out that he felt like he was about to cum so I continued. I was alternating between sucking his thick cock and sucking and massaging his balls and he was loving his balls being sucked just as much as he was enjoying my tongue roiling around the head of his cock and along his shaft. I went down to suck his balls again thinking I had plenty of time before his load would shoot forth. My timing was a bit off because once I was on the balls he shot the biggest load up into the air and it landed on the both of us. I realized his cock was viciously bobbing and spitting so I tried to coral it again with my lips as it shot spurt after spurt of warm cum into the air. I managed to wrangle it on the last 2 squirts so that I could enjoy the thick baby batter that was to be my reward. He was coming down from his intoxicating euphoria with his cock gently throbbing against my tongue when his wife squealed and started to squirt from her vagina just as he was finishing up. They both got off and that was a first for the both of them. His wife had never squirted before and was quite shocked by her own body's reaction at it's height of sexual arousal. I think she scared herself and her husband had a huge smile on his face. He thanked me for being the fist man to make his wife cum without even touching her. It was such a wonderful experience and we will be meeting up on a regular basis now to try to duplicate that experience.

 

[MrTMT]

Reading some of the replies, this reminded me of an encounter I've had many years ago when I was in late 20s. It happened around this time, black Friday to be exact. It was a sunny mid afternoon and the weather was typical cool on that day. For whatever the reason, I found myself around Manhattan, NYC.
Weird as it may sound, but I was at the stairway entrance to NYC subway, it was crowded with people either were going up or heading down. Then, here came a nice looking, slender white young man around my age on his way up the stairs with 2 shopping bags, the type that from a Department store (seemed like he went for Christmas shopping). We instantly locked eyes, flashed each other with big smiles and the conversation started, I don't remember details on the conversation, but what I can remember was that I turned around and followed him and talked along the way. Next thing I know, we ended up at his place. He lived near there, a very nice place - more of the high ends type apartment.

I followed him in and walked up the stairs as he lived on the 2nd floor. His bedroom was on the front side. Without any more conversation, we're both naked and he let me fucked him raw (no condom), right there on his bed. First, I did a doggy-style and finished in a missionary style, shot my cum in him, the guy was moaning and seemed enjoy the entire time. I don't remember we did any foreplay (jerking each other or sucking) we just went right into fucking.

He has a decent size, slightly upward and smoothly type curved cock, circumcised. He jerked himself off while I was fucking him in the missionary position. He came about the same time as I did. It was as hot as fuck at that time.

Once done, I cleaned up, got dressed and left, that was it. There was no exchange of contacts nor did I stop by his place any time after that.

 

[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.

 

[illusionguy]

I have posted about this before but here goes as it fits in here as unexpected. It happened in mid January.

I had recently arranged for a friend of a friend to mow my grass and when he arrived the first time it was really hot and he asked if he could have a shower after he finished because he had to pick his kids up. I had met him a few times before so I told him that would be okay.

While he showered I got us both a beer for when he finished. He came into the lounge naked, and still drying himself, to get his beer and I got a surprise to see that he has a really big fat uncut cock that was half hard. I commented on the size of his cock and he asked if I wanted to take pics of it but stupidly I didn't. He had a drink then asked me if I would like to play with him. I could not turn him down so we started kissing until I said we should take it to the bedroom.

When we got there I stripped and we kept kissing licking sucking. He said he was a bottom and I told him that I was mainly top so we could be a good fit. I rimmed him for about 10 minutes to get him wet and loose then he sat on my cock and rode me for awhile before I got him on his back and pounded him. Just before I cum he asked me to cum on his face and he got on the floor and as I cum on him he wanked himself until he blasted over his chest.

Up until that time I had no idea that he was into men as well as women. We have since got together whenever he mows the grass and even at other times. One day while fucking him I asked him if he knew how big he is, but he didn't, so I measured him. He is 8.3" x 7.2" of beautiful uncut cock.

 

[Godslittlejoke]

I was working in an adult bookstore/head shop. Dude in his 20s came in. He was lean, good looking and nervous. He was asking a ton of questions about coverings and straps. He couldn't find one big enough and asked if I had any that might work. I found my biggest one which was actually a men's leather wrist band and told him to try it on. Instead of going into the changing room he just stepped to the end of the counter, pulled down his pants and asked me to help him. We never did get that strap on him. It wouldn't have fit anyway. He was definitely over 9 inches and thick. My jaw hurt for the rest of my shift but it was worth it. There were a couple of regulars who watched but they were to scared to join in. He came back after closing. My ass hurt until we opened the shop back up in the morning. Word got out and business really picked up for a while.