Most unexpected sexual encounter

[Plasticroad1]

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

Hey man, tried to send you a PM but it said your privacy settings don't allow them. Anyways, crazy story! That's absolutely wild

 

[deleted1827711]

This wasn’t necessarily sexual as it was erotic. I used to live in NYC and one day the train was packed. I was standing holding the overhead bar and someone behind was standing opposite holding bar. We happened to be the exact same height and it was so crowded that our butts were smushed against each and rubbing. He had a plump juicy ass too. Was so hard while it was happening we both looked back at each other few times but we both couldn’t do much cause it was so crowded

 

[ericbear]

Years ago, I was taking a short course for work at UC Berkeley. I was staying in a hotel in San Francisco, and taking the BART train into Berkeley every morning, along with all the other commuters. One early morning as I'm waiting for the train, I see this cute young man (like half Daddy's age) who looks like he is trying to find his way home after a rave last night. I think he's crusing me. I move to a place under the stairs, where no one would normally stand, and sure enough he follows me. He smells faintly of weed, and seems still just slightly buzzed. A taste of his lips confirms this. We embrace, and he starts to grope me, but then my train pulls in. It's for work, so I've got to go, but he follows me on board. He sits on my lap on the train, and we start kissing. For the whole trip, surrounded by morning commuters, we sucked face, as he sat on my lap and throbbing cock. (It was San Francisco, in the pre-gentrified days, so no one really noticed.) When we got to the Berkeley station, he wanted to find some place to fuck, but I really had to go, as class was in 15 minutes. My memory is hazy, but I think I did run into him later on another, personal trip to SF, and we took care of things.

 

[xguy311]

This wasn’t necessarily sexual as it was erotic. I used to live in NYC and one day the train was packed. I was standing holding the overhead bar and someone behind was standing opposite holding bar. We happened to be the exact same height and it was so crowded that our butts were smushed against each and rubbing. He had a plump juicy ass too. Was so hard while it was happening we both looked back at each other few times but we both couldn’t do much cause it was so crowded

Oh I have some GREAT subway stories too! Biggest thing I miss about the crowded trains is unexpected hard on and butt touching ;-)

 

[deleted1827711]

Oh I have some GREAT subway stories too! Biggest thing I miss about the crowded trains is unexpected hard on and butt touching ;-)

Would love to hear

 

[tippindascalez]

Would love to hear

I've had my ass grabbed on a crowded train and my dick was grabbed as well. Never never knew who did it...but it wasn't a pleasant feeling.

 

[theplayerking]

I was in Santiago, Chile for work a few years ago. I had just taken a shower and only had a towel wrapped around my waist when a male housekeeper (the only male housekeeper I’ve ever seen in any hotel anywhere) knocked on the door. I let him and noticed he was pretty young and very obviously gay. After I closed the door I let my towel fall around my ankles and started playing with my cock. He came over, looked through the peephole on the door for his coworker and locked the door. He then dropped to his knees and started sucking my cock.

I pulled down his pants and we started 69ing on the floor. I don’t speak Spanish and he didn’t know any English so I just said Activo/Passivo? Unfortunately he didn’t want to fuck. We kept sucking each other until his coworker knocked on the door. Once she went away he shot in my mouth, zipped up and snuck out with his cart.

I got dressed quickly and went down to the lobby so they could clean my room.

That’s the only time I’ve had truly unplanned sex. I used to answer the door for food delivery guys in my boxers, but they were never hot enough to play with.

 

[CockMySuck]

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

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

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

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

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

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

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

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

 

[chrisrobin]

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

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

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

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

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

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

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

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

Hopefully soon you'll get together, get naked and at least suck each other off if nothing else. Just go for it, take whatever comes.
Sometimes out of this situation great things happen, a chance word. an action and hey presto you go for broke and end up enjoying things.
At least you know the cock on Josh shoots well and wow, one delight to blow! Keep us posted

 

[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.

 

[chrisrobin]

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.

Must have been an Italian do do it so beautifully. I was on the Grand Canal one time, working when this guy caught by eye and when we had a break I headed in his direction. He lead me to a quiet corner,dropped to his knees and sucked me off expertly. When he'd swallowed he just nodded thankyou and wandered off.

 

[Nkw17]

I've been having a lot of unexpected encounters! I'm here to tell you about the that 2 happened today.
Soo to start my day off I went to go drop something off at Goodwill & as I was putting my things in the bin a hott 5'11 Hispanic looking guy walks in & I notice he's kind of flopping around in his shorts. After I went to my car & said to myself let me go take a look around & be seen. I saw him & he kind of looked at me; Next thing you know I was going to go pee but I saw him go to the bathroom 1st. I hesitated to go but as soon as I went in he was standing sideways at the urinal showing off, I looked & he looked at me then turned all the way to the side to let me stroke it. It was the biggest dick I've seen in person!!! It was about 8 1/2in Tan colored, thick & uncut looked vey similar to Preston Parkers (no exaggeration) He teased me with it & said that's enough as I stroked it. Omg He had me feeling Hott after that, I wanted to suck it but he was just showing off.

Later on I went to the mall because I was still feeling hott.
I walked around eventually ending up in Ross but on my way out this guy (5'7 with a face similar to Casper Smart) coming from the isle looked at me & I looked him up & down. I headed to the bathroom right across & he followed. As I was in the mirror he kept turning around & I started making eye contact with him. He was smiling in a hott way; telling me to come in the stall; when I did he began squeezing my ass pulling my pants down then started stroking me. Next he started unbuckling his pants & pulled an uncut 5 1/2-6in I couldn't tell his nationality but he was most likely Puerto Rican. I was stroking him & he began fingering my ass & squeezing my nipples but it didn't feel good. After that he whispers for me to suck him. I pulled out a condom & he said No. I said I can't do it w/o a condom. Soo we just kept going & he began to get soft. I think he got offended? Lastly I went down in front of him like I was going to & he said kiss my balls, I did & put my tongue on them a little. He then put his pants up & left.

That 1st guy was the one I really wanted. I wasn't expecting to see a huge penis today but it was Niiiiice!

 

[stretch8888]

I travel alot for business so have had a few fun times at hotels . message me for more details

can't message you cause of your setting but have many stories from the road

 

[deleted5698211]

I gave a 75 year old a blowjob as a dare haha. I thought it was a mad joke until he pulled his pants down. He said it was the first orgasm he had in 3 years lol.

 

[SpruceBringsteen]

Pretty much every one!

 

[tippindascalez]

I gave a 75 year old a blowjob as a dare haha. I thought it was a mad joke until he pulled his pants down. He said it was the first orgasm he had in 3 years lol.

LOL Older fellas need to bust a nut too!

 

[Thequestionis]

I was working at a pub for over a year and we were hosting a wedding reception. After everyone had left the staff sat and drank as the day after the pub was closed for cleaning. After a few drinks we heard a knock at the door and one of the guests had been left behind, an 18 year old lad. We invited him to drink with us until his lift came.

We talked about all sorts of shit for hours and were quite drunk. It turned out that the lad’s lift wasn’t coming so he’d have to stay at the pub with us. There was only one bed in the building which two guys were going to share and I was going to take some cushions and sleep in the office. Now we had this lad with us he couldn’t be left unattended in case he took stuff. I took him upstairs to show him where the toilet was and where he’d be sleeping and BAM! Out of nowhere he clamps his face onto mine. At first I pulled away, then I realised I’d be a fool not to. This lad was about 9 years younger than me, fit as fuck, I couldn’t let this pass. Long story short, we did everything bar fucking and it was an amazing end to the night. Never saw him again and never got a name, but fuck what a night.

 

[MrTMT]

I was living in a small town right outside a large metropolitan city after I graduated from college and started professional work. Been single back then, I enjoyed took the bus or the high speed train into center city at night on weekends. I lived about 15 minutes of walking to the public transportation terminal.

I remember one Saturday night, I was walking home after I went to see a movie in the city. I was kind a late, around 11PM or near mid-night, it was a cool night like around this time of year. Since it was late, the street was kind a empty, although it was well lighted. Suddenly, there was a Jeep pulled over next to me and stopped, I looked over and saw a nice looking younger guy in the driver's seat. He asked me if I need a lift, if so, he offered to drive me to where I needed to go. At that time, my sense of personal safety just went out of the windows, as I was often aware of not getting into stranger's car. I did accepted and jumped on in the passenger's side.

I wasn't sure why I accepted the ride with this guy, even at that time, I knew I was about 5 minutes from my house, I could've continues walking home. Maybe I was flattered for the offer and was physically attracted to the guy. The guy was a few years younger than me, I guessed he was about 18 or19 years old. I never did ask for his name or his age.

So back to my story, after I get in, he started asking me how my day went and why I was still on the street that late. I replied that I went to a movie and provided him the name of the movie. He started to drove pass my house but I didn't say a thing because I was enjoy been in his company. We're chatting along and by the time I knew, he drove into a middle school parking lot a few blocks from my house and parked facing the street. The parking lot was partially dark. The guy was well dressed, looked like he just came out of a party or some kind of formal celebration like a wedding or significant even.

This was the time that he started to let me know that he found me attractive and wanted to watch me jerking off and cum for him. He started to unzipped his pants, showed me his nicely hard cock bugled out of his brief. He lifted his shirt and the t-shirt underneath and motioned me to reach over and touch his cock. At the same time, he reached over and lifted my white t-shirt and started to play with my chest and my nipples. I started to notice he had a very nice smell of some sort of cologne. A minute later, I pulled down my shorts and my boxers and started jerking off while he was attentively watched each of my hand movements. At this time, he finally pulled down his brief and started jerking his cock. I must admit, he has a larger cock than mine, it is nicely thick, cut with a side-curved. However, he complimented that I have a nice cock and wanted to see me cum. I did shoot my load let out a few moaning. I shot my load directly on top of my stomach. I then reached over and played with his cock, then he took over and started to shoot his load. He gave me a big smile right after he came. Looking back, that was completely unexpected but also hot as hell.

The car windows and the windshield started fogged up from the heat.

Once done, he rubbed and cleaned his hands on his underwear. I pulled down my t-shirt pulled up my shorts.

He dropped me off in front of my house.

 

[lbj15]

I'm actually legendarily terrible at reading signals -- once in high school a way-out-of-my-league-cheerleader took me to the lake, parked, and eventually put her head down in my lap. I remember scratching her back thinking "I wonder if she's into me? Is this a signal?" Eventually she drove off. I'm probably borderline asperger's, and don't read signals well in general.

Which is a way of saying: To one degree or another almost all of my early-to-mid sexual encounters were unexpected! In a way, especially as I got older, this has been almost as much of a help as a hinderance; I do pickup techniques without even realizing it ("Why is he ignoring me? No guy ignores me.")

###
But two stand out, both on a similar theme. The first was on a company retreat. We met up at the hotel bar with some people from different branches. This guy in our branch was notoriously bad at getting laid, and I was working furiously to get him with this cute girl from a different branch. Every time she'd say something to me I'd redirect toward "Bob," kept talking him up, etc.

So at some point I got up to use the bathroom which was down this hallway. I came out and she was standing there waiting. We made eye contact for a second before she marched up and kissed me. Things went pretty quickly to her hotel room from there. Got one of the nicer compliments of my life: "I wasn't planning on having sex with you until I felt your dick through your pants." Also, that it really bugged her that I kept trying to fix her up with Bob. Oh also Bob didn't talk to me for months.

###
Second one, I was at a month-long training event. There was a hot girl who was a "club girl", which has never been my type and vice versa (I'm sort of an All-American guy who usually dated/fucked girl-next-door types; "extremely cute" or "very pretty" girls, rather than hot girls, if that makes sense?). I dated more Jennifer Love Hewitt, and she was like Megan Fox, so I never really thought much about it, other than that she was hot but not my type, and was just sort of indifferent toward her.

Toward the end we were in this boring training session at this huge conference table that seated like 50 people. We were seated next to each other at the end opposite where the presentation was. I felt a tap behind me. She passed me a note. I don't remember what it said, but I responded. The notes got increasingly flirty, and then she suggested we play "three truths and a lie" where we took turns writing down three truths and one lie. Things quickly escalated, to where she was writing things like "I've never eaten pussy" (false) and "I love anal sex" (true). Afterwards my co-workers laughed because they figured out exactly what was going on -- "I don't know exactly what she wrote, but you must have loved it, because you were beet red." Anyway, her last one was "I really want to fuck you" three times and "I don't want to suck you" which pretty much got the point conclusively across. There was a mandatory happy hour/mixer afterwards which was the longest two hours of my life, after which we left.

We got into the elevator to the temporary apartments they had rented for us (20th floor) and immediately started going at it. At one point I had her leg up under my arm and was cupping her ass; she had apparently taken her panties off in a bathroom before we left and was absolutely soaked. I commented on this as I started to finger her from behind and she said "I've been like this for 3 hours. It hasn't been very comfortable. Why didn't you just take me into a hallway or bathroom or something at the mixer?" My cock was obviously hard and the head was sticking out of my pants, and she was just slowly and gently squeezing and stroking the head.

When we got to my apartment, the first fucking was over in two minutes, just me bending her over my bad, both of us still fully clothed, but I'm pretty sure we both came. We ended up going at it all night long, and I gotta say there's a lot to be said for club girls! At one point between sessions she said that she thought I was just a big snob since I didn't hit on her and thought that I was too good for her.

Both of these events were pretty instrumental in my understanding of female psychology and led to me getting laid a LOT more; understanding that hot girls could be intimidated/bothered by me, and that maintaining a little bit of distance is hugely effective.