Most unexpected sexual encounter

CalifornianSTUD

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I have a ton but I would say the absolute most unexpected was when I was leaving an escort job at a pretty fancy with a pretty attractive young rich guy. As I’m learning I stop by valet and a cute little Latino guy is working. I hand him my ticket and says “we both have Kias”. I smile and say “oh, nice”. He then says “most people who stay here drive very nice cars”. I say “they are over compensating”. And he says “like you mean they have small penis?” So I say “yea, something like that”. He says “so does that mean you have a big one?” I said “no, it’s not big, it’s huge”. He says “must be nice. I wish I had a big one”. I say “do you want mine?” as I slowly unzip. He pulls me into his little booth and I whip it out. . We start making out and I undo his pants and lower them enough to where his ass it out. I flip him around and spit on his hole and then go to town. He moaned ‘ay, ay, ay, ay, ay... for 45 minutes straight. When I was done he asked what room I was staying in but I told him I wasn’t staying there. He asked why I was here at 4am so I told him “I was paid by a guest to fuck them for the past 3 hours”. He then asks “you fucked him for 3 hours then came right to me?” I told him yes. He then asks how can he find me, so I gave him my number.

Sad part of the story, he was deported a week later.

Less sad part is, I flew down to Guadalajara a month later to see him. He was fine but had 8 roommates. When I stayed there he told them all to let me fuck them, so during that week I had a house of sexy little Mexican guys at my sexual service.
 

Oztrich

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This past weekend I was invited to go on a motorcycle ride with three other guys. I new one of them, but had never met the other three. All four of us are bookish types and the motorcycles were a Moto Guzzi, a Triumph, a Laverda and a BMW. The ride took us on a circuitous route to a restaurant in a small country town, then to a spot by a nearby small lake. It was a great ride!

The ride to the restaurant was sedate and nice, through beautiful country that winds back and forth along a highway that ought to be called a laneway in spots. We stopped at the restaurant to eat and talk and found a good table close to the back of the restaurant that also had the benefit of a great view of the mountains. During lunch it became clear that the two men I didn't know were a couple. They were both articulate, nice guys who had been together as a couple for several years. The conversation throughout lunch was light and interesting, just as I like it, and, after the tipping the server, we all paid our own share and left.

The lake is close by and accessed after going up over a rather substantial hill, through a series of sharp bends and by entering an area managed by the state. We rode down close to the edge of the lake and we all dismounted and sat together by the lake shore. The talk was light as it had been in the restaurant and I did not think much about any of it. One of the men excused himself so he could use one of those forestry-maintained restrooms. The guy who invited me got up and followed, heading to the restroom. The man who was left looked at me and, out of the blue, half asked and half stated, "You know we're gay? Right?" I told him I had figured they were as they did nothing to hide it. He followed that with, "Did Mac say anything to you about our routine when we go for a ride together?" I repeated to him that I was told the ride would be a ride to a restaurant, down to the lake, and back over the mountain to town again. He asked, "Did he say anything about where we go after the ride?" I told him, honestly, that he didn't. He was quiet for a while, but finally said, "We usually go back to our place (referring to his and his partner's home) or Mac's and spend some time there." All I could come up with was, "Oh... Okay..."

About this time Mac and the other guy returned from their visit to the restroom. The guy I had waited with, Eric, asked Mac, "Did you say anything about what we do after a ride to [me]?" Mac responded, "No, I wasn't sure if I should... I was nervous about it..."

From there I learned that these three men ride together regularly and always finish the ride at one or the other of their homes and "play." Mac apologized and said he thought I might be bi or gay and had gotten shy about approaching me about it. I told him he was half right and said, "I'll let you off the hook... I'm bi..."

At Eric's house it did not take long for the four of us to be sitting around naked and talking. Four middle-aged guys together, butt naked and getting set to get up close and personal. The day ended at almost midnight on Saturday night. I was still hard from the little blue pill as was Mac. Eric and his partner wanted to go to bed and that left Mac and me to go our separate ways. Outside, standing by the motorcycles, Mac asked me if I wanted to go to his place and I told him I did. I followed him back to his place and we went right in and right to the bedroom, we had sex and slept until almost nine on Sunday morning. Mac got a call from Eric's partner, James, who asked if we had slept together to which he said yes we had. Mac invited James and Eric to come over for lunch and the day was spent with all four of us united in sex play.

The whole thing was totally unexpected, and I have seen Mac every day since then.
 

LuckyO

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My (then) wife and I lived in a large apartment building. She taught school in an adjacent town. There was a couple living in the apartment above us that we went out to dinner with sometimes. She worked in a bank that closed on Wednesday afternoons. She was absolutely gorgeous. One Wednesday I came home at lunchtime to change into a suit for a briefing I had to give that afternoon. I changed and as I was coming out the door, my gorgeous neighbor was coming home, walking up the stairs. She asked what I was doing home in the middle of the day and I told her. She asked if I have any lunch. I told her that I had not. She invited me upstairs to her apartment to have a bite to eat. I had a little extra time so I told her, "Yes,' and followed her upstairs to her apartment. As soon as we got inside her apartment she turned to me and said, "I am your lunch; eat me." Apparently my wife had told her that I was good at eating pussy.

After some good foreplay I went down in her and over about 30 minutes gave her there orgasms, the first time she every had multiple climaxes. We then has sex. Afterwards she said, "We need to do this every Wednesday;" and we did, for about two years, until we moved away.
Enjoyed
 
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Fontenoy

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The cruise was a two week deal with a lot of island stops along the way. We had sex eight or nine times before the cruise ended and it turned out he like m/m sex as much as I do.

Was a great cruise with even better sex!

Thanks for sharing such a great story!
If you had time, would love to hear more about it. Did he overcome his shyness? Did he get to last longer? How adventurous did he become? Thanks again.
 
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A number of years ago, my (now) wife and I were visiting an upscale nudist resort in Florida. At the time, we were dating regularly, but not exclusively. On the morning of our last day there, I noticed 2 older ladies (mid 60’s or so) whom had not been there earlier. Both were nicely tanned all over and in good shape, but one of them in particular caught my eye as she had an awesome rear end and seemed to be showing it off a bit.

About mid morning, my wife asked me to go back to our room to get her a new pack of cigarettes. Even tho we were only about 100 feet from our room, with the resort layout, to leave the pool area I had to go up about 15 steps to the main club house, thru the clubhouse, down a slight hill and across a parking lot to our room. It wasn’t planned, but as I got to the foot of the clubhouse stairs the older awesome butt lady also got there at the same time. Being a gentleman, I let her go first and followed about 2 steps behind her.... just enough for her beautiful derrière to be at my eye level!! At the top of the steps, I opened the clubhouse door for her and initiated some small talk which continued as we approached the rooms. At that point, I asked her if I could pay her a compliment. She looked at me and smiled broadly and said “of course.” At that point, I mustered the courage to say “You have the perfect (brief hesitation) ass!!!” She sorta chuckled and said “thank you. It’s talk like that that may get you some of it.” I replied “promise?”

At this point, we were at her door. She unlocked it, cracked the door slightly, looked at me and asked “ got a few minutes?” I said “sure.” She then opened the door and nodded for me to follow her. Once inside, I stood at the foot of the bed as she went over to a table and took something from her purse. She told me “get ready to put this on” as she handed me the condom. As I was tearing into the foil wrapper, she dropped to her knees and started sucking my cock. When I was throbbing hard she got up and bent over the side of the bed and spread her legs as I unrolled the condom on my shaft and started to push into her from behind. With the excitement of the moment and the thrill from the view I had as I fucked her, the entire encounter was much too brief, but is maybe the hottest single sexual experience in my life.
 

LuckyO

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A number of years ago, my (now) wife and I were visiting an upscale nudist resort in Florida. At the time, we were dating regularly, but not exclusively. On the morning of our last day there, I noticed 2 older ladies (mid 60’s or so) whom had not been there earlier. Both were nicely tanned all over and in good shape, but one of them in particular caught my eye as she had an awesome rear end and seemed to be showing it off a bit.

About mid morning, my wife asked me to go back to our room to get her a new pack of cigarettes. Even tho we were only about 100 feet from our room, with the resort layout, to leave the pool area I had to go up about 15 steps to the main club house, thru the clubhouse, down a slight hill and across a parking lot to our room. It wasn’t planned, but as I got to the foot of the clubhouse stairs the older awesome butt lady also got there at the same time. Being a gentleman, I let her go first and followed about 2 steps behind her.... just enough for her beautiful derrière to be at my eye level!! At the top of the steps, I opened the clubhouse door for her and initiated some small talk which continued as we approached the rooms. At that point, I asked her if I could pay her a compliment. She looked at me and smiled broadly and said “of course.” At that point, I mustered the courage to say “You have the perfect (brief hesitation) ass!!!” She sorta chuckled and said “thank you. It’s talk like that that may get you some of it.” I replied “promise?”

At this point, we were at her door. She unlocked it, cracked the door slightly, looked at me and asked “ got a few minutes?” I said “sure.” She then opened the door and nodded for me to follow her. Once inside, I stood at the foot of the bed as she went over to a table and took something from her purse. She told me “get ready to put this on” as she handed me the condom. As I was tearing into the foil wrapper, she dropped to her knees and started sucking my cock. When I was throbbing hard she got up and bent over the side of the bed and spread her legs as I unrolled the condom on my shaft and started to push into her from behind. With the excitement of the moment and the thrill from the view I had as I fucked her, the entire encounter was much too brief, but is maybe the hottest single sexual experience in my life.
Hot unforgettable experience
 
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nburbsbiguy

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A number of years ago, my (now) wife and I were visiting an upscale nudist resort in Florida. At the time, we were dating regularly, but not exclusively. On the morning of our last day there, I noticed 2 older ladies (mid 60’s or so) whom had not been there earlier. Both were nicely tanned all over and in good shape, but one of them in particular caught my eye as she had an awesome rear end and seemed to be showing it off a bit.

About mid morning, my wife asked me to go back to our room to get her a new pack of cigarettes. Even tho we were only about 100 feet from our room, with the resort layout, to leave the pool area I had to go up about 15 steps to the main club house, thru the clubhouse, down a slight hill and across a parking lot to our room. It wasn’t planned, but as I got to the foot of the clubhouse stairs the older awesome butt lady also got there at the same time. Being a gentleman, I let her go first and followed about 2 steps behind her.... just enough for her beautiful derrière to be at my eye level!! At the top of the steps, I opened the clubhouse door for her and initiated some small talk which continued as we approached the rooms. At that point, I asked her if I could pay her a compliment. She looked at me and smiled broadly and said “of course.” At that point, I mustered the courage to say “You have the perfect (brief hesitation) ass!!!” She sorta chuckled and said “thank you. It’s talk like that that may get you some of it.” I replied “promise?”

At this point, we were at her door. She unlocked it, cracked the door slightly, looked at me and asked “ got a few minutes?” I said “sure.” She then opened the door and nodded for me to follow her. Once inside, I stood at the foot of the bed as she went over to a table and took something from her purse. She told me “get ready to put this on” as she handed me the condom. As I was tearing into the foil wrapper, she dropped to her knees and started sucking my cock. When I was throbbing hard she got up and bent over the side of the bed and spread her legs as I unrolled the condom on my shaft and started to push into her from behind. With the excitement of the moment and the thrill from the view I had as I fucked her, the entire encounter was much too brief, but is maybe the hottest single sexual experience in my life.

I'm curious. Did you ever tell your (now) wife what happened?
 
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Oztrich

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Thanks for sharing such a great story!
If you had time, would love to hear more about it. Did he overcome his shyness? Did he get to last longer? How adventurous did he become? Thanks again.

He got braver and more comfortable as the cruise went on. He would cum very quickly every time I ever took him in my mouth, he never got over that. I don't know how to answer about his adventurousness except that he became quite open about what we were doing. It was a very pleasant time.
 

nburbsbiguy

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Yes. We dated for 3 years non-exclusively before becoming engaged. During that time, we both had multiple FWB arrangements and numerous one night stands.... she more so than me.
Nice! Ever have a threesome with her and someone else?
 
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Nice! Ever have a threesome with her and someone else?

No. We’ve both had numerous 3sums, but not together. All of them happened years before we ever met. We have discussed it and I think I have an interested participant, but wife is hesitant to get back into it.
 
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Fontenoy

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He got braver and more comfortable as the cruise went on.

Thanks for taking the time to reply. To me it's a perfect 'most unexpected sexual encounter' story, and very well written too. What I meant by asking if he became more adventurous, was did he recipricate in oral sex and if so, did he get into it?
Thanks again.
 

SamMann75

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My son's class parents hosted a fundraiser for a charity, all dressed up and dinner and drinking and dancing (just the parents no kids), a good time was had by all.

After the event we were walking with another set of parents and the light snow was getting heavier and the wind picked up. The other dad asked where we were parked and as they were closer offered to drive us the extra block to our car. As we live a good hour outside the city I thought about getting a room at the hotel we were passing. They came in and waited to see if we got a room before going along. My wife chatted with them in the lobby as I went to the desk. I got the only room available and returned to our little group and said all they had was a 2 bedroom suite, why don't you come up instead of driving in this? His wife said you have been drinking dear and the roads are not getting better.

When the elevator jolted I think we all felt a little more buzzed then we realized as we all bumped into each other grabbing anything to steady ourselves and pulling each other further off balance...and had a good laugh. This couple was a good 15 years older then us. We got into the suite and I half collapsed into the couch, his petite wife gently sitting beside me as he swept through the room to the floor to ceiling windows commenting on how lavish the room was. He called to my wife who was still standing near the door, then walked over to her saying she had to see this view. He walked her across the room, up the three steps to the area in front of the windows that had a love seat and 2 chairs, and right up to the window. He stood behind her and leaned over her shoulder and softly said isn't the harbor beautiful in the snow? My wife purred, his breath must have been warm on THAT spot behind her ear...he put his hand on her hip...his wife put her hand on my knee and said your wife is truly beautiful...I know I had a conversation with his wife about mine but I can't recall anything I said...I just watched as his hand slid up her side, then slowly lowered the zipper from under her arm on her strapless dress. The dress fell to the floor as he pressed up against her, her hand coming up onto the window near her shoulder, I could see her bare breast pressed against the glass and she gasped and said it's cold and he softly said in her ear and your so hot and then he kissed her neck right behind her ear....his wife now telling me how the moment we showed up tonight he's been talking about what a magnificent dress she was wearing...his hand on her hip I watched his hips press forward and my wife gasped...then the window fogged momentarily as she exhaled and moaned your so big as she pushed her hips back against him. Still gripping her hips he pulled back slowly and pressed forward...further and she moaned your so deep...oh god I need this. His wife said don't worry dear he's not really that big as her hand slid up my leg and grabbed my hardon through my pants...and she leaned into me and whispered ok for her maybe it feels really big as she gave my dick a squeeze. We sat there in silence with her squeezing my dick through my pants as her husband took long slow deep thrusts into my wife, my wife pushing back to meet his thrusts, her body trembling, her legs shaking her moaning loudly the glass fogging around her hands and face and breast pressed up against the glass. We watched as she had two very intense orgasms, and after about 15 minutes he grunted he was going to come and she yes give it to me and she had her third orgasm as he buried himself deep and lifted her off her feet into the window as he came.

When he pulled out my wife turned around and kissed him before getting on her knees and and start cleaning him off. He certainly wasn't big by my wife's standards, but he was better then average and fairly thick. His wife whispered that she'd suggest we take out turn but...and I felt her squeeze my dick...which was no longer hard and felt sloppy. I'm not sure when I came but soon I found myself between her legs giving her oral listening to her husband moan and exclaim in surprise that he was getting hard again. Moments alter I heard my wife grunt and moan...his wife said your wife looks incredibly sexy on all four. I heard my wife grunt again and again and I turned to look over his wife's thigh to see him taking her doggy style, her panties were gone but she was still in the garter belt thigh highs and heels, his pants were around his ankles and his shirt was open as he knelt behind her and was not giving her long hard fast thrust, which she was pushing back against and rolling her hips in what she calls the figure 8. She moaned oh yeah give me that big cock hard, he pulled her hair back and slapped her ass saying you like it rough and she replied I do right now...I felt a hand on the back of my head and I resumed performing oral listening to him pounding away to my wife's enjoyment. After three orgasms (no idea how long) she pulled my chin up to her surprising firm stomach, I laid my head on her stomach watching my wife now on top of him riding him with her breasts in his face. For 40 minutes I laid between her legs on the couch, my head on her stomach her hand playing with my hair and her foot rubbing my hard again cock watching our spouses fuck in several positions, my wife having several orgasms before he came in her again. About 10 minutes before they ended his wife said goodness he's going to have to go back to the chiropractor after your wife's done with him..and with her foot rubbing my cock through my pants I came again.

After they finished and were just laying on the floor breathing heavy she stood me up, letting her dress fall off she took my hand and wearing just bra and panties led me to the bathroom, undressed me and cleaned my off with a warm face cloth before rinsing my underwear in the sink and hanging them up to dry. She took the hotel robe and put it on me and led me back out to the couch and sat on my lap, started telling me how incredibly sexy the two of them looked together. He was laying flat on the floor and my wife was once again seeing to the cleanliness of his softened cock. Licking and sucking it gently, her nipples looked swollen I don't think I've ever seen them so big. I think it was a surprise to us all as he started to stiffen again. He said are you up for it, my wife said I might never get the chance again as she climbed up his body and onto him. They were gentler this time, a few short periods of hard and fast but mostly gentler. In the light as they changed positions I noted how red my wife's ass was, and there were marks all over her breasts as I remembered he had sucked on them a lot during their second round.

The next morning he joined my wife in the shower and then we left and went to our separate homes. We see them at school all the time and talk like old friends. We've never done anything since, we've never even talked to them about it since. It's like it never happened.
 

TypicalWhiteGuy

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I ran into a gay kid from high school who I used to bully and beat up a lot for being queer (I was still closeted) at a bar about 10 years after we graduated. Ended up talking with him for about half an hour, then his boyfriend showed up... I topped both of them, lol
 

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I grew up in one state and moved to another. This girl from where I grew up was in rehab I believe in the state I moved to. I picked her up, took her to a party that was going on at a friends house, fucked her in an empty bedroom at the party, left the party and drove her back to rehab. It was bonkers. And she had the biggest tits and super skinny. Really blew my mind and probably led to me getting my first beautiful slampiece from the state I moved to.

It was a surreal moment but I remember most of it vividly.