Most unexpected sexual encounter

[Redheadchi]

So in my mid 20s I was walking out of the mall during Xmas time and this guy comes running up from the parking lot and goes "oh my god babe I am so sorry I am late. Please don't go!"

I'm like "excuse me?"

"I'm so sorry for making you wait for me. Let me take you to lunch to make it up to you."

It was so corny but creative and he was cute. We went to lunch and the chemistry was wild. He walked me to my car and we started making out and he got noticeably aroused and there were lots of people around, but neither of us wanted to part just yet so we drove around to find more secluded spot. I "handled" him while I drove.

We found a more quiet spot and fucked in my car. It was the quickest meeting to fucking I have ever experienced. Like less than 2 hours. I was Christmas shopping and certainly did not plan on my day ending up like that. It was hot as hell ngl.

That's hot!!!! Guess I can't try this if I ever run into you

 

[indyfrat79]

Last year I stayed at an all inclusive hotel in Playa del Carmen. I went to the restroom by the pool one day and was taking a leak at the urinal. One of the maintenance guys also came into the restroom and stood at the urinal next to me. He was early 30s, nice stubble, appeared to be hairy, nice soccer build. We made eye contact briefly and I could tell that he was staring at me. I looked over and saw his big uncut dick, looked at him, and smiled as well. He told me to follow him. I said ok and did. He quietly snuck me into the maintenance room on the back side of the pool restrooms. He immediately began feeling me up. He wasn't into kissing and pointed at his wedding ring. I smiled and went along with it. I could feel his growing cock and got on my knees. He began fucking my face and came within 3-4 minutes. It was a huge load for me to swallow. He wouldn't suck my dick but told me to spit on his hand so he could use some of his cum to jerk me off. I too came quickly and shot my load on the floor. He pointed me to the door and I took my seat back near the pool with hubby, telling him only that I had to run up to the room for a minute. I didn't see my friend again but wondered how many guests have had that beautiful uncut dick in their mouth.

 

[bighornso]

My first year in College, I met an older man who was in his 40s and very hot. He had a huge collection of sexy underwear. Being my first year in College, I didn't have a car so he would pick me up. We lived 5 minute drive away from each other. Once in his apartment, he would turn on porn, and start sucking my cock, licking my balls, and rimming my ass while I played with his junk in his hot undies. Eventually the undies would come off and I would play with his cock. He would take my load in his mouth and then drive me back home. This continued for almost a year or two. Anyhow, one Friday afternoon, I was able to borrow my cousin's car to run some errands and decided to stop by his place to see if he was home and we can mess around. I knocked on the door and some other guy opened the door wearing nothing but white boxers. You can tell he was sleeping on the couch and had woken up to the knock on the door. He told me he was the nephew and his uncle was at work. He invited me inside so I took my chances and came inside. We sat talking for a bit and one thing led to another and we ended up messing around. It was hot. Like his uncle, he was smooth and had a nice thick cock with big balls.

 

[San Clemente]

Last year I stayed at an all inclusive hotel in Playa del Carmen. I went to the restroom by the pool one day and was taking a leak at the urinal. One of the maintenance guys also came into the restroom and stood at the urinal next to me. He was early 30s, nice stubble, appeared to be hairy, nice soccer build. We made eye contact briefly and I could tell that he was staring at me. I looked over and saw his big uncut dick, looked at him, and smiled as well. He told me to follow him. I said ok and did. He quietly snuck me into the maintenance room on the back side of the pool restrooms. He immediately began feeling me up. He wasn't into kissing and pointed at his wedding ring. I smiled and went along with it. I could feel his growing cock and got on my knees. He began fucking my face and came within 3-4 minutes. It was a huge load for me to swallow. He wouldn't suck my dick but told me to spit on his hand so he could use some of his cum to jerk me off. I too came quickly and shot my load on the floor. He pointed me to the door and I took my seat back near the pool with hubby, telling him only that I had to run up to the room for a minute. I didn't see my friend again but wondered how many guests have had that beautiful uncut dick in their mouth.

You slut, I love it

 

[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.

 

[indyfrat79]

You slut, I love it

What can I say? I'll never turn down a load from a nice uncut dick.

 

[londonhas]

my (male) mate and I were out on a pub crawl with my (female) friend, it was the first time they'd met and she was flirting with him all night.

anyway she lived the closest to where we partied so ended up at hers to sleep for the night. we got watching some porn and she went to her room and jokingly invited me in... as soon as i walked into the room, she closed the door and stripped naked and started going to town on me!

it was definitely one of the strangest experiences... my mate (legend that he is) ended up in the front room continuing to watch porn, fap, and crashed on the sofa..

 

[illusionguy]

Had an unexpected encounter yesterday.
I got chatting to a random guy in his 30s when I went shopping. Invited him back to mine . We had a couple of drinks then ended up both naked trading blow jobs for about 30 minutes, then got into a 69 where I ended up up rimming him for awhile before I fucked him.
It was such a hot unexpected way to spend a Saturday afternoon.

 

[Thom Hewson]

Most unexpected encounter was the one that launched my sexual awareness at age 53..a salesman at Jos A Bank outright came on to me in an otherwise empty store. Late at night, just before closing. Trying on pants and he started running his fingers everywhere while taking measurements. Soon we were both pantsless and ready to fuck on the dressing room floor....

I prefer to remember moments stolen with my love (we are both married, but sadly not to each other... met him when invited over to dinner at the home of a doctor friend ... the evening started in the living room for drinks and ended with three of us showering together then both topping our host in bed)...

Most every visit was an unexpected pleasure... my love and i enjoyed long walks on forest trails near his house two hours from mine...smuggling pizza and beer into the drive-in and rubbing each other throughout the movie... grilling together after bailing out the basement of his antebellum home ... nodding off together on the couch .... waking up to him in the morning rolling over me, rockhard and gently sliding in... there were other less poetic moments too, rubbing his throbbing stick shift while getting a ride home, finding spot on a dark street to make out inside steamed up windows and suck each other off....cumming in him the first time he'd had a man inside...

But by far the most unexpected erotic moment was laying naked together in the hammock in his back yard, with only the sun as a blanket as we kissed and held each other tightly. Not really the best place to make love.. i had visions of getting injured rolling off together.. but that singular moment of kissing, hugging, and stroking each other with unbridled passion will always define everything we feel for each other....

 

[Thom Hewson]

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.

@HorseHung40's what year did you graduate NU?!

 

[Brazn]

Most unexpected encounter was the one that launched my sexual awareness at age 53..a salesman at Jos A Bank outright came on to me in an otherwise empty store. Late at night, just before closing. Trying on pants and he started running his fingers everywhere while taking measurements. Soon we were both pantsless and ready to fuck on the dressing room floor....

I prefer to remember moments stolen with my love (we are both married, but sadly not to each other... met him when invited over to dinner at the home of a doctor friend ... the evening started in the living room for drinks and ended with three of us showering together then both topping our host in bed)...

Most every visit was an unexpected pleasure... my love and i enjoyed long walks on forest trails near his house two hours from mine...smuggling pizza and beer into the drive-in and rubbing each other throughout the movie... grilling together after bailing out the basement of his antebellum home ... nodding off together on the couch .... waking up to him in the morning rolling over me, rockhard and gently sliding in... there were other less poetic moments too, rubbing his throbbing stick shift while getting a ride home, finding spot on a dark street to make out inside steamed up windows and suck each other off....cumming in him the first time he'd had a man inside...

But by far the most unexpected erotic moment was laying naked together in the hammock in his back yard, with only the sun as a blanket as we kissed and held each other tightly. Not really the best place to make love.. i had visions of getting injured rolling off together.. but that singular moment of kissing, hugging, and stroking each other with unbridled passion will always define everything we feel for each other....

That’s a very sexy collection of memories. So erotic...

 

[Redheadchi]

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.

I don't live far from there and work in that area. I'd live to have this happen haha

 

[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.

 

[hotbtminla]

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.

This was super hot, and being from Los Angeles I know it's true because of the way you described that particular elevator in that particular hotel lol.

 

[Nosuportneeded]

Current wacky ltr is my most unexpected. She’s much younger and hotter than me

I was feeling scrubby and scruffy and “not so in the game”

Best fuck of my like was not expected. Great relation with a truly special person

 

[thongboy]

I was standing in line outside in the dark, waiting to get into a movie. I was with my gf and wearing a black muscle shirt and skintight black leather jeans. A young dude joined the line behind me and all of a sudden he pressed himself against the tight leather of my ass and his hand reached around and started stroking the bugle of my cock. I could feel him getting hard as he pressed against me. Cindy saw what was happening and started laughing, and the kid pulled away.
Later in the lobby I had a good look at him and saw he was a young dude who sometimes came into the sex shop where I worked.
He was in a tank shirt and wearing French stretch jeans that looked as though they'd been painted on. Cindy saw my interest and whispered "3 way?" in my ear. I didn't think so — there was something too obsessive about him, even though I was wondering what it would be like to fuck him. He followed me into the men's room and said I this was not a good time and told him I was only interested in dudes who were bi. I left him in the washroom looking at himself in the mirror while he adjusted his cock. That was the last time I saw him.

 

[8589801]

damn

 

[OctoGun]

This was super hot, and being from Los Angeles I know it's true because of the way you described that particular elevator in that particular hotel lol.

haha I’ve had a few messages saying the same thing. I didn’t realise the elevator was so infamous

 

[chrisrobin]

Gozo, November a few years ago Brilliant and before it got to "discovered". Mornings spent shopping and sightseeing, meeting friends for coffee, walking from deserted beach to deserted beach just seeing the odd fisherman. Secluded corners for nude sunning, absolute bliss.
Back to the hotel for lunch most days, afternoons being social and ending up as the sun went down by the hotel pool relaxing before a dip and dinner and finding out what the evening had in store.
I soon realised that every afternoon there were the same people also relaxing before dinner, in particular this mother and gather and son. I soon became aware the son was watching me and when I did begin to talk to his family was very attentive. Anyway they were on a break and the son was on a gap year before uni, currently working in the family business. This holiday was a belated birthday present to their son who had turned 18 during the summer. The mother was a well set up very well turned out matron, the farther wore shorts with creases, white socks and sandals and managed to look uncomfortable in leisure gear but the son, tatty T shit, baggy shorts and bare footed and a little pudgy with baby fat, crowning glory was an amazing shock of black hair.. Me I suppose short sleeved shirt and short shorts. As the sun went down they always left together to dress for dinner, I always got a look from the son. Once they'd gone I'd have my last dip, a couple of lengths and then to the changing rooms for a shower before also getting ready for dinner. I think after a couple of days of passing the time, discussing where we'd been it came out that I always had a final dip before dinner. So as usual I was showering after my swim a day or so later when I heard a noise and there he was coming in from the pool carrying his shorts but wearing the smallest budgie smugglers I'd ever seen, well packed and pubic hair poking over the top. Missed you he said as he took in my naked all over tan found , nice tan, I've got lines - as he striped of the minuscule coverings and doing a twirl. Yes he'd got big big tan lines and a big big cock with a semi lob. He turned on the jet next to mine, found soap and lathered all over, under his legs and balls and ass as I tried not to look to much and control the urge in my crotch. He was chattering on and watching me as I to soaped and rinsed and tried to avoid frontal views - he had no such concerns by now sorting a full on boner. Always happens he said waving it at me, see it happens to you as well,. He looked round and as usual it was deserted. His hand reached out and grabbed my cock. Wondered what it would be like he said, really nice and with that he pulled me in so out cocks touched and pressed and bodily contact all the way up as his lips touched mine - an electric moment. Dam I wanted to make out but dam I was over twice his age and it was pretty public. His tongue found my tongue, his hands gripped my buttocks but I pulled away. Not here I said, noting the look of rejection on his face, my room later if you can make it.
At dinner sitting at my table for one (not a social animal) I watched him enjoying dinner with his family. As I watched I wondered what they'd have thought had they seen him earlier Then. after coffee I wandered off, took the elevator up to my room opened the door to the balcony and stood there enjoying the evening breeze and late night perfumes from the gardens below. I poured a drink, put one side light on and took stock of the day. God he was a delight to hold, puppy fat yes but mmm so nice to feel and hold and that cock, hard and eager., but really far to tempting so maybe steer clear.
When there was a light knocking at the door.
He stood there in his baggy shorts and torn T shirt grinning and holding a bottle. He pushed past, kicked the door shut, turned and put his arms round me and kissed me, dragged me to the bed and laid on top of me while groping me, feeling me and wildly kissing my neck and ears and giggling as I tried to work out why I was being seduced and enjoying it and beginning to reciprocate. Drinks he said getting up and pouring more into my glass and filling one for himself. Cheers. Now lets get naked Oh he was hard, oh he was eager and oh he was fucking sexy. He laid frotting and kissing as he sort of explained things. Yes he was gay, yes he'd been about and no they didn't know and yes he wanted to be with me Plus apart from a hot gardener I was the hottest totty about! And he liked maturity more than kids my age he said as he eased me onto my tummy and laid on me, his uncut cock wet ended up my bum crack. His fingers found my hole, wet fingers, entered as he whispered in my ear do you? as his end pushed and pushed and slowly he filled me, expertly till I could feel his bush pressed into my buttocks, my hand went round and found huis balls nestling between my legs as I then rose for him to fuck me.
His hands caressed my nipples, my cock and balls and his lips and teeth worked on the nape of my legs as he steadily rose and fell sending waves of enjoyment through my body until he grunted, pushed harder and wow I could feel his cum going down his cock over my sphincter and flowing into me as I let my own load shoot into his hand. We laid back, slowly he withdrew, turned me over and kissed me. Thanks he said, thank you I said. He looked at his watch, sighed, I have to go, washed off in the bathroom, dressed. Sorry, but I really do have to go, tomorrow?
And everyday after that after dinner we had sex. We fucked each other, he liked to sit on cock, sucked each other off and I introduced him to the fun of frotting. Each afternoon I'd sit by the pool reading and maybe chatting and admiring his body, his eyes and white teeth and grin and the way he walked. Each night after dinner I'd be waiting like a teenager for his knock and kiss and smell and taste.
And then the holiday was over, they were returning the day before I left. Our last evening was very passionate with promises to get in touch when we were home.
I saw their taxi drive off to the airport, no wave, no looking back and blowing kisses. That night was very odd, no hip thrusts or hard tongues, no spunk.
They say the weirdest things happen when you don't expect them, that holiday romances are the sweetest - but also the saddest but if you get the chance to embrace it. Over many years I have been noticed in a variety of places but this was the most unexpected and open. I didn't feel like a dirty old man screwing with a youngster but more as a sexual equal, and I didn't use my age as a weapon for he'd had quite a lot of experience under his belt.
So I left Gozo with mixed feelings, said goodbye to friends who lived on the island and after a boozy lunch flew home.
One message on my phone. Call me.
i

 

[suejam]

i was 18 on holiday in croatia on a nudist beach