Most unexpected sexual encounter

[4552511]

ok, it's like you are inside my head and writing my masturbation fantasies!!! lol
loved this

Hahaha. Half to hear. But no fantasy. Real life experience and still have a few more to share.

 

[4552511]

Hahaha. Half to hear. But no fantasy. Real life experience and still have a few more to share.

Meant to say Glad to hear.

 

[deleted4500261]

There was a very popular girl at my high school who was a cheerleader and most of the guys really lusted after her. She had dated a guy from another town that had already graduated so she was off limits.
After I graduated I ran into her at a gas station and she asked if I wanted to come over to house that night out of the blue. I didn’t even really know her.
I wasn’t going to say no so...
I showed up at her house and it was her, her room mate and another guy that the room mate was hanging out with.
This sounds made up but it isn’t. She said she was going to take a bath but for me to come and talk to her while she did. Ummm...ok.
She had a great body and we were both 20 years old at the time. She was tall, small boobs, long legs, great butt and really cute wih big brown eyes.
We talked while she took a bath and I coulen’t stop staring at her wet body.
She got out of the tub and we went to the kitchen and had a few drinks. We got a bit drunk and headed up to her room.
We did the usual stuff and I remember that doggy style was awkward because she was as tall as me so it was a weird angle. We had a lot of fun and stayed friends after but never had sex again. It was so random and I never would have guessed I would have ever slept with her.

 

[o_wells]

Hahaha. Half to hear. But no fantasy. Real life experience and still have a few more to share.

Can’t wait to hear them!

 

[4552511]

Monday couldn't move any slower for me to meet up with the Gardener again. Then it got me thinking. What's wrong with me? I've always been the one doing the fucking when it comes to girls and guys. How did this guy take a hold of me? Why did I not want to fuck him but instead I'd rather be fucked by him? Why was I day dreaming at work recanting our experience over and over in my head? Now here I was on a Thursday during my break,day dreaming when my phone rings interrupting my moment of wood. It was my cousin. I picked up
Me: Hello
Cousin: What's up brother?
Me: Hey what's up? How are you?
Cousin: Doing well. Guess who's going to spend the weekend with you?
Me: Ummm...
Cousin: Me! I'll be in town friday evening! Get to catch up with you!
Me: oh cool (not really). For how long?
Cousin: The weekend, and I know you have mondays off so I will leave Tuesday morning
Me: In my head (oh no!). But couldn't lie or not let him know something was up. So I responded cool!
My cousin is fun but I'm a clean freak so him staying with me was my nightmare. He is the very masculine carefree, weed smoking, in shape always chasing tail guy. While I'm Bi (not out), masculine but very meticulous, hardworking, in shape masc guy. This was going to be interesting.
The weekend was uneventful. Just filled with me cleaning up after my cousin and us eating and watching movies while I kept an eye on my calendar lol.
Now it was Monday morning. Door bell rings, I start running downstairs, my cousin straggled out of his room, to see who it was, I tell him to go back to bed that it was my gardener. He asks me why he is ringing the door bell. I respond he is helping me fix something.
Opened the door, Alfonso was about to give me his normal hug when he heard a room door slam shut and looked at me and I whispered my cousin is upstairs. He then tells me he wants to show me something in the garage and tell him I'll meet him there. Went to the garage through the second living room so I could bolt the walkway door from the inside leading to the garage and then lock the garage door too. Once I was in, Alfonso hurried up to me kissing me and slamming me to the wall. He pulls up my tshirt and start to suck on my nipples (damn!), he remembered one of my weaknesses and it also seemed he loved nipples. I have a huge chest from bench pressing and pushups. He spends some quality time on them while I tried not to squeal. This guy had me. He had me good. He then takes down his pants. This time he was wearing Adidas track pants and a tshirt . I see he wanted quick and easy access as opposed to the jeans and boots he always wore. I got on my knees and did my thing. Sucking on his dick like a vacuum and then using my tongue to twirl on his head. He shivered and I thought he was about to cum. Then i realised because he's uncut, his head is quite sensitive. So I spent some time twirling my tongue. He pulls me up and asks for a condom. Damn it! I left it upstairs. He then says can't fuck with no condom. I responded okay. In a quick moment he pulls my shorts down and turns me around leaning me on the sink slab in the garage. I hear him spit on his dick and I thought to myself oh man I've never played raw and I dont know about this. He spits on his hands and uses the saliva to lube between my inner thighs, pulls them together and sticks his saliva'd dick in between and begins to stimulate sex. He pulls me close to his chest with his arm around my neck and sticks his tongue into my ear. Then proceeds to bite my ear lobe softly, sucking on it and then goes back to rimming my ear. He went back and forth like this while pumping away till he pressed into me and I could feel his cum spurting out in between my thighs into my boxers that was around my ankles. When he was done he stumbled backwards heaving and holding onto his waist. This guy was magic. The place spelt of his spunk. I quickly removed my boxers, used it to wipe off the spunk between my thighs, on the floor, on the cabinet door below. As I put on my shorts, He came close to me, ground his dick into my dick while c look benching my ass, kissed me, and said "we go again?". I was like no Bro and pointed upwards "my cousin". He responded "oh sorry" and we both chuckled. I quickly made my way to the walkway unbolting as fast as possible the doors so I could run to my room upstairs to drop the boxers in my dirty clothes hamper before my cousin saw me and my wood. He went back out to the backyard and started the lawnmower. I dropped the boxers in the hanper, got new pair of boxers, didn't change the shorts so not to raise any suspicion. As I opened the door to my room, there was my cousin. I stood there looking at him wondering what was up. He then broke the silence with "where were you?". "I've been looking all over the place for you". I responded oh the gardener was showing me something with the sprinkler timer and how to save water. He was like oh that's a good guy there. He said he likes it when people show care rather than just do the job expected and leave you to figure things out. Then he said anyway, he wanted to know if he could take a swim in the pool. I told him to go for it. He was super stoked and ran downstairs. I collected myself and went to the pool area where my cousin was busy swimming and the gardener was busy mowing. Alfonso looked up and saw me, winked at me and wagged his tongue at me and chuckled. I looked over and my cousin was busy with his laps, I scratched my head, looked at Alfonso and chuckled. Alfonso knew he had me like a bitch and I was loving it. He really knew how to make one feel good. Yup he got me whipped. And he knew it.

 

[halcyondays]

Her name was Joyce. When I was in grad school she was a postdoc. I was 24. She was in her mid-thirties. We worked in the same professor's lab. Sometimes late nights were required. She was tall with beautifully styled auburn hair and big tits over a narrow waist. She always dressed to kill in tight dresses and heels. Only once did I see her in jeans, sweater and sneakers. That was on a Saturday. Even then she wore a skin tight sweater which showed off her bust and hourglass.

Most profs had a little break area in their labs with a couch and/or a few overstuffed chairs where they and their students could relax in comfort without hiking to lounge somewhere. A mini-fridge, coffeemaker, microwave completed the space.

Her flirting/signaling had included comments like if only I were ten years younger and if I weren't married and you're a handsome devil.

One late night in the lab I was slouched on the couch taking a break when she poured herself a coffee and plopped down next to me. She kicked off heels and stretched out long smooth legs. While we were chatting she playfully lifted my leg with hers and let it drop. I did the same to her leg. We went back and forth doing this until we stopped with our legs twined. When I turned to her we kissed. Soon our hands were all over each other. Hers held my jaw then opened my jeans and felt inside. Mine cupped and moved her breasts through dress and brassiere and ran up the insides of her thighs and found wet sex. She straddled me. We necked. My lips found her cleavage. Whatever finger full of fragrance she had traced there still lingered God she smelled good.

Tell me you have a rubber, she said.

When I nodded she climbed off and wiggled out of panties under her dress. I pulled down jeans and undies and rolled on a sheath.

You are huge, Joyce said watching me do it. Soon her hands wrapped around it and seconds later she straddled me. Her fingers guided me in. She pushed on urgently.

The lab was dark except for the light shining out of incubators. The double doors to the hallway were locked. Night janitors were long gone. The only sounds besides the air vents and hum of lab equipment were her gasps. She bucked and bounced for maybe five minutes and was done. I pumped from underneath for a few more until I came.

She got off me and pulled panties back up.

My husband will kill you if he finds out, she said, watching me unsheathe.

Not you? I smiled, knotting the filled condom.

He'll kill both of us, she said. Seriously. He's insanely jealous. We can't do this again. It has to be a one time thing.

You have my word, I said. It wasn't the first time I had heard a death threat from a taken woman. It wouldn't be the last. Besides she knew I was engaged.

Good she said, pushing into heels and straightening her dress. Go flush that. You can't leave it in the trash.

She giggled when I pretended to help with her dress but cupped her breasts instead. I lamented not getting to see them. We went back to work.

Two hours later we did it again. Despite the ferocious air conditioning we took off our lab coats for that one.

Do you always have more than one condom on you? she sighed, squeezing me with her pussy.

It's a necessity, I said.

I can't imagine why, she said.

We didn't work late alone together often that year but had at least one quickie each time. The work stressed her. I was happy to help relieve it some. Each time she said we wouldn't do it again.

She came to my apartment a few times so I got to see her magnificent breasts. We enjoyed each other much longer than five minutes those times.

 

[pinokio]

Two years ago I went to camping on lakeside during summer holidays, alone. My friends were going to arrive a day later and I did not want to change the booking. I bought myself a beer and went to sit on the beach and enjoy the sunset. As I was sitting there on the pier, I saw and heard a couple of late teenagers (18/22 as I learned later) talking about fashion and career in modeling. A boy who was handsome and quite self confident said he wanted to start this. I told them some advice about it because I've been modelling a lot. Then they recognized me from media pictures, which was funny. They were excited and invited me to join them. We partied all night together, girls made out and boys with girls had sex... And also boy with a boy, as it appeared. Everybody turned to sleep apart from me and this handsome guy. He was completely drunk and sitting under a large towel or blanket to get warmer. I came to him and pitying him being tired, I gave him a very little massage to his shoulders, through the blanket.
Suddenly he said to me 'Come on, give me a head'. I was surprised but, also being drunk and horny, I agreed. He spread his thighs wider and opened the really huge blanket to cover me, as there were still some people walking around on the beach. I knelt and pulled his swimming trunks down to his ankles. I started to suck his dick, it was already erect. 'Come on, make me cum', he said. I liked blowing him although he smelt a bit of wet spandex. I touched his balls and ass a bit. The cock was not small at all, normal but fat and throbbing. I moved my lips up and down around it. Once stopped for a moment to check if anybody's around, and he covered me deeper He had a nice body too because he used to play football (a few months later he got too big but then slim and fit). I asked if he knew I wanted to make out with him and if he does it often with other guys. He agreed to both. He also suddenly grabbed for my erection and started to kiss me in the mouth. I suggested going to my camping place and then, I dont remember how exactly, our meeting finished. I did not want to make him cum outside and wanted to take him to my room and also get more tender, maybe spend the rest of night together in one bed. He went to sleep to his place. The next day I met him but shortly and he seemed unwilling to talk. I also discovered he blocked me from his social media, which did not make a problem when some months later he wrote to me if I can lend or even give money to him because he's in trouble. I said I won't because it seems we do not even know each other, right? And wished him luck. He dealed with those problems, I guess. Still in touch with other people from that meeting, his family included, but with the guy not. Maybe he felt bad because I was about ten years older, still I felt rejected too. Anyway, a hot memory... and with time, I also start to understand why he reacted this way.

 

[Reg]

My most unexpected was when I was traveling on a regular basis. I had been staying in hotel down the street from the clients office. It was not unusual for me to work late at the office and walk back to the hotel, have dinner and then to the room. This night I went to the bar to wind down and sitting at the bar was the companies presidents secretary. She saw me and motioned me over to sit next to her. I ordered me a drink and her and refill. We talked about for a few minutes then she put her hand on my thigh and ran her hand up between my legs and stroked my cock. She stroked me a couple of times and I was quickly getting hard. She leans over to me and whispers "I assume you have a room" then laughed softly. I stood up and said "I sure do" and she followed me upstairs.

That was an amazing encounter that lasted for 3 months while doing my project.

 

[Euphoriasbliss]

My most unexpected encounter happened sometime last summer. I went on a coffee date with this guy I met on a dating site, we decided to take our coffees to go and went to the beach/boardwalk. After walking and talking for a while we ended up in a bit of a secluded area and started making out, there was still quite a few people around so we decided to go back to his truck. Once we got back we started making out some more, next thing you know I was bent over awkwardly giving him a blowjob. We somehow ended up in the back seat where he fucked me doggy style. We weren’t at it for very long because it was getting crowded and didn’t want to get caught, before dropping me off at home, we stopped at a grocery store’s parking lot. Usually that parking lot is pretty empty but winded up being packed, we thought this would be as good as it’ll get and decided to give it a shot. I gave him another blowjob to start off and when it seemed to be going well we decided to fuck again but stayed in the front this time, I got on top of him and rode him in the driver’s seat. We parked facing a busy street and I’m pretty sure every car driving by saw us lol.

 

[MrMartini]

Flew into Portland on a Sunday afternoon and when traveling I was always looking for good outdoor nudist places. Rooster Rock outside of Portland is sanctioned nude but I'd been there and wanted something different so I drove up to Bagby Hot Springs on Mt. Hood. Great place. Very rustic and very laid back. In the tub areas it's CO but most were nude. I picked a larger tub that had 3 other people, 2 guys and a chick, and asked if they minded if I joined. Of course they didn't. They were all three nude and so was I. We had a couple of jugs of wine we were passing around (even though alcohol is prohibited). About half an hour in another couple showed up. They asked if they could join but didn't come into the tub nude. Both were wearing swimsuits. He sat on one side of the tub and his wife slid in next to me. OK, that's a little weird I thought but what the hell. The chit chat continued as the sun went down and before long you couldn't see under the water in the tub. The guy was a Toyota salesman and all he talked about was how wonderful fucking Toyotas are. His wife said almost nothing other than greetings. All at once I felt a hand on my knee and then sliding up my leg. Yep, the hand went right to Mr. Johnson. In less than 30 seconds I was bone hard and standing straight up. About the only thing I heard her say was almost a whisper, "Holy FUCK!" as she found out how big I was. I tried to sit still and look normal as Mr. Toyota rambled on. Figuring I should somehow reciprocate I put my hand on her inner thigh and started to get under her swim suit bottom. Quietly she said, uh uh (no) and moved my hand away. I was content to let her work. She worked me slow and never got rough. It only took between 5 or 10 minutes before I was ready to let a load go. I signaled that I was ready by putting my hand on her leg and squeezing. She got the message and grasped the head of my cock so she could feel the cum shoot and the head throb. With the hot water, the wine and the ejac I was VERY relaxed. But didn't lose the erection. She took note and we did it again. The second time it took a little longer but the contractions were even stronger. After that he asked if she was ready to head home and she said yes. So they got out of the tub and wandered up the trail towards the parking lot. As they left the other three were looking at me and the chick giggled a little. I said "What?" One of the guys said, "Did she get you off?" I sort of stuttered and could feel myself turning red. He said, it's ok, they're regulars. Then he said they come to the tubs, slip into one where there's somebody they don't recognize and she can handle some strange cock. Then they go back to the car and fuck outside in the dark. I never made it back to Bagby but I'm sure Mr & Mrs Toyota did.

 

[candy1990]

I was in my early 20s and living with my friend at her dad's place, he was late 40s, he was friendly, handsome and recently divorced. I'd taken a Friday off and i guess he wasn't aware of this as i caught him completely naked on his way to the washroom when i got up that morning, we both froze and i couldn't help but check him out i mean he had a nice body for an older guy and he was soft but it looked big i was just staring at it until he put his hand over it and apologized saying his didn't realize i was still home at which point i retreated to my room. Later that day he approached me and apologized again, i told him it was fine then said something about him having a nice body for an older guy, we continued talking but i couldn't help but notice the bulge in the front of his sweats and after a few glances he caught on and with a bit of a laugh asked if i wanted a closer look, i was embarrassed that he caught me but i said yes and he actually pulled it out, i was pretty horny and went with it and he fucked me right there on the kitchen counter. We continued fucking for the next six months or so until i moved.

 

[J32]

A couple years ago I had this downstairs neighbor who was a massage therapist. She would always flirt with me when we ran into each other. Now besides the obvious mistake of hooking up with your neighbor the reason I never acted on it was because she wasn’t all that attractive. She was chubby and never wore any makeup (a little would have gone a long way) so I would always make small talk for a minute and say goodbye.

One day she asks me if I could pick up her mail while she’s out of town. I say yes and when she returns she offers me a free massage. I hesitate on taking her up on the offer...I didn’t want to be naked on her table and send the wrong signal....but then she told me she was moving at the end of the month. So I agreed to the massage.

When the massage happened I thought I could maybe get a happy ending from her but that’s all I wanted. She starts massaging me and uses no draping and isn’t shy about massaging my ass. We’re making small talk but then when I was face up she tells me that she used to listen to me having sex with my ex all the time. Often playing with her pussy while she listened. I started getting hard as she was telling the story and she just said “do you want to fuck” and in the moment, with my dick hard, I said yes. It wasn’t bad. She sucked a good dick and had nice nipples. Funny enough she ended up staying in our apartments for another few months and it was very awkward every time we ran into each other.

 

[4097701]

i was there to get stuff for my lawn and there was a guy kinda walking with me. i went to the bathroom and we were in stalls next to each other. he started jerking off and asked me to stick my cock under the stall. after playing with it he came into the stall and asked me to fuck him raw. i came in his ass and we noticed the guy in another stall was jacking off while we were fucking. we could see his shadow. i kinda waited outside the bathroom to see who was jacking off and it was an employee

thanks for that... hot!

 

[A_dub]

I was in my early 20s and living with my friend at her dad's place, he was late 40s, he was friendly, handsome and recently divorced. I'd taken a Friday off and i guess he wasn't aware of this as i caught him completely naked on his way to the washroom when i got up that morning, we both froze and i couldn't help but check him out i mean he had a nice body for an older guy and he was soft but it looked big i was just staring at it until he put his hand over it and apologized saying his didn't realize i was still home at which point i retreated to my room. Later that day he approached me and apologized again, i told him it was fine then said something about him having a nice body for an older guy, we continued talking but i couldn't help but notice the bulge in the front of his sweats and after a few glances he caught on and with a bit of a laugh asked if i wanted a closer look, i was embarrassed that he caught me but i said yes and he actually pulled it out, i was pretty horny and went with it and he fucked me right there on the kitchen counter. We continued fucking for the next six months or so until i moved.

Was he a good fuck? How big was he?

 

[Intoit414]

About 5 years I was at Put in Bay (an island west of Cleveland) on my boat. We had to raft off of another boat that was owned by a couple in their 50s. I just started talking to them about how nice their boat was and they invited me to check out the cabin so I did. I was genuinely interested in the boat. We went in the cabin and his wife took off her top and he told me I was welcome to play with her tits. I was completely shocked but I started to feel her up. She took off my shorts and started to blow me. We eventually started to fuck while he was watching and then he got naked and I watched them fuck. He turned around and started blowing me ( first time I’ve ever had a guy blow me). I played with his balls while he fucked his wife. Kept switching back and forth. I came on her tits and he licked her clean. I would pay to find that couple again to relive that experience. That’s the reason I am bisexual now.

 

[Buddie]

This reminded me of events I hadn't thought of in decades...
I was in college about 500 miles from home. Far enough that flying home didn't make sense financially and I didn't have a car either so it was for a few years that I was taking 8-12 hour Trailways bus trips.
I was shocked the first time a guy offered to blow me on a dark bus with few passengers and those few were either asleep or all the way up at the front. After the first time, it wasn't a surprise at all. In fact, it happened so often that it became something to look forward to on those long boring trips.

things happen for a reason

 

[DiamondJoe]

Here's an odd one, and there wasn't even any physical contact.

I was with the missus on a bus going down Oxford Street in London one afternoon. We're sat upstairs front left, I'm in the aisle seat. We've only been sat down for 5 mins and two men get on board, climb the stairs and opposite us, front right.

I cast a quick glance and ascertain they're both fuckable - and the one nearest me sees me looking at him and flashes a very quick smile before looking away. I chance my arm and wink back...

And from then on to the time we got off the bus, both myself and this guy were silently flirting whilst sat next to our partners.

As I say, nothing actually happened but the encounter had an electric quality to it.

 

[nikeyboi90]

I was on my lunch break, trying on clothes at a Zara in London.

Apart from myself and one other, the fitting room was empty. The individual cubicles are mirrored on both sides and if you and the person opposite don’t close your curtains fully, you can see everything.

Looking in the mirror, I noticed the guy changing opposite hadn’t closed his curtain properly and we were both completely on show to eachother as we changed. He was early 30s, muscled, with tight white CKs. We started teasing eachother, spending longer in just boxers, him in briefs, inbetween changes. Eventually he stopped changing and was visibly hard. He stood there in the reflection grasping at his hard cock.

At that moment, his friend appeared and swung back the curtain to offer him a shirt in a different size. The guy managed to take the shirt without the friend noticing what was going on. I got dressed, headed to the counter and left.

After leaving, I noticed the pair were headed in the same direction, following from a short distance. I made my way to H&M to see if they would follow - they did.

I grabbed some shorts and headed straight for the fitting room. Again, they were completely empty. Almost immediately after, the hot guy from Zara followed me in and went into the cubicle opposite. We both left our curtains pretty much fully open - we were at the very far end and unlikely to be disturbed. We stripped to our underwear - both rock hard. He pulled his thick cock from his tight white briefs. It was huge and still had a nice flop to it. He had thick trimmed pubes with perfectly smooth balls. He, quite brazenly, stepped across into the entrance to my cubicle and tugged at my meat. He dabbed his finger on the ever increasing wet patch my throbbing cock was causing on my boxers, before taking it out and thumping it against his. We played with each others dicks briefly, before he stepped back into his cubicle, we both got dressed and left.

5 minutes later, I was back at my desk.

 

[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.

 

[OldWise]

I was in my middle 30s, divorced, sitting in a Starbucks, working away at a business plan. I didn't see them until they stood in front of me. Two tall blondes, two attractive, fit blondes, one about 5'9", the other about 5'11' one was in her early 30s, the other in her early 40s, both smiling at me.They both knew me separately, but I didn't know that they knew each other, let alone that they were close friends. (Interestingly enough one was a defense attorney for Mafia types and the other was a prosecuting attorney, so I assume they would be on opposing sides.)

They told me that they had decided that since I shown them such kindnesses and favors, I needed to be rewarded; thus, they decided to give me a good time, as in threesome good time. When asked if I was interested, I replied, "Wow! This dying and going to Heaven thing is a lot better than I expected it to be."

We walked to the younger woman's apartment, which was nearby. As soon as we entered her place, they stripped before stripping me. It was a good time, as they did most of the work—until it was time for fucking. Normally, in FFM threesomes with your wife or girlfriend and some other woman, you worry about showing the other female too much attention. Not this time. I was the special guest, the star, the recipient of all their attentions. Their goal was making me as happy as possible. They succeeded. As one sat on my face, the other fucked me cowgirl. Two tongues licked my balls and cock at once. My hands delighted in comparing their breasts and ass cheeks. My cock sampled their mouths and vaginas, evaluating little differences. Even my nose tickled at sniffing their different perfumes and intimate scents. The older woman repeatedly told me that I wasn't to try to make them happy; it was their job to make me happy. I had license to be as selfish as I wanted.

If they had only half as much pleasure as I did, then they had a fucking great time.