Most unexpected hook up?

[zotique]

When I was 20 I was on my way to Mexico from Canada and stopped in L.A. to visit a school friend who had spent a year in Canada when her parents bought a vacation home there.

We were always kind of sweet on each other, but were going out with others when we knew each other so nothing happened. Nothing happened this time either; she had a boyfriend and I had a gf back home.. But we went out to the philharmonic together and to a concert.

Her bf was kind of jealous so one Friday afternoon he came by and said "there's a girl at work that says she's going to go out to a disco tonight and meet some guy to get laid. I told her that could be dangerous, you never know who you'll end up with." Then he looked at me and said "Do you want to meet her ? I told her there was a good looking young guy staying over here."

I agreed and later that night she came and picked me up. She was about 30 and kind of plain and a little plump, but what the hell. So she took me home and thoroughly fucked me. The only thing she didn't want to do was get eaten out, but she agreed to suck my cock to get me hard again after the first two times we fucked. (as if I needed a blowjob to get hard for the third round at 20, but it was nice to get sucked like that) We did this for two nights running on her black silk sheets on her water bed then she bought me a carton of Marlboro and dropped me off at the highway on-ramp for Phoenix Arizona.

She was only the 3rd woman I had ever fucked and her cunt really wet and sloppy gushy compared to my gf back home. Maybe she was just more aroused than my gf ever got.

 

[Cindy69love]

My older neighbor. I'm 32 he's in his early 60's.

 

[Grindallnight]

A girl that I used to fuck at college, we went to an NHL game together. I figured there was a chance I might get laid that night, but didn't expect what happened at all. We got back to her place and moved quickly into the bedroom.

She told me that she was something along the lines of a "born again virgin". I figured that meant no sex. She said that anal sex didn't count (the way she was figuring it, I guess).

We ended up with her bent over in the shower and me going to town behind her. Condom broke, kept going, and I pulled out and finished on her ass under the stream of water.

Was a pretty memorable night. I think that's the last time I've seen her in person.

 

[Lost_Yonder]

Must admit, I've had a few unexpected trysts. One of my earliest ones was after college was traveling across country to move in with my then girlfriend. Along the way, stopped at a good friends in Aspen to spend a few days enjoying the mountains. He was living at home himself and I ended up sleeping in their finished basement family room for three nights. His parents and two younger sisters were all home, but it seemed pretty natural to have friends staying for several days. Most of the days were full, hiking, climbing, hanging out in town. I didn't really interact with his family much at all. On the third night, before I was leaving in the morning, around midnight I was woken up by someone. Turns out it was one of his sisters. She sort of rocked me awake and once I came out of my sleep, literally just jumped on me. I was scared as shit, but who was I to resist a very cute young lady. After two rounds she slipped out and none seemed to be the wiser of it. Was half tempted to delay my trip and stay another night, but my friend himself was heading off in the opposite direction so I had no excuse to stay on. In the morning I didn't even see her, but the other sister had a bit of a smirk on her face - though never sure if I was over reading it or not...

 

[HoldYouDown]

Hmm.

In college I hooked up with a girl named Kim. I don't remember much about her but she was very petite. Anyway a week or so later, her good friend (or maybe not?) Becky came after me.

Another time, I went out with a female friend (Janice) and HER female friend (Angie) whom I only sorta knew. We went back to Janice's apartment and I messed around with Angie while our mutual friend Janice slept (or tried to) in the next room, no door.

More recently, went on a date with a girl but she couldn't go home with me because she had an early morning flight. Otherwise I know she would have. Said goodbye and went to a party - wound up fucking the hostess that night.

I guess these sound tame but there you go.

 

[DeckardNYC]

I was about 20, back in semi rural Pennsylvania, at an outdoor summer party with a wide range of people. Bumped into prettiest little scots-Irish girl, dark hair, mischievous smile. There was an instant connection, for the next two hours we flirted and sparred and did that little tango of young, urgent, not to be denied lust. Then we went to my car and fucked like rabbits, and then went back to the party.

Epilogue: we tried to date for a few weeks but we were too different and ran in different crowds.

 

[HoldYouDown]

I was about 20, back in semi rural Pennsylvania, at an outdoor summer party with a wide range of people. Bumped into prettiest little scots-Irish girl, dark hair, mischievous smile. There was an instant connection, for the next two hours we flirted and sparred and did that little tango of young, urgent, not to be denied lust. Then we went to my car and fucked like rabbits, and then went back to the party.

Epilogue: we tried to date for a few weeks but we were too different and ran in different crowds.

Attraction is a curious thing...

 

[DeckardNYC]

Attraction is a curious thing...

Very much so. And for something sudden, attraction is very dependent on a time, a place, how you feel, etc., i.e., factors that might not be the same if you met under different circumstance. Life is fun!

 

[haventdonethat]

Payback

Many years ago I was having a drink at a bar and noticed a very good looking young woman wandering around talking to just about everyone. She approached me with the story that her and friends had run out of gas just down the road and needed someone to go back into town (20 minute drive) to get them gas.
After some hesitation I agreed. The friends were a couple who had driven 150 miles to pick her up. We all piled into my truck, drove to town and back then fuelled up their vehicle.
I was sitting in my truck with the engine running, watching in the mirror to make sure theirs started. It did. They were standing about talking a bit when the woman tossed her pack in the bed of my truck, opened the passenger door and got in.

Quite surprised I asked “what up?” Her answer is forever etched in my memory.

She replied “payback”.
“Take me somewhere and fuck me”

How could I refuse.

 

[starpower96]

Many years ago I was having a drink at a bar and noticed a very good looking young woman wandering around talking to just about everyone. She approached me with the story that her and friends had run out of gas just down the road and needed someone to go back into town (20 minute drive) to get them gas.
After some hesitation I agreed. The friends were a couple who had driven 150 miles to pick her up. We all piled into my truck, drove to town and back then fuelled up their vehicle.
I was sitting in my truck with the engine running, watching in the mirror to make sure theirs started. It did. They were standing about talking a bit when the woman tossed her pack in the bed of my truck, opened the passenger door and got in.

Quite surprised I asked “what up?” Her answer is forever etched in my memory.

She replied “payback”.
“Take me somewhere and fuck me”

How could I refuse.

That's awesome...and a great reward for a good deed!

 

[haventdonethat]

That's awesome...and a great reward for a good deed!

That was only half the story.

The night did not end well.

Care for the rest?

 

[Iwant2havefun]

Yes please! I'll wait.... : )

 

[haventdonethat]

Things Go Awry

It was not a good ending to the night.

Her friends had left.

We had a very pleasurable night of fucking.

She came clean and told me her friends had come to pick her up and take her home after six months in a mental institution.
That’s when things started getting freakish. Talking to herself and looking for someone or something in the corner. Maybe her meds were wearing off.
I was getting nervous.
She said she had to get home and hinted I should drive her. That was impossible. I was almost out of gas myself and was down to my last twenty dollars.
I drove her back to town, gave her my last twenty and dropped her off at the bus station so she could make her own way home. I think my rear tires were smoking when I pulled out of the station.
I read the papers constantly for a few days and did not see any instances of horrors on the bus so figure she made it ok.

 

[diablo1986]

Neighborly Love

When I was a kid I used to be babysat by our next door neighbor and her husband. They were a kinky couple but I didn't know it then. As I grew up, my neighbor (we'll call her Cindy, real name is similar) started to get more and more touchy with me. Always wanted to pat my ass whenever I gave her a hug hello. The hugs started happening pretty much every time we met up and one day when I was about 19 and visiting from college, I was a little more excited than usual. I guess I was just having some random wood but hey, that's how it goes when you're young, dumb and full of cum, right?
Well, Cindy felt my bulge during our hug and instead of pulling away she pulled me closer and pushed her pelvis up against me and said, and I quote, "Oh, to have a young man again." We laughed and she moved her hands down to my ass and tucked them in my back pockets. Mind you, we're right outside my house, next to hers, and this is happening. At this time, when we were together, she was probably 50? This is pushing 15 years ago now. Maybe slightly younger. 5'6" with a killer body and big titties. Not much of an ass but holy shit was she good looking. Half white, half something else? Nobody could guess her ethnicity.

Long story short, she asks if I'm around later in the week and I of course say yes. We end up having dinner at her place and she tells me she's divorced, her ex husband (who I always thought was a really cool guy) was apparently a douche, and now she's lonely. After some food (and some booze, to my surprise) she brings out a photo album and shows me polaroids of her getting fucked by other guys. Apparently, she and her ex were swingers at the time they were babysitting me. I'm practically shaking I'm so excited, and I'm looking for a way to leave because I have no clue what to do. I'm 19, it's weird to have a hot neighbor flirting with me, and especially someone I've grown up around. I'm stuttering and stammering like a fool and she spreads her legs and shows me her pussy. Verbatim she said, "Do you think you could fit in me?" And like a badass I said, "Only one way to find out!" I had no fucking clue what to do, but thank god she led the show from that point on.

We fucked for hours. The whole neighborhood could probably hear us. I pounded that pussy like I was the last man on earth and she squirted all over her mattress. Hence my lifelong love of squirting women. I came, she sucked me til I was hard again, and we fucked until I came again. And then again. My balls were drained and sore but it was worth it. Came on her tongue, her tits, and in her pussy. As we're lying there, my cum drizzling out of her, she turns to me and says "You have a bigger cock than your dad." EVERYTHING about this experience was unexpected!!! And yeah we fucked other times after that, and I'll share those stories another time. But yeah, Cindy... you made me a man

 

[tmmmbrrr]

.....

 

[Iwant2havefun]

It was not a good ending to the night.

Her friends had left.

We had a very pleasurable night of fucking.

She came clean and told me her friends had come to pick her up and take her home after six months in a mental institution.
That’s when things started getting freakish. Talking to herself and looking for someone or something in the corner. Maybe her meds were wearing off.
I was getting nervous.
She said she had to get home and hinted I should drive her. That was impossible. I was almost out of gas myself and was down to my last twenty dollars.
I drove her back to town, gave her my last twenty and dropped her off at the bus station so she could make her own way home. I think my rear tires were smoking when I pulled out of the station.
I read the papers constantly for a few days and did not see any instances of horrors on the bus so figure she made it ok.

Very sad. You tried to help...twice....so you did what you could do. Pretty horrible for her friends to leave her like that. Thanks for sharing

 

[Misshotndeep]

A childhood friend of mine was a porn star. So I thought I would give it a ride. He totally sucked. I mean a waste of time sucked! Never in a million years as we were growing up would we have thought we would have had sex. Not once. We had known each other since we were 9. Then again I never would have thought he would be a porn star either. Life is full of crazy twist and turns.

 

[zotique]

Niagara

Later that same year I was 20 I was hitchhiking to Niagara Falls from Toronto and got picked up by two women From San Francisco in a VW van.

While on the way to Niagara Falls, one of them said "How do you know we're not serial killers and we're just going to kill you."

You're gonna have to rape me first," I said.

We parked right at the falls and while one slept up in the loft of the pop-top, the driver, who was this cute 27 year old who worked at a massage parlour fucked me in the main bed. Twice before going to sleep and once more on waking.

We wrote one month later and she called me "My gentle man."

 

[Doctor Joe]

My older neighbor. I'm 32 he's in his early 60's.

Sounds so naughty! I'm sure there's quite a bit more story here!

 

[Lost_Yonder]

gotta give this a bump - love the stories of unexpected encounters

 

[hardbiker82]

A married woman that I've known for nearly 30 years, I never knew she liked me. Then one day, she asked me to call her -- out of the blue. She was married, and even as much as she liked me, I couldn't get myself to see her. But, it eventually happened. And the first time we saw each other, after not seeing her for about 5-6 years, was an explosion. We hit it off! Found so many common interests, and our sexuality was the same. We both love sex. Her sex life was dull, until her and I hooked up. Definitely, an unexpected hook up.

 

[mjolnir_1]

I wore her out literally haha.

I was a young airman and somehow this older woman took a shine to me, I don't even remember how or why. She was a bit rough and I was more than ready.

We hooked up and over the next 12 hours I must have fucked her close to a dozen times. I went through a whole box of magnums and by the time I had nothing left she couldn't walk right. I guess she liked what I brought to the bed.

She past her last afternoon with me massaging my back and ass as I knocked out my coursework before I left to go overseas.

Never saw her again

 

[mjolnir_1]

I had her first lol.

Another woman a little younger than me. We wound up hooking up and I had a bad back at the time, so I walked with a bad limp. She didn't seem to mind and we wound up in my place music cranked and nice and dark. I wound up a position I have not been able to do since where I had her legs wrapped around me and she was sitting up right while I was leaned back and then I pulled my myself tight up against her so that I was buried so deep in her.

I know I came so hard so deep in her I almost blacked out, and she was just a whimpering moaning mess. I think I passed out soon after and she was gone.

I found a letter from her a day later she left behind thanking me for the most incredible sex of her life. I was out of the country days later and come back and found she got married to a guy in my squadron but different section from me.

He was a bit of a dick towards me, but I remember drinking beers with my buddies saying yeah he married it, but I just look over with confidence and get a little smile from her knowing I wore it out first.

 

[Misshotndeep]

Another woman a little younger than me. We wound up hooking up and I had a bad back at the time, so I walked with a bad limp. She didn't seem to mind and we wound up in my place music cranked and nice and dark. I wound up a position I have not been able to do since where I had her legs wrapped around me and she was sitting up right while I was leaned back and then I pulled my myself tight up against her so that I was buried so deep in her.

I know I came so hard so deep in her I almost blacked out, and she was just a whimpering moaning mess. I think I passed out soon after and she was gone.

I found a letter from her a day later she left behind thanking me for the most incredible sex of her life. I was out of the country days later and come back and found she got married to a guy in my squadron but different section from me.

He was a bit of a dick towards me, but I remember drinking beers with my buddies saying yeah he married it, but I just look over with confidence and get a little smile from her knowing I wore it out first.

That's one of those stories you give a high five for.

 

[Lost_Yonder]

Another highly unexpected encounter was when I was working in western Africa. I was with a team mostly out in a regional capital, but whenever I went to the capital city I often stayed at the home of one of the embassy staff people I got to know - they loved having company and it was quite luxurious after months living with no running water and intermittent electricity!

One evening there was a party at the ambassador's home and a number of us returned to my friend's home to continue the party. Slowly the numbers dwindled, even my friend crashed, must have been 2 or 3 in the morning. There were three of us left - me and two women. One was a young peace corps volunteer who I had my eye on and was flirting with all evening and was quite hopeful she would be staying the rest of the night with me. The other was a pretty attractive looking marine embassy guard. Not my type at all and I sensed my wannabe peace corps lover was not into her at all. Well, the night didn't go as planned as soon the volunteer was crashed out on one of the couches inside and the the marine sat on my lap and told me outright she wanted to fuck. Who was I to argue!

She was quite active, shall we say, almost aggressive, liked it rough - hair pulling and all. She was noisy too, but everyone was passed out. We actually became lovers for a while, at least whenever I was in town. Don't ever know if she was involved with others or not while I was away as it was months before I'd be in town. The friend I stayed with finally had to put a halt to it as she was a bit wild and loud for his taste and she obviously couldn't host as they lived in a shared space.

Some fond memories!