That brief fling

[Nellie60]

A while back, I had a brief encounter with a work colleague who was married. It started the usual way...some flirting and it became pretty exciting and one thing led to another leading to an once off sexual encounter in her car. It wasn't full sex but was an incredible handjob, partly due to my insistence at the time. I still remember to this day how amazingly experienced she was. Whatever it was probably the fact she was in another relationship took the experience evener higher. Unfortunately she didn't take it any further and we both just left with memories. Needless to say it was tough seeing her after that.

Anyone else out there experienced these brief flings then it doesn't go any futher? But wanted more?

 

[SharesMe]

I bet as in a relationship many years ago, was stuck in Chicago after flight cancelled. (He wasn’t with me) Ended up at a pretty nice hotel. Down at the little pizza restaurant/bar this guy and I hit it off really well. He kept complimenting me, and obviously staring at my tits. Admittedly I was really getting turned on. A couple more drinks and I invite him back into my room. In the elevator he pulls down my top, starts sucking on my nipples, and I reach out to his bulge, growing. Door opens on my floor, as we’re walking to my room his phone rings and he’s talking to his wife. (Who’s in his room asking when foods ready). I smile, tell him I’m good for a quickie. He fondles me a little more, teases my nipples and says he has to go. Bummer! I went back to my room and masturbated hard!!!

 

[jehoram]

I remember camping with a friend of mine whom I will call Alice. We were getting cold, so I suggested that we share my double sleeping bag. We did, and we got it on. But I made the mistake of mentioning it to my girl friend. who was also a friend of Alice. My GF hit the roof, even though she'd made it clear to me earlier that she didn't consider our relationship to be monogamous. GF and I visited Alice the next day, where Alice assured her that she wasn't going to steal me away. GF and I broke up a few months later, and I think that the fling had a lot to do with it. By that time, Alice moved away. When I ran into her a few years later, we didn't have sex, although I wanted to. But she'd moved on, she said. When she told GF and I that it was strictly a one-night sand, she meant it.

 

[sixfoot4]

I bet as in a relationship many years ago, was stuck in Chicago after flight cancelled. (He wasn’t with me) Ended up at a pretty nice hotel. Down at the little pizza restaurant/bar this guy and I hit it off really well. He kept complimenting me, and obviously staring at my tits. Admittedly I was really getting turned on. A couple more drinks and I invite him back into my room. In the elevator he pulls down my top, starts sucking on my nipples, and I reach out to his bulge, growing. Door opens on my floor, as we’re walking to my room his phone rings and he’s talking to his wife. (Who’s in his room asking when foods ready). I smile, tell him I’m good for a quickie. He fondles me a little more, teases my nipples and says he has to go. Bummer! I went back to my room and masturbated hard!!!

Lovely story. I have other short erotic stories which might produce a similar result...

 

[Rockymtnman]

Had one in Ireland a few years back. There for a rugby match between Ireland and the New Zealand All Blacks ( fucking cracker of a game). At a pub post game and there’s a lovely mid 30’s, pale, slightly ginger gal about 5’3, long curly hair, thin but fit. I’m wearing a USA rugby jersey and she wanders over to ask if I’m from America. Which, I am. We get to talking, she lives a few blocks away, I walked her home and when we get about a block away she says the lights are on my husband is home so we backtracked and we go to my hotel.. my godamn friends are back. Strike two. We end up finding a somewhat secluded area of the hotel we’re we fool around, she gives me a handjob and I her. Was leaving the next afternoon so never was able to pursue anything more.

 

[positiveflirt]

I feel the tension here! Sometimes I feel like the "almost" stories are sexier for all the frustration they carry.
A few years back I met someone stunning at a bar, had seen her around but now we could speak (even if LOUDLY OVER THIS BAR MUSIC) we hit it off well. All good right? Wrong, I'm being tailed romantically around town by someone who doesn't get the message at all. I lose the pursuer and my new friend and I sneak off to my apartment and are locked in a passionate embrace half naked when the bell to my apartment goes. Fine, no worries, don't answer it. And then, a knock at the window, and *then* my phone starts ringing off the hook. We laugh about it, quickly make each other come then she sneaks out the back door with plans to come over another time.. which never happen.
We're in touch still and laugh about it, I can't help but feel if we got our own way the story would be much less remarkable

 

[ilovetoeat42]

At a conference 10 years ago....was only for the weekend, but damn best sex I ever had. She wanted me to do anything I wanted with her.

 

[CockSparrow]

A few years ago, my then brother-in-law asked me if I could give his wife - my sister-in-law - some help with putting together a plan for a business idea that she had. I suggested that the pair of them come over and have lunch with his sister and I, make a pitch, and I'd see if I thought the idea had legs. They did. And it did. And halfway through the second bottle of wine I said that I'd be happy to give her a hand.

At first, I think that Annie was a bit surprised at how much homework she needed to do. But, to her credit, she got on with it, and before too long she and I were touching bases about once a day.

Things between Annie and I started out friendly enough - and just got friendlier. And, over the weeks, friendly became almost flirty. And then definitely flirty.

About three months after Annie got her business up and running, she asked me to go with her to an industry conference in another city. To be honest, I wasn't going to go, but my wife thought that I should since it would be Annie's first time with some of the big players.

On the evening of the second day of the conference, Annie and I decided that we had had enough of all the people, and went off for a quiet supper-for-two at a little Italian place the concierge at the hotel had suggested. We decided that the 'rule' for the evening was no shop talk. And so our 'colleagues' supper' ended up becoming 'a hot date'.

Back at the hotel, Annie invited me to her room for a nightcap. I can't remember if we had a drink or not. But I know that we wasted not time in getting naked and getting into bed. And then, for some reason, we both just lay there. 'This is probably not a good idea,' I said, eventually.

'Probably not,' Annie said.

The following year, both of us got divorced. We still caught up from time to time. Annie still flirted. But we never took it any further.

 

[Nellie60]

A few years ago, my then brother-in-law asked me if I could give his wife - my sister-in-law - some help with putting together a plan for a business idea that she had. I suggested that the pair of them come over and have lunch with his sister and I, make a pitch, and I'd see if I thought the idea had legs. They did. And it did. And halfway through the second bottle of wine I said that I'd be happy to give her a hand.

At first, I think that Annie was a bit surprised at how much homework she needed to do. But, to her credit, she got on with it, and before too long she and I were touching bases about once a day.

Things between Annie and I started out friendly enough - and just got friendlier. And, over the weeks, friendly became almost flirty. And then definitely flirty.

About three months after Annie got her business up and running, she asked me to go with her to an industry conference in another city. To be honest, I wasn't going to go, but my wife thought that I should since it would be Annie's first time with some of the big players.

On the evening of the second day of the conference, Annie and I decided that we had had enough of all the people, and went off for a quiet supper-for-two at a little Italian place the concierge at the hotel had suggested. We decided that the 'rule' for the evening was no shop talk. And so our 'colleagues' supper' ended up becoming 'a hot date'.

Back at the hotel, Annie invited me to her room for a nightcap. I can't remember if we had a drink or not. But I know that we wasted not time in getting naked and getting into bed. And then, for some reason, we both just lay there. 'This is probably not a good idea,' I said, eventually.

'Probably not,' Annie said.

The following year, both of us got divorced. We still caught up from time to time. Annie still flirted. But we never took it any further.

Interesting story, shame couldn't go further since you are both divorced now....

What I learnt was everytime I saw her I would imagine her wildly masturbating me in the back seat of my car...it was both very arousing and painfully at same time and strangely I wanted more. When I saw her with her husband at functions I would imagine the same..even now after some time...

 

[HumpDayHoratio]

Was sitting at a hotel bar one afternoon. Just a few people, not crowded, when a girl walks in and sits a couple of stools over. We strike up a conversation. She’s from Minneapolis and got extended for some reason and had been in the hotel for a few days.

She was a beautiful mix of Asian and Caucasian, long straight black hair, paler skin with a sprinkling of small freckles across her nose, and blue eyes. The best personality. For my part, I was a little out of practice at this point being married for close to ten years. She was married also. We really hit it off.

We have dinner together and as things are kind of reaching a natural conclusion, she looks across the bar and asks me to escort her out of the bar as a dude that was hitting on her the previous evening was giving her the once over again.

We walk out together and now I’m thinking, “maybe this is going to happen?” I escort her all the way to her room but realized I had walked down the wrong wing by accident! A happy accident? We both nervously say a sweet goodbye, shook hands and I never saw her again.

I often wonder had either one of us just said a word, brushed a hand? She was one that got away.

 

[zoso682001]

Was sitting at a hotel bar one afternoon. Just a few people, not crowded, when a girl walks in and sits a couple of stools over. We strike up a conversation. She’s from Minneapolis and got extended for some reason and had been in the hotel for a few days.

She was a beautiful mix of Asian and Caucasian, long straight black hair, paler skin with a sprinkling of small freckles across her nose, and blue eyes. The best personality. For my part, I was a little out of practice at this point being married for close to ten years. She was married also. We really hit it off.

We have dinner together and as things are kind of reaching a natural conclusion, she looks across the bar and asks me to escort her out of the bar as a dude that was hitting on her the previous evening was giving her the once over again.

We walk out together and now I’m thinking, “maybe this is going to happen?” I escort her all the way to her room but realized I had walked down the wrong wing by accident! A happy accident? We both nervously say a sweet goodbye, shook hands and I never saw her again.

I often wonder had either one of us just said a word, brushed a hand? She was one that got away.

One of those experiences that you'll wonder about for the rest of your life .

 

[tristantrotsky]

I bet as in a relationship many years ago, was stuck in Chicago after flight cancelled. (He wasn’t with me) Ended up at a pretty nice hotel. Down at the little pizza restaurant/bar this guy and I hit it off really well. He kept complimenting me, and obviously staring at my tits. Admittedly I was really getting turned on. A couple more drinks and I invite him back into my room. In the elevator he pulls down my top, starts sucking on my nipples, and I reach out to his bulge, growing. Door opens on my floor, as we’re walking to my room his phone rings and he’s talking to his wife. (Who’s in his room asking when foods ready). I smile, tell him I’m good for a quickie. He fondles me a little more, teases my nipples and says he has to go. Bummer! I went back to my room and masturbated hard!!!

Never, ever turn down the opportunity of a quickie... that chance will never ever come again, and you will live with the regret...

 

[haventdonethat]

Anyone else out there experienced these brief flings then it doesn't go any futher? But wanted more?

I have two, this is the first one that happened years ago.

GF and I were going to spend a few days fishing with another couple we were friendly with. Quite friendly . We had seen them naked many times as they had seen us. Last minute work problems meant that we (me and the other guys GF) would get dropped off at the tent site, then they (my GF and the other guy) would join us the next afternoon. No problem.

So we get dropped off, set up camp and the tent, get a fire going and eat a large supper. Afterwards we relax at the fire and enjoy some drinks and a couple puffs until the night sky is totally black, then it is into the tent and our separate sleeping bags, naked of course..

I am horny and very hard so I start stroking very quietly while we continue talking. Not quiet enough though. She abruptly sat up, switched on her flashlight and said something like “if you’re going to jerk off I want to watch”. I wasted no time flipping the top down and showing her my now super hard cock. Again, I can’t remember the exact words but something along the line of “Oh my! That’s a big one” as she reached over and started jerking me very skillfully. I would like to say that we had sex all night long but it didn’t work out that way. I orgasmed very quickly, shooting cum all over my chest, she wiped her fingers on my arm, covered up in her sleeping bag and went to sleep. Damn!

Nothing further ever happened and no mention of this incident was ever made, as far as I know.

 

[Nellie60]

I have two, this is the first one that happened years ago.

GF and I were going to spend a few days fishing with another couple we were friendly with. Quite friendly . We had seen them naked many times as they had seen us. Last minute work problems meant that we (me and the other guys GF) would get dropped off at the tent site, then they (my GF and the other guy) would join us the next afternoon. No problem.

So we get dropped off, set up camp and the tent, get a fire going and eat a large supper. Afterwards we relax at the fire and enjoy some drinks and a couple puffs until the night sky is totally black, then it is into the tent and our separate sleeping bags, naked of course..

I am horny and very hard so I start stroking very quietly while we continue talking. Not quiet enough though. She abruptly sat up, switched on her flashlight and said something like “if you’re going to jerk off I want to watch”. I wasted no time flipping the top down and showing her my now super hard cock. Again, I can’t remember the exact words but something along the line of “Oh my! That’s a big one” as she reached over and started jerking me very skillfully. I would like to say that we had sex all night long but it didn’t work out that way. I orgasmed very quickly, shooting cum all over my chest, she wiped her fingers on my arm, covered up in her sleeping bag and went to sleep. Damn!

Nothing further ever happened and no mention of this incident was ever made, as far as I know.

 

[Nellie60]

Wow thats very hot, thank you so much. I would gather the 2nd situation wasn't quite as hot but....

Still would love to hear more details...you know what was she was really like when she finished you..was she verbal, quiet etc. I ask cause with me she was very enthusiastic and verbal... permanently embedded in my mind

How was your relationship after the boyfriend arrived etc.

 

[Nellie60]

Never, ever turn down the opportunity of a quickie... that chance will never ever come again, and you will live with the regret...

 

[haventdonethat]

Wow thats very hot, thank you so much. I would gather the 2nd situation wasn't quite as hot but....

Still would love to hear more details...you know what was she was really like when she finished you..was she verbal, quiet etc. I ask cause with me she was very enthusiastic and verbal... permanently embedded in my mind

How was your relationship after the boyfriend arrived etc.

She seemed almost aloof and quiet, like jerking me off was just a job. The next day was ok even when the others arrived.
Second situation was hotter but for different reasons.

 

[Nellie60]

After weeks of flirting it was difficult to turn anything down and absolutely don't regret it. The experience provided just how lucky some guys are. Its not often you meet someone in random circumstances thats is just so hot and she was married.

 

[Nellie60]

She seemed almost aloof and quiet, like jerking me off was just a job. The next day was ok even when the others arrived.
Second situation was hotter but for different reasons.

 

[Nellie60]

Gosh you would think she would be more intimate? Like kissing...asking too much ha ha.. Thanks for your reply

 

[Nellie60]

She seemed almost aloof and quiet, like jerking me off was just a job. The next day was ok even when the others arrived.
Second situation was hotter but for different reasons.

Can you remember details of the 2nd situation and why it was hotter you say?

 

[FantasySharer1]

A co-worker and I were taking classes at the same college for a work-training program. Once she had taken public transit there directly from work and told me she wished she had gone to her apartment, gone home, and gotten her car. It was 9pm and getting colder so she asked for a ride since she was on my way home.

I gave her one and as I'm dropping her off she goes: "You can come up for dinner, I have leftover pasta and it's enough."

I went upstairs, ate my fill, having no intentions on doing anything else WHATSOEVER. We had a great friendly work relationship so we had a good time just talking.

I wash the dishes while she's cleaning up and am getting ready to leave and she just comes up to me and says: "I'm not looking for a relationship with you, and this would never happen again, but if you want to just have fun tonight, I'm open. But the whole thing dies here after we're done. You have to go home and we never ever talk about it again. And if it ever gets to work you'll just be the worst person on the planet."

She was strong-pretty, a little body fat but really really strong, REALLY cute face, and perfect breasts that were outsized for her frame. I always had a work-crush on her. I promised her it'll never go beyond tonight. She told me to come into her room in ten minutes.

Now the stupid part - we fucked bareback. She told me she's on BC so we just had a great time. It was excellent sex, a lot of tension and stress released, very simply missionary. Nothing particularly amazing except that it felt great and the taboo of finally having my pretty co-worker really made it better. Thankfully the bareback had no consequences.

We lay there for a bit after we finished, and she told me she's going to shower in the morning but I'm welcome to use the shower and go home. I ended up declining the shower, joked around for a few minutes, told her I had a great time, and just went home.

We never talked about it again or changed our relationship despite working together for two more years. We had already worked together for two years and had a good bit of trust which is what I imagine made the whole thing possible. Still a great memory that makes me smile.

 

[davenjenn]

On a plane coming back from Europe. We chatted. He was very sweet but also confident. Eventually he started rubbing me through my dress. When we were home went to his car and made love

 

[Nellie60]

Wow you did well. The fact she explained everything what to expect afterwards made it easier later and you feel good having her and no one's hurt. Great story.

 

[the_single_gal_unconfidential]

A few years ago, my then brother-in-law asked me if I could give his wife - my sister-in-law - some help with putting together a plan for a business idea that she had. I suggested that the pair of them come over and have lunch with his sister and I, make a pitch, and I'd see if I thought the idea had legs. They did. And it did. And halfway through the second bottle of wine I said that I'd be happy to give her a hand.

At first, I think that Annie was a bit surprised at how much homework she needed to do. But, to her credit, she got on with it, and before too long she and I were touching bases about once a day.

Things between Annie and I started out friendly enough - and just got friendlier. And, over the weeks, friendly became almost flirty. And then definitely flirty.

About three months after Annie got her business up and running, she asked me to go with her to an industry conference in another city. To be honest, I wasn't going to go, but my wife thought that I should since it would be Annie's first time with some of the big players.

On the evening of the second day of the conference, Annie and I decided that we had had enough of all the people, and went off for a quiet supper-for-two at a little Italian place the concierge at the hotel had suggested. We decided that the 'rule' for the evening was no shop talk. And so our 'colleagues' supper' ended up becoming 'a hot date'.

Back at the hotel, Annie invited me to her room for a nightcap. I can't remember if we had a drink or not. But I know that we wasted not time in getting naked and getting into bed. And then, for some reason, we both just lay there. 'This is probably not a good idea,' I said, eventually.

'Probably not,' Annie said.

The following year, both of us got divorced. We still caught up from time to time. Annie still flirted. But we never took it any further.

I would have sucked your cock. at least.
it's exciting to carry a tidbit of out of bounds things in your life?