one night stand

[Mandalorian]

Was in Chicago for a conference in Feb 2020, weeks before Covid lockdowns. Was sitting in the vip lounge reserved for conference vendors (I wasn’t but got a free pass from friend) which had free drinks and snacks. I was sitting alone enjoying cocktail #3 and realized I was sitting across from a very sexy tanned blonde Milf type in a tight skirt (which is almost the uniform for trade show floor spokespeople). Struck up a conversation about the day’s events, where we are from etc. tried to be funny. She leaned closer to talk since it was getting loud. i took a chance and put a hand on her lap and she put her hand on top of mine and it was go time. Ended up fooling around in a dark corner under the escalators and ended up in her room. 2 hrs later we had a quick bite in the hotel lobby and I had to split to see my colleagues. Her name was Heather from Madison, Wisconsin.

 

[Oliverleo]

Was in Chicago for a conference in Feb 2020, weeks before Covid lockdowns. Was sitting in the vip lounge reserved for conference vendors (I wasn’t but got a free pass from friend) which had free drinks and snacks. I was sitting alone enjoying cocktail #3 and realized I was sitting across from a very sexy tanned blonde Milf type in a tight skirt (which is almost the uniform for trade show floor spokespeople). Struck up a conversation about the day’s events, where we are from etc. tried to be funny. She leaned closer to talk since it was getting loud. i took a chance and put a hand on her lap and she put her hand on top of mine and it was go time. Ended up fooling around in a dark corner under the escalators and ended up in her room. 2 hrs later we had a quick bite in the hotel lobby and I had to split to see my colleagues. Her name was Heather from Madison, Wisconsin.

That sounds like a wild and memorable experience. It’s interesting how spontaneous things like that can happen in unexpected places, especially at events like conferences. It’s always fun when there's a mutual connection and things flow naturally like that. Heather from Madison definitely made your Chicago trip one to remember! It’s funny how these kinds of moments can stand out, even with everything else that was going on at the time, especially so close to the lockdowns.

 

[Mandalorian]

In general conferences and trade shows are ripe with people away from spouses out for a good time. Expense accounts make the liquor flow well.

 

[henrybogo]

Trade show here too, it's one of those places where you bump into all kinds of people. I accidentally found myself talking to a guy who wouldn’t stop going on about his business and his achievements. He seemed wealthy maybe but had the kind of voice that just kept droning on. At some point, I drifted toward another group, and I joked, “If only you had a mute button.” That earned a few chuckles, and we all shared a moment of light convo. Among the group was a woman who stood out, though at the time, I had no idea she was the talkative guy’s wife. She laughed at my joke, but there was something about the way her eyes lingered on mine. I noticed it but didn’t dwell on it—just one of those fleeting moments you brush off. Time passed, and eventually, I found myself heading to the bar for a drink. That’s when I saw her again, sitting alone and looking a bit bored. Feeling a bit spontaneous, I borrowed a pen and scribbled my room number onto a piece of paper. I folded it into a paper airplane and sent it flying in her direction. Surprisingly, it glided smoothly landing near her. She looked at the note and then turned, meeting my eyes with a curious smile. I returned it, stepping closer. She stood up, and followed me toward my room. The second the door closed behind us, I scooped her up, and she kissed me hard. I threw her onto the bed, and from there, things got intense and fun. We spent the evening together, and by the time she left, it was well into the night. The next morning, as I was leaving to catch my flight, I saw her again but she was with her husband. Very awkward as I made eye contact with her and pretended I didn't notice.

 

[Oliverleo]

In general conferences and trade shows are ripe with people away from spouses out for a good time. Expense accounts make the liquor flow well.

Absolutely, Conferences and trade shows often create a relaxed atmosphere where people are more open to unwinding and having fun. It's a great way to mix business with some leisure.

 

[star003]

Trade show here too, it's one of those places where you bump into all kinds of people. I accidentally found myself talking to a guy who wouldn’t stop going on about his business and his achievements. He seemed wealthy maybe but had the kind of voice that just kept droning on. At some point, I drifted toward another group, and I joked, “If only you had a mute button.” That earned a few chuckles, and we all shared a moment of light convo. Among the group was a woman who stood out, though at the time, I had no idea she was the talkative guy’s wife. She laughed at my joke, but there was something about the way her eyes lingered on mine. I noticed it but didn’t dwell on it—just one of those fleeting moments you brush off. Time passed, and eventually, I found myself heading to the bar for a drink. That’s when I saw her again, sitting alone and looking a bit bored. Feeling a bit spontaneous, I borrowed a pen and scribbled my room number onto a piece of paper. I folded it into a paper airplane and sent it flying in her direction. Surprisingly, it glided smoothly landing near her. She looked at the note and then turned, meeting my eyes with a curious smile. I returned it, stepping closer. She stood up, and followed me toward my room. The second the door closed behind us, I scooped her up, and she kissed me hard. I threw her onto the bed, and from there, things got intense and fun. We spent the evening together, and by the time she left, it was well into the night. The next morning, as I was leaving to catch my flight, I saw her again but she was with her husband. Very awkward as I made eye contact with her and pretended I didn't notice.

smoooth…wish you could give little more elaboration about her looks that evening and how she was dressed..

 

[Robert Mugabe]

That sounds like a wild and memorable experience. It’s interesting how spontaneous things like that can happen in unexpected places, especially at events like conferences. It’s always fun when there's a mutual connection and things flow naturally like that. Heather from Madison definitely made your Chicago trip one to remember! It’s funny how these kinds of moments can stand out, even with everything else that was going on at the time, especially so close to the lockdowns.

Sure it wasn't Ashley from Madison. ?

 

[Oliverleo]

Sure it wasn't Ashley from Madison. ?

Haha, definitely not Ashley, but it sounds like she’s left an impression on you, maybe Madison has more than one unforgettable lady.

 

[Foodoo19]

I know this is going to sound like a Penthouse Forum bullshit story, but I assure you it's legit.

It was summer 2006 and I was in Winnipeg on business. I met a woman on Lavalife (my god, how I miss the heyday of that site!!) who was looking after her parents' house for the weekend and just wanted a boink.

And here's the kicker -- she was a stripper and was absolutely stunning.

She gives me her address and I was hesitant, like this was too good to be true. But when I arrived, she answered the door without wearing a stitch of clothing, says little more than 'hello', leads me to the living room and proceeds to give me an amazing blowjob before we made our way to the bedroom to finish up.

Had a few one-night stands, but nothing quite like this one before or since.

I was a single fit 30 Y/O and living downtown at the height of Lavalife and the early days of Plenty of fish. I was crushing it. Two of the hottest chicks I have ever banged were on the same day from 2 separate 1st dates. As dad bodded 50 y/o now I still think back to those days!

 

[Oliverleo]

I was a single fit 30 Y/O and living downtown at the height of Lavalife and the early days of Plenty of fish. I was crushing it. Two of the hottest chicks I have ever banged were on the same day from 2 separate 1st dates. As dad bodded 50 y/o now I still think back to those days!

Wow, those must have been some wild days, sounds like you made the most of that prime time on Lavalife and Plenty of Fish. It's always fun to look back at those unforgettable experiences. Even as a dad-bod rocking 50-year-old now, I bet you've still got some great stories to tell.

 

[JeanGary Diablo]

I was a single fit 30 Y/O and living downtown at the height of Lavalife and the early days of Plenty of fish. I was crushing it. Two of the hottest chicks I have ever banged were on the same day from 2 separate 1st dates. As dad bodded 50 y/o now I still think back to those days!

Those who know .... KNOW!!!!!!!!!

We're the around the same age. I consider the Lavalife heyday to be its own micro sexual revolution -- not a lot of people were privy to it. I had a high school friend who'd never had much luck with the ladies; great guy, not bad looking, but really shy. I told him about Lavalife around 2002/2003 and he signed up. Within days he was scorin'!

Lavalife's golden age was about 2000 to 2010. It had the best dating site ever, bar none; like, as in no platform even came close to being as good. All genuine REAL people looking for some bedroom fun and getting it. Tinder and Hinge cannot hold a candle to it.

Sadly, the site revamped itself around 2011/2012 and it is now a ghost town, a mere shadow of its former self in its glory days, but man, those were the days if you were around for it!

 

[Foodoo19]

Those who know .... KNOW!!!!!!!!!

We're the around the same age. I consider the Lavalife heyday to be its own micro sexual revolution -- not a lot of people were privy to it. I had a high school friend who'd never had much luck with the ladies; great guy, not bad looking, but really shy. I told him about Lavalife around 2002/2003 and he signed up. Within days he was scorin'!

Lavalife's golden age was about 2000 to 2010. It had the best dating site ever, bar none; like, as in no platform even came close to being as good. All genuine REAL people looking for some bedroom fun and getting it. Tinder and Hinge cannot hold a candle to it.

Sadly, the site revamped itself around 2011/2012 and it is now a ghost town, a mere shadow of its former self in its glory days, but man, those were the days if you were around for it!

For sure!
I used to by a bottle of wine and settle in for the night to score some prospects. I had a daytime 1st date once with a nice looking woman. We met at kensington market and day drinking ensued. After a few early awkward 1st dates of sitting across from someone and essentially interviewing each other, I developed a hard and fast rule of no sitting. Moving. Finding funny things to talk about in the surroundings.

We ended up going back to my place drunk. We were heavily teasing each other by then and I was rock hard. She sat on my steps just inside the foyer and asked for my cock. I obliged. Fornication followed with anal. I walked her to the ttc streetcar stop on Dundas near trinity bellwoods and said good bye. The sun was still out. Went home and had a nap. Glorious.
Never saw her again. Except a few days later I saw her walking hand in hand with the guitarist of one of Canadas most famous alternative bands. I guess they were a couple lol.
Made me feel even better.

 

[opieshuffle]

Conference. Large group of acquaintances. Short, cute red-head was there. Had a "pre-drink" party in my room with a group before evening closing party. End of conference she tells me she "left something in my room". BOOM! She was/is the hottest sexual encounter I've ever had! The making out, groping, dry humping lasted hours... to the point the final deed was almost anti-climactic. The chemistry was off the charts! 20 years later thinking about that night gets me instantly hard!

 

[xyphy]

I remember the lavalife days as well. There was one time on the chatline I started chatting it up with some rando and we decided to meet. She knew of an apartment near Queen/Bathurst that had a fitness room that was never used, she had been house sitting for a friend and kept a key. We met in front, went inside to the lockable bathrooms where she gave me incredible head and then analized her until I pulled out and came in her mouth. We straightened ourselves up, left and never heard or saw her ever again. One of those moments that I can't believe actually happened. Also, she was super hot, kind of cool/normal and would have and should have gotten her deets.
To this day I am thankful I wasn't mugged, could have been such a setup and I was too horny to even think about it at the time. this was probably around 2001

 

[xyphy]

There was another time that I was at some party and was chatting to some girl who asked why there were so many gay guys there. I told her I wasn't gay, she didn't believe me. I suppose I am too clean cut and well dressed. LOL. anyways, she's like "prove it". Asking her how is a guy supposed to "prove" he isn't gay. She said that a gay guy would never let a girl suck his cock. Went to the bathroom, proved that I was straight. I became her BJ Booty call for the next 6 months.