Most Unlikely/Surprising Sexual Encounter

What's your most unlikely or surprising sexual encounter?

For me, it was at a formal dinner reception, you know the deal 10 seats at each table, all couples with wives or SO's. This absolute "TEN" at our table is slying making eye contact and discreetly flirting all evening to the point where I was afraid others might catch on. So I excuse myself to go to the restroom and to my surprise she has followed me!! She walks up to me brushes her hand against my dick, keeps walking, turns and says follow me. We go into a small room in the hotel and she says "I just love quickes so let's do this"..lol She pulls up her formal dress, no panties on, bends over the table, and lets me hammer away like it's the last fuck on earth! After we finish she says "Thank's that was great! See you back at the table" WTF!!! The chick acted like nothing ever happened and I never saw her again....

Congratulations

Most unlikley was at the beach when I was 20. A buddy and I were driving down the beach looking for a good spot. There was a VW Westfalia set up and three young women in bathing suits, so we pull in close by. We go out into the water and start showing off. One of the girls walks out into the surf a appears interested. So I go over and start my hustle. Turns out that they were nuns on vacation.

The most surprising was when a co-worker asked me to come over and tune up his motorcycle. After finishing he said that his wife had lunch ready. She was a smoking hot woman he met in the Netherlands when he was in the Air Force.

We had lunch followed by a few drinks. Then he showed me his cartoon collection. I was wondering how a guy who collects cartoons wound up with this woman. Life is funny sometimes.

Then he set up a projector and screen and started threading on a movie. This was back before DVDs or even VHS. I was expecting some Looney Tunes and was thinking up an excuse to leave.

He started the movie and it was not a cartoon but a porn movie. We were sitting on the couch with his wife between us and she starts taking off her clothes. It was the biggest WTF of my life up to that point. It turned out to be a total three way with DP.

Most unlikley was at the beach when I was 20. A buddy and I were driving down the beach looking for a good spot. There was a VW Westfalia set up and three young women in bathing suits, so we pull in close by. We go out into the water and start showing off. One of the girls walks out into the surf a appears interested. So I go over and start my hustle. Turns out that they were nuns on vacation.

The most surprising was when a co-worker asked me to come over and tune up his motorcycle. After finishing he said that his wife had lunch ready. She was a smoking hot woman he met in the Netherlands when he was in the Air Force.

We had lunch followed by a few drinks. Then he showed me his cartoon collection. I was wondering how a guy who collects cartoons wound up with this woman. Life is funny sometimes.

Then he set up a projector and screen and started threading on a movie. This was back before DVDs or even VHS. I was expecting some Looney Tunes and was thinking up an excuse to leave.

He started the movie and it was not a cartoon but a porn movie. We were sitting on the couch with his wife between us and she starts taking off her clothes. It was the biggest WTF of my life up to that point. It turned out to be a total three way with DP. Originally Posted by JohnMacnab

NICE!!

1 - Vacation with then girlfriends family. I sleep in one morning while everyone else goes to the beach. Get up walk in kitchen to get advil and water for hangover with nothing on but boxers, I close the fridge and father in law's new girlfriend is standing there with 2 piece on and all oiled up ready for beach. Without a word spoken, we both look down and see my johnson poking thru my boxers and rising quickly. We both sleep in the following 3 mornings....

Most surprising for me was when I was in my 20's. I was dating a hot blonde from Florida, and she had an equally hot (but considerably more slutty) roommate. She always warned me about the roommate, but I thought she was being overly critical, until one night around midnight when the roommate came knocking on my apartment door, came in, and gave me one of the best blowjobs I've ever had. As she left, she had to take a jab: "I know _____ doesn't swallow, but I love to. Call me whenever you need it again."

I did.

Oh, I like this game.
My buddy came to town with his wife one time and stayed at a local hotel.
His mother-in-law drove down to visit and we all hung out at the pool most of the afternoon drinking.
About midnight my buddy's wife says she's got to go pass out and tells me and her mother not to try and drive because they have an extra bed in the room.
A couple of hours later I was bumping uglies with the mother in law while they slept in the next bed!
Don't know if the wife or dad-in-law ever knew but my buddy gave me a high-five!

ONE of my most surprising encounters in the hobby recently was a visit with Caramelqtee Mila! I already had an idea the girl was sexy as hell but when I saw her in person . . . . she was a must have! As if that wasn't enough I I trained hard for our meet just to keep up with her, and thank god I did cause that was intense!

A couple years after I got out of college and into the work-force, my parents decide to book a family cruise from L.A. to Mexico (Cabo, Puerto Vallarta, Mazatlan). So my sister and her BF are off doing their things... I find myself on a sailing excursion with this 19 year old from Vegas who'd been eying me during the "assigned" seating dinners... Her mom, her dad, and her sister all "approve" of me (don't ask me why!) and we spend a bit of time chilling in the casino back on ship... her dad starts getting drinks for me and her before he then takes off to spend some time with his wife. Needless to say, we didn't get much sleep that night!

One time when I was in high school I got a phone call in the middle of a school night.
There was a sexy sounding girl on the other line that started asking me questions and moaning. Eventually we had phone sex, I got my nut and never heard from her again.
Really fucking strange but awesome at the same time.

sounds like penthouse forum....

sounds like penthouse forum.... Originally Posted by live4fun

Are you saying they are all TGTBT ?? LOL !!

This sounds like Penthouse Forum. I've never had anything close to what u guys are saying.

This didn't end in sex, but it was unusual and fun. I saw on the cover of a national magazine (long gone, called "Look Magazine"--it was like Life Magazine) a close-up head shot at the beach of the most beautiful girl I had ever seen in my life, with golden blonde hair blowing in the breeze approaching sundown. I was a camp counsellor in the mountains with a bunch of 13 year olds in my cabin. I come back to the cabin and remarked that I had just seen a picture of the most beautiful girl I had ever seen, on the cover of Look Magazine. One of the campers says, "That's my sister. She is coming up here (1,000 miles from where the photo was taken) next Tuesday. Would you like to meet her? I was head of the waterfront and had that day off. So I take out the water ski boat, and just this girl and I spend the whole day and early evening together in our bathing suits out on the mountain lake by ourselves. It was a different era. If it had happened even five years later, we would have shacked up. Or if I had been more experienced at the time. Oh, and I will add--she was a 10/10 on the magazine cover, but only an 8/10 in real life, maybe a 9. But if she had been a 10, I probably would have been even more shy about going for gold.

One time when I was in high school I got a phone call in the middle of a school night.
There was a sexy sounding girl on the other line that started asking me questions and moaning. Eventually we had phone sex, I got my nut and never heard from her again.
Really fucking strange but awesome at the same time. Originally Posted by Dirk182

I'm in my office late one night, many years ago. I get this call. It is from a really sexy female voice, asking me to come over and fuck her. I can't leave that night, but I (thought I) knew who it was--a girl that I had been going hot and heavy with for a while (but no "going all the way" yet), and who I had seen just the day before. She sounded different, and I worried that maybe she was high on drugs or something. So the next day, I go straight over to her apartment. I"m surprised she didn't mention the call, but nevertheless, this time I "granted her request" and we had sex.

Many years later (earlier this year), an old female acquaintance of mine (someone completely different who doesn't know the above girl) let me know, apologetically, that she had once had a friend of hers, as a joke, call my office late one night and ask me to come over for sex with her. They were both on the line together and wanted to see my reaction.