Most Unlikely/Surprising Sexual Encounter

I did my girlfriend's mom, and then her aunt . . . Does that count?

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

Oh man, was that you? I'm so sorry.

And quit calling me a girl.

I'm kidding.

For me, I was 18 and ran cross country. Went into a local discount furniture store to buy a stool for the counter in my new apartment. Two ladies, in their 50's working the register. When I approached with the stool, they giggled. One nodded to the other who leaned over and whispered to me, "have you ever just wanted a very random blow-job?" I don't even remember getting back into the stock room it happened so fast.

Did you go back furniture shopping there at least once a week after that?

Oh man, was that you? I'm so sorry.

And quit calling me a girl.

I'm kidding.

For me, I was 18 and ran cross country. Went into a local discount furniture store to buy a stool for the counter in my new apartment. Two ladies, in their 50's working the register. When I approached with the stool, they giggled. One nodded to the other who leaned over and whispered to me, "have you ever just wanted a very random blow-job?" I don't even remember getting back into the stock room it happened so fast. Originally Posted by Gulf2

For me I was 13 years old and yes still a virgin.My Aunt had got into an argument with her best friend (23 and smokin hot) and made her cry.After they made up she asked my Aunt if I could spend the night at her house to cut her grass the next day.She agreed and I wanted some extra money so I agreed too.As I was sleeping in the guest room I swear I had a dream she came into my room and asked me to sleep with her.A few mins later she woke me up and asked if I wanted to sleep with her.I asked her if I was dreaming and she took her knight gown off and turned to her bedroom. I seen her big beautiful Butt and I didn't care if I was still dreaming or not.I jumped up and had sex with her all night long.The next day she told me she hadn't been with a guy (I know I was just a boy still)since moving to Houston in over 6 months.I wound up cutting her grass for free even though she offered to pay me.

Back in the late eighties, I got tired of getting the solictation phone calls particularily about time share. So I decided to give this one girl a hard time. She gave it to me right back so I figured I get her off the phone by making lude and sexual comments. She gave it right back to me. This was getting interesing. I asked her what she looked like. Sounded good not great but hey what the hell. We decided to meet at bar in a motel. If she was a dog, I could leave. I got there she looked pretty good. Had a few drinks and she then invited me back to her apt.
This was the first time I had a women lick my ass. She loved it. She was wild. I fucked her for hours. I didn't want to see her again cause I had just started going out with someone. Needless to say, she had my phone number and called numerous times. I had my roommate answer the phones for screening purposes until she stopped calling.

Nothing remotely like these stories has ever happened to me. Looking back on my teen years I can think of one attractive neighbor in her 30's who may have possibly been sending me subtle signals but I was too dense to pick up on them. Now, if she had just been as bold and clear as the women in these stories I would have happily been all over her.

Did you go back furniture shopping there at least once a week after that? Originally Posted by JohnMacnab

Yeah. I have now have the world's largest collection of bar stools. For some reason, everytime I sit on one, I have this strange craving to smoke a cigarette.

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.... Originally Posted by EastDago

That is freaking hot dude.

for me mowing yards from 12 to 16, got my ass from 20 and 30 something yeard olds that took the time to teach me the right ways to please a woman, and be great at oral sex, mowed 20 yards, 10 a week, over 25% taught me and paid me. I wish this could happen again!!!!!!!!!!!!!!!!!!!!

this is a great thread!

In the early days of ASPD, Amber had some sort of quicky get together, just some friends to hang out. She lived in an apartment over by Richmond and Wilcrest. I was just hanging out and bull shitting when one of her neighbors came over. Amber and I went over to this ladies apartment, and I was introduced to the owner of the apartment and said hello to one of her ladies.

Come to find out, they were doing some sort of pay for phone sex setup. Amber left and I just was sitting on the couch, my eyes and ears on fire. I don't remember much about the owner, but one of her fellow phone sex talkers was a big titted milf, about 35 or so years old.

The hot blonde got on the phone and was apparently getting pretty turned on by her fake orgasms while on the phone. She handed the phone to the apartment owner and came and kneeled right in front of me. Next thing I know, she is yanking my pants down and gave me a bbbj/cim, while I played with her huge tits (she took her top and bra off).

I never even knew her name, and never saw her again.

I did manage to say thank you.

Hanging out with the proper people in the early days of ASPD could be a good thing.

I did manage to say thank you. Originally Posted by DEAR_JOHN

But, of course, sir. You being such a gentleman and all......

But, of course, sir. You being such a gentleman and all...... Originally Posted by bbkid

To say I was surprised and overwhelmed by the whole thing would be an understatement.

Hanging out with the proper people in the early days of ASPD could be a good thing. Originally Posted by DEAR_JOHN

Truer words have never been spoken. In the early days, the social event after parties were truly epic. Getting on that guest list was like getting the golden ticket to Willy Wonka's factory.

I'm waiting and hoping one happens while I'm still able to enjoy it!