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Weirdest thing that's happened to you

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The thread about "open the door" made me think about it. Standing at the door for a few seconds can feel a little awkward, but I'm sure most of us have had a lot more uncomfortable situations.

Mine wasn't seeing an escort, but a married woman I'd met on line. We were going to finally get together at her house. I parked out front and was walking to the door when her husband unexpectedly pulled into the driveway. Talk about awkward.

I had no idea if I was busted, or if he just forgot something. He got out and I said "Hi, are you selling the laptop on Craigslist?" He said no and we agreed I must be at the wrong place. It was all I could do to walk slowly back out to my car that suddenly seemed very far away. Every instinct I had said "run away!"

It's one of the best memories I have of my escapades, and I never even got in the door! I was kind of proud of myself for coming up with something on the spot. Even though my heart was pounding, I don't think he suspected anything. She and I laughed our asses off about it later.

It's all about experiences. You can't buy memories like that. Or, well, maybe you can!

So what's your best "uncomfortable situation" story?

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Mine was simply knocking on the wrong door at a hotel, both times the main problem was wrong hotel. Could here someone on the otherside of the door, probably looking out the peep hole. yikes.gif

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From back in my Capitol Hill days:

Went to an incall, realized I left the covers in the car. Realized when I went back, my keys were locked in the car! The uncomfortable aspect was the police contact as I was trying to get back in(to the car, not the incall).

Had a SW that would occasionally knock on my apartment door when she was looking for a few bucks. Normally, it would have been ok; but once, she knocked while I was sexing up my GF at the time(Yay Cap Hill!)

But, by far the most uncomfortable:

Did an overnight at a local hotel. All went well until about 2 days later. Received a call from LE. It seems there was a violent crime committed in an adjoining room and they wanted to know if I'd heard anything! "No officer, I was too busy!"

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I was in another city, and arranged a two-girl outcall to my hotel room. We had a rocking good time, greek on girl one, greek on girl two, and then a DP on girl one with girl two using a strapon on her. WOW!

Not only was it an unusually wild and great session, but during the whole affair one of the ladies had left a bottle of baby lotion open on her bag on the room's sofa. The ENTIRE bottle spilled out and soaked into the sofa cushion.

That night I toyed with the idea of just bolting in the morning and saying the mess was already there, but my conscience got the better of me. So the next morning, when checking out, I mentioned the sofa, the spill, and ask to be notified if there would be clean-up charges.

Two days later I got a call at home, from the hotel manager, a woman. She thanked me for the notification on the spill, and said there would be no charge because the prompt notice allowed them to get to it before the stain set. Then she said:

"Most gentlemen don't tell us when their lady guests make a mess. Thanks again."

I don't know if intended or not, but as she hung up I could hear her laughing out loud.

Hilton Hotels. I haven't had the guts to book another Hilton for over a year.

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I had two knock-on-wrong-door incidents, and both were awkward in their own way.

First was back in the day, when "Pleasures" was still around in Boulder. My third (or so) trip there, the girl on the phone asked me if I needed directions. I said no, been there before. Turns out they had moved. I knocked & some mousy middle aged lady answered- she seemed to know exactly why I was there & was none too happy about it.

The second time was even worse. I made an appt with my ATF, who lived in a small mobile home park at the time. I had seen her often enough, that I would just walk in when I arrived. After a 2- or 3- month dry spell, I booked again and she didn't tell me she had moved to the next trailer down the street. So, when I walked in, I found myself face to face with a half dozen homies. I don't know how I got out of there alive.

Ah, the memories.

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Mine was simply knocking on the wrong door at a hotel,...
Very similar, two hotels share the same name downtown, but on one floor, they don't share the same room numbers. I confirmed about three times with her and all three times it was Hotel A. Of course, she's at Hotel B. Finally, get to her hotel and of course the good ol pass key to get to elevator is needed. When the front desk asked her name and room number I said, "ummmmmm her nickname is this but not sure what her legal registered name is, let me call her!"

Very awkward and still one of the main reasons I despise downtown hotels!

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I knocked at the right room number, but wrong hotel. A very attractive YL answered, but not the one I had seen several times before. She said I was the 2nd guy that morning to make that mistake.

Called my YL and she directed me to the hotel next door. I gave her a hard time, jokingly, about her instructions but she said I was her first of the day.

I suspect the wrong woman was a provider too.

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The line between "Weird" and "Normal" are kind of blurred in this hobby. For me, the weirdest moment was my first hobby experience, which came in my mid 40s not that long ago. Knocked on door, loud music playing, no answer. I'm so nervous, I just think, "Ah, forget it." I knock once more, music turns off, dogs start barking like crazy. The whole neighborhood is alerted to my visit.

She answers the door...the weirdest thing, which is incredibly normal FOR THE HOBBY was that she was naked and kissing me within five minutes of meeting me. I was so floored, so mystified, so baffled by this. I finally stopped and said, "I can't believe this is happening. I just met you." She just smiled, giggled, and said. "I'm going to give you the best blow job of your life."

Normal? Yes. Weird? For me, at the time, it was supremely weird.

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"I can't believe this is happening. I just met you."

It took me several visits to stop thinking this even though it was why I was there. :)

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When I met what I call my first "real" provider, I told her I'd had a bad experience. At the time, there was no sex at home at all. Once we got into it, I looked down at her and said "Wow. I'm fucking a woman." She didn't miss a beat and said "That really was a bad experience!" I'd have laughed if I hadn't been so terrified.

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LOL: I had two REALLY hot trists with a beautiful young woman (early 30's). Fast-Forward a few months...I have just taken a new job.....I am really clicking with one of the "older dudes" he and I see eye-to-eye about projects, customer support, and technology. I have a meeting with him in his office, I show up before he does, and IHe look at a photo he has hanging on his wall. WTF??? Is that the woman I just had happy times with a couple of times?? I am staring at the photo, (and just realizing that it IS HER) when he comes in behind me.... He KNOWS I am staring at the photo....he PROUDLY starts telling about his daughter, and how she excelled in college, and about the great career she has now.....I am like "Uh, Bluh, Duh????) This dude really likes me, he slaps me on the shoulder and says "I can bring her to the next company picnic....you REALLY should meet her" Me: "Uh, Bluh, Duh" HIM: "No Really, she needs a good man with a career" ME: (thinking about the WORST social circumstance EVER) "Uh...actually, I have a girlfriend....I am so sorry....I should not have even been LOOKING at that photo...." HIM (slapping me on the back) "No worries....she is beautiful....any man is going to look at her".....ME: "uh, yeah, she is beautiful"

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Needless to say, I never scheduled another appointment with her....She has since retired, hope she found that good man with a career:)

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She just smiled, giggled, and said. "I'm going to give you the best blow job of your life."

Was it?

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The line between "Weird" and "Normal" are kind of blurred in this hobby. For me, the weirdest moment was my first hobby experience, which came in my mid 40s not that long ago. Knocked on door, loud music playing, no answer. I'm so nervous, I just think, "Ah, forget it." I knock once more, music turns off, dogs start barking like crazy. The whole neighborhood is alerted to my visit.

She answers the door...the weirdest thing, which is incredibly normal FOR THE HOBBY was that she was naked and kissing me within five minutes of meeting me. I was so floored, so mystified, so baffled by this. I finally stopped and said, "I can't believe this is happening. I just met you." She just smiled, giggled, and said. "I'm going to give you the best blow job of your life."

Normal? Yes. Weird? For me, at the time, it was supremely weird.

Pleeeeeeeease tell me you wrote a review. :D

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I've had so many embarrassing moments, I could write a fucking book.

1. I'm banging a hooker in some skeezy location. Her dog comes in and takes a giant dump in the corner.

2. Standing outside a hotel room, while two hookers behind the door debate whether they should "let in a big black guy."

3. I order incall, hooker shows up with a tranny. Wants me to do a threesome.

4. A hooker trying to "chase" me away with her Rottweiler (I'm not afraid of dogs, since we've always had a German shepherd in th family. More funny than scary).

5. I show up at an incall and the girl turns out to be into bdsm. Tries to upsell me to a threesome with her....wait for it......mom.

The list goes on and on....

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I've had so many embarrassing moments, I could write a fucking book.

That could be a best-seller!

  • I met a very drunk escort at the bar of a hotel. She couldn't walk on her own so I dragged and carried her up to the room. She fell down on the floor of the lobby, puked in the elevator, hallway and bed. Nothing happened and I was outta there!
  • Had a session with a lady with a cute pit bull who stayed by the bed trying to get me to play with him. YL said if I did not behave she would have doggy bite my dick off.

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While seeing a well-reviewed lady for the first (and only) time, I exited her incall at a private apartment to a sea of cops in the parking lot. My heart immediately jumped to 180 bpm and my body wanted to freeze, but somehow I managed to put one foot in front of the other and make my way to my car. I have no idea what the cops were doing there, and I never did find out. I sent the lady an email afterward telling her that her parking lot was crawling with officers.

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LOL, I remember that one, if it was the same lady, we cancelled that day because of that.

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When I was living on the East Coast, I frequently went out to Silver Spring, Maryland, to bang these two illegal Colombian chicks who were whoring themselves out off a fleabag motel. The room was so small, when one had a customer, the other went into the bathroom for a smoke.

So, one day, I'm over there, but sort of have a bad feeling. I decide to leave my pants on. I'm plugging away, quickly bust a nut, leave....and about 10 minutes later the damn place gets raided.:eek:

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Was it?

It actually was not the best blowjob of my life. My wife can tie a cherry stem with her tongue, and back in the day she shared her talents on me with wonderful regularity. I sure miss it.

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Pleeeeeeeease tell me you wrote a review. :D

She is retired now, av8r. Another weird thing was that we were intently watched by four dogs, including one on the bed. I guess that's not so weird, now that I read all these dog stories.

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If that dog had tried to join in --- THEN you'd have a good story for this thread :-)

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When I walk into the room, I am introduced to the dog wagging its tail. The provider & I quickly get to the fun stuff. I am sitting on the couch with her straddling me. We are in a steady rhythm when all of a sudden she screams!!

Her dog sniffed and licked her ass.:eek:

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Lets see something weird. I once hit something that belonged to the hotel with my vehicle. I didn't damage my vehicle though.

I meet a providers security/drive. once. She introduced me to him after seeing her a few times. She swore it wasn't her pimp. Whatever he was it was super awkward.

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Justina's tongue ring story is the greatest of all time.

http://www.theotherboard.com/forums/showthread.php?t=40061

(scroll down a bit)

I can top that now:

Had a lovely Gentleman with a very well trained ass...

Long story short: Butt Plug got lost in his ass. :eek: After everything was done, I sent him to the shower to retrieve it (solo) and then I went shopping for some bigger and sturdier items. :D

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More amusing than weird; Back when I was very green, an Asian woman on BP interested me so I gave her a call. She sounded American-born and I mentioned this. I also asked her if she had any reviews. This totally pissed her off and she ranted about how she never knows what she is getting into with new clients, so why should I have the benefit of reviews? Then she accused me of racism because she thought I was interested in an Asian fresh off the boat, and then hung up.

OK, so she is maybe not the most stable person in the world, I thought, but I had a hotel freebie which was about to expire, and since this provider only did outcalls I decided to try once more. This time I avoided the sensitive topics and we had a pleasent conversation and set a date. I guess she did not save my phone number into her assholes folder. ;)

I met her at the hotel and we hit if off rather nicely. We had some mutual interests and we laughed easily with each other. We must have talked for a half hour before activities and she did let me know the clock would not start until after our talk.

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I can top that now:

Had a lovely Gentleman with a very well trained ass...

Long story short: Butt Plug got lost in his ass. :eek: After everything was done, I sent him to the shower to retrieve it (solo) and then I went shopping for some bigger and sturdier items. :D

Again, I have no clue how you ladies do what you do. None. Just handling the "non weird" is too much to even ponder.

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I can top that now:

Had a lovely Gentleman with a very well trained ass...

Butt Plug got lost in his ass. :eek: . :D

I simply cannot imagine an ass wide enough, loose enough, used enough, to lose a buttplug in. Those things have flanged ends to prevent that sort of thing.

What were you doing? Fisting him up to your shoulder?

:eek: indeed!

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I simply cannot imagine an ass wide enough, loose enough, used enough, to lose a buttplug in. Those things have flanged ends to prevent that sort of thing.

What were you doing? Fisting him up to your shoulder?

:eek: indeed!

This is my point. It's "weird" but it's just part of the job. These women know things that I simply don't want to know.

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