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Late night trip to Denny's ends with a Craigslist encounter confession
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This is inspired by the guy posting CL confessions. I miss CL and have had some similar experiences to him. Here is one of my more memorable ones.....

It was the summer of the 2016 presidential elections. I was in Texas about to head west for work. I posted an ad in the city I was going to be in for a couple of days, as usual expecting little to no response, and if I got one it would be a scammer or bot. My email alert went off and we started talking. She was interested in my ad, and as long as I wasn't a "Burnout" or "Killary" supporter, let her know when I got into town. I sent a "fansign" pic letting her know who I was likely to vote for and hit the road. I checked my email a few times to let her know I was still steaming that way, that it would be late when I got there, etc. She said she was a night owl anyway, was familiar with where my hotel was and to let her know when I got settled and we could meet at Denny's.

I got there, got to the hotel and sent the email and expected the "it's too late, I am tired kinda cop out/excuse" email that ends a planned encounter for whatever reason. Instead she said I will be there in 20 minutes and described her attire. I walked over a few minutes later and soon she arrived.

Typical late night Denny's crowd, so I don't have to describe the scene too much. We looked like a "normal" couple who were there for a late night meal, mixed in with the other eccentrics/drunks/weirdos who were there. I was a little hungry and said what are you having, her answer was she brought her own metabolism tea and she was fine. Odd, but hey. CL.

We sat in that booth for over an hour. Talking. Weird stuff at times. Stuff that comes form late night conspiracy shows on the History Chanel. Aliens. Government stuff. She was an off and on paralegal and had all sorts of "people done wrong" stories. It was fascinating but it also left me with that "do I want to be alone in a room with this person I met on CL an hour ago" feeling. At one point she asked me straight up, am I coming back to your room, and I gave a sheepish answer that oddly she understood. I think she could read that I wanted to but had apprehension.

She hit the bottom of her tea cup and the crowd had thinned enough that the waitress was coming by with the frequency of hey, buy something or GTFO. I said let's get outta here and she gathered her stuff, I paid and out into the night we go.

Standing in the parking lot at nearly 1 a.m., with locals walking past us we were still deep in the weird conversation we were in, and I looked at her and got a "what". I said are you lips as soft as they looked. Her answer could not have been scripted any better...."get in the van and find out". Just like in the movies. It was the kind of van you are imagining....really. Older, messy, but I couldn't stop myself. I jumped on the tail of this comet because I wanted to see where it went next. She was 59 to my mid 40s btw. Her lips were very much soft. I could see the potential/possiblity of a porn scene developing in her van there in Denny's so I said, hey I need to go, I'm on foot and it is late. She said nonsense and insisted on driving me to my hotel. I had decided that it wasn't the night, thanked her and waved as she drove into the night.

20 minutes late I got an email with a pic looking down the full length of her body saying "I just got in bed and am thinking of you"......to which I did the only sensible thing and replied, "I wish you were here".......the reply was "what is your room number" and I sent it. See you soon she said. Frantic nerves. If this goes sideways I am the only one to blame. I freshened up and brushed my teeth. Ran as much of my "stranger coming to my room" security protocol as I could. Soon came a knock on the door and there she was with a smile on her face.

My ad was for a random act of muff dive (RAOMD) kind of experience, and as I had said, she was interested in that as well. Soon she was undressing, and we moved to the bed and she lay down. I began to get acquainted with her body, and, well her pussy. I will tell you what I told her and my intention of how I hoped it would land, and how it did land, and how I saved myself from offending....

You've seen them. Mastabotory pussies that are replica of you favorite porn star. You can buy one and "fuck" your favorite porn star. Well, she had a very beautiful pussy. And I said "you have a porn star pussy". And she took it as "you look look like a high mileage slut". And I tapdanced my answer out and she understood and I began to lick.

The tone of this story is more how weird a CL encounter can be...and I imagine a Tinder or Bumble encounter can be if it is just sex and not looking for a relationship. But she had a weird free spirit sensual nature that was very attractive. She absorbed the licks and moaned in a way that made me want to keep licking. At one point she said "I wonder how many fingers you can get inside" and I will be discreet by not answering, but it was very eroitc.

I licked and fingered and she came multiple times, until eventually it was about 4:00 a.m..

Just like there was some sort of unspoken communication at Denny's, she understood it was time to go, and she said something to the effect that she had to bake a casseroul for a church group in a few hours, got dressed and out the door she went.

There is a part 2 to this story, the next night . Depending on if you want to hear it.............

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4 years ago