My Very Brief Weekend Dating “Adventure”

My Very Brief Weekend Dating “Adventure”

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Last Wednesday I received the sweetest note on FetLife. The subject was “Interested, so very interested”. The message that followed was so charming I checked out his profile.

He’s only 26. Not much there for a profile, but I don’t have much either. Just pictures, and only one kind of with my face.

He didn’t have any pics posted online, but he addressed that in his note:

The way I see it being loud is like cheer leading, lets me know I’m doing a good job, and you can break as much of my skin as you like πŸ˜‰
Hi, I’m “RS” (short for Rock Star) and I’m hoping that we can get to know each other.
What kinds of things are you into (both vanilla and kink)
I don’t have any pictures on my profile right now, but if you’re interested I can send you some via email or KIK.

Note: Rock Star is not his name on FetLife

I responded. He sent pics. He was gorgeous. We emailed a couple more times and then exchanged numbers. He’s new at the kink thing and so am I. We had common interests in rope/bondage, wax play, switching and also similar personalities and interests outside of the bedroom.

After my Thursday evening dating snafu, I was looking forward to something a little different. He asked me out for late drinks on Friday. We met at a bar and 3 hours flew by as we talked. Conversation flowed smoothly. I only had a couple weak bar drinks so I was fairly sober, he had a couple beers…

I really, really liked him!!

He walked me to my car and sat with me while it warmed up. We talked for another minute or two and he leaned over to kiss me…

His kisses tangled tenderly with mine. His tongue gentle, but not invasive. His hands caressing my back…

I want to write this in a sexy story kind of way, but my weekend didn’t end quite like it started.

We had perfectly-timed, amazing front seat car sex! I say perfectly-timed because, as soon as I got my pants back on, someone got into the car next to us πŸ˜‰

RS winked at me and said, “I kept checking to make sure that no one was coming our direction.” I giggled and looked around. There was a car in the row behind us with its parking lights on. I’m fairly confident whoever was in that car watched the entire thing. (Hahaha! Kinda kinky, right?)

What a great way to break in my new car!!! (I’ll tell you about the car later.)

We texted briefly Saturday and Sunday afternoon he asked if I wanted to spend that night with him. I had Monday off, car sex with him was fun, so I thought What the hell? Why not enjoy a youthful frolic with this young gentleman and see where it takes us.

Not very far, it turns out.

I dressed up in my fuck-me boots and some patterned thigh-highs, short skirt, low cut shirt, favorite bra… I looked and felt amazing!

When I got to the hotel, we sat and talked for a while. He told me he really liked my stockings and my boots. It was comfortable when we kissed. It was comfortable when he took off his clothes and stood naked and glorious in front of me.

It was comfortable when I sucked his dick and when he entered my pussy from the front and from the back. I came so many times I can’t even count. His cock thrust so deeply inside me.

Slow…. Then fast. His hand on my clit sometimes… He grabbed my ass-plug and tried to put it in without lube. I reminded him, after a screech…

He played with the ass-plug while he continued to thrust into me. He was like a bunny. My legs were almost complete jelly when he entered my ass. He’s only the second man to have that hole and it still makes me a little nervous. Alaska was so gentle and good to my asshole… RS thrust a little to quickly and completely at first, but slowed when I asked.

I came again and again until I couldn’t hold my legs up underneath us any longer. I said, “I don’t think I can…” and collapsed on the bed, still convulsing from the aftershock.

He pulled out and went directly to the bathroom where he spent a really long time cleaning himself off. So long, I started to wonder if I had “messed” him up and he didn’t know how to say so.

Eventually, he emerged and sat down next to me. He was awkwardly uncomfortable and stood up again to grab his underwear before he said, “I should put these on before I tell you this. I feel so stupid.”

“What’s up?” I asked. Honestly concerned that something had gone wrong. “Did I do something? What happened?”

“Oh, no no! It’s not you at all it’s me. I know it sounds corny, especially with what was just happening, but I can’t do it.”

“Is it the age thing? Seriously, I don’t have a problem if you tell me whatever’s wrong. I’m grown. I can take it.”

“It’s not that, Smitten. I feel so stupid thinking it or even saying it because I haven’t even met her yet, but I think I’m in love with another woman.”

Honestly, I had not ever anticipated this scenario. I was completely speechless.

“I’m sorry,” he said. “I was really a jerk to think I could do this, but I can’t.”

“I really liked you, RS,” I said as tears welled up in my eyes. I wanted to hold them back, but then I didn’t. What difference did it make that this guy saw that he made my cry.

“I like you too, Smitten. Friday night I completely lost track of time while we were together. When you told me how late it was, I was genuinely surprised. I was even looking forward to learning things from you and together with you, but it wouldn’t be fair and I just can’t do it.”

He was so sweet about it. We hugged a lot of times and talked more as I got dressed and then I partially dressed him. He cried with me; he saw my hurt…

I said that usually all I want to do was cuddle after brain-mangling sex like that, I didn’t know how to react to what he’d told me. But I thanked him for giving me the opportunity to learn something new and being completely honest with me.

I know he was young. I knew it couldn’t last.

I was just hoping for some kind of connection. Even if it was only temporary.

This was just Fate looking out for me long term, I’m sure…

When I got home at 10:30PM, I sat in my car and cried. It took everything in my power not to text Alaska.

Monday my willpower was not so strong…

OnlineDating

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15 thoughts on “My Very Brief Weekend Dating “Adventure”

  1. *throws several red flags out on the playing field*
    Okay, I call BS on this young man’s excuse. And that isn’t online dating…that was just an hook-up, free sex, booty call, hit it and quit it moment. Not the beginning of a relationship, unless you were trying out the guy for a long term friends with benefits relationship. *grins* That’s fun all in it’s own right!

    But I wonder, what are you really looking for? A sexual relationship or a romantic relationship? They don’t have to be one in the same or even the same person. Yet they start out very different from each other. This weekend is a good example of a sexual relationship only start.

    1. This weekend was supposed to be the beginning of a sex only relationship. I still have feelings about how it ended, though. If he had a problem with me, I wish he would have told me that instead of concocting that stupid story and then being so nice to me…

      Aside from that, I thought the pictures were cute.

  2. That sucks, I’m sorry. A couple things came to mind when reading this. First, is it seems from your writing that you are engaging emotionally pretty quickly – meaning you’re quick for your head to get to the “oh I like him” place. That’s pretty dangerous especially when you are pursuing just sex. If you can be a bit more cynical until you’ve met someone a few times, it could help. Second, even with casual sex, I think you’re opening yourself up to bad situations when you have sex on the first meeting. It might seem counter intuitive, but unless you really don’t care, you do open yourself to having more men bail after a couple of meetings.

    1. Thank you, Ann ❀
      Men bail on me after a couple meetings whether I let them fuck me or not – I've tried it both ways. And maybe I don't understand what you mean, but I always thought I should want to like someone in order to hang out with them again – either for sex or not. But I agree with your comment on being more cynical.

      I’m not trying to be argumentative or bitchy. I hope this didn’t come across like that πŸ™‚

      1. Nope doesn’t come across like that at all. I just caution you against that immediate hope because it takes a few dates if not more to really suss out what may happen with someone. Of course you have to like them – it’s the expectations that can be an issue. Unspoken or not.

        I agree some men will leave no matter what, but it’s a matter of whether you want to put yourself out there sexually with them right away before you get bailed on. I’ve felt better generally when I haven’t fucked someone and they disappear. Unless I didn’t give a crap either way.

  3. Oh my lovely … me, I would look at it this way – you did connect – for a while – and it was glorious x as you are glorious and he has to a degree shown you that there are good men out there …

    1. Thank you, Sweetness! I am looking at this in many good ways ❀
      The hurt is acknowledged and passed. He helped christen my car and find it a name πŸ˜‰

Talk to me :-)

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