Fu*king the oldest guy ever

The Agent and I leave together. I’m obsessing about being able to take my contacts out so we go to my place. We get to my place by taxi. I’m a horrible host…don’t offer him anything to drink. We just start kissing and go upstairs and then we are naked except he’s still wearing his boxers. I recall thinking he has a very good body for an old guy. He has his hand between my legs and it feels very good. The last thing he said to me before I pass out was “I can’t wait to be inside you”.

I wake up at 6am and my head is throbbing; I feel horrible. My mouth feels like something died in it and my contacts are permanently adhered to my eyeballs. I’m tucked in beside the Agent, head on his arm. That at least feels nice. I don’t panic when I look at him…he still looks good in the light of day. He gets up to go pee then I do the same and then realize I need to puke. My bathroom is an ensuite so I run the water and the fan and hope to god he doesn’t hear me – because there’s nothing classier than a woman who fucks on the first date and gets so drunk she pukes.

We go back to sleep. Wake up at 9am. The medicine and puking helped and although quite hung over, I don’t feel like death anymore. He starts kissing me. Hand between my legs. I find myself wishing for NIM and how he touches me. The Agent’s skin looks old…not his body. I’m thinking this as he’s kissing me, mouth on my breast, hand between my legs, and I’ve got my hand on his cock. My inner dialogue is something like this:

  • Wow his skin has lost its elasticity. I guess that’s what happens when you are older.
  • Arms are okay, nice chest.
  • I wonder if he waxes his chest. He certainly has enough money for manscaping. No, I think he’s just hair free.
  • Hmm. Decent size cock.
  • He gets it up easily enough. Good sign. Didn’t take Viagra. Good sign.
  • I wonder how long he’s going to last?
  • Focus, dammit!

In contrast, with NIM, the only thing in my head is “oh my god, oh my god, oh my god, oh yes, oh more, oh my god”.

The Agent pulls me on top of him and off we go. He tells me I feel amazing, so tight, so wet. Could stay in me all morning. It’s nice. He’s nice. I do have a couple lovely orgasms. He actually does last a while. He cums with a flourish.

I realize I should check that Katherine is okay. I don’t have my iPhone…and The Agent has a text from The Developer asking for my number because I left my phone at his place. Yikes. He’s left it at the front desk for me to pick up.

It’s 10am and I need caffeine. He gets dressed, I throw on a nightgown and we go downstairs and make coffee and talk. For over an hour, he talks almost non-stop about the various properties he has bought, sold, developed. Some of the stories are interesting. He’s obviously extraordinarily wealthy. I’m not inherently impressed by this except that he is self-made. While he doesn’t ask me much about myself – actually maybe nothing, now that I think about it – he seemingly listens when I speak and peppered his stories with “I’ll have to show you that”, “You would really like that I think”.  I find myself wondering if this might be a guy who would take me to dinner, because a dinner would be swell.

He asks me to put my contact information in his phone, which I do. It makes me wonder if he’s forgotten my name.  His name is the same as my faraway lover. Is it bad that it made me happy to say his name during sex, because it reminded me of the other one?

He gives me a kiss – not lingering – and says goodbye. I’m not sure I care if I see him again, but of course I hope he’s interested…even just to reassure my ego. When I don’t hear from him, I’ll have my answer. I’ve become a cynic. But we’ve proven that going to nice bars is probably a better option than online.

Katharine stayed at the Developers apartment until 4am. Her summary? “We went there. It was half decent. Nice cock. Decent body. He was very into it. He’s very smart. Very sweet. But you gotta know that guys like that don’t date girls who fuck on the first date”.

0 thoughts on “Fu*king the oldest guy ever

    • Thank you Marian! It makes me sad too. Katharine and I had a debrief last night over dinner (chicken nuggets…we ate what our kids ate)… I have a post rambling in my head about the double standard out there. Why women are told to wait, but more importantly, why. What men thinks it says about the women who don’t.

  1. Great story.

    Unfortunately yes, there is truth in that last line, no matter how hard we fight it.

    I for one figure if they think any less of me because I’m a sexual being then they are the ones missing out no? I’m more than just “she put out on the first date” and if they can’t see past that then do I really want to be with a guy who thinks that way?

    No, I don’t think I do…

  2. “…because there’s nothing classier than a woman who fucks on the first date and gets so drunk she pukes.”. – I love that line! I literally just Laughed out loud!

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