It’s the Sex, Stupid!

It’s been an interesting week of sexual encounters. I have three men “in the hopper” and I slept with two of them! So on paper, that’s exciting. But in practice… it’s… something.

First was Schlomo. He is divorced and while we don’t have a ton in common, he is clearly attracted to me and was pretty forward on our first date. He smelled my hair! He told me he wanted to taste me! (And he didn’t mean my lips!). So I was hottttttt for our second encounter.

It did not disappoint (well, not exactly). We met up at a new, fancy but quiet cocktail bar near my place. I hadn’t been before so I didn’t realize there is a little separate room from the main bar, where he snagged a table. Good thing, because we basically made out the whole time at the bar and didn’t do too much talking. And we only had one drink. The conversation was a little forced - like I said, we don’t have too much in common - but the chemistry was 💯💯💯

We wrapped up the drink and I invited him back to my place. He wasted no time in saying yes. Once at mine, we didn’t really do any talking, just got down to business. And what a business it was! He was entirely focused on my pleasure - which of course, love that! It wasn’t until after he had made me come four or five times using just his fingers and we sank back for some pillow talk that it occurred to me - we hadn’t actually had sex. We hadn’t done P-in-V, losing-your-virginity sex. And to his credit, our pillow talk started with unraveling that mystery.

While he was married, he barely had sex because his wife suffered from the condition where penetrative sex is very very painful. He said he went almost ten years without having sex. And now he has sort of a complex about penetrative sex. He’s working on it - and based on his incredible digital performance, I’m happy to participate in any way he wants - but that it takes time to unwind that. Which I can 100% appreciate.

So overall, Schlomo was deeply satisfying but - no penetration.

Then there’s Cali Cool Guy. I was so nervous for our date - my feelings have been building for him for a while. This would be our fourth date (though first in almost three weeks) and we hadn’t slept together yet. So when we went to dinner, I was trying to figured out where our sexual tension was. And I couldn’t. I also really wanted to ask him where we stood, and I chickened out. I asked him what he was trying to get out of Bumble - and he gave me a super generic answer about just wanting to meet women. I was trying to figure if his heart was open, if he was looking for a relationship and I really whiffed the follow up. I ask hard diligence questions for a living! How did I mess this up!

When we finished dinner, we chatted while we walked. He sorta suggested going to his apartment (which was the entire point of me suggesting dinner in his neighborhood). We hadn’t even kissed yet at this point in the date! I said something about “yeah I wanna make out with you”. To which his reply was to kiss me on the street.

But once at his (gorgeous! Well designed! Tastefully decorated!) apartment, it felt a little forced. As in, I felt like I was forcing him a bit. At one point when we were just kissing, I pulled back and said “you know we can just make out or hang out” and he said no and pressed forward.

There was not much foreplay (ok, fine by me). But it also was very…. Random? Rote? Mechanical! I was into consummating our connection but the chemistry was just absent. Not in a good or bad way - just a vacuum.

And the sex itself - very short. Maybe not “The Minuteman Liftie” short but - I hadn’t really gotten started. In addition, no offer to help me out. Fingers work (we know that much!), so I was surprised because he’s been such a gentleman about everything else up until this point. It was just…. Weird.

I left once it became painfully clear he was done for the evening. I did text him about hanging out again - not quite ready to give up on the connection. But it does seem like this saga is headed more for Friendship Forest than Love Island, especially if the sexy side of things keeps up like this. We shall see…

The big takeaway from this week is: sex is weird! And undependable as a stable aspect of a new relationship or connection. I promise not to take good sex for granted! So yes, I will set up another time to hang out with Schlomo. If I broke the seal on “no having sex with Trump voters”, I might as well make the most of it…