I met SK online. She is a few years older than I am. Notably, she’s past the important 30 mark. Though I’ve dated a bunch of older girls, that was when I was younger, and I’ve never before dated anyone over 30. We only exchanged very few messages before she just gave me her phone number and told me to call her. But when I did call her to ask her out, she made me qualify myself by chatting for about 15 minutes before she’d agree to go out with me. I knew right away this girl would be trouble.
Our first date was for coffee on a Saturday morning. She is cute for her age and has a big, warm smile, but clearly her best days are behind her. I’d say she’s a 6.5, though at her prime she could have been an 8. Her best feature now is that she’s a great conversationalist. As I checked out the waitress, I really enjoyed talking to SK. I walked her almost to her home (she seemed reluctant to tell me where she lived) but didn’t try for a kiss because it seemed like she specifically didn’t want it.
For our second date, we had dinner on a week night. Again it was a nice time. She made a serious offer to split the bill. I tried to insist on paying, but she gave her credit card to the waitress and told her to charge half. I figured this was her way of signaling her non-interest in me, so I didn’t try to kiss her when I walked her home, and I didn’t expect to take her out again.
But she suggested a pretty forward third date: we’d eat hash brownies and look at pictures she’d taken while traveling in various third world countries. If that sounds exactly like an excuse to get stoned and have sex, congratulations, because that weekend we got stoned and had sex.
This was actually the first time I had sex while high, so it was an interesting experience for me. She gave pretty good head, let me finger her ass, the whole deal. She was exceptionally horny and she had three orgasms, one from fingering herself while I played with her breasts, one from me fingering her and another from the actual sex. I did enjoy it, but she’s not so attractive so that aspect was a little laborious.
We kept up a routine for a few weeks of seeing each other two or three evenings a week and then sleeping together. She’s enjoyable company, except she has the annoying girl habit of picking fights. Fortunately, because I’m so much more desirable than she is, I could just stare her down and not let her intimidate me. It also helped that I was consistently seeing other girls at the time, so I didn’t feel like I needed SK for anything.
After a while, she realized that I didn’t want anything serious with her and that I was just having a good time. Because she’s over 30, she has to get really focused on finding some guy who’s going to be with her for the rest of her life. Since I know that’s not me, I totally expected her to break it off. When she initiated a breakup conversation, I told her straight up that I didn’t want to get serious so fast, and that she should take some time to think about it and if she wanted to keep seeing me. Then when she got back to me a couple days later, I could hear her voice cracking and wavering; she clearly didn’t know what to say or how to say it. So I came out and said that if she doesn’t know if she wants to see me, that is her answer: she doesn’t want to see me. And that was that.
Overall, this experience was not life-changing, considering that she’s not so attractive and the sex was good but not great. But I will always remember SK fondly as the first girl I successfully gamed into bed. By “gaming” I mean that this is the first time for me that having sex was not “getting lucky,” but something that I earned by saying and doing the right things at the right times and in the right ways to reach that goal.