(Blogger's note: I know, I lied. It's been a rough couple of months, what can I say??)
I had 'met' (i.e. exchanged emails) two different women on Craig's List. One had responded to a post I wrote, and one (amazingly) had written a post of her own that I responded to. And she wasn't spam!! A rarity in the world of CL, my friends.
Gina and Diane. Both were available only on Saturday of that week. I could have put off one of them to the following week, I suppose. But who the hell wants to wait?? So for the very first time, I did it.....dates with two CL women on the same day.
I tried to at least space them out. Not that I'm an old man or anything, but I can't exactly cum a million times a day like back in the teenage years (ah, the memories). So I wanted to allot as many hours of recovery time as I could. Gina was the evening date, and I didn't want to embarrass myself!
I met Diane for lunch. Afterward, we made our way to a local hotel and had great sex. A little too great....she wanted a round two after we had finished! God damn it, why do round two's only come around at times like these?? I couldn't exactly tell her that I had to save myself for my next date a few hours later, so what could I do? Yes, round two occurred.
After leaving Diane, I was nervous. Guys, you know that feeling you get after have multiple rounds of sex? Like, feeling all good and relieved, but kinda done for the time being? That was how I felt. How was I going to have adequate sex with Gina??? Should I cancel with her and just reschedule? Fuck it, I decided to just give it a shot. What's the worst that could happen? I suck, and she doesn't want to see me again. Oh well, there would be other proverbial fish in the sea.
No food with Gina, she just wanted to meet in the hotel room (damn, dinner would have bought me some more recovery time). I wasn't feeling quite as done as I was earlier, but I didn't exactly have a raging hard-on either. What helped was that Gina was gorgeous. Blonde, curvy, amazing smile. And very sensual. And luckily, very into foreplay. We made out, and slowly explored each other's bodies. I spent alot of extra time going down on her....my rationale being that if I had any performance issues, that at least I could hang my hat on having given her a couple nice orgasms with my tongue. Then she started going down on me. I was fighting off some nerves and intrusive thoughts (thinking during sex is BAD), but the blowjob went well. Again, not super hard, but adequate.
Now would be the true test. As the condom went on, the nerves rose again. Nothing kills a mediocre erection faster than a tight condom. So, my plan was to get it on and get in as quickly as possible. The more lingering, the more chance for issues. I put it on, jumped on her, and put myself inside. Starting fucking her hard and fast. She was one of those types who kind of moans throughout so you can't really tell when they're cumming exactly (see one of my previous posts), so I reached a point where I didn't want to risk going any further. And I came. She might have too, who knows. Overall, I think it was a respectable effort on my part considering.
So yes, I had sex with two CL women on the same day. It hasn't happened since, but I'll always have that memory. Wish I hadn't allowed it to stress me out so much so I could have relaxed and enjoyed myself a little more, but what can you do. In the end, it worked out pretty damn nicely.
By the way, I never saw Diane again, but did have more fun with Gina......
