Encounter #12: Two Women, One Day

(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......

Two Women in One Day

At long last, a prelude to our next encounter.....

Going into this whole Craig's List conquest, I had a few primary goals. The first, of course, was to have as many fun, no strings attached encounters as possible and create some nice memories. After that, my other biggest goal was to fulfill as many of my own personal sexual fantasies as possible. I think every guy has their own little bucket list of sexual fantasies that they want to indulge in while they can, and I am certainly no different. Most of these fantasies are things that most guys share.....threesomes, semi-dangerous public sex, etc. All good stuff.

I share these fantasies, as well as several others. One of these others is the idea of having sex with two different women on the same day.

Difficult to achieve? Definitely. Particularly when you are single. Probably the most realistic way for people to achieve this is when you are in the course of a relationship/marriage, and then have another encounter on the side on the same day you have sex with your significant other. So it really only entails seeking out one other person. The challenge when you're single is finding TWO separate people. And not just fining two separate people, but two people who are willing to fuck you on the same day! Not easy, my friends. It takes careful planning, both as far as scheduling the encounters, and proactively ensuring that you are 'ready' for both encounters (the fantasy could fast become a nightmare if you are not recovered enough for encounter #2).

So, why do I speak of this as if I have some first-hand knowledge of the situation? Well, do you really need to ask? Details to come.......

When Life Interferes....

So, clearly I lied in my last post. Not intentionally, of course. I truly expected to get right back in the groove of cranking out two posts per week. But alas, life interferes again. Nothing terrible or traumatic (or exciting, unfortunately), just long work hours, physical and mental exhaustion, and the lack of time and mental energy to write. It's interesting, being a relatively new blogger, I always figured that no matter what else was going on in life, there would always be the time and motivation to write. It really seemed like such a low-maintenance hobby. But I underestimated how the desire to write (or at least to write solid, non-half-assed posts) can definitely be diminished by mental fatigue from other aspects of life. Well, lesson learned!

I'd like to promise that there will be no more long posting droughts like this again, but obviously it would be silly to make such promises. For now, I'll just say that I will try my best! Thing are slowing down now, so hopefully there should at least be some improvement in the short term.

Thanks for your patience......next post is coming shortly (I promise!)

Encounter #11: Fun with Porn

(Blogger's note: Sorry for the long delay in posting, things have been crazy busy lately with work and life in general. But I am hoping to get back on track with 2 posts per week again now....thanks for your patience!)

I have to admit.....it was my idea.

I was emailing back and forth with "Amanda" who I had met on CL, and she asked me if there was anything I wanted to do that would be a little 'different' when we hooked up. So I thought about it. What had I not done during any of these encounters yet that could be fun and spice things up a little bit. And then it came to me.....porn! Wouldn't it be fun to have sex with a total stranger, while watching other total strangers have sex?? It sounded good to me, so I suggested it to her. She was game. We made plans.

We arranged to meet at a local motel that often advertised free pornography as one of it's perks. A little sleazy perhaps? Yes. Typically I prefer to meet my encounters in nicer hotels so we can be more comfortable. But the point of this encounter was to be a little different, a little dirtier. So we were both willing to tolerate the tackier accommodations. I mean, honestly, as long as they had a bed, was there really any other major deal-breaker?

The room turned out to be fine. We both had a laugh at the mirrors on the ceiling and heart-shaped designs throughout the room. Clearly, we were not exactly the first couple here just to engage in naughty activities. So, we started out by getting comfortable with each other, making out a little, etc. After the ice had been broken, I went for the tv remote with a smile. Of course, I had to make a crack about how she just wasn't doing it for me so I was going to catch some of Sportscenter....thankfully she had a sense of humor!

I turned on the porn. We laid together and watched. It was pretty hot.....the scenes were very raw and explicit. As we watched, we would slowly touch each other, teasing. We were both getting incredibly turned on, as evidenced from the heavy breathing from both sides of the bed. Was it each other having that effect or the porn? Or both? Did it matter? I tend to think it was both. But in any event, we were soon pleasuring each other orally, and then enjoying several positions of fucking. Of course, there were a few positions that were in the porn where we just looked at each other like, yeah ain't happening! One of the downsides of trying to emulate porn actors....normal people just aren't that flexible. Ah well.

The sex was good, and the porn did spice things up. I had fun. Afterward, she started asking me questions that lead me to further understand the potential downsides of porn (particularly for the insecure). Was she as sexy as the women in the scenes? Did she turn me on more than the scenes did? Was it disappointing that we couldn't do every position? I tried to reassure her, but I could tell she wasn't totally convinced. But what could I do? She was attractive, and I certainly would have had fun without porn. No way to prove that to her though. Looking back, I hope the insecurities don't stand out in her memories as much as the fun of the experience.

Would I suggest this again? Probably not for a NSA encounter like this. Like phone sex and cyber sex, it's a better thing to use in the course of a longer term relationship to add a new wrinkle. Or, of course, for a fun solo experience  ;)