Confidence & Courting

I enjoy flirting. I enjoy playful conversation and texts. I enjoy when a kiss is just a kiss. My point is that sex isn’t my endgame. If I meet a sexy person who is a potential partner, I relish in the chase; in the playfulness of each discussion and each encounter; in the not knowing where this might be going. By appreciating this person in this way, I’m never disappointed because whether we end up friends or lovers, I feel as though I’ve come out ahead.

This is not new for me, to some extent I’ve always behaved this way. Even when I was younger and sex was definitely meant to be the endgame, I was still happy if I made a new friend along that journey. The difference when I was younger was that I was not at all confident. So you can imagine how most flirtations ended.

There’s a fine line between confident and cocky

What is new for me is playing with confidence. Flirting with confidence is incredibly hot and sexy. At the same time, there’s a fine line between confident and cocky. Since re-entering the dating pool a couple of years ago, I’ve had plenty of failures on either side of this fine line. Failures where I was too timid, and failures where confidence came across as cocky and got me shut down. I do think that I’ve learned from this and really found my stride now.

Becoming confident began when I was getting to know Justina and going on our first date. Reflecting on my courtship with her, I could have been a little more confident when discussing specifics. But I was generally confident in my desires and did not waver in my intentions and attention towards her. My philosophy was that I had more to lose by not expressing myself than by being confident and being told that she wasn’t looking for the same thing. It paid off.

Connecting with Anne

Since The Great Pause has kept us all at home, I mentioned Anne and a hot video sex session that we had. (Well, I never did follow up and write about that sexy vidchat, but there’s a bigger story to tell today.) Like Justina I met Anne through my music and dance community and we became friends right away. I got to know Anne and her wife, even making an introduction to Jeannie at one of the rare raves she attended. The friendship changed last summer when I was dancing with Anne, her wife, and their friends who are a gay male couple from their hometown.

One of the guys was very friendly but also very forward and was asking me a lot of questions. (I learned later that he’s very protective of Anne.) At one point he asked, “You are gay, right?” Anne turned and, slightly offended that he was so forward said, “he’s married to a woman.” Then I added, “Yeah, but we’re open and both bisexual.” Anne and her wife both turned to me and seemingly at the same time said, “so are we!”

A few weeks later, Jeannie and I had dinner with Anne and her wife. We had a great time and we had a lot in common, but there weren’t necessarily any sparks, so we all left as friends. As Anne and I got closer as friends, we shared a lot of intimate stories and it was also slowly revealed that we both had an attraction to each other. Then Anne was (suddenly to me) going through a divorce and I was trying to be there for her as a friend.

While trying to just be a supportive friend, I was also finding my conversations with Anne to be very playful, so I kept dialing it up a bit. I was very much thinking that my confidence would be rewarded physically, or she’d shut me down; but our friendship foundation was strong enough that she wouldn’t “toss me away.” Not only was I correct, but we were soon sharing mutual desires to explore some casual kinks, especially her desire to be tied which is also my favorite kink.

So we began plotting a ropes session and were debating between a BDSM party and a private session. While I most definitely had a sexual attraction to Anne, at this point I was envisioning the ropes session being more platonic. She quickly dissuaded me of this basically saying, “well, if you tie me well, I know I’ll want to fuck you.” It was very easy for me to hear this, since I shared that desire. But it was also a pleasant surprise and I feel that the confidence we both expressed in our flirtations made it easy to just be honest with each other.

The Long Game

It was a bit before New Year’s that Anne and I started planning a ropes session but life was conspiring against us. We finally got a date on the calendar for late February, but as it approached something forced that date to change. Next we had a new date on the calendar for late March, then The Great Pause changed everything and that date was impossible. During this time and throughout isolation, Anne and I continued to be flirty and confident, mostly over text.

At one point in our text exchanges she said, “I hope your dick is as big as your Big Dick Energy!” I said with confidence that it is and got the response “well, it’d better be, now!” (There’s an entire post needed to address the question “does size matter” and how this takes shape in flirtations. Let’s just say for this story that even “objective” size is subjective since everyone’s experience and desires are different. So I had no idea if I would seem big or small to her.)

We finally hatched a plan to see each other at the end of June and it was every bit as hot as we’d hoped. Many times in the text flirtations she had said, “you really are just going to make me wait for this, aren’t you?” And I would always reply confidently with some version of, “Yeah, and I’m worth it.”

Was I really sure I was worth it?

This begs the question, “was I really sure I was worth it?” The answer is, of course, NO. I mean, I think I’m a generous lover who knows what he’s doing and has a lot to offer. But even if there were such a thing as a perfect lover, everyone’s desires and expectations are different. So there’s really no way to know for sure if I’d be worth it.

But playing the long game, and playing it with confidence, really earned me the right to be with her; and the chance to live up to my hype. Was there a chance I’d fail at this? Oh, hell yeah. Was I concerned about this? Oh, hell yeah! But I met her the other night with the same confidence that served me well throughout our flirtations and this continued to serve me well. Regardless of the size of my dick, my Big Dick Energy prevailed and we had a wonderful time together.

There’s one other great thing for me in having been with Anne – she’s absolutely a FWB. This is important to me for several reasons. First and foremost, I’ve really never had a casual relationship that included sex and I really wanted to experience this. Now that I have, I can say that I like it. I wasn’t sure that I would; I kinda thought I might have regrets afterwards. Second, I don’t have the capacity for another serious relationship right now. I’m incredibly happy to have my lovely wife and another steady partner. Third, while I was playing the long game, Anne found a new primary partner, and while this partner is embracing the idea of a non-monogamous relationship, they haven’t done this before, so there’s no telling how they’ll really handle it.

To wrap this up, I want to re-frame something I already stated. When in doubt, be confident. (But don’t be cocky!) You have way more to lose if you don’t try, and likely way more to gain if you express yourself fully and completely. There will undoubtedly be rejections, but those will serve to teach you and perhaps how to read a partner better in the future. This is my experience and it has served me well.