Embrace Your Insecurities Day 4: Sexual Incompatibility and Innovation

Before I could write this post I felt blocked. Even though I was doing a great job of shedding other insecurities, whatever was holding me back from writing (without second guessing everything I wrote) was running rampant. So I busted out my journal and asked my Limitless Self what was happening.

Limitless Self, what insecurity makes it so hard for me to write easily?

You have an expectation about writing that cuts off your natural flow. You think writing should look polished and concise and professional, yet some of your favorite bloggers are raw and pure, not polished and professional. Be raw and pure yourself and you will flow.

How do I be raw and pure?

Raw means real, authentic, unrefined. You care more about honesty than you do presentation.

Pure means 100%. Whatever you're being, be it 100%. You don't hold back or hedge. You don't need to fact check or create foolproof arguments. You simply share thought-provoking ideas and piercing insights.

People taint their purity by trying to always be right, or always sound smart, or not offend anyone, or not look bad. They forget that every story needs a villain, and that you are often the villain in someone else's story. If you try to prevent that you will be bland and boring. You won't be the villain in anyone's story because you won't be in anyone's story. You will be unremarkable and overlooked.

Stop trying to placate imaginary critics and start passionately imparting your perspective. You will never be right in everyone's eyes, so just honestly share what you see through yours.

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After writing that out I felt much freer. I don’t need to stress out about topic and presentation, I can just share what’s most on my mind and trust that whoever’s meant to read it will find it.

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Sexual Incompatibility

I’m not sure what it was, but I couldn’t seem to stay aroused. I could get it up for short periods of time, and even engage in intercourse, but I would lose focus, and certainly never came close to coming. Everything else was so perfect about her, why couldn’t the sex be perfect as well?

When we had sex again the next morning, I was in a better place and more focused. But still my normal passion and playfulness were replaced with effort and attachment. Sex is a huge part of an intimate relationship for me, so it felt like I was putting a lot of pressure on myself to make sure it was good. So of course that backfired and caused me to be so in my head that I couldn’t be in the moment.

Ironically, even when she came, which is normally the highlight of any sexual adventure for me, I didn’t light up inside and get excited to join her. Instead I felt like a distracted dad unable to take his eyes off a sports game while his son took his first steps just a few feet away from him.

Was there something wrong with me? Was I trying too hard? Were we simply sexually incompatible?

All of these possibilities raced through my head. Luckily we had established the habit of total openness, so instead of trying to sweep it under the rug with some excuse, we discussed all manner of things that could have been at play.

• Did I respect her too much to feel dominant?
• Did I have a habit of making love to insecure women, using my displays of love towards them as an indirect means of loving my own insecurities?
• Did I not feel safe enough around her to be vulnerable enough to orgasm?
• Did the fact that she was used to partners with less stamina cause her to not be calibrated for someone with more sexual experience?
• Did I need to get better at receiving pleasure instead of focusing on her so much?

After discussing all these possibilities and more, openly and without either of us getting defensive or fighting, we kissed goodbye and she went home.

After she left my ex texted me, wanting to come over sometime next week. It was so tempting to fall back on the 7+ years of sexual chemistry with her and enjoy the ease and comfort of reliable mutual orgasms. But I knew if I said yes to that I would be stringing her along, and using the past as a crutch, instead of stepping boldly forward into the unknown.

The Sexual Training Simulator

After talking things out with both the ex and the new girl, I decided that maybe part of what was driving me to want to get back with my ex was the fact that I still hadn’t ejaculated. And that maybe making decisions like this (with a loaded gun) was not offering me the most objective perspective. So I did what any solution-oriented soul would do in my situation, I laid down to masturbate.

I didn’t want to masturbate to porn, or fantasies I knew would reliably get me off. I wanted to use the freedom of my own mind to map out the sexual destiny between me and the new girl. Clearly she was different than anyone I’d ever been with, so maybe there was somewhere different that being with her was supposed to lead me.

I explored many fantasies looking for what would excite me most about being with her: Domination/submission, blowjobs, anal sex, vibrating anal plug… but the first thing that actually got me super excited was something totally unexpected: yelling out her name during sex. I’ve never yelled out someone’s name before, much less had a fantasy about it, but here I was masturbating in bed, getting off to the thought of yelling her name during intercourse.

Then, the thing that set me over the top was actually even more vanilla and unexpected. Going down on her. I don’t know why those thoughts did it for me, but within a few seconds of thinking that and few images flashing through my head I had a different kind of orgasm than anything I’ve had before. It felt like a heartgasm. Even though my penis still ejaculated, it was my heart that led the way. And the ejaculation seemed to be a byproduct of what my heart was feeling, not what my mind was thinking or my hand was doing.

Afterward, I explored the meaning and feeling behind these two fantasies, and why that was the combination that got me off. It kinda sounded like the sexual fantasy equivalent of yelling “Beetlejuice, Beetlejuice, Beetlejuice” and then blowing Michael Keaton. But as I reflected on what they actually represented to me, it felt like yelling her name was like invoking a god(dess) or saint. And then after that goddess energy was activated, oral sex was like speaking the Divine into physical manifestation. But instead of speaking words I used my tongue itself for physical stimulation.

Sometimes an Obstacle Is Really Just an Opportunity for More

What seemed like something that was getting in the way, was actually something leading me to so much more. That heartgasm was a game changer. I can’t imagine what it would be like to experience a fullblown heartgasm during sex, or trying to go back to just having sex with my genitals afterward.

It makes me wonder, what other opportunities am I missing out on because the obstacles seem too big? Maybe the bigger the obstacle, the bigger opportunity. All I have to do is see past the part of it that makes me feel small, to discover the opportunity to grow so much bigger.

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Thanks for reading!

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Embrace Your Insecurities, The Full Series:
Day 0: Exceed Your Love Limits
Day 1: Coming Out of the Closet
Day 2: The Transformative Power of Insecurity
Day 3: Opening the Door to Love