Becoming a Pussyboy, Step #2: Getting to know your pussy.
You want to be a better pussyboy? First, you’ll need to train your hole before you can really call it a pussy. Don’t skip this step. Take your time with it. Enjoy it. The thing is: your entire life, it’s been clenched—like spending decades with your knees bent. Now, you’re reconditioning that and adopting a new normal. That can take time, especially if you don’t have much prior experience using your hole. So, that’s the physical component.

Just as important, however, is the mental component. As guys, we’ve all spent our teenage years discovering our cocks, with the understanding that playing with our cocks is just what guys do. We figure out what makes it tick. Its anatomy. What feels good? What doesn’t? What gets it going? What makes it cum? Later, when we start having and exploring sex, a lot of us realize that our dicks may not be the be-all-end-all of our sexuality. Maybe it’s our mouths, more so. Maybe it’s our holes. If sex always involves an equation of giving and receiving—the fucker, and the fucked—maybe we’re the receivers. One day, you realize: “Okay, I’m a bottom.”

So, you’re a bottom. Still, so much of the way you think about sex revolves around your cock. Because you’re a guy, right? Sex is over when your cock cums. Getting fucked is fun, sure. Sucking cock is fun. But it doesn’t feel good in the way that stimulating your cock does. That’s because you understand your cock. The rest of it, you probably don’t. You’re only getting half the story, at best.

Want to be a better bottom? Explore.

For a long time, my ass was this arcane thing. I barely even knew what my asshole looked like on the outside, let alone the inside. I didn’t understand its anatomy, let alone what makes it feel good—or what doesn’t, what gets it going, or what makes it cum. Truth be told, it’s as complex and as sensual a sexual organ as any other. The more you explore, the more you realize that.

So, here’s your first step: forget about your cock. Not forever, necessarily—though some do find that appealing. Just forget about it, for a while. For a week, don’t jerk off. Instead, play with your ass. Imagine it’s a pussy. Imagine it’s all that’s there. Feel it. Finger it. Use your toys. Touch yourself elsewhere, if you like—work your nipples while you enjoy the sensations of it, perhaps. But don’t play with your cock. At least, not at the same time.

Just one session like this, and you’ll begin to understand: there’s a whole world of fun you’re not having because you’re too focused on your cock. Now that you’ve trained your pussy well enough to separate the pleasure from the pain of it, you can explore this. With just a finger, feel the outside of your pussy. Push inside. What makes it tight? What makes it slack? Push it deeper. Feel around. Feels good, doesn’t it? It did all along, but you were searching for the wrong signals. You’ve always thought of pleasure as being the feeling you get from touching your cock. This is different, but it’s just as good—for some, it’s better.

Set aside some time, every now and then, to forget about your cock and rethink what “pleasure” means, separate from your cock. That time might be spent playing with yourself and your toys, or getting fucked—or, a personal favourite and a strong recommendation: being eaten out, nothing else, no “ultimate goal” of cumming, just a hot mouth servicing your hole the same way you love to service cocks. For once, be a little selfish when it comes to your pussy. Give it the same time and focus that you gave your cock all those years. You’ll be rewarded.

That’s your homework for now, pussyboys. Keep me posted.

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