Ask Beastly: Is My Penis Too Small to Please a Partner?

You’re not too old, too small, or too late—you just need a little rewiring.

I was raised a conservative Christian and was doing the whole waiting until marriage. It was only as I turned 50 that I dropped that nonsense. I am generally attracted to cis and trans women. I attempted to top for two different trans women but failed to get my cock to insert into their anus/rectum. I did all that is recommended. My penis was as hard as it ever is and I used plenty of lube. Having a conservative Christian message playing in my head, I thought it wasn’t God’s will for my life or my penis is too small between 4-5” erect. What are your thoughts? I want to try bottoming, but I am not into the whole rectum cleansing thing. At 58, perhaps I am too old for it all.

Babe,

Sex continues long after 58, at least among my friends, so let’s do away with that idea.

I am not sure what actually happened when you tried to fuck. Your penis was hard. You could not insert it because it was too small? Normally guys with smaller penises have an easier time getting it in but might struggle to please their partners once they’re in. Really big dicks are the ones that some people simply can’t get in—because they’re too big, too painful for the bottom.

I don’t see how being too small kept you from physically penetrating someone. So it sounds like something mental was going on—something related to your upbringing, your past beliefs.

But, again, I'm not entirely sure. Your question isn’t clear. If you felt shame and had to stop, it’d be evident what needs to be worked on: shame. If that were the case, I’d say to get more sexual practice and invest in connections (friendly, sexual, romantic) with people who challenge your shame, discomfort you, and push you. In your case, you should be around more trans women and queer people — and see them not just as sex objects but as people to learn, love, and listen to.

And, obviously, a therapist. If you’re not talking to someone about your sense of self, your identity, and your sex life—particularly after your upbringing—it’s time, babe.

However, I’m not entirely sure that’s what happened, either. Your question doesn’t really state why you had to stop. So I don’t know what the problem was. But I assure you that your penis can do the job, and more to the point, it has to because it’s what you have. Life must be, if nothing else, the journey of learning to love what we are given, including these unique vessels we live in. If your penis is not enough for someone, they're not a match for you. It will be enough for someone else.

The messages in your head can quiet, especially if you replace them with new messages—if you immerse yourself in queer culture, youth culture, rock and roll, techno, kink, wild sex, and basically anything in culture that acts as an antithesis to the Christian beliefs you were raised in. Like learning a new language, you can only learn to reject that toxic religion and the toxic culture it fosters by immersing yourself in a new one. Welcome to the church of sin.

Get a therapist.

Love, Beastly