Inability to orgasm during sex

It's a common issue here man.

There are many factors that come into play.

First, you probably have porn-induced sexual dysfunction. What is your porn use? Do you still watch porn? Have you tried nofap in the past?

Second, how do you masturbate? Do you use the prone technic? Do you use the death grip technic? If so, you have probably numbed the nerves of your penis, which aggravates your ED.

Third, you may experience performance anxiety because of your consecutive failures.

Fourth, and it's probably the worst, you probably carry a lot of TOXIC SHAME. It's something I discovered recently about myself as I'm working 8 hours per day on fixing my own shit. I know exactly what you're going through, because I went and still am going through the same shit (I'm now literally avoiding having sex because of it). Problem is man, shame and anxiety are a deal breaker in terms of erections.

You have to work on your shame man. Where is it coming from? How serious is it? If you feel ashamed to the point you won't even see a doctor or a psychologist (like I was for like 10 years of my life), it means you carry a LOT of internalized shame. You need to release that shame if you want to be able to have proper erections and be able to orgasm. In your situation I think seeing a psychologist would be a great idea. Opening up is how you start releasing your shame.

For me personally, I started therapy 4 months ago. My first session was horrible. I spilled a bunch of puke all over the place. It was the first time I admitted to anyone that I was a porn addict (among another bunch of issues, childhood, teenagehood problems, professional problems, romantic relationship problems). I never spoke about it again. But 3 weeks ago I realized I had so much shame, it was probably the cause of my inability to orgasm with a girl (I can now maintain erection but I can't O from normal sex, and very hardly from BJ even if I know I'm THAT CLOSE to cumming (it's like it just won't come out)). In one week, I opened up and told 4 friends about my porn addiction. I was so scared of their judgment. It turns out they don't give a shit and don't see me differently. Some support me. Some don't. I don't care.

You have to accept the fact that you aren't perfect man. Read my journal, read my posts on the Shadow self. Maybe you've denied your primal needs and it now causes you ED.