[32M] Should I wait or gain some experience? /u/Money_Prompt_8345 Sex

I haven’t had sex in years, and truthfully, not a ton of sex experience on its own either. I do have plans running in the background to have sex with my best friend. We aren’t together but could potentiallyyy end up that way (which is what I would want and would at least prioritize having sex with this woman as something I have to explore at some point in the near-future). We’ve essentially just been waiting on me to do an STD test just to be positive that I’m clean.

I am worried about me either orgasming prematurely or having trouble getting erect. I’ve had some issues with this, not always, but I could see me needing some practice. I do want to explore masturbation in terms of enhancing endurance though.

We’ve put off having sex for months and is not something we actively discuss, but we still flirt and it makes sense that we’ll become sexual partners still. I don’t want to put this off much longer.

I’m very tempted to have sex once or twice before this because I am worried about my performance. Is this a good idea? I’ve thought about it with full clarity and I tend to think I shouldn’t do it, but not too much either. It seems potentially smart as long as I make sure I’m clean after. Obviously I would enjoy it. But it maybe seems excessive. I don’t know. Thoughts?

I haven’t had sex in years, and truthfully, not a ton of sex experience on its own either. I do have plans running in the background to have sex with my best friend. We aren’t together but could potentiallyyy end up that way (which is what I would want and would at least prioritize having sex with this woman as something I have to explore at some point in the near-future). We’ve essentially just been waiting on me to do an STD test just to be positive that I’m clean.

I am worried about me either orgasming prematurely or having trouble getting erect. I’ve had some issues with this, not always, but I could see me needing some practice. I do want to explore masturbation in terms of enhancing endurance though.

We’ve put off having sex for months and is not something we actively discuss, but we still flirt and it makes sense that we’ll become sexual partners still. I don’t want to put this off much longer.

I’m very tempted to have sex once or twice before this because I am worried about my performance. Is this a good idea? I’ve thought about it with full clarity and I tend to think I shouldn’t do it, but not too much either. It seems potentially smart as long as I make sure I’m clean after. Obviously I would enjoy it. But it maybe seems excessive. I don’t know. Thoughts?