I think it goes without saying that working this issue out is better suited with a professional therapist and not the internet regardless if it's an internet community like this or online pornography, which just provides an exceptionally warped view of sex and sexual relationships.

Well, I value the eclectic feel of intersubjective thoughts and opinions on the matter which is manifest on these forums. I don't really have money for a therapist at the moment.

I'm quite conflicted about the issue but it doesn't cause me to be anxious or anything. Just trying to be Stoically adept at the issue.

The deeper issue here is that I suppose, apathy and depression. I don't have the desire to establish a relationship with anyone. I'm pretty much a loner.

That's about it...

I've had sex very few times in my life and I can say they have been expensive in some ways, for example: I worry a lot about STDs, also, I worry a lot about pregnancy. Not to mention the fact that the woman I have sex with and I are almost never in sync with each other: we are almost never equally horny, we are rarely horny at the same time; sometimes I really want to have sex and she has stuff to do like taking care of her brother's baby; sometimes she has to go very far to work and I'm not able to see her. All these things frustrate me and I cannot complain at all. So at the end of the day much of what I've taken out of sex has been frustration and anxiety. It may be because I'm a beginner but still I have asked myself if it's even worth it. I hope that when your first time arrives you don't get the same things out of sex as I did. However, you are very likely to do so and if you feel depressed I don't recommend adding anxiety and frustration to that. The problems will outweigh the pleasure that comes with sex the first times, I guess that will change over time, right now I could not tell. If I were you I would work on my depression before anything and I think you should ask for help. Here in Mexico we have public hospitals and people with economic difficulties can access Quality healthcare and that includes both psychiatric and psychological treatments. You may search for something similar where you live. I mean, I never had depression but therapy has been really helpful to me nevertheless.

However, you are very likely to do so and if you feel depressed I don't recommend adding anxiety and frustration to that. — Alan

Hmm, I guess that is a good point. Maybe, there's some fantasizing on my part about the whole thing.

Anyway, I guess there's a multitude of factors at play here in this thread, which I have delved into and addressed on my part. I'll have to analyze the situation a little more in depth on my own.