I've been having problems recently because I'm so lonely that whenever I try to masturbate I can't actually cum because I can't stay focused on the horniness; the loneliness keeps seeping through. I haven't had a lot of positive sexual experiences in my life so its hard for me to masturbate without feeling like there are holes in my imagination. It makes me feel kinda empty and hollow.

I think this is literally the exact opposite symptom compared to you but overall I think the causes are similar. We both are unable to understand and express our sexuality the way we want to, to others and ourselves, because of our complicated histories and lack of comfort-ability with our sexuality in general.

You could try writing in detail exactly how you feel and why. Maybe you'll find a way to express it that is more palatable to other people. Honestly though? Just fucking ask them. Hey I have some awkward things I've been wanting to vent about, is it ok if I talk to you about something relating to some sexual/sexuality related issues?

Even if they say no you're still showing that you value their opinion and view them as a confidante. Better yet think of something fun to talk about right after so you can change the subject real quick. Maybe next time you have something fun happen and you're going to tell someone just wait until after trying to vent to them. That way they won't really remember it the awkward thing.