I hear that per the frustration.
First up, with the condoms -- I see you're in California, so I want to make sure that you know about this program for free condoms in your state: https://www.teensource.org/condoms/free
. You can also call in to your local public health department and see how they're doing condom distribution during the pandemic. You may be able to get more free that way, too.
Yeah, by all means, the not being able to feel things much isn't just about your pleasure (and even the idea that you won't experience pleasure or will have less pleasure by using a strap on and harness is also quite an assumption and a pretty simplistic way of thinking about pleasure, but we can talk about that more later if you want). It's also an issue wen you're learning how to engage with someone's anus and rectum, the delicate tissue there, and how it all works with the muscles. By all means, we can feel some resistance and some give with a harness and dildo, but nowhere near the far more nuanced sensations we can usually feel with hands and fingers. That way of anal sex also gives you both practice communicating with this kind of sex, too. So, I'd always suggest starting there first for a ton of reasons, very much including because that tissue is so delicate and it is easy to hurt someone unintentionally, especially when you're also new to strapping on.
When it does feel like time, your best bet will be to hit up an independent sex toy shop, which can be an option once he's 18. That way, someone in person can help. Or, you can find one online, and ask for help via email. Another way to do good research about this is to read some toy reviewers on these kinds of toys and tools.
I've got a couple articles here that also might be of use to you now and later:
• https://www.scarleteen.com/article/bodi ... e_of_entry
• https://www.scarleteen.com/article/advi ... ex_lowdown
• http://www.scarleteen.com/article/bodie ... every_body