This is one of those situations that demands honesty and vulnerability. "Hey, I know this might be awkward, and I'd like to think we could remain friends no matter what, but I just wanted to let you know that I like you quite a bit, and if you felt the same way, perhaps we could go out sometime. If not, that's totally fine; I really enjoy our friendship for what it is, and I'd not let my feelings interfere with that." Then, see what your friend says. There's a chance your friend won't be able to look at you the same way, but there is also a chance that this could be the start of something amazing!
It isn't wrong to fantasize about getting fucked by a horse or to use a dildo to help you enjoy that fantasy. Thoughtcrimes aren't really a thing unless you internalize a lot of shame. However, that said, your partner might not be able to understand or empathize with this desire very well, so it may or may not be something you need to share with your partner. It might be a good idea to discuss how your partner feels about kink and paraphilia more generally before admitting that you yourself have this particular kink, to gauge how your partner might respond. If it turns out your partner wouldn't really like to know about this kind of fantasy, you have the option of keeping it to yourself. How you masturbate isn't really something anyone else has a right to determine for you unless you are in a power exchange relationship; make sure you aren't doing anything risky or that falls outside of your relationship terms, and you can safely enjoy your kinks in private where they cannot damage your relationship. It is certainly a better idea to be fully open and honest, but only you know whether your partner would be able to receive that information in a loving and empathetic way.
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As a top, you will frequently be expected to be in control of the situation and to be self-assured. You can still project those qualities even if you need some help with getting hard. Practice becoming confident with your pump and making it a sexual part of foreplay. "Now we get to make my penis hard so I can fuck you" sounds a lot hotter than apologizing for needing a pump and making it sound like a bad thing. It's all about how you present yourself and the confidence you have.
It might be a good idea for you and your parents and him and his parents to all go out for dinner together in order to develop comfort and some kind of rapport. It's much easier to say no to someone you don't know than it is to say no to someone in person. When you and your parents make it clear that you're not a threat, there is a good chance his parents will become more okay with him spending time at your place.
Model the behavior you'd like to see from him, and when he does open up to you, make sure you're accepting and non-judgemental of what he says, even if you aren't happy about it.
Physical attraction is only a small part of attraction; if you like everything about the person otherwise, there is no reason that lack of physical attraction need to stop you.
No, that is perfectly reasonable. You are unlikely to get what you haven't asked for — go ahead and advocate for your needs!
You can't force it; you can put yourself out there, but pursue a relationship only when and if you feel that kind of connection with another person.
Break up with him; that will probably get his attention.
Yes! That's quite common. Single furs and couples tend to be the units by which furs join and exit packs.
