I think the OP needs to cut Simon some slack. I understand how important gender identity feels, particularly at that age, but the fact is that if Simon is into guys then a trans guy, normally lacking in certain physical attributes, may very well not ever be in his attracted-to group. Yes, using the term 'not a real man' was unfortunate but it sounds like he's apologetic and clearly from the context he was using it to refer to the sorts of people who he'd find sexually attractive. Trans people are fully aware of the fact that they're not "real" members of the gender they identify with, or at least they should be, and should not be so sensitive to it being pointed out.

I'm a straight talker, so if easily offended please skip past. With that out the way... What is a 'Real Guy'? I'm in my 40's and have never definitively been able to answer that. My sister is straight; She watches sports, drinks beer, and is generally a representation of a stereotypical man. So for 'Simon' (and many many others), it has to have come down to a physical thing, d**k. Which is understandable given that your school is still probably teaching the same thing that they were in my day when it comes to biology. NGL, the whole gender debate can get confusing as heck, so I imagine it's even more so for young teens that are trying to discover themselves. Cut him a break. You said it yourself, this kid's only told 2 people that he likes guys/d**k. You're all still learning, don't get too hung up on this kind of c**p. Focus on being kind, caring, loyal, and supportive friends. Then you'll find that little else matters when you have friends that would fight, bleed and die for you.

Give Simon a chance to learn from it. It sounds likes he's been a good friend, but has to do some thinking about both gender and sexualtiy. It also sounded like he didn't know what he was going to say until it was out of his mouth, and it may not have been the right wording. Or it might be the right wording but he now knows he needs to change his way of thinking. Or this might be the beginning of the end of the friendship. But it sounds like he deserves a chance to think things through, to consider your perspective, and confront some latent homophobia/trans phobia. It might take a few conversations, but give him a chance to get there. If he doesn't take it, it's ok to distance yourself.

In my mind, as a trans guy, he could be forgiven for the original "I've never kissed a guy before", but doubling down and saying that you're not a real guy was super sh*tty of him, and I personally wouldn't really want him in my life anymore since he doesn't respect your identity

I am friends, or acquainted with, (counts) 7 different people who have biological sex markers or whose assigned gender does not align with their mind/brain. And I've noticed my immediate perception of them--before I have a chance to think about it, to process anything--shifts slowly over time. So there's a lot of correcting myself. And correcting others! In my friend circle, we don't punish ourselves for getting it wrong; we know it's a process. We just keep correcting until eventually we approach having that visceral, immediate perception of them as their actual gender. It does help for them to look like their gender / sex; I have a harder time at the beginning, before hormone treatments. Yes, it's horribly embarrassing for me, as it must have been for Simon; but all the knowing it intellectually isn't the same as knowing it viscerally. And sexual attraction is all about the visceral. Give him and yourself time; Simon's uh, viscera will likely, hopefully, think of you as a man yet!

He kissed you because you were there, willing to be kissed. Its not a comment on his gayness or on your gender or on your attractiveness. Its good for you to learn now that somebody being physical with you does not necessarily mean that they like you or find you attractive. Yes, that can be confusing and hurtful, even for adults! But he did make an explicit comment on your gender, and thats the part worth focusing on. Of course that was hurtful, but only you can judge whether or not his behaviour otherwise is validating, safe and supportive as a friend.

I think the concept of trans can be difficult for many people to accept, particularly if the person in question (OP) hasn't physically transitioned yet, so maybe a bit of slack is needed here. But I would make it clear to Simon that if he can't accept me as a guy, then it's time to say goodbye.

As a teenager, not-yet-transitioned, trans man myself; I say you aren’t the AH, but neither is your friend. I’ve had plenty of friends call me ‘not a real guy’ or say that it doesn’t count. Sure, hurts like hell, but also… yeah- I haven’t transitioned and it makes sense that many people still see me as fem. I WILL say- however- it’s okay for him to mess up his words etc, but if he doesn’t apologize [or at the least say he won’t call you a ‘not real man’], then he’s at fault.

Simon isn't attracted to females, that's what he is trying to tell you.

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He is right. You are not "a real guy". You are a girl.