 

This is going to have to have some explanation. Bear with me. Throwaway because he might find this.

Marked as NSFW because I'm not sure if mentioning nude art of someone is nsfw or not. Might be.

I've known this guy for years. He's been home-schooled most of his life and is slightly autistic, which have both combined into a lack of a filter, inability to read rooms, and poor social communication skills. His memory is also shit. We came together and bonded to become pretty good friends due to our friend group and common interests.

A while ago, he decided to pursue his dreams of being a more feminine guy. I supported it and wished him the best. 

I had a girlfriend a while back. We're split, but good friends. He, at one point, drew her nude. It was an odd thing to do. I don't know the entire situation, but it was shitty to be told this by her. I talked to him about it and he denied he was trying to get with her. We all came to an understanding and I trusted him.

Months later,he was being increasingly lewd to my then-girlfriend and I think he drew something else of her. I talked to him about it and we again came to an understanding. Things were fine for a while afterwards. I trusted him again.

A while later, he was moving forward with his feminine guy process. But, he told then-GF that if her and I don't work out, then he'd basically be a girl with a dick, knowing she likes that, and to consider trying him out. I'm essentially quoting him with that statement. This came unprompted. I was absolutely livid. He defended himself by saying that he didn't mean it, and it felt weird as soon as he said it. He tried to take it back.

I laid into him for how shitty of a thing that was. We didn't come to an understanding. He couldn't remember the past two times after I brought them up because of his shitty memory. We resolved the situation eventually, sort of.

It's been years since that. Maybe two or three. We still talk nearly every day, and I fucking hate him most of the time. Other times, I feel conflicted. Sometimes, I feel fine around him. But, if I could choose, I wouldn't be his friend. But that would mean causing a huge rift in the friend group. I don't want to do that to them. Especially when I feel like I should have gotten over it by now.

I am genuinely mean to him.  I know it's absolutely unfair and shitty to do. I can't help how I feel about him and I know I should control myself. But it's really damn difficult. I still haven't let it go. I've apologized to him multiple times for this.

I can't stop making connections to "being basically a girl with a dick" to who he is. These connections make it terrible to hear his voice. It's difficult to hear him laugh. And I feel like an absolute monster because of it.

I am afraid to talk to him again about this. Nothing he can say to me will change how I feel, as made evident by his attempt at apologizing after I tried to talk to him about this earlier.

Reddit, AITA? What the hell should I do?