Awesome content and thanks for posting!
Regarding your query: I suppose no one knows. There are 3 options I guess:
- It could become weird.
- Nothing would change.
- It could become awesome.
2 out of those 3 are ok. Personally, I don't see why crossing that boundary would affect your friendship negatively. I think it would strengthen it, but this is me. Are you scared of him developing feelings for you? Talk with him about that!
What are you planning to do?
I have never heard of that "intercrural sex". Interesting.
I don't think anal sex is necessarily intimate. To me, it is just sex. I have had sex with guys in a way that is just... transactional. They fuck me so we both get off. But if you are not comfortable, you shouldn't do it!
How old are you guys btw?
Let us know how it goes! This is the most content this sub has had for a few months!