So my family have started to call me a male name and use male pronouns, and I'm grateful they're trying even though they slip up a lot. However it just sounds awkward and feels awkward when they do it. How long does it take until it feels natural?

I guess in the beginning there was a slight feeling of 'well you're only using that name and those pronouns because I told you so.' So I'd be overthinking it. Eventually it just happens though, and feels natural. You just stop noticing that you haven't heard your birth name or female pronouns for a while.

I'd agree with Kam for the most part.

As you progress you start getting use to it more and more and then start to notice that the more you're enjoying the correct name/pronouns the more the old ones stick out like a sore thumb and that might irritate you more ect.
Of course it varies per person and so on.

For me it took a few months of getting used to hearing the new name. My brain still sometimes even says my old name (like say if I go "Omg what were you thinking (insert name here) and instead of my thoughts saying my new name it automatically goes to the birth name which irritates me lol. Of course I've lived with that name for 27 years so it'll take time.

But yeah, as you progress and give it a good solid 6 months or so of constant hearing it, it'll get tons easier and then it'll become second nature really.

IMO, it feels awkward if it is awkward for the person doing it. There's still obvious awkwardness when my mother calls me by my name, because the effort in her voice is clear. People who only ever knew me as me, there's no "obviously working to get this right", no awkward.

I agree with blink. My mom has gotten very comfortable and used to my new name, but she hadn't gotten used to my pronouns yet, so when she calls me he and him, it sounds forced. She remembers about half the time, and she hasn't caked me by my birth name in months, which makes the screw ups all the more awkward, even more so than the correct ones.

I struggled with this too, and still do now with words like  "son" and "brother" etc from family members. It took about 6-12 months for the name to stop feeling awkward, but now it would feel really weird to be called my birth name.  It definitely takes a little while for new names and pronouns to stick , but if everyones on board and supportive, it'll all fall in place with time

I also feel really awkward...but in a way like I haven't earned it yet. Like I'm not worthy of being perceived as male. Very weird.

For me it's been tough to remember that someone is talking to me when they say my name, which is kind of a blessing since they're at least using it. I think I need to record someone saying my name and make it a ringtone or something so I hear it a little more often and get used to reacting to it.

People mainly say my chosen name at work, I answer to it right away. What's weird to me now is if one of my family members use my birth name. I honestly feel like they're talking about someone else.