Does it really get easier?

[Kratos Aurion]

If you are happy then that's fine. It's was just that your friend's reasoning for not letting you start on top was a massive red flag.

Rather than pulling out, holding still until the pain subsides is much better. Otherwise you take a few steps back in the opening up process.

I'll definite try holding still next time. Now that I think about it, him pulling out last night knocked the wind out of me lol.

 

[Infernal]

Your body is experiencing something totally new to it. It may take a while for things to connect in a way that you really enjoy it. Maybe some self exploration is needed, or it could be that maybe this isn't something you'll ever enjoy. Some men just don't like anal play and that's totally fine.

 

[Dave NoCal]

Like others who have responded, I am concerned that your friend seems to not be very considerate of your situation and feelings. These first experiences are particularly important regarding whether you will come to find anal to be pleasurable. As others have noted and, as I did earlier, not everyone comes to like. For some, even when they have learned to open up, it still feels more like an uncomfortable medical procedure than sex.