How to pin easier

This is probably a repetitive question but how on earth am I supposed to be sticking the needle in my butt cheek. I pin usually in my ventral glute or glute (I try to change locations often).

BUT unfortunately as my gf explains to me I was blessed/cursed with a plump woman-like ass so every time I try and pin it just pushed my skin down instead of puncturing the skin.

i genuinely think at this point i am doing it wrong. I was never taught as well besides the piece of paper they gave me that might as well have been printed by wikihow lmao. I tried just shoving the needle in super hard to avoid this onetime and it hurt like hell so now I’m here asking for advice.