So after a month of playing with my buttplug, I bought my first dildo!
Maybe I went to far or my hole wasn't used to the bigger size, but I got some pain tingling and stopped, knowing that I could get some light bleeding (like my first time with my buttplug aha).
So yeah, even if I stretched a bit with my plug and put extra lub, I wasn't able to take the bigger size... any tips? I tried that position from pic

Smaller anon here struggling to get my deeper toys in consistently, what am I missing? I've had the most success with a large size chance, but only in some positions. Or is everyone else just using poppers.