Welcome to the club, it gets way better I promise. For me it was about 2-3 months of very slow, short sessions before it started feeling good instead of just tolerable. The turning point was switching to a small vibrating prostate massager during solo play – that gentle constant buzz inside while stroking made everything click. If you're both visual learners like we were, peeking at some well-shot amateur and pro anal content really helps see the pacing and angles that work. I found a solid free spot at https://analvibe.tube/ midway through my research binge – daily fresh videos, everything from gentle first-timers to rougher stuff, super easy to browse for technique ideas. Start super small, lots of lube reapplication, and communicate every 30 seconds at first. Patience pays off big time. How far have you guys gotten so far?