I was 12 and playing with a kid who lived across the street. Neither of us had very big dicks and we struggled getting them into the holes, also because we had no clue about lube yet. All we ended up doing was lining them up with our holes and then we'd shove them to try and get them in but they would just slip up the crack. We tried again a couple weeks later after we found out about lube. This time we were both able to get them in but they didn't go in very far. When I felt my hole stretch and his dick start to move inside I loved the combination of feelings I was having down there and just couldn't wait to try more.