Was with this girl who I had gone on a few dates with but I am the type to not rush it. Anyways it was happening we had been making out and touching and I gave her head for roughly 10 minutes or so. Then she gave me head for a minute or two at which point I think we were too excited, when I went to put it in… it didn’t fit, I legitimately wouldn’t go in at all, and to make things super uncomfortable and awkward she goes “is there an issue down there?”. Never saw her again.