Ok, hopefully I can explain this all clearly. My g/f and I are attempting to have sex for the first time with each other - for her, it's her first time. She's on NuvaRing and is currently in her 4th month on the ring. We've now tried to have sex twice and both times haven't worked out, as a few things are working against us. First, she's a virgin. Enough said. Second, she's very tight. When she went to the gyno they had to locate the small tools for her. Still, we've tried to do what should be done. Get her relaxed, work her with fingers first to ger her ready, and use lots and lots of lube. This is where the problem may be though. We're using KY Natural Feeling Liquid. The two different times we've tried to have sex, though (two separate nights, btw), she's started getting a burning sensation in her urethra, with the second time being worse. The pain in her vagina apparently wasn't very bad, just some discomfort, but the burning urethra was unbearable - she said it felt similar to UTIs she used to get as a kid. The sensation went away in the shower rather quickly. What we are thinking is that the KY could be getting into her urethra causing this burning. However, KY is EVERYWHERE before we try for sex and nothing - oral, fingering, etc. - causes this burning sensation, but the two different times we've tried for intercourse this burning has gotten to her. She thinks it may just be the positions allowing for it to get in. A side note, we are using latex condoms (Crown) but neither of us has a known latex allergy (we both work in research labs and have worn latex gloves for hours on end). So, has anybody here ever experienced this? Are there other possibilities for the burning sensation besides the KY? Any other advice or recommendations are greatly welcomed.