First time having .. sorry if it's dumb..?

If you're talking about pain from the hymen breaking, just gotta do it at some point. If you're talking about pain from the entrance being tight and unstretchy, it's better to do it naturally and do a lot of in advance over a number of days. (Pro-tip: trim your damn fingernails!) Start with the pinky if necessary, then work your way to the thumb. It's even better if she fingers herself and stretches herself a few times a day at home. Once she can handle two fingers together (man's middle and index) then the next step will be his . She may get a minor skin tear along the entrance (closer to her rear) which will be painful when stretched even a little and moreso if salt from sweat gets in. Give it 3 days to heal each time that happens, but try to have every 3 or 4 days to keep that skin down there a bit stretchy. If you don't have for a while (2 weeks+) it can tighten back up, and she'll have to go back through getting those tiny tears that sting. I'm a bit thicker than average (not a lot) and like to last a while, which produces more tears; these guidelines have reduced my female companions' discomfort and eventually allowed me to have with them frequently and for longer periods of time.