Koolaid - do a lot of foreplay, to get her wet in her vagina, use a lot of lubrication (KY jelly, not vaseline), and a lubricated condom. Put a pillow under her butt, have her spread her legs wide, and have her help guide your penis into her vagina. Do it slowly, a little ways in at a time, then a little more, until you are all the way in. Make sure you are going in at the right angle - her vagina angles upwards, and if your erect penis has an unward, "banana" curve like a lot of guys have, it should go in easily. If it goes straight out when erect, or curves downwards, adjust your entry to match her curve (which you can determine by inserting your finger in her vagina during foreplay). If she still has her hymen (the skin covering the vaginal opening, in part, that most girls have, unless they have broken or lost it from horseback or bicycle riding, masturbation, etc., there could be a little blood when you first enter her. There is no way around this, and have a towel ready.
I still dont think that him on top would be best. My boyfriend currently has a HUGE dick, we still have to start with me on top like 95% so he doesnt tear me. The problem is most men dont know when what they do hurts.
Say "ouch" so he will learn. Never suffer through pain for sex that can easily be remedied or avoided.
I found the opposite, for the most part when a man has his dick in a pussy they dont seem to give a shit that what they do can hurt and hurt alot
