According to the gynecologist, I am a "perfectly normal virgin girl"... who just happens to be extremely tight, to the point that tampons are not an option for me. (Those are the doctor's words, not mine.) Her suggestion on dealing with this problem is to be "a little tipsy" the first time I have sex to relax the muscles. Personally I'd rather deal with the issue now, a good few months before The Boy and I are planning on having sex, so it isn't as much of a stressor later, and also because I want this to be as good of an experience as possible for both of us.

Basically what I have done so far to start is to use a well-lubricated tampon and insert it very, very slowly, letting myself get used to the pressure and the feeling before pushing it further, which hasn't really worked very well. (I have also discovered that I hate KY Jelly and will be trying something more slippery.) I will be trying the bathtub-and-finger method as soon as I get a chance. Is there anything else I should try? About how long should I expect to work on stretching before I feel results?

(The Boy, by the by, is aware of this issue and knows to take it easy. Of course when we are both in the grip of hormones this may be harder to accomplish, but I know him well enough to trust that if I say "No, we need to stop here for now" he will (of course I will make it worth his while. ;) ) Any suggestions for positions, &c that would make this easier? I know that the first few times are not exactly earth-shaking usually, but I do want to make sure that this will be a positive experience for us both.)