OK, so this is mostly walkthrough for men not for women... but... if you are woman, you can give it a try as well :o).
1) identify the problem - thats very important, if your girlfriend/wife suffers from huge vaginal pain when you try to have a sexual intercourse, maybe she suffers from vaginism
2) go to see a specialist - gynecologist or sometimes even psychiatrist could help first to identify whats goin on in here (if doctor tells you: "I see nothing in there, there is no physical cause", then the doctor is an asshole and go to see a different one, so dont be shy to see a doctor - you have to first make sure that the pain is not from a different reason than vaginism).
3) if your woman of your life is wet like hell, thats not sign you can rush in and penetrate, because it does not work like this, you have to make her feel comfortable and! try for even couple of months with smaller objects than your dick is (unless you suffer from hormonal desease called micropenis, lol, but thats a different story and I cant help you with that ;o)
4) every woman has a different reason for the traction of the muscles in her vagina, maybe she is shy, maybe she is afraid of the terrible pain that will happen in a few moments (because of the past experience), maybe she is bigot catholic who thinks she will die in hell if she has orgams... reasons are endless (thats if you cant help her with this walktrough, then psychologist can help identify the reason).
5) so your mission is not to repeat the painful experience, you have to make her calm, make her feel comfortable, make her used to be naked in front of you (if the shy thing is the reason), works great if you fool around a bit and she comes in front of you (in a way that you ask her to show you what she does to have an orgasm - this also has to take a time, to win her confidence, this walktrhough is not written for a reason that you will succeed in two days, we are talking months in here)
6) when she is got used for the nudity and stuff in front of you, you can start just with adding your hands with hers - like you will make her come with YOUR hands (now we are still talking about the non-penetrative shit, she has to feel comfortable that anyone esle is playin on her playground)
7) vaginism does not mean she is frigid, so when the girl is now used to feel comfortable and is used for the pleasure that orgasm gives her (with your effort), you can start slowly about using your fingers (again, start with the smallest one and in days you can use your bigger fingers, later you can try two fingers and much much more later even three) - but again!!! anytime you feel contraction in her vagina (which means therefore you are causing her pain, not pleasure, back off and start with the one finger shit again from the start... or use your tongue, thats good as well)
8) crucial part is the patience, making her comfrotable and slowly trying bigger and bigger objects - you have to teach her that putting something in her vagina does not mean pain (thats why you have to in time try bigger objects - like a dildos of different sizes etc. if you have succeeded on the "fingers" part). But again if you try to put your finger inside you can e.g. lick her or play with clitoris (like you will take away the attention bit from the penetration thing).
9) again be gentle, be slow, do not rush anything and the more you practice the better (like everyday practice is a perfect story, but maybe your wife is not a nympho so she does not want to have several orgasms a day)
10) after you feel like she is comfortable with objects that are of the size of your dick (you can take to this point in weeks, in months... but there is a 99,99 % success rate, what differs is the amount of time which it takes to get there), you can finally try to fuck her properly :o)
11) if you have succeded, now you have put your ass into a tougher shit, because if she has had in past years only clitoral orgasms, she feels now that the "fucking" thing is not adding anything to it, hahahaha.
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