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By 2nd base you presumably mean touching breasts.
In general women like to have their breasts touched, so she will be looking to allow it to happen as soon as she feels that the time is right. But, if she is not comfortable with her partner it isn't going to happen.
So the partner has to make sure that she is comfortable with him(her). The basic elements are usually that he(she) has done all the preliminary work of establishing trust and intimacy and had some kissing that has worked well.
Boys in particular tend to skip stroking and caressing all the other important places before making a beeline for breasts. Don't rush it. Build trust by taking your time and stroking her neck, chest just below the collar bones, upper back, face, running fingers through her hair and kneading upper buttocks. Talk to her, tell her nice things.
If she is young she will take base to base progression slowly, and this particular partner may be a few years or months too early to ever hit 2nd. Its tough, but respect her decision.
For adult women its usually no big deal and 2nd follows the first kiss by about 15 seconds.
Im a girl myself so i know how boys start:
1. start to hold her hand
2. start to kiss her
3. start laying her down and put your hand up her top and hey presto! there you go! just a few tips:
Girls like to know a guy well before they start to become serious so take it slow and make sure shes comftable with it first
Make sure your good in progress and hope it go's to third and then all the way! but go slow and as i told you before... TAKE IT SLOW AND MAKE SURE SHES COMFTABLE WITH GOING TO THIRD AND ALL THE WAY FIRST! good luck!
The best time is during a long make out session, just wait for the right moment and do it gently.
Ensure you are running at the same speed. That way you will arrive at first base simultaneously. Assuming you started from the same point.