This point is absolutely key as it is a conversation and both of you working together towards a common goal (even if she doesn't know what that goal is *evil grins*). If you are going to try and make her squirt and she knows that is the goal -- but she has never squirted before, well, she could be nervous about it and all in her head. This is no good this kind of mindset does not lend itself particularly well towards orgasms of any kind. So when would the best time be to try it? After she's just cum like a maven. That way she is all floppy and relaxed, satisfied and therefore impossible to disappoint. With no expectations, she's in the ideal headspace to cum more.
Also, squirting has a whole bunch of expectation built in for a woman...and she's probably going to be thinking a whole ton (too much) about what is going on. And what she really needs to do is it back and relax without a worry in the world. Y'know, kinda like that post cumming bliss.
Now it's time to give her instructions and guide her towards a new and fun experience (but don't pressure her in any way).
1. Once she is laying on her back, insert a finger or two into her (you may wish to build this up a little, kissing her thighs before licking her bare pussy...and then work your way up to inserting yourself in her...but I'll let you be the judge of when she is ready).
2. Tell her, "Squeeze down on my fingers." With
any luck, you will feel a tight squeeze on your
fingers. But I'd say half the time you feel...nothing. She scrunches up her face and makes it look like she's squeezing somewhere...but it ain't your fingers! If that happens, tell her, "Great, now can you squeeze in a different sort of way?" or "Try pushing on my fingers and try to force them out of you." The idea is to work with her so you give her feedback when she is squeezing and pushing properly. You can tell her to flex her muscles just as she does when she stops herself from peeing or do the opposite and 'open up' like she doesn when she pees. Also, you should reassure her that she can't pee while sexually aroused (ok, not totally true as I have taught my slave how to do this, but it takes practice! At first she would try and try and could not pee even though I'd made her drink a pitcher of water and then waited till she had to go really bad. But that's another story.)
3. Once she has zeroed in on the right muscles, encourage her to alternate between squeezing and pushing. You will feel her muscles squeeze in on the side of your fingers when she squeezes and more on the tips moving down when she pushes.
4. Continue to lick her clit, play with her nipples, etc and get her to push harder and hard as she does so. Make you tell her to push! Often. Begin playing with her g-spot more and more as she gets more aroused. Get her close to orgasm...and let her relax in between big powerful pushes.
5. You should be feeling her bear down on your fingers and her cervix pushing against you finger tips. As the cervix pushes against your finger tips, back out of her pussy so her cervix is just at your fingertips...and keep guiding her to push as bear down farther and farther so your fingers move further out of her. After she is done pushing, move back into her as it helps to have something to push against.
5. As she gets closer to orgasm, use the 'come hither' technique I describe in the 'how to squirt' post and at the same time, tell her, 'PUSH!' And as she cums, order her now, 'Push harder! Push your orgasm out!" As she orgasms, her cervix should push your fingers 100% out of her pussy -- and as this happens she will squirt!
Note: You can also do this but keep your fingers aggressively massaging her g-spot as she
orgasms...but I have found that her muscles are sometimes not strong enough to cum and squirt while fingers are in her. If she has stronger muscles, removing your fingers (at the right time) still makes it easier to squirt.
6. Bathe in her glorious female ejaculate! Lick her beautiful pussy and tell her how much you love her shejaculate. Taste it (because female ejaculation tastes fucking great!) Swallow her squirt! Breathe in her squirting orgasm. And then fuck her with the massive hard on her wonderful squirting has given you!
7. Sleep in the wet spot. (It may be a bit cold...but it's still awesome.)