I would say they do break in, but don't really stretch, and more in the width/forefoot than in the toes as they shape to your foot. I have a pair of mens 38 sprints for everyday and mens 39 KSOs for running. The sprints would be a little tight in the toesies if my foot expanded with socks on (as it does during running; they'd probably be okay barefoot) and the KSOs are a little tight over the top of my foot as it is, but the larger size means I have a little extra room in the heels - too much and it could lead to slipping/blistering. They fit my foot width-wise exactly. I didn't dare to try womens sizes, though it might be okay because of how they fit.
Anyway, your toes shouldn't come up to the END of the pockets, and it shouldn't "hurt" between your toes for the shoes to be there. You might try on one size smaller too just to see how they would feel if they were too tight. Also, if you plan on wearing them most often with socks, you might want to try them on with socks (it makes a little difference, though mostly it just feels like more filled-in space between the toes). The KSOs do have a top section where the strap is that can feel tight if you wear them for a long time and have a higher instep/wider foot.
If you are concerned about sizing, you might want to just wear them indoors (and probably with socks, or clean not-sweaty feet) for a couple of days and see if you got it right.
I saw a guide to VFFs on birthdayshoes.com that should be easy to find. It was a few "slides" about the different shoes and how to size/fit, with a couple of tips.
I wish they were more common, you're lucky to get to try them on before you buy!!



) for a couple of days and see if you got it right.
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