Dont "soak" it in neats fot oil, that could actually ruin the bag...if the bag seems too stiff, a "light" application of neats foot oil with a finger tip or soft rag to the smooth side every month or so will eventually soften the leather quite alot with a bit of use and time, especially time.
(Note:be sure you store the used oily rag in an air proof sealed jar or something so it doesnt spontaneously combust as it dries).....I also use mink oil rubbed into the leather, especially the seams, and will even work it with my finger tips it into the rough inside of the pouch to assist softening a particurlarly stiff outfit if needed....lately some of the "craftsman" grade veg tan leathers seem to be especially stiff right after wetting,sewing and finishing, but they seem to soften right up if given the above treatments and some time....not as good as better grades of leather, but well enough I think.
On that note: they say some of the lower priced commercial veg tans are now coming up from south of the border and are kind of "iffy" right off the bat, too dry and a bit "off" from the get go, so I have started to buy only the higher end live oak tans, and plan to use dealers like "Wickett and Craig" who sell only consistently good quality American leathers exclusively...initially they cost more per square foot, but in the end I really think its worth it and feel much more comfortable ordering and using it. At least I know what will arrive and what the quality of my finished project is likely to be. Its also worth noting that veg tan leathers are just plain stiffer than chrome type tans naturally, and will never get crumply soft, especially the heavier wt. stuff, say in the 5~6 oz range and higher...also note that belly leather will tend to be alot softer in hand than sholder stuffs, but bellies can stretch, or cheaper grade belliy cuts can actually uncontrollably shrink...each hide is a bit different, but finding a dealer that can give you predictable and consistent quality is more than half the battle, at least it has been for me lately anyway.
Hope that helps some...and your pouches look great, thanks for sharing the pictures.