You would have to hold the case while pulling the gun up, which means you're either going to hit that roll of fat above it or wind up pushing the holster into her waist, and you have to avoid blocking the sun, which is coming in at a sharp angle here, and would likely trigger her subconscious and cause her to wake up. Also, if you're wearing any kind of cologne or scented deodorant, or if you just stink, that's likely to trigger her subconscious and wake her up. Plus she's sitting on what looks like a clipboard, which means you would have to lean further over to avoid shifting it, making the whole process even more unlikely to work. And unless you're 8 feet tall reaching over from behind her, it's going to be impossible to not lean on her a little.
