I really like how you painted the whole head and then applied the bubbles. Smart, IMHO, because unlike with metal shims which are pushed into the sculpt, your sculpt remains intact without that line. Your final castings should be virtually seam-free. Very nice.
As for the casting of latex in silicone, yes you can as long as you can ensure that air can get to the deepest areas, as MA stated. I cast my hands in silicone molds. Scott Marshall casts all his latex masks and suits in silicone molds. As MA stated, it can become difficult if areas are too deep and you can't get airflow to a particular section, even with the mold split and using a heater fan or heat-gun. It really depends on the sculpt and the mold created. Gene ran into this problem with his silicone head mold because his mandible jaw is so long and narrow and is forced to remold it. The ends of his mandibles simply do not get enough air flow to cure the latex, so it never cures. I've had issues with the studs in my left hand mold not curing unless very thin layers are painted in and then encouraged to dry via heat gun. Even then, I've encountered some issues. The thing with a two-part mold is you have to do each side independently and then seal the joint with a butter coat prior to closing it. Then, you have to blast it with warm air because otherwise the moisture simply will/can not go anywhere (Silicone is waterproof as opposed to porous material like UltraCal, which is Portland Cement and Plaster of Paris). Make sense? Silicone is awesome for detail, but without thinking ahead when creating your mold, it can get tricky. Though, I tend to over-think things, too, lol...
Sorry for the hijack, MasterAnubis. As you were,

Dying to see your first pull!