Overview:
Vector Paint
Auto Trace to create a mask from the paint.
Details:
Vector Paint:
Paint on with white, outlining the cloud, but try to keep the outside of the stroke on the inside edge of the cloud (the outside edge of the mask is where the mask will be)then when you’re done, change the parameter named “Composite Paint” (at the bottom of the Vector Paint plugin) to “As Matte”, then…
Layer>Auto Trace, Threshold and Tolerance to 1, uncheck “Apply to New Layer”, then M reveals the two masks created, delete mask to, the inside mask. Change mask 1 to Add, and uncheck Vector Paint (turn vector paint off). That should do it. MM Reveals the mask properties, you can feather the mask or expand/contract, change mask opacity there.
Also, here are a few tuts:
This one does what you want but you need to fill in the space (your cloud completely.
Rotoscoping with Vector Paint
https://library.creativecow.net/articles/oneil_bill/as_matte.php
and
Turning Paint Into Masks in After Effects
https://library.creativecow.net/articles/kurkoski_tim/paint_to_mask.php