Originally Posted by Penance

You need to practice each of your individual side escapes until you're able to do them well against moderate static resistance (this means they just use their weight and strength to resist). At first, you don't want them to switch to another side control position when practicing.

Then you need to start linking the escapes together and be able to flow from one to the other smoothly as your opponent changes positions to keep up with you. Your goal is to "get ahead" of them in the sequence or get them to make a mistake.

You won't be able to do this sparring against a heavier person. You need to practice this during warm ups where you can tell your partner how much and what kind of resistance to give you.