You can try an SSL MITM(Man in the Middle) Proxy, these are available, both commercially and open source(ly).
Two things to be aware of thought, if iTunes does strict checking of the certificate fields this might not work. And as mentioned by @MDmarra above device UUIDs might be an issue. This is completely application (iTunes) dependent.
... proxied HTTPS requests are terminated by the proxy and resent to the remote webserver. The server certificates presented to the client (i.e. a web browser) are dynamically generated/signed by the proxy and contain most of the same fields as the original webserver certificate. The subject DN, serial number, validity dates, and extensions are preserved. However, the issuer DN is now set to the name of the proxy's self-signed certificate and the public/private keys of the proxy are used in creating the forged certificate. These forged certificates are cached (in memory) by the proxy, for better performance.
Also a good run down of issues by someone who tried the same thing:
There's an application called iOS SSL Kill Switch noted in that article. This is not specifically what you need but it might be a piece of the puzzle.