Over the past two years I've been working on a cross-platform crypto library for Python. One of the aspects of it is that it doesn't require a compiler (it uses ctypes or cffi), and works with the cryptography libraries shipped via your OS.

Part of this library is a TLS implementation that uses SecureTransport on OS X. If someone is inclined to get requests (and pip, etc) running on the system Python on OS X, it should be possible with the guidance outlined at https://github.com/wbond/oscrypto/issues/10. Unfortunately, it isn't something I have time to work on right now.