What are the possible ways to work after OPT expires


My OPT STEM is going to expire on January 2015 and unfortunately I did not applied for H1B. But my employer is ready to apply for 2015. Is it possible to continue working untill October 1st if I file for H1B before my OPT expires? Will I be able to work if I file after my OPT expires? I also heard that there are some H1Bs where we can apply throughout the year. Is that true? I sit a good idea to 2nd masters to obtain CPT to continue working? Please help me its urgent.

Thanks in advance.