Depends. I'd need more info. But yes, on the face it it is possible.

Depends on if they have issued a warrant for you. This "stops" the running of the time. If no warrants were issued prior to the time running out,...

Depends on the original charge, whether it is a first offender sentence. Question can't be answered without more info.

Can they legally hold my boyfriend being a first time offender without bond because of breaking a stay away order?

Yes. Aggravating Stalking is serious. No bond status may be modified with a superior court bond hearing.