Can I transfer my guildmaster status to my other pirate?

[Dr. Zeppers]

Sven is correct.
There is one other option, but not really what your looking for necessarily.
You can transfer your GM pirate (the pirate, not the status), from one account, to another, if you have another account.
This does require contacting customer service however.

[JM Ohara]

No, you can't have more than one guildmaster per guild. Assuming I read that right. You can guild yourself however, even if both pirates are on the same ID. With your GM in came hit F then click the guild tab. Do Create Invite, let it generate a single use code. Go get the other pirate. When they get in hit F, Guild, Redeem Invite, and punch in the code. Hit enter and boom, you guilded yourself.