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Headmasters 

TransFormers which have a Nebulan (humanoid) companion who transforms into the head of the transforming robot, and does not form part of (but can usually drive or otherwise connect to) the large robot's vehicle and/or beast mode/s.

Sometimes used to mean the large robot, sometimes the small figure/head. (Japan only: some heads were brought out without bodies, and all heads were interchangeable between robots, making more sense of the term "headmaster").

Of course, it also means a male head-teacher (now rarely used for PC reasons) - presumably it's a play on words (used as a model for later names such as Powermaster, Targetmaster etc.). Initially appeared in series 4 of generation 1.

Also, the first series of the Japanese Transformers cartoon (the 4th series overall) is called "TransFormers Headmasters".
The Headmaster Mindwipe, a Decepticon who turns into a bat, has a Nebulan companion, Vorath.

OR

The Headmaster Vorath is binary bonded to the transforming robot Mindwipe.
Headmasters by Andy April 19, 2004
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headmaster

headmaster, n.

(1) the principal of a school or similar educational institution

(2) someone who is really good at oral sex
I got sent to the headmaster.
headmaster by IKEA May 12, 2004

Headmistress of The Pit 

Someone who convinces others to engage in nefarious, prolonged substance abuse against their will. An enabler or bad influence. A leader of Pit Dwellers. A loud, flamboyant party-goer of questionable sexuality.
Sam: 'I can't do this anymore, stop being a Headmistress of The Pit'
Jamie: 'You will Pit Sam, don't make me drag you into the Pit!'

Headmaster

head·mas·ter
/ˌhedˈmastər/
noun
(especially in private schools) the man in charge of a school; the principal.
The headmaster appears to have everything under control.
Headmaster by kaosmoker September 30, 2018

headmaster's duty 

The act of soliciting for the purposes of prostitution, i.e. a girl "working" in a bar, usually with unnecessarily revealing skirts and tops.

Has its origins in South London; etymology rumoured to be an oft-absent headteacher caught soliciting in the late 1970s. In order to avoid direct reference, the claim that he was doing his 'duty' evolved into 'headmaster's duty'.
I think she's probably up for a bit of headmaster's duty

headmaster

a girl who is popular/well-known for sucking a lot of cock (often in a particular area or place)
Yo! Yesterday, after the party, the headmaster gave me a nice ass bj!
headmaster by Con Artist 101 December 2, 2004

bullis headmaster 

the most annoying and biggest stickler of them all..the stupid ass quaker...farquar
Damn...that bullis headmaster farquar sure is an ass!
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x:"Girl your fit chewed today!"
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