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!
by Con Artist 101 December 02, 2004
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.
by IKEA May 12, 2004
Head Master - a person who is particularly proficient at felatio.
Marcia is a head master; she sucked me so well that when she was done, I couldn't even walk out of the car.
by IMKessel@yahoo.com October 18, 2007
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.
by Andy April 19, 2004
Headmaster is a person who is extremely proficient in luring girls in (of any shape and size) to receive head. Also known as fellatio for you virgins out there.

However do not make the mistake to assume the headmaster is not a virgin. In most cases, the Headmaster is almost always a Virgin.
Monzy: Oi i got head from Raveena last night. She nearly ate my dick off

The Boys: Raa! Naa, how'd you pull her? You're defo the headmaster akhi!
by virgin4lyf October 21, 2014

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