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The one that's part of the Headmasters Pet part 2 where you try to put the medium dildo in for the first time.  The quest task is called advanced disciplinary techniques, the one where you have her spread on the desk.

Take picture and do search standing, paddle her over desk, massage inner thighs otk. No matter who did first 4, make you are disciplinarian for next two: spank her in straddle position, then put her on desk for medium dildo.  

Thank you!

I did them all and I have 1 AP left, and yet I still have Pain 5/9 and Pleasure 5/9. Humiliation is maxed out.

How do I complete all of them?

Since I listed six, you did not do all of them. If the sixth isn't an option for you, you haven't finished dildo training.

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Ok, then how do I do it? As far as I can remember, I didn’t get to put any dildos in Rachel, she’s just doing splits at night while doing her homework. 

Also, what does “otk” mean? You wrote it in your initial reply.

-.- Odd game to play, not knowing otk. No idea where you are, but most likely you should be spending afternoons practicing with Rachel in office. 

Don't know, man, I'm not used to a lot of English slang. It's not my first language.

Anyway, yeah, I'll practice more. Thanks for the assist!

For whoever is wondering: OTK means: over the knee (in this context), one true kill or one true king.