Oh man, is that urethral? Haha, ouch.

Introducing the multimassive_penetration tag. Seems to be more appropriate than huge_insertion or double/tripple_penetration in this case.

this is more like quadruple penetration

You forgot to count the mouth.
Septuple, technically...

And is there need for also having double, triple, etc.?

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They are not men. They are flying dicks.

This is entirely do-able. The urethral, I mean. Otherwise I think it's hard to fit more than 3 hips down there.

Urethral sex is entirely possible. It's just a matter of WHYYYYYY.
And semen in the urethra is bad anyway.

I thought these were arms; one of the two in her vagina (to the left) seems to have an elbow. But google translate sez:
棒入れ - stick holder
一人の女子生徒の中にどれだけ沢山肉棒が入るか競う競技 - Competition to compete how many cocks get into one girl student

Unless this is just the preparation phase....

where is this from?