Hexus: I think you're looking at it wrong, its not going in, its caressing her with the underside of one of its arms. What else would those filaments be for.
Charmscale: No, it's caressing her. Trust me, the right kind of rubbing over the girly bits can feel overwhelmingly good. And I think the tentacle creature is secreting the juices from the undersides of its tentacles. Notice how all the tentacle undersides look at least a little wet.
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