In the left half, he seems to think he can handle her. She's unimpressed, and her face silently says, "Oh, really?"
In the right half, she's decided to give him a try: "You think you can handle my pussy? It's swallowed dildos bigger than you, but be my guest."
In what I would hope would be the third image, his feet are the only part of him sticking out of her lips, and she's brought her finger to bear in order to press the rest of him inside. She's smirking, and you can tell from her expression that she's thinking "When I said 'be my guest,' I meant it literally. Enjoy your stay; I know I will."
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