Obadiah takes a slow, measured breath, allowing Tony (and himself) a moment to adjust before beginning with the next segment.
It's longer, and tapers out to be thicker, and Obadiah is even slower with it than he was with the first part. Here is where it would have been nice to have Tony on his stomach, unable to see what he was being penetrated with and thus unable to make any kind of guess about how big it might be and how wide the stretch might get before it's all over.
But being able to see him - to see the look on his face and the little ways in which his body happily betrays him - is still better than that, and having tricked him into thinking Obadiah is using something far bigger on him isn't a bad plan B.
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It's longer, and tapers out to be thicker, and Obadiah is even slower with it than he was with the first part. Here is where it would have been nice to have Tony on his stomach, unable to see what he was being penetrated with and thus unable to make any kind of guess about how big it might be and how wide the stretch might get before it's all over.
But being able to see him - to see the look on his face and the little ways in which his body happily betrays him - is still better than that, and having tricked him into thinking Obadiah is using something far bigger on him isn't a bad plan B.