Does it hurt - Yes. Do you want me to stop - No.
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When the rag is in place take the ass. Nice, hot video!
You would, I think if he wants more of the same try to make it as comfortable as he can. Smart man, knows how to work her, making her believe it is what she wants. But it is most likely what he wants
To ease the pain, jerk
Says someone who has never experienced it. The need comes from want to please someone who always wants more, never satisfied..