As Kristy is based on shynessincarnate herself anyone who has read her dare threads knows she can handle the pain quite well. We also know from the reports from the last punishment thread for being late in this story that she isn't exactly the best at keeping her self from orgasm in a prolonged situation. So to make it a situation ware Kristy can handle the situation I vote for option 2.
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Trust is important but if you aren't willing to get to know someone how will you ever know if you can trust them?
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