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if Yukino joins, then I'll put death flag on her
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I'd put a waitress flag on her. Fairy tail can never have enough waitresses
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So forcing a woman to strip herself completely naked in front of her comrades, and expelling her is not going too hard on her?
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Technically, he told her to do it and she complied. It's not like he ripped her clothes and she was all like "Nooooo~!", although I don't doubt he would have done it, had she shown any hesitation. That and well, losing a life bet usually results in death, I think the only reason she made it out alive is because Kagura owns her now.
P.S: Love the faces of the Quattro-puppy members on the first page