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I'd have to say the wierdest request I've gotten from one of my exes was to rape her. I was VERY reluctant to do it because a) I was in love with her, and the thought of hurting her in any way hurt me as well, and b) I was afraid of fulfilling her fantasy unexpectedly and actually raping her without her prior knowledge (she wanted it to be a surprise).
Well, we compromised. I would fulfill her fantasy, but it wasn't going to be a surprise. She would have to say, "Rape me" and then I would do it. So we did...I dunno, it just wasn't my cup 'o' tea. According to her, it was the most amazing sex she ever had, so I obliged her a few more times, but then told her that the whole experience, whether fictional or not, made me uncomfortable because it made me feel like I was hurting her. She understood.
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