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Reading this post I wonder if you have considered the situation fully. Are you attracted to her in a, 'I her and want a relationship with her' way or just sexually? If it is just sexually, and therefore because she is a challenge, I'd say step away. If you successfully draw in an insecure person, and they fall for you while your intent was just to 'give' them some thing they didn't have before (an orgasm) then when you are done and feel happily accomplished then what for her? At best you'll destroy her and further damage her self esteem. At worst you can end up with a stalker. SB seeking for SD. My personal rule, from experience, is never be someones first.
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