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I've observed that most of you all here have significantly more life experience than myself - and some outside insight pertaining to my situation would be helpful.
Sounds like a Typical American Girl--ie., A Spoiled Slut that wants and feels entitled to it "ALL"..
Dude, no need to be so rude or give such awful advice. The first time, you should only put one in her cooter and go no deeper than the first knuckle. Depending on how well they know each other, he can also stick one in her stink hole. That's like etiquitte 101.
If you are respecting the fact that she has a **** buddy she doesn't want to give up, then you're not nearly as confident as you think you are.
Why do guys care about dumb **** like 'kinda sorta seeing someone'? I'll respect a wedding band, but the correct response to 'I'm kinda seeing someone...' is always 'So? Let's have drinks sometime.'