First off: IMO the message won't get you what you want. It's too forward and assumes an awful lot, and if she's as innocent as I'm imagining, it will put her off.
I'm not sure I understand your motives. You want to get laid and perhaps bragging rights that you got the 'cherry' of this hot girl? I could be wrong but it seems like you're not as interested in her as a girlfriend, yes?
Jill is an insecure, scared young lady. She values her virginity enough to hold onto it this long. But the fear of how scary the first time will be is wearing on her, so she's tempted to "just get it over with" and sleep with whoever. Clearly it means alot to her.
You asked our opinions. I'm a woman, and I can sympathize with what Jill is going through. I've got to be honest. As a woman I'm not sure I like your text or your intentions. Jill is waiting for the right moment and for the right guy to come along; someone who respects her and who won't make a scary moment even scarier. Forgive me for saying this, but it sounds like you're scheming a way to get her to put out for your own reasons and may not have her best interests at heart. Therefore you are the WRONG person to be asking her for it, and it's not justifiable with saying it's "helping her". (in my opinion at least-- others are welcome to disagree)
Your prowess in bed is not what a scared virgin girl needs. It won't mean anything to her, and your forwardness between the sheets may scare her further. You may also find youself quite disappointed in the experience, since it sounds like you are very experienced and she quite obviously is not.
This is a 'good' girl who sincerely sounds like she's waiting for a meaningful experience. If you want a good time, my advice is to hook up with someone else (i.e. someone who's been around the block). If you want a chance at a relationship, go call her and ask her out to dinner or drinks or something, and patiently see where it goes. It sounds like she's a wonderful young lady, and you might be missing out on a change at a great relationship by just rushing into things.
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