Here's how I would play it, if you really want to bone her.

Does she know you're a virgin? I assume so.
Talk to her on the phone, if you can do it in person then better. make sure she initiates.
Tell her how horny you are, how you're going to and want to fuck every piece of ass you see. (Sell it, tell her about other chicks you're dating/seeing)
Tell her how you once believed about saving yourself for someone special but now think its bullshit.
Tell her that's just the way your parents raised or brainwashed you.
Hint that you want your first time to be a little memorable with someone that you somewhat know.
And that your super horny and want to have marathon sex.
Tell her you jack off and 2 mins later your already hard again (depending on how well you know her you may want to leave this one out)
Don't mention you want her (she'll get the idea)
Play it see how she responds, make your move. Be a little more overt if she still doesn't get the hint.
Fuck her at HER place (this is important for your next move)

Fuck her and after you cum, just straight bounce. Just say "Thanks" and LEAVE this is why I suggest her place. Do it nonchalantly as if its not a big deal. Pretend you have some big assignment or w/e excuse. Don't talk to her don't answer any her questions, just say something came up. Insist its really important.

Give her radio silence for 4-5 days. The longer the better honestly. This way YOU have the power. It's science, the feeling of out of control is the same feeling as love. If she feels like she doesn't control you she may not "love" you but she will start being attracted to you. She will be soooo confused about your exit she will initiate contact first. And she will probably think your out boning other girls.

The only outcome you should go for is a fuck buddy.

Now, here is what you need to be ready for.
A: Huge possibility of her saying "I just wanna be friends" you can try and play it like it won't affect the friendship you're just horny
B: She declines and ignores your request, now its official time to drop her and move on
C: You fuck her and the power of the vagina makes you fall in love. DONT she will be soo turned off and never talk to you again.
D: You pull this off and become her fuck buddy. Assuming you don't completely suck the first time around. And assuming you can actually sell your bullshit and you're half decent at lying and can hide your emotions.

Heywood, please tell me you're a motivational speaker, you're like one of those really aggressive speech givers and it seems to work pretty damn well. I just regard myself as not the best looking guy 'cause I've been put down over the years for my looks, I'm in very good shape, I exercise very regularly and have done for years, without sounding like too much of a dick, I have a lot of talents... My problem is when talking to ladies is I never really get all up my own about those talents but I think I could easily use them to impress girls.
I'll keep trying the challenge, I want to get to a level where it's basically just a natural thing and I do it whenever without even having to think about it, as though just introducing myself to girls is a reflex. But as you quite clearly put across, I need to stop being a pussy about it and get on with it, which I will be doing!

I have always wondered, I've seen some guys out with girls and it makes me wonder, but I guess it just comes down to your social skills at the end of the day... I figure a ridiculously handsome guy wouldn't get girls if he was socially retarded. I do need to build up confidence!

And that's some pretty sound advice, I wouldn't just tell a girl straight away that I'm horny 'cause it just seems desperate and weird, but I guess I could sort of play on some things you said to sort of put it across.

I wouldn't either but consider it a last ditch effort. And no there is nothing wrong with saying your horny, embrace your sexual needs, don't be ashamed of it. Its not about what you say, its HOW you say it.

There is a high probability that my advice won't work. The lesson is you got out there and tried.
If you fail who cares? You have plenty of other girls to test it on. You'll learn that she isn't really the friend you need and you'll know you've tried everything. It will be easier to move on since well you've pretty much layed out all your cards. and the question of "What if?" is completely thrown out the window.

Don't be so hard on yourself. Everyone gets rejected, take it as a learning experience of what not to do and then use your experience on other girls. Eventually it will become natural.

Rome wasn't built in a day neither will your sex life/game. It takes work!

No I'm not a motivational speaker, I am a part time physical trainer, and hold several leadership positions with my employer. One of those is the collection of unpaid debit. Something nobody seems to ever "want" to do, ask for money when owed. That boils down (for me) asking people to do something they don't think they can do, I convince them otherwise.

Just as I know these people can pay their debit, I know you can do THIS. If it takes being blunt to get that across, blunt is what your going to get.
Now you have earned my pride Bro.

List your "talents".

Bragging about your talents is ....needy.

USING you talents is NOT.

Also I would like to know the scariest most dangerous fucked up thing that ever happened to you?

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They call me the cat whisperer, cause I know exactly what the pussy needs.

Some of my talents include being a multi-instrumentalist, a calligrapher, I used to do a lot of art, I know it wouldn't really count now, but when I was a kid I used to compete in horse riding... And now thinking about it, bar being a multi-instrumentalist which tails out into a few things, I don't have many more talents, I just do things that an average guy doesn't / can't do, but not specifically talents.
None of these are really talents I can use on the go unless I set it up for that, they'd just be talking points.

As for the most dangerous, fucked up thing that's ever happened to me, I'd have to sit for a lot longer to think of something, I've had my fair share of weird and dangerous things before, but nothing so bad that it was branded into the front of my head my whole life.

Hey, Heywood I really liked your challenge, because it was a really similar situation to mine, girls were always using me but never want to be with me, and same user mentality exists with some male friends where I help them and they don't return the favor. So not only am I going to accept the challenge for not giving user girls my attention until I lose my Virginity ( feels so good to admit that), I'm going to cut off all users until I feel I can handle the management of them so I won't be used in the future. I'm gonna be a boss, lets do this!

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The true man wants two things: danger and play. For that reason he wants woman, as the most dangerous plaything.
Friedrich Nietzsche