@Eden: more answers

Eden, you get your own post baby: To answer your question, my average one lasts about 3 to 6 months. That is, with the good ones. One lasted 1 year+, and one, my first one ever, even longer than that. Some, with SB's that I found no real chemistry with, even though we may had slept together a couple times lasted 2 weeks. Others, with self proclaimed SB's but who were in fact escorts in disguise: 1 day or less.

How would you initiate the discussion yourself:
The first question is where. Many men may be taken aback if you stop them literally in the middle of the street. So let's get off the street and go into a bar / restaurant. Where would you sit? At the bar, and just wait for the average handsome man dressed in a suit to come in after work alone or with friends and sit near you? You may have to do some leg work and scout for the right place, and precise time of day. You will need military precision here as to increase the probability of success.
The point is to make this whole thing seem as natural as possible, even though you may have other motives in the back of your mind. You want to make this as if they are the ones initiating the whole thing. And then you could actually ask: 'I was hoping there would be some type of pampering here. A girl has to pay for college you know' (as long as you are of college age, that is).
Or do you hang out in business hotels? This however has bad connotations. I personally think it is a fine line you are trying to walk. You will be hanging by yourself with no girlfriends to spoil the whole thing. Of course this means less security for you.

How would I prefer it to be initiated by the lady:
A smile at a bar after a hard day, and a casual comment to put me at ease. Maybe a question about my profession, as many of us like talking about business stuff. This can also bring you to the subject of $$$ which may be of help to you as well. Or maybe a little comment on your part about how hard school, or you first job ever, is.
I tell you though, since I, specifically, have done this so many times I would make you in the first 10 seconds. You need an unsuspecting 'victim'. And you need to be as un-manipulative and natural as possible. And a subtle compliment to us, goes a long way. After we have started talking, buy me a drink as well. That is so intriguing to me, will make me feel just great like you appreciate the company and you want to extend the encounter. It could also get you return in spades. Plus, I love free drinks.

Hope this helps. If you need more personalized attention you can email me.