For me it is a sign of chemistry, trust and synchronicity. I always have my best sessions with a dance partner who does cum. I almost always repeat with a woman who has reached orgasm and seldom with ones who don't (or who don't show the prospect of getting there). When a woman is able to orgasm it demonstrates an openness and presence in the moment. If a woman is interested in her own pleasure, as well as mine, the combined sexual energy always rises to a higher level. It opens up channels of communication that go beyond the the physical. Tonight a woman looked at me deeply in the eyes and thanked me for coming to visit her at the shop and said she really needed the orgasm, as if some unspoken burden had been released in the moment. Earlier this month another texted me after I got home in the evening and invited me out with her on a social adventure (which I had to decline, sadly). And I have been offered discounts or money back as I'm heading out the door.
I find it a fascinating process to open the mental door and to walk through the corridor of a woman's sexual desires - each different and unique. Yes, it is a commercial transaction, but a peculiar one where we wear no armour and speak freely about our deepest desires. This canvas of physical and mental nakedness affords the curious an opportunity to spill paint and get messy. By doing so, I've learned a ton about sexuality (mine and hers) that would have been stuck in a bucket otherwise. Sometimes I am the painter, and sometimes I am the canvas. I find that the giving of pleasure heightens the receiving of it, and makes for more beautiful art.
So expect, no; wish, yes.