How would you connect...

[Guest ff-whole]

I was waiting for an ATM to get some cash out of the wall, and as it happened there was a platinum blond in shorts in front of me and when she spoke I heard a deep and husky voice....
Damn, was that a Transvestite? Breast beautifully sculpted, strong facial features... I was mesmerized so when she / he turned I gave her /him my best smile...

It was in a very small town and I think she/he might not be a local since many tourist from across the pond are known to visit this small touristy place. She/he might be out of my league still she/he is not the youngest but still very hot...

Next time I'll meet her/him, I might want to start a conversation, like if she lives here... Hopefully not, because if she is on holidays she might not be 'working'... Am I to assume right?
How would you handle this situation and how would you guys try to connect, if being in the same situation and interested to go one step further...?

I don't have much money but love to get to know her a bit further and if possible having some great sex. Probably not if she decides to ask for the 'usual' fee for the rising opportunity... I would in her place.

[wonderfulfuture]

You connect by saying something rather than walking away. Simple as that. If she's into you, she'll continue the conversation even if you can't think of anything interesting to say on the spot. If she's escorting, she's a pro, and will recognize your interest and take the lead. If not, you go home and whack off to what could have been.

But I guess you know that. Check Grindr, doublelist, backpage, etc. Cruise the same neighbourhood around the same time if you're desperate. Don't fuck up next time.