I had a long post written but totally messed it up, then deleted it. I was on the phone at the time and upet about my relationship (not my wife), and just couldn't think straight.
Anyway I do try to flirt with older men, and sometimes tease the old guys by showing too much cleavage. Unfortunately this has resulted in 60+ year old men staring at my boobs, and having a few guys using creepy ways to look down into my top and bra. Guess this might lead to going braless in a thin top someday.
My breasts are large enough and not very saggy yet.
So I'll make this real short:
1. Dress well, but not too sexy, or too casual. You only need to look a bit more classy than the group you're in. Men will notice.
2. Don't over-do your makeup. I'm old (as you know) but found I look better when age isn't being totally hidden or caked over.
3. Sit someplace that's near other people, yet in an area where you can be easily approached by men who want to talk.
4. Stay safe and comfortable by having a convienient exit planned. (needed if you're very unsure of the place you're in)
5. And most of all - don't be afraid to smile and say "Hi" to someone. No need to be agressive in this approach, since that one word said in a simple and polite way can draw a man into opening up in a nice conversation.
And yes, I'm in a relationship with another transwoman, but that doesn't stop me from flirting a little. Anyway, these guys could never make me an Empress the way my girl does.
You'll do fine Suzi.
