Okay, I haven't even bothered to read everyone else's post. I'm evidently now a cougar, since I've been called one three times since December, all of them by young men who obviously wanted me to chase them, and were flirting with me, not the other way around.
While the term "cougar" is supposed to apply to older women who chase young men, it's usually used by young men who want that older woman to chase them.
So I find the title of your thread totally apt. Seriously, I'm tempted all the time. We are more confident and we're usually only insecure that someone will judge us for behaving in a cougar-like way. In fact, I was on chatroulette.com last night and this totally cute, innocent, adorably bashful 20 year old man tempted me so much that I hit a moment where I very quickly, but politely, hit "next" before I became naughty and told him to meet me in a hotel room. Yes, it's a fantasy and it could be all yours.
So the first rule is this: If you want to be caught by a cougar, "Do not ever call her a cougar." Men seem to believe that it's a compliment, while 100% of the women I've asked consider it an insult. Don't insult her. Tell her she's beautiful. Tell her you think she looks 25 (if she really looks young) or 29 (if she looks a little older) years old and say it sincerely. Seriously, it's probably the sexiest thing you could say.
If you want a kinky cougar, then it's even easier. Go to a "Munch." Look them up online for one nearby. The women would love to eat up an eager young thing, and many of them are very hot. Seriously, it's the lion's den. It's more reliable than Craigslist and your results will be much more satisfying. A "Munch" is a luncheon in a safe public place where you can meet other kinky people face to face and talk about anything, but especially whatever kink you want to indulge in. It's better than Craigslist because you see what they look like, they're experienced kinksters, it's public and safe, and there are usually other people there who have had sex with them who can testify to their lack of complete craziness or their impressive skills.