Hello, Dan. I have an older neighbor, about age 60, who is married. I am married also. FYI. My neighbor, who is old enough to be my mother, is a flirt, but she only flirts with me when I'm with my wife. I want this older woman. I want to see her in heels and a sexy dress. I want to watch her pose while I jerk off. Because she turns me on. How can I approach her to let her know I'm interested? I'm scared that if I say the wrong thing to her it will get back to her hubby or my wife. Can you help me?
Wanting Older Woman
I can't help you.
Not because I'm against older neighbors hooking up with younger ones, WOW, and not because I'm against marrieds hooking up with other marrieds. I can't help you because this woman clearly isn't interested in dressing up and posing for you while you jerk off. Or anything else.
The evidence? She only flirts with you when you're with your wife—she only flirts with you when you can't return the flirt—and never flirts with you when you're alone. So one of two things is going on here:
1. The flirting is malicious. Your neighbor flirts with you in front of your wife to antagonize your wife. She's a shit-stirrer, WOW, and she's trying to create conflict in your marriage. And conflict is all she's after. Drama, not dick.
2. The flirting is innocent. The old neighbor lady just wants to get her flirt on—she wants to wink and twinkle—and she assumes there's no risk of escalation and/or misunderstanding if your wife's there. She may even be trying to pay your wife a bank-shot compliment. ("Your hubby's a hottie, girl, good for you!") She likely further assumes you wouldn't be interested in an old lady like her, WOW, seeing as she's old enough to be your mother and all.
Either way, WOW, this isn't happening. And things would only get weird—they'd only get weirder—if you misgroked your neighbor's intentions and floated the dress-up-and-pose idea.