Shyness

I'm really shy, especially when it comes to meeting people. I've always thought it would be hot to fool around with an older woman but I have no idea how to bring about that type of opportunity. Does anyone have any helpful hints/tips? Maybe suggest something I should wear, show more bulge?, how to come onto an older woman in public?
*I'm 19, by older woman I mean older than 30*

Hey, you are a cute boy and any women would be lucky to have you.

Hell I would love to have you. Oh sorry looks like you do not swing that way.

This is LPSG, tell us or show us your cock.

Shy?? You have a webcam porn business! Sheesh.

If you're getting a summer job, I suggest working someplace where the women you like hang out. Country clubs, caterers, pool maintenance, dog walking, upscale women's retail. Any place you come into contact with the sort of woman you're looking for. Places they spend their leisure time are your best bet.

OR

You could just put an ad on Craigslist. There are a lot of cougars out there and they would LOVE to teach you all sorts of things.

And here's to you, Mrs. Robinson...

So the older guys weren't enough for you? Hmph!

I'm shy in person. Just looking for some advice PLEASE!?

be a pool boy for a summer. DO IT!

I do nude modeling and make amateur vids but i'm pretty shy in person. I can relate. Thank God i'm married because i'd hate to be single and trying to land a decent date.

Just talk, and learn how to begin and build a conversation.
Start with people who aren't intimidating, then move to people who are only slightly intimidating, and so on, until you are able to hold a conversation with anyone.

If you are really super extra shy, start online, then move to initiating convos with the people who do not live in your computer.

Also, remember whatever insecurity you have most others share it. And, unless you have someone specific in mind, I'd start with a bit older than 30, maybe a full on cougar 40ish woman. She'll teach you something, hahaha.

P.S. use condoms and be safe :)