A Few Ideas
If you're still in contact with him, cycle back through your buddy's mom. If she was intrigued at one time, she'll enjoy the fact/fantasy of seeing you again "all grown up." You can take it from there.
Let us know if she's a possibility, and I'll pop back in with some more thoughts.
If she's not, these guys are right - CL or a comparable site can be a lot of fun. I even see a lot of that sort of thing on VW. Keep an eye open for one in your area, and let the fun begin.
Beyond that, the major advice I'd give a young guy looking for older women is to think beyond the pickup or the hookup or the "bang." Think in terms of an affair. Even if you don't want that, she does. And if you can teach yourself to engage women (esp. older women) on that level, then you'll find your world full of intriguing, lovely and very sexy ladies.
You're at a great time in your life. And if you play this right, you're going to have stories to tell for the rest of your days. Enjoy, and let us know how we can help.
Peace ~nobus
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