The age of the woman doesn't matter per se. It's how it's relative to your age that matters. For example:
At 19, I screwed a 38-year-old. MAJOR win!!! Still a life highlight.
At 38, I messed with a 40-year-old. MAJOR fail. I hang my head in shame.
This stuff all depends on where we are in our lives. I'd encourage anyone up to age 24 to go as old as they want and have fun. But once you get older, it stops being fun real quick for a bunch of reasons. One is that there is no "novelty" aspect. The other is that older women don't really expect much from much younger guys, but they're often entitled uber-bitches to men their own age....which is why you want to go younger when you're older...
At 19, I screwed a 38-year-old. MAJOR win!!! Still a life highlight.
At 38, I messed with a 40-year-old. MAJOR fail. I hang my head in shame.
This stuff all depends on where we are in our lives. I'd encourage anyone up to age 24 to go as old as they want and have fun. But once you get older, it stops being fun real quick for a bunch of reasons. One is that there is no "novelty" aspect. The other is that older women don't really expect much from much younger guys, but they're often entitled uber-bitches to men their own age....which is why you want to go younger when you're older...