"can we keep on winning"? if what you mean is consistent win without losses, then of course that is impossible.
After every winning streak, comes them losses. Infact, to me it, doesn't matter if the losses are more than the wins, as long as you're not taking too much of the risk, and you have what you spare out to keep up with the fun. Enjoyable! The only time there's real problem with gambling is when you expect too much from the outcome, sometimes because you've risked too big. The "Never bet what you can't afford to lose" phrase is so commonly used now that I doubt one would still make simple mistakes about it.
There is severe misery about gambling but many of us might not really know about that. There is no way anyone can be gambling without losing money to gambling. There are different ways we can lose money to gambling and we might still not know what's happening until it is realized that every attempts to recover past loses is no more working.