I'm actually in your exact position, 27 and still a virgin. Hell I haven't even kissed anyone yet so I'm probably in a worst position. I've thought about your question quite a bit in my own life. I have mixed feelings about it.

On the one hand I think it would be nice to tell. A woman who will sympathize with you and go slow at your own pace would definitely be great. Having said that at our age more and more women are settling down. The few ones who are available probably want an experienced man. This may not be true of everybody but I do think it's safe to say that finding a woman like this will be tough. The expectations in dating are simply different when you're 27 than when you're in high school or college.

That's why just letting nature take it's course should be a serious consideration for you. There's a lot to be said about just doing things without overthinking. I've noticed these types of people tend to go far in life, whether it's in their career's or personal life. I'm not saying be reckless and become some kind of daredevil, but after you've given it some thought just go for it. Women in general like it when a man takes charge. They don't like it when men are too open with their feelings or insecurities. But then I don't exactly have any female friends so this may be my own insecurities talking. I have however seen many women stay with men who don't treat them right so maybe I just have some nice guy bitterness. Who knows?

As you can see I haven't told you what to do. What I have done is given you some things to think about. I hope you will and make the decision that is best for you. Good luck! And tell us how it goes!