Recently, in two completely separate and unrelated conversations, I was told by two people who don't even know each other (and are practically from different planets), that "first-time sex is always awkward."
I'm no expert, but I have had my fair share of first-time sex. In my experience, it isn't always awkward; it is sometimes awkward.
It's really no different than a first date. I think we can all agree that most women probably have more first dates than they do actual relationships. When you meet someone, you think there might be a connection - but there's no way to know for sure until you go out. But for all the first dates we have, few lead to a second. Even fewer lead to an actual relationship.
A lack of conversation, or a disagreement over the date activity, or a boring time, or whatever is a sign that it just isn't going to work. This relationship isn't meant to be - and that's fine. We gave it a shot, and now we know. Rarely do we invest so much in first date that we get upset if it doesn't work out. Really - nothing is lost (except maybe a few hours and a few dollars, which is really just a cost of dating).
Sometimes, first dates eventually lead to first-time sex. Personally, I think if it's awkward, that's also a sign. Just like the signs a date isn't going well, awkward sex is a sign that you have different desires, preferences, fantasies, or rhythms. Whatever it is, you're just not in sync.
That should be fine, too.
Just because you got to the point of wanting to have sex does not have to mean that he is The One. You have to keep looking if you're going to find him, right? Sex is just a part of that search. It would be an important part of any relationship you choose to pursue.
Sure, if you've decided to wait until you're married before having sex, and your first time is awkward, then it's something to work on. But if you're having sex early on, why is it something you have to "give a chance?" If you found out that the two of you wanted different things out of life, or a relationship, or finances, or family, would you try to "work it out?" No? Then why give the sex a chance?
Maybe the awkward sex is just the the sign we need to know it's time to move on. I think we need to cut ourselves some slack and realize that while we're looking for Mr. Right, we're going to have sex with a few Mr. Right Nows. It doesn't mean we're sluts, or have poor judgment, or make mistakes.
It means we're trying to find what we want, and what makes us happy, and we know that sex is a piece of that puzzle.
*Note: Yes, I encourage casual sex and/or sex early on in a relationship. I think it's important for women to know what they like, and casual sex is a good way to learn. I also believe sex is an important part of a healthy relationship, and you need to know if it "works" with a person before the relationship continues. However, I encourage safe and responsible casual sex. Safe means protecting yourself; responsible means being honest with your partners about your situation, including if you're not monogamous.