I haven't felt awkward about entering my partner but I have thought of it as somewhat of a violent act. When I am in a heightened sexual state I tend to be aggressive as I penetrate her. But she says it's that initial entry that gives her the most pleasure. Because of this I will often spend some time just penetrating and completely withdrawing repeatedly but I don't thrust my penis all the way in, just the head and maybe a bit more. After a while she tell me to put it all the way in. It's exciting to me to watch as my penis enters her.
When I have mentioned to her about my thought of it being a violent act, she says she doesn't see it that way. All she knows is the sensations she feels during the initial penetration is the best part besides the orgasm.