"In other words, I feel less of a man because I couldn't inspire the same awe as she felt for her first."
That may be a good thing you know. My first was very painful.
However I'd suggest basing your choice to have sex on the woman herself and not whether or not she's a virgin. It may turn out that way but... virgin or not, what will really matter is how much you love her.
When it's the right person the past doesn't matter really.
Am I wrong for wanting a virgin for my first time?
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"In other words, I feel less of a man because I couldn't inspire the same awe as she felt for her first."
That may be a good thing you know. My first was very painful.
However I'd suggest basing your choice to have sex on the woman herself and not whether or not she's a virgin. It may turn out that way but... virgin or not, what will really matter is how much you love her.
When it's the right person the past doesn't matter really.