my boyfriend and i have only had sex once and we used a condom, but it seemed like when we were having sex that he couldn't break my hymen. I realize that the first time is generally pretty painful, but I was wondering how likely it is that my hymen is already broken and that the pain was just my vagina stretching...
It might take you a few tries to manage to accomodate his entire penis - nothing to worry about, it's quite common. Things that might help could be having him put a finger or two inside of you to help you get used to the sensation of having something inside of you.
You'll also want to make sure you are feeling really aroused, as this will make things easier. Lubricated condoms (and extra water-based luricant) might also help.
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