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Probably either lack of lubrication, or you are going too long (and again lube is the problem, as a girl will start to dry up after a while). According to Dr. Drew, after about 10 min. or so it's pretty much "Ouch!" to the girl.
BUT, if you are having sex frequently, why don't the two of you start on hormonal birth control pills??? They are the EXACT same chemicals as the day after pills that she is already taking, but in lower doses so there aren't as drastic side effects.
ALSO the morning after pill is only 85% effective if taken right away!! Daily BC pills are 99.6% effective.
In any event, hope this helped. I'm glad to hear that you are trying to be responsible.
Good Luck!!



Why does the condom always break?
My girlfriend and I have been together for 7 months now, I love her to bits but almost every time we have sex the condom breaks... Anyone know why and what I can do about it? Thx