If she's relaxed and not dry, it shouldn't hurt. If she's hurting in her lower abdomen, that could be a sign of endometriosis. If she's on birth control pills, that might hinder her from getting moist.
KY makes some good vaginal lubes and there are spermicide suppositories that are great for also keeping things nice and wet.
Many years ago, a sex expert did a demonstration on tv to dispel the 'condoms are too small' myth by stretching one over a teenage boy's head. If it feels like it's restricting blood flow, you don't have it on all the way-it's probably rolled up a bit. The tip should be loose, not wrapped tightly around the head of your cock and the condom completely unrolled. Make putting one on part of foreplay-have her do it while you play with her and get her 'ready'. Never jam...start slow, tease her clit and vagina with your cock. Go slow, move it up and down; you'll feel her getting wetter as you do and you'll know how and when to continue.
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