Spend as much time with her as you can during the days before and on the day. Do it somewhere where she is comfortable and feels at-home. Make sure it is somewhere where she isn't worried at all about getting caught or interupted. Take the phone off the hook. Maybe play some music that she likes; something that will get her relaxed. Take things slowly; plenty of foreplay. Also, use lubrication (KY jelly or similar). Again, take things slowly, and talk. Stretch the hymen, my husband and I were recommended this on a CD by Dr. Ed White and it was extremely helpful and simple. It takes time and patience though. I feel that it made our first experience much better. It also helps to not pressure her. If she feels pain don't push it until she has adjusted to the feeling and it helps to not pressure for sex in the first night. I wanted to but couldn't so we waited and kept stretching and it worked out great.
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