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The pain factor also varies wildly. I know some people who say they cried; others say it didn't hurt at all. Being fully lubricated and aroused makes a big difference, so get as much foreplay in as possible and don't be scared to "check" yourself with your finger to see how wet you are before go ahead with the deed. Have you had oral sex with him? If you haven't, start experimenting with that first. It should definitely help to get you ready. No matter how much foreplay you do however, be prepared to feel at least some discomfort in the beginning. In my case, it hurt for a good 10 seconds, was uncomfortable for maybe another 30 seconds, and then it all went away after that. His size in this case also adds to the discomfort/pain level.
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