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Hi Sara,
You may or may not bleed the first time. There is no guarantee that you will. You can also bleed AFTER your first time. You can't really prevent it.
It happens. You know it can happen. He should understand it may happen too. You don't have to be scared.
Yes it can hurt but if you both take your time it will be more comfortable for you. Don't rush things and use plenty of lube. He shouldn't expect to go in quickly or deep. Talk to him. Let him know if it hurts.
You may be sore for a few days after having sex too. That's normal. You've never used some of these muscles so they can be sore.
Good luck.
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