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Hi Random,
How old is your boyfriend?
Forget about trying to please him. You're likely to be in pain from having his penis in your vagina and also from him likely tearing your hymen. Expect some, possibly lots, of blood too.
Hopefully, if he's experienced, he'll make sure that you are good and wet before he slowly enters you. That'll help.
Just try to relax.
Remember, he puts a condom on before he touches your vagina. If there are any problems, like the condom is on backwards, you use a NEW one. Never reuse a condom. If you have sex again, use a NEW one. He needs to hold the condom on while pulling out too.
Good luck.
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