I think you should, because it’s going to come up eventually and it’s important for you and your boyfriend to prepare for it now.
Sex, unlike the movies will have you believe, is not some romantic Ryan Gosling Kissing You In The Rain And Laying You Down And Knowing Exactly What To Do fantasy experience. Sex takes teamwork and empathy and passion and effort. And all of that is firmly rooted in clear, unapologetic, honest communication.
My advice is to bring it up with him some time soon, before you think there’s a chance that you two will end up having sex. It doesn’t have to be an overly complicated conversation – something along the lines of “I really like you and I want to let you know that I don’t have a lot of experience. When the time comes, you might need to be a little careful with me.”
That’s it. Two sentences and all of your cards are on the table. Your boyfriend/guy you’re dating will know, be patient with you, take things slow, and work to make sure that you enjoy sex. You’ll both be happier that way.