We actually have quite a few things designed to help you with this decision! The first one I recommend both you, and your boyfriend, look at is this article: Ready or Not? The Scarleteen Sex Readiness Checklist
. That piece goes through all the different things to consider when making the choice to be sexually active, so you can figure out what things you are, or are not, prepared to handle and go from there. You can also go through this list to help figure out what sexual activities you and he are both interested in: Yes, No, Maybe So: A Sexual Inventory Stocklist
. After all, there's way more options than just vaginal sex, and you may find things on there that you both want to try and are comfortable with the risks of.
Preparation is definitely something to aim for when it comes to being sexual with another person. There are a lot of cultural messages about how sex should just "happen naturally." But in reality, sex where people take time to a) think about their choices and b) communicate about what they want and prepare for the experience is usually way more pleasurable (and safer) than sex that "just happens."
When you mention buying bananas, are you thinking in terms of using them as sex toys?