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You go to the mall together and grab a drink. He listen to his hobbies and passions. At the beginning you are a bit too shy to talk, but later, you also speak about yourself, as much as you can without revealing your swapped sex.
He is completely honest with you about his intentions. He doesn't know for sure, if all this work out for the long run, but he is excited to actually go on a date. He also thinks you are smart, cool, and look pretty. He also has never seen a girl naked before or anything the like. Most of the time, he focused rather on school and his hobbies.
When you are alone, you remember he had never seen a girl naked before, so you decide to become his first. If you can give a boy such joy, why not? You remember how much this means to them since you have been once yourself.