Tell your BF one more time that you’re not going to send him naked pictures, now or ever. But this time, try telling him more sternly. Say it’s never going to happen, and you’re sick and tired of him asking. You don’t need to explain why you don’t want to, but if you feel like that might help, just let him know the reason. Don’t let him try to talk you into doing it. Be firm and don’t let him guilt-trip you.
If he still doesn’t stop asking, maybe it’s time to make an ultimatum. Let him know that while you love hanging with him, you don’t love being pressured to do something you don’t want to do. Tell him that if he doesn’t cut it out, he might not be your boyfriend for much longer. That may seem harsh, but no girl deserves to be with a dude who pressures her into doing anything she’s not comfortable with. If he really loves you and is a good guy, he’ll stop. If he keeps doing it, it just means he’s selfish and not ready for a relationship. And you definitely don’t want to be with someone like that.
What’s on your mind? Heather can help! Send her your question at firstname.lastname@example.org