No reason why you can't have fun too. Men do like a tease as long as you put out eventually. Make him chase you a little first, play cute when he askes for them "nope sorry can't show you my underware again" "why?" "not wearing any" (it's fine to lie if it's a tease) "no really that's cool send anyway" "hmmmm no" "plz" "I have an idea" wait 5mins to build anticipation "okay ready?" "Yes" then send a normal one and say you just changed for it. That's just an example of how a text interaction would go, other ideas could be asking for a nude in return and stuff. tl;dr: send them when he askes for them but make him work for it a little he will enjoy it more.
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Be careful, if you give him nudes, you give him a powerful revenge weapon if you two ever break up.
Not more than twice a week. Do NOT include your face.
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Once you send a nude, it's always in someone else's hands. Are you ok with that?
He won’t get bored. That’s not how it works.
As much as possible
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