#1: Make sure it's cool first
Unsolicited and/or unwelcome sexual messages can and will be considered sexual harassment, so make sure the other party is a willing participant before progressing too far. A signed waiver is the safest approach...
I the undersigned, agree to have my world rocked via electronically transmitted messages......but that might dampen the mood you were hoping to establish. There are more reasonable ways to test the waters, as described below:
An Example Bucholz: Hey sexy. I think you're sexy. Karen: LOL. I think you have the wrong number. Bucholz: I think you've got the RIGHT number, if you want to know about dudes not wearing a shirt right now. Karen: Please stop texting me. Bucholz: Oh right. I should probably explain before we get much further. My name's Anderson Cooper, and I'm doing some research on the topic of sexting for my show, Anderson Cooper 360. Your number was selected at random by a computer, and I was hoping you'd be willing to help me with my research. Karen: How do I know you're Anderson Cooper? Bucholz: I'll prove it to you. Here's a picture of me I just snapped right now with my camera phone. FILE ATTACHED-selfportraitpic.jpg
Karen: That looks an awful lot like a file photo. Bucholz: Thank you for implying that I'm always camera ready Karen. But I shall prove it to you harder. Pick a number between one and four, then tell it to me. Karen: Ok. Three. Bucholz: Here's a pic of me holding up exactly that many fingers. FILE ATTACHED-selfportraitpicv2.jpg
Karen: Wow! Bucholz: So we're good? Sext ahoy!
#2: Adults only
Related to the previous bit of advice, but important enough to deserves its own entry. Especially if you've never physically met the person you're sexting, like in some kind of chat room situation, you're really putting yourself at risk of having every misspelled euphemism for your penis read out slowly in front of an elderly judge.
"Wangprong? Really? That's worse than Fuckcudgel."
An Example Bucholz: Before we get too much further, I should check, are you over 18? Karen: Yeah, I'm 28. Bucholz: Hmm. Do you remember the Macarena? Karen: Yes. Bucholz: Ok, your story checks out.