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As a rule of thumb, you should avoid sending dick pics all together. There is nothing attractive about them, nor sexy. Sorry, not sorry. Ask any girl you know, she's most probably going to tell you that she's not about that life.
Once a male suitor sent me a photo of his erection in which he was completely naked...except for a pair of white socks and his running shoes. I repeat, his running shoes! He took the photo standing up, with the phone pointing down at his penis. It was indeed a lovely penis, but all I could stare at was those glaring white tube socks. When sending a dick pic, either take off all your clothing for an actual nude photo or perhaps pull your dick out of your jeans and hold it with one hand in a tasteful manner. Do not get buck naked except for your socks. Also, when taking a dick pic, do not stand in front of the mirror in the funniest thing a dude can wear: a T-shirt and no bottoms.
I know your dick is nine inches long. You told me the very first time we had sex, and my vagina quickly figured it out as well. I also now understand why your email address and social media handles all include the number nine. Adding a ruler next to your penis in your dick pic to remind me once again comes off as (pardon the expression) a bit cocky, not to mention wholly unnecessary.
A stone-faced, seductive dick pic has its place. However, if you want to goof around a little bit that's totally allowed. Sex is supposed to be fun, and sometimes adding goofiness to a dick pic can make it that much more endearing. I would laugh my ass off if a guy sent me a dick pic with a smiley face drawn in marker on the head of his peen.
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