So you've been chatting for a little while and it feels like things are going the right way. You want to seal the deal — or maybe you want to warn her that you've got a huge dick. Why not send a pic of your big dick? That would absolutely do it, right? Stop right there.
When is the right time to send a dick pic?
There is only one answer to this question: if and only if it is asked for. If the recipient hasn't asked to see your dong, then do not show them your dong. End of story.
Doesn't matter if it's going well. Doesn't matter if you've had sex already. If it wasn't asked for, then do not send it.
For one, most women do not like receiving unsolicited dick pics, and a lot don't even like getting dick pics at all. You might be thinking that you'd have absolutely zero qualms with getting a tit pic or pussy shot in your messages, and if that's totally okay. But just because you want to see her naked doesn't mean that she wants to get up close and personal with your engorged member.
On many dating apps such behavior can get you banned. In Texas sending unsolicited nudes is considered a crime, and other jurisdictions have enacted or are considering similar legislation.
Say it with me: Only send a dick pic if a dick pic is requested.
Be prepared for others to see it
As with posting anything online, the moment you send an image to somebody else it leaves your control. Sure, sharing those images without your consent could be considered illegal in many places, but that doesn't mean it will stop people.
This is especially true if you have a very large penis. Humans are fascinated by the unusual, and a huge dick is definitely unusual. Don't be surprised if it gets shared, either in a "look at this picture on my phone" manner or straight-up sent to other people.
There's a school of thought that this might not be a bad thing for the well-endowed. The theory goes that the more people that know you have a huge cock, then the more people might be interested in having sex with you. And to some degree that is correct: when word gets around about your endowment it can absolutely lead to more sex with more people for you. Which is great if that's what you want, and there's nothing wrong with wanting that. But if you're looking more for something serious, then everybody having seen your turgid member isn't going to be of much benefit (at least maybe until the next time you're on the market).
That said… people will still talk. Men, women, doesn't matter. They'll tell a trusted confidant about you, who will tell somebody else, and before you know it people you barely know are coming up to you and saying "I heard you have a huge cock." That's not necessarily a bad thing — after all, a large penis is a socially desirable trait — but if it's something you want to keep private then that can be frustrating.