I am upfront about my penis size when dating.
I think that there is a point to being upfront about it, at least when you're on the larger than average side of the spectrum like me. Maybe if youre average or small, there isn't as much point to bring it up.
If you have a big dick, and you have warmed a women up to a state of being very aroused, and you are completely filling her pussy and she feels that subtle pressure of your large penis gently stretching her and filling her up... There are some women who will start orgasming uncontrollably from that feeling, and there are some women who will wince in pain, and jump off of you and the moment is over. (there are surely other types of women, and a myriad of scenarios inbetween, but for the sake of this argument, let's generalize to keep things simple)
I'm not the type who rushes into sex. I am that weird anomaly who actually likes to get to know the girl first. I have also been rejected by more than one woman because of being too big.
The fact of the matter is, there are lots of women out there that find the sensation of being filled by a large penis as a horrible feeling. They do not find it sexy, or attractive, and having their cervix hit or their vagina stretched is a feeling that is a complete mood killer for some women out there. I say this only from experiencing these women.
The reason I decided to be upfront with women about the fact that I have a large penis, is that I don't want to go through all the motions of flirting and dating and leading up to sex to find out that they don't like what I have to offer, and I'd rather not waste my time trying to get them to come around to my size and find ways to enjoy what I have to offer/
Especially when there is also a large number of women who fucking adore and love a big cock.
I know what I'm into, and I know the role I like to play in bed, and the fetishes I have, and there are so many women out there, I wouldn't advise men looking for women to waste time with women who don't love what they have, because there are lots of women who would go bonkers to date a guy they liked who also had a big cock.
This goes for any other physical or emotional trait. I wouldn't advise people to try to seek the approval of someone who doesn't appreciate the unique qualities that make you, you. If they don't love your uniqueness, then don't try to change yourself for them, or change them to appreciate you. Just be yourself, and be the most yourself you can be, and be with someone who loves those things about you, and adores just how you, you are. If you want to change anything, focus on yourself, focus on how to be the best version of yourself, for your own reasons, not for anyone elses.
It's for these reasons, that I like to be upfront with my penis size when dating.
No, you don't blurt out to the woman on the first date "hey I have a huge cock, you dig that shit?" No. Don't do it like that.
But as you're getting to know her, and you have already established the basic connection, and mutual atraction, (which is usually established after one or two dates) then I think its a good thing to bring up. If she likes the huge cock, then youre golden, and the anticipation leading up to sex will be incredible, and if she is turned off by that, then you've wasted only a couple hours and then you move on.
I don't think there's any point in telling someone your size first. Either that person has experience with your size, so when you tell them they would already know that they could handle you, which you would have found out anyway once you were in bed with that person, or that person doesn't know if he can handle your size, which could only be discovered by attempting to have sex with you. Either way, there's no point in mentioning it.