Advising a woman

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I may have preferences to varying degrees for a lot of things, but if a dude made a point of bringing up that they're of average endowment or below average endowment it would likely read as an insecurity (to me, not saying others would interpret it the same way). If I liked a person, their genital specifications aren't going to make me stop dating or not fuck someone. Even back when I did casual/NSA/FWB/etc I usually did know what prospective partners looked like, but never once were their genitals the deciding factor on whether we met up.
 
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rtg

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Sarcasm, the last great form of humor
I think it's the first great fork of humour.

As to your question... don't mention it unless you know she's a size queen. It may show you are insecure. She may also just wonder why on earth you've brought it up. And as has been said, we choose the guy not his cock.

Sure, when I'm interested in someone I wonder what they are packing. But I just assume they aren't well endowed so I don't have any expectations. If I like someone enough then it's always workable, no matter what size.
 

AlteredEgo

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Tell me about a weird penis as soon as we start talking about sex. Make it funny or flirty. Or show me a picture of the weirdness if you can get me to agree to looking at a dick pic. Do not winge. If it is oddly shaped, has a very tight phimosis that needs special care, is much smaller than average (like, 3.75" or smaller) or much larger than average (8" or more) please just find a way, a fun or interesting way, to let me know. I learned from a 2.5" dreidel-shaped penis that I don't like that kind of surprise. On the other hand, I saw a picture recently of a really weird dick, and because he was proud of it and descriptive about how he wanted to wield it, I was pretty excited about it. Rather than a weird dick, it was a hot novelty. On the other hand, if like him, you can't follow through, I guess you say nothing.
 

nailz

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At what point in the dating cycle should you advise the lady that you are not well endowed if at all

Never.
Whether she wants to sleep with you or not has nothing to do with the size of your wiener ;)
 

Tattooed Goddess

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You also don't want to ask her about your penis size if you end up being sexual together. If she feels like she has to constantly reassure you about your penis size you start going into the friend zone pretty quickly.
 
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Tight_N_Juicy

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I'm the one who brought it up. If a guy wants to get friend zoned just keep bugging her about your penis insecurities.

I saw that, deleted my post. Sorry OP. I do still hate that term though.

If a guy gets pissy for me being his friend, he belongs in none of my zones. Just my humble shiz..