When should I tell her

I am a 43 year old male. I've just started dating a girl. We haven't had sex yet. What I am wondering, is should I tell her I'm small before we do.
I am a little under 5 inches hard. I have cuckold fantasies and small penis humiliation fantasies...have had for twenty years.

So, does this make sense, for me to tell her "I'm not very big" before we get to the bedroom?

The confession alone might turn me on, but it might be too weird for the girl.

I thought maybe I could wait until after we'd fucked a couple of times...then she'd know I'm lacking big time, and I could mention it that I would be ok if she had a bigger one on the side...

Start off by giving her lots of oral and manual sex. Give her enough orgasms that way then she will not be too concerned about your size. Get your tongue working hard on her clitty and your fingers streatching her pussy entrance. A cock, however small, when going in and out of the pussy lips fast can make a woman happy, especially if you keep her dry by wiping away her juices with a tissue every now and then. . Keep her happy in these ways for a while, create a solid bond between you and then, ONLY then think of sharing her out.

I agree with SA Taylor. I would indeed start off orally pleasing her, often....statrt with it...do it in the middle....and end with it if she will allow you too.

Ensure she orgasms this way often. She will know you are to small, and she may not comment on it for a while. Provide her orgasms orally without reciprication (sp) increasingly more often. When she asks why not you, jsut tell her that you enjoy her satisfaction.

intime you wil notice that she does not really get off on your little one.

the broach the subject, although it may take time