Back when I was single, I don't think laptops came with internal cameras (at least mine didn't) and webcams were less mainstream. Live video chatting didn't really take off until I met my girlfriend (now wife). I'm not complaining, but had I been single a little longer here's what I think I would have done in terms of cybersex/video chatting:
In terms of cybersex, when I would chat with a woman, it was always with locals (or local enough that I would be willing and able to drive to their town to meet in person). I never chatted just to chat. It was always with an eye toward meeting in person for an actual hook-up. Of course, it didn't always work out that way, but I never went in knowing I would not be able to physically meet this person. The chatting with these local women was more Q-and-A, descriptive accounts of past experiences and frank discussions of interests/preferences/talents. It would not be the typical cybersex like many describe: "Now I'm taking off your panties ... now I'm flicking your clit wth my tongue." I have as much writing ability as the next wordsmith, but it just always struck me as a waste of time. We would turn on one another plenty by discussing our pasts, interests, and plans for what we'd do to each other once we met.
Now in terms of webcams, I would have no issue showing my live, erect cock on a webcam to a potential hook-up. However, I think I'd do it in such a way as to not display my face in the same shot as my cock. I wouldn't want to be put on some porn site against my will, and that sort of thing can happen. Last thing I want is for my friends and family to see me with my dick in my hand sitting at my computer. I suppose I could show my face at a separate time in the same conversation, but I would be very careful about pairing dick with face.
Number 2 about webcamming, and I put a lot of thought into this in theory despite never having done it in practice. Again, I would have no qualms about showing my package so the woman knows ahead of time that I have a big dick. However I wouldn't masturbate in front of her to the point of ejaculation. I know many people use webcams specifically for this purpose, but if I were to ejaculate in front of her, what would be the point of meeting in person. Again, that is the whole objective. There has to be something left behind. Yes, I have a strong cumshot and I tend to shoot a hell of a lot of semen. I'm sure it would translate to video very well, but I could just see a woman keeping it a cyber relationship if I did that. I don't mind giving her a teaser - 'if we meet, this is the dick you're going to see and have inside you,' kind of thing. But I don't wan the first time she sees my cum to be online. Let her have the option of rubbing it in, tasting it, etc.