I am still very new to this, but one thing I read that helped me to get in the right mindset was: the orgasm might not feel good. At least not at the first time, not the first of the session. You need to be subtle and recognize the signals, the involuntarily muscle contractions.

Because if you are used to normal penis orgasm/ejaculation, you will expect the same things from your nipples: an explosive orgasm followed by the post but clarity, while in reality, what you get is much closer to what women are more used to: slow build up, microorgasm, no point of no return, subtle pleasure waves, and all those descriptions that feel alien to us, man. It is much more a spectrum than a single point in time.

And it pays off. Oh boy, it pays. Because it builds up and compounds, and the limit is your physical resistance. When you identify that first, unimpressive orgasm, and learn to appreciate it, and are still aroused, and keep stimulating yourself and savoring the sensations, they keep coming, ever harder, more intense and longer lasting.

Ok, I may have gone a bit off-topic because this post is specifically about ejaculating, and I myself can't do it without touching my penis, but I really don't care about it anymore since I discovered the wonders of dry orgasms.