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You can with someone and without. If you do it you jack-off and come and that's a organism right there. If your with someone having sex and come inside them, that's another organism.
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Yep, you should be able to have an orgasm without any issues. The male orgasm is pretty straightforward for most guys. Just masturbate (jack off) and it will come. You can use some lubricant if you want, and experiment with different amounts of pressure, different speeds, etc, and you should cum without issues.
If you masturbate regularly but you've never ejaculated, well, that'd be concerning and if that's the case here, I think you ought to see a doctor. Some guys can't ejaculate, but they still get orgasms. That's called dry orgasm.
Have you ever had wet dreams? That should be a good indicator that you can ejaculate.
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