So let me start from the beginning. In my previous sexual relationships, let's say 1997-2003, during a full session, I'd cum once and that'd be it. Back then, it was extremely uncommon for me to have sex without a condom, so maybe that was a factor.
Side note here: It usually takes a while, around 20-30 minutes, to cum. That includes oral, manual, and vaginal stimulation, or a combination of all three. Even with masturbation, it can take some time.
Now, fast forward to meeting the woman who'd go on to become my wife. We met in 2003, married in 2005, and are still married to this day with 3 kids all teens. With her, sex has always been amazing. In the beginning, we sporadically used condoms and abandoned them completely around late 04 or early 05. We noticed that condoms just didn't work for us from a pleasure standpoint. But back to my main point. During oral or manual stimulation from her, it'd still take me a little while to cum. But with vaginal sex, i was cumming within a matter of minutes. This would happen regardless of any length or type of foreplay. However, without stopping or even pulling out, I'm able to maintain, or at least with minimal effort, easily regain a full, and more often than not, an even harder erection for a full penetrative session. After the first orgasm, i usually cum again 15-25 minutes later. If it's a really hot and steamy session, 30-45 minutes. The second orgasm has always been the lip biting, body clinching, heavy breathing, loud grunting, knee buckling coup de gras.
In the beginning with my wife, the first orgasm was usually small and she'd hardly notice or feel it at all. I'd feel a small gush shoot out and that'd be about it. But over the years, it has gradually evolved to become almost as intense as the second.
Now, for those of you wondering about my wife's pleasure, and I know there's a few of you out there, trust me she's well taken care of. She usually cums two or three times. At least once from oral and or manual stimulation, and once from penetration. If she does cum a third time, it's normally right before my second orgasm. She had said the excitement and feeling me get bigger and harder, and the increased vigor of my thrusting as I'm about to cum is what gets her off. And I'm okay with that ;-)
This is extremely rare. But, if we're not to exausted by this point and I'm still somewhat hard, i can keep going to cum one last time in another two or three minutes. However, it often pales in comparison to my first and second orgasms, and she doesn't really get a lot of satisfaction out of it either. So we usually just end things after my second to rest and reset.
So the point of this story isn't to brag or boast. But just to share my experience with being able to ejaculate more than once.
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