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Everybody's different. When I was younger (I'm at the half-century mark) I could go again in a few minutes, with a little stimulation with my sweetie. But I knew guys who could just do it the once and had to wait a good long while.
Guys above the age of 21 or so who can go routinely go three times in an hour are fairly rare, although I'm sure somebody here will shout "me, me!" I tried it a few times, and though I could sometimes keep it hard on the third try back in those days, there really wasn't anything left to give, and it was more like work than anything else.
Chemicals will help, of course, but if you're under 30 and want to try those, I'd consult with people here about dosages or you might end up with the dreaded four-hour hardon.
Speaking naturally, the best thing for extra stamina is to have taken in a lot of high protein, high-energy food earlier in the day. Protein, baby, with good carbs and not a little fat. Eating a heavy meal right before sex is not a good idea, but having serious reserves on board does help with stamina and your ability to come more than once in a short time. For me, sex and hunger are a bad combo.
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