Mmmmhhh

It really depends on so many things, and no session can ever be the same.  
I’d say anywhere from 2 to 4 times, but hey it can be less or more as we are all different !

Mmmhhhhhh

I don’t do overnights …..

It has only happened on a few occasions, and the women for those were absolutely determined to get a 3rd. In one case, the girl went a bit past the two hours to get it done. Never have done an overnight so cant answer that one.

For me 2  was the most in an hour. But usually i like to just go once and have it a bigger  orgasm and bigger shot. If i go for 2 hours I would def like to go twice.

Back in the late 80’s I remember a once in a lifetime marathon session at the world famous Julie’s.  I was single, had just gotten my holiday bonus (stupid me should have invested the cash instead) and ended up banging 6 or 7 of her gals (including 3-somes). At one point the entire place including Julie were trying to get into the action and separate my cash from me. Came 13 times in a 4 hour session. The girls wanted no more of me after I was done.  Being in my mid 20s with a hyperactive thyroid no doubt helped.

3 in 2  hours

never done an overnight but did a 4  hour appointment and came 4 times

When I was younger... Twice in an hour was common. 3-4 x in 2 hours.  Now? Twice in 2 hours maybe 3x if the gal tries really hard in a PSE.  But I'll stick to 2 in 2 for a more comfortable time.
My record was 6 times in 12 hours on an overnight in 1996. When I was 28.  Now I am almost 54 and have gained 65 lbs since then.  Did an overnight recently where it was 2x before sleep and once in the morning and I was happy.