Wauw! Intense experiences, thanks for sharing.
The deepest I have gone with meditation was when I experienced something called Kundalini. I never heard of it before I got it, I looked it up later to find out what the hell that was because it was a combination of sensations I never felt before.
It happened after I started meditating at 3-4 months, pretty consistent every day in the evening at least 20min in complete dark, absolutely quiet. It was like a burst of energy shot up my spine reaching my head, the third eye if you will, when it got there my whole body started vibrating not physically but energetically like electric and then I got really hot. Very strange experience but I'd take a Kundalini over an orgasm any day It felt that blissful!
Cool he saw Richard Alpert live. He's definitely worth listening too, you can find a lot of material on him on the internet. He know what he's talking about after hundreds of spiritual explorations