Help me understand what happened?

You are right there! Super o land,but you don’t know what you have yet lol. But since you’ve only started to re wire,the body and brain are a little confused as to how to sync up but that will come. I had all quakes and stuff at the start with little to no pleasure. When you say you had a half second body wide O,it was likely somewhat of a startle. That’s the time to remain focused on your relaxation and just let things be as they may. Just enjoy any good feelings that come without worrying if they’ll grow stronger. You could try throwing in a little erotic fantasy at this point.

True,soreness may have put you off a little,maybe go every other day. You are doing it right. Practice and experience will prevail. Don’t try to rush or chase,they murder sessions.

Well done resisting the Jack off finale,maybe put the jacking off on the back burner for a while. Only clear the pipes out if you really need it.

Bin off the disappointment,that needs kept in check,and see the positives in all the checkpoints you’ve reached already. 

Keep grinding brother 🙂

Posted by: @quench

Questions
Is it normal to feel less orgasmic the first few times?
Will it get stronger with more sessions?
Does it seem like I'm making mistakes that I'm unaware of?
Any tips are welcome! Thanks.

Posted by: @quench

This went up and down in intensity for roughly 20 minutes before I couldn't take it anymore.

I'll focus on the questions, hope this is not too direct  : 

What's "normal" or should I say, what's to be expected, is to feel close to nothing the very few first times, very subtle sensations.  So you did very good/ you're probably a natural which is like drawing the winning Aneros ticket. What you are describing is a good, solid Super-O, but you did not get the feelings associated with one, probably because you (your body, mind, Ego, or whatever) have no experience in processing similar feelings and you got locked/focused on the body action It's pretty unusual to get this far this quick, so it's hard to say how things will progress, but basically you should get more acquainted with the feelings over time and it will start to feel better, and that 1/2 second feeling will expand and last longer and longer. 

It would be easy to say clenching instead or relaxing was a "mistake", but on the other hand, can you really talk about mistakes this early in the game, I don't think so.  My advice is don't change anything, focus inwards even if things are going crazy on the outside, and progress should come relatively quickly without too much work. Relax, breath, go with it. 

Oh and welcome aboard, and congratulations on achieving your first Super-O ! 

@zentai An error made my reply disappear, so I'll try to remember what I wrote

Thanks for the quick answer.

Posted by: @zentai

because you (your body, mind, Ego, or whatever) have no experience

This is so true. After lurking and reading for a month, I had a "I'm gonna make this happen!" attitude, and probably expected too much.

Posted by: @zentai

focus inwards even if things are going crazy on the outside

And this is amazing advice. I was so caught up in what was happening physically that it likely was a distraction. Maybe I'm over-analyzing too. But thanks for setting my mind straight and helping me let go of the disappointment. I didn't realize how much I had achieved already so it's no time to get greedy.

Finally, I decided to end session 2 with a traditional, and ended up having the longest, strongest ejaculatory orgasm of my life, 25-30 secs. I created an ocean on my belly

@quench

My pleasure ! Helghast's advice just above is also great, pretty sure just making small adjustments will keep you on the right path. 

The forum software is a little fickle, emojis will make your message disappear more often than not, links will do this too, sometimes. Nowadays I copy everything to the clipboard before posting just to be sure, not ideal but it saves a lot of frustration ! Anything more than a couple lines, I copy in a text file. 

Yes, greed is bad, and over-analyzing, while intellectually simulating, can wait a bit until you have things more dialed-in, else you risk paralysis from analysis which is a very frustrating place to be.  

Posted by: @quench

Is it normal to feel less orgasmic the first few times?

Yes, as @Helghast & @Zentai noted these sensations are subtle but as you learn to focus your mind upon them their apparent intensity will grow. This is part of the 'rewiring' process.

Posted by: @quench

Will it get stronger with more sessions?

Most likely yes but there are many factors which influence any one Anerosession, some sessions will be 'duds' that is why you will so often here the phrase "...no expectations...".

Posted by: @quench

Does it seem like I'm making mistakes that I'm unaware of?

No, in fact you have already had remarkably good results. I am an advocate for new users to practice semen retention as an arousal amplification technique to accelerate your rewiring. Please see the threads Are you "aroused"? , Aneros, Arousal & Abstinence/Semen Retention , 21 day challenge post & @divine_o 's thread Arousal building methods.

Posted by: @quench

I achieved what I think might be a prostate orgasm, but it felt dull and I don't know why.

Nothing to worry about here, your body has already shown you that it is reacting well to the stimulation, it is just that your mind has not yet gotten into synchronization with what your body already knows. Don't try to analyze the process during the session, just focus on the sensations your body is producing and provide positive affirmations/thoughts for those sensations you do experience and enjoy. Things will get better as long as you let your body lead you and you don't try to control the process.

Good Vibes to You!

@rumel Thanks. I'll read up on the links. After the session had ended, I was left with a worry that this might be all there is, but I'm way past that now thanks to these helpful comments. Since waking up today, I've had random waves emanating from the prostate and up my back into the arms, at the most unexpected times, standing in the kitchen, sitting by my desk... It's like something has been unlocked.

Posted by: @quench

It's like something has been unlocked.

An awakened prostate can be an awesome force which can lead you to higher levels of pleasure and consciousness, enjoy!

Good Vibes to You!

Congrats on your termed unlocking.  I second your reasoning to try silicone lube with your Maximus Trident.  Early on for me, silicone lube made a difference, since for that newbie, comfort generated more confidence, which kept me “plugging away”.

@quench

Any update ? I don't want to pester you, but I'm sure I'm not the only one who's curious about your progression since things went so well right from the start. How are things shaping up? 

YEA !! Quenchy! How’s the sessions going? 😉

@helghast @zentai

Hello guys, I appreciate you asking! Some good things have happened, some bad.

BAD
I bought Pjur Med Premium Glide silicone lube and double triple checked that the plastic material in the Maximus can tolerate it. Also couldn't wait more than two days before attempting again. The soreness had not gone away, so I had to stop after a short time. Sphincter area burned upon insertion, and everything (anus, rectal lining) felt uncomfortable the whole time. My butt tightened around the Maximus in a bad way, like it was desperately trying to prevent it from moving.

I have IBS which is mostly under control due to exercise and diet, but sometimes I slip up and eat something that causes a loose stool, which was the case that day. There's definitely some soreness from overuse, but I'm speculating it was aggravated by enzymes (or something, idk) from gut content being rushed down too soon due to IBS. To clarify, I remained clean during the session, but I probably started way too soon after emptying, and didn't douche.

Some things I've learned (that work for me, at least) are not to force a session out of determination; the session has to call for you.
Wait some time after bowel movement before starting. And wait enough days for soreness to pass before attempting again. Nothing good will come out of trying to ignore the pain. And, I actually rushed insertion in the heat of the moment—Big dumb.

I will now wait at least till next week (~5-6 days, whenever it feels right) before attempting again. I also suspect I've been reacting to the glycerin from the water lube. It gave me rashes everywhere it touched my skin. I have extremely sensitive skin and the slightest scratch with my nails will leave red trails exactly where I scratched, like I can draw on myself. I couldn't feel the lube-induced rash, only noticed it in the mirror post-session. Maybe the glycerin has contributed to my rectal soreness?
Anyway, today I visited the only local sex toy shop and bought Pjur Back Door with jojoba, and a Swiss Navy glycerin free water based lube. Tested them both on a patch of skin on my belly. The Pjur silicone does nothing, but the glycerin free Swiss lube created a rash too! I don't know what to use for my silicone plug anymore 🙁

GOOD
In the evening on the day after the failed session, I went to bed with a feeling that I can only describe as prostate horny. Ever since the supposed Super-O, I've had a lovely glowing sensation in the prostate when I think about prostate play. It's like forgetting that you have a penis, and still being horny. Anyway, I went to bed and was frustrated at myself for being so impatient and making the soreness worse.
But then I thought: This Aless thing that people keep talking about... In my mind that was something that only a few very advanced users could do, so I went in with zero expectations.
I lay in a semi-fetal position on my right side and relaxed, which was easy because I expected absolutely nothing.

I managed to find the glowing prostate feeling and applied it to a fantasy. First, some precum and semi-erect. Then lost focus and got flaccid. Each time I managed to focus and the erections returned, they got stronger, until... Around 5 involuntary twitches of the penis and a moan? I usually keep it dead quiet. It all took maybe 5 minutes and I was shocked.
Prostate play really is almost entirely in the mind! At this point, my penis was drooling pre and I lusted so hard for something to press against the prostate, but the soreness would've ruined it, so I kept going toy free. I managed to bring back the short bursts of contractions maybe another 10 times before I got too tired and went to sleep.

I felt like I was at the edge of a cliff, and I would've achieved orgasm if I dared to jump.
But every time I approached the edge, I got so damn excited with rapid heart and nearly hyperventilating that it pulled me right back again. At most I managed to peek over the edge, but never jump.
I'm seriously struggling to keep it calm when the "this is it, it's finally happening"-moment comes.
And then it never actually comes. But it's amazing to know that Aless is (kinda) possible for me to do already! Can't wait for the soreness to truly go away so I can resume using the Maximus.
Finally I want to add that whereas I never even thought about my nipples before, now they are so sensitive that it occasionally feels exciting just to have my shirt rub against them as I walk.

So what do you think? Further advice?

Posted by: @quench

Some things I've learned (that work for me, at least) are not to force a session out of determination; the session has to call for you.

Yes, this is very important, don't let your ego try to dictate this process, rather listen to your prostate's whispers for attention.

Posted by: @quench

Nothing good will come out of trying to ignore the pain.

Pain or soreness of any kind are session killers. It is best to resolve any such issues before attempting an Anerosession.

Posted by: @quench

I also suspect I've been reacting to the glycerin from the water lube. Maybe the glycerin has contributed to my rectal soreness?
I don't know what to use for my silicone plug anymore.

Yes, it sounds like you may be mildly allergic to glycerin. May I suggest you try some natural oil lubes such as coconut oil, olive oil, almond oil or check out the suggestions in the Bestlube... thread.

Posted by: @quench

Prostate play really is almost entirely in the mind!

So true, you might find @rook 's thread Whole Body/Whole Mind - the mental side & @SteelColdiron 's thread Aneros: The Essential Mind State insightful. It might also help you to read @Neros 's post The truth behind how to "rewire".

Good Vibes to You!

Posted by: @quench

I don't know what to use for my silicone plug anymore

I had discomfort when I started with Aneros (Helical's beginnings).  It may have been the lube.  While glycerine-free, perhaps my body didn't like plant cellulose or guar.  In June I tried "Coconu".  I wrote, the lube has hardly a sent and sensually melts.  This pricey oil was set as an offering before the "inner sanctum" in hopes if I treat it right, I will remain in good graces.  It won't react with acetal or silicone Aneros toys- it's petroleum-free.  I'm on my second tube.

Posted by: @quench

I'm seriously struggling to keep it calm when the "this is it, it's finally happening"-moment comes.

Perhaps refer to @zentai 's Overcoming Obstacles to Progress (Fears) .  But you're doing great and  your early more or less proving Aless to yourself is also remarkable.

@quench

For toy play,get the lube that suits your body and wait till the derma issues are patched up. It may be worth looking at astroglide,they have one that’s free of a lot ingredients the regular ones have.

If you need to have a session toy free,do that,largely you do what you do with a toy,you’ve had some a-less success already,seen it,believe it,now you can build it up.

Posted by: @quench

Nothing good will come out of trying to ignore the pain. And, I actually rushed insertion in the heat of the moment—Big dumb.

More like -- big unexperienced, but yes, thinking you'll just get over it and have a nice session, this never works. 

For the lube, @rumel and @helical are right on the money, natural oils formulation are great, coconut oil being a favorite for lots of guys. 

Posted by: @quench

In my mind that was something that only a few very advanced users could do, so I went in with zero expectations.

Posted by: @quench

Prostate play really is almost entirely in the mind!

It's interesting how these reverse psychology things go, you expecting it not to work made it work, because you had no expectations (of it working?). Aren't they the same thing? Our minds are really messing with us a little bit too much sometimes.

Posted by: @quench

I'm seriously struggling to keep it calm when the "this is it, it's finally happening"-moment comes.

That's up to practice, and maybe a little bit of fear of the unknown. You'll tame this feeling as you go a little bit further each time. Or maybe it's just excitement, then it's a question of giving in to it. This may appear to be a bunch of Cheshire Cat answers, but it's not really more complicated than this. 

Had another a-less before sleep and just wow! It feels almost unreal to say this but.. Many minor peaks over the course of 20 minutes, each stronger than the last. I was still feeling panicky when approaching a peak, but each time I got calmer. Had a pee break and shivered violently with excitement the whole time, which is totally new to me. After getting the tension out by flexing every muscle in my body, I went back to bed for more. This time the waves hit harder than ever and for the first time I thought "this is actually orgasm now" but there were hardly any contractions. Nothing super, but definitely orgasm. An hour later of exploring that feeling I went for another pee break but I just couldn't pee. Instead I had an accidental minute long orgasm while sitting on the toilet and it was probably the strongest one of my life. Walking back to the bedroom I had another "accident" while standing on the floor. It just kept coming. It was like trying to ejaculate but it never comes, and so you're just stuck with the feeling. I think I lost 3-4 hours of sleep over this, but totally worth it.
I must have run out of pre, because it got completely dry after a while.

I think I understand what people mean when they say it's waaay different from traditional O, and when they feel like there's always a stronger level beyond what they've experienced.

I just want to thank everyone and the whole community for the advice and everything. It only seems to be snowballing from here.

@quench 

Atta boy!! Easy street! Sack off the toys while you heal. You’ll be grand with your A-Less.

Approaching them peaks,just stay level,and breathe. That’s all you gotta do,you won’t die lol. Orgasm doesn’t cause self destruction of the human body lol. 
Stay chilled and watch them peaks soar to new heights 😉