New user-gctid145555

I think expectations play a large role. It could be that during your first time you were unsure what you might feel, and so opened yourself to feel whatever might come along. Then in the subsequent sessions, you wanted to repeat the same feelings, so you might have been trying to steer the ship a little too much. Just a guess. It's a real mind-fuck sometimes.

After reading up, I tempered my expectations on how well my first time would go.

Excellent! However, @Clenchy is quite correct in his assessment and that's one of the points I make in the introductory PM I sent you (check your Messages folder).

I used a progasm ice, and within 60 seconds of insertion, I started feeling like I was going to orgasm, it was amazing! If an orgasm is a 10, I was riding a solid 9 for about 20 minutes, I was amazed! I am not sure if I achieved a 'prostrate orgasm' or not, but I had to be close!

Congratulations, it sounds like you may very well have had a prostate orgasm. You need to understand that prostate based orgasms are qualitatively different from penile induced ejaculatory orgasms, please see the thread What's an Orgasm? for a little more info.

I was super excited, and figured I just had a VERY cooperative prostate, which was great.

You've also identified a very important aspect of successful Anerosessions, namely starting your session highly aroused (see the thread Are you "aroused"?).

Can this be common that the first time is amazing, but then you struggle after that?

Your first experience was NOT the typical experience reported but it is not extremely rare either. Aneros guru @B Mayfield had a Super-O on his first ride but then labored for nearly a year before he had another one. Aneros guru @darwin practiced for nearly three years before he had his first Super-O, so you can see there can be a wide time range for each man's experience to manifest.

Another question, is there such a thing where your prostate is more cooperative if you haven't massaged it in a while?

I suppose you could term it like. Your body's receptivity to induced sensual/sexual arousal is influenced by many factors and time elapsed from the last massage is certainly one of those factors.

In case it matters, I took two nights off, and I plan on trying again tonight. Hopefully I can catch that dragon again!

Beware of the trap you may have just set for yourself, namely chasing after the orgasm. It is probably better to think in terms of allowing the orgasm to "catch" you! The Super-O is a stealthy beast, always stalking you during an Anerosession but if you are constantly looking for it, it will stay at bay. It loves to pounce when you least expect it!

It's a real mind-fuck sometimes.

Yup!
Good Vibes to You !