What is your feeling?

Posted by: @alanross

Do you constantly contract and release?

You can, if you think it helps. But, typically... no, it's not required or even desirable.
But in the early stages, it's about exploration, and discovering what different things feel like.
Don't get too hung-up on what physical technique you're using. Contracting and releasing is a part of it (or can be), but you need to also factor-in what you're feeling in the moment.
Paying attention to subtle feelings and focusing closely on minor sensations, might be something you're not used to doing... but it's what the journey looks like for most people.

How can you tell if your prostate is touched?

That's a very hard question in some ways, because it can be hard to separate sensations in that area, at least I find that to be the case. There have been times where the feeling is very focused and specific, other times where it's more spread out.
And times where there is almost no feedback sensation, even though I'm sure I must be hitting the prostate.
I think I'd describe it as more of a two-way street... you don't simply supply stimulation to your prostate and get a proportional response in exchange. It's much more of a negotiation and a team effort. When the prostate is awake and active, it can respond pleasurably to almost no movement, or just pressure.
Which brings me back to your first question... you have to experiment and learn how your body responds... and learn where your mind needs to be.

Though maybe I haven't really answered your question... for me, I measure prostate contact in terms of pleasure. If "both sides" are doing their job, then there will be pleasure.

Maybe a good way to visualize it, is that while the aneros can reach towards the prostate and cause stimulation, so too can the prostate reach out and hug the aneros and tremble against it. It can be a very different mindset compared to penis masturbation. Rather than "beating your meat" or "choking your chicken", your prostate isn't there to have pleasure forced out of it by physical means. It's way more of a dance than that.

Posted by: @alanross

I've never heard of a prostate orgasm before.

If you Google the term you'll get about 48,900,000 results but what is strange is that most men will never get to experience the exquisite pleasure of this type of orgasm. Welcome to your learning center and I ask you to read through and follow the links in the Introductory Message to New Members.

Posted by: @alanross

I probably spent an hour last night using my device. I never felt it make a difference.

Initial sessions with a prostate massager for newbies are often felt to be uneventful because your prostate is not yet awakened. This awakening takes time to occur so you will need to be patient.

Posted by: @alanross

Do you constantly contract and release?

As @clenchy noted that is one of numerous approaches and a good place to start developing your own technique. Please read through @b-mayfield 's thread B's Keys and B's Best for suggested introductory techniques and information.

Posted by: @alanross

There might have been a cramp where my bladder is. My prostate, however, was never touched by it. How can you tell if your prostate is touched?

What you felt may have been a cramp was more likely an initial indication that your Aneros was in fact contacting your prostate. A more frequently reported signal is a feeling like an urge to urinate which will soon pass as you become more accustomed to the massage action. You've just begun a unique journey of learning and it will behoove you to do the reading I've pointed you towards.

Good Vibes to You!

Posted by: @alanross

Do you constantly contract and release?

No,you do not. Any contractions should be delicate. Holding tension in your pelvic floor is much more important.