Am I on the right track, guys?

@netvvork Congratulations on your decision to re-introduce Aneros. I am curious which Aneros model(s) you own?

To answer your question about frequency, as long as your mechanics of sessions is good (cleanliness, lube, contractions, etc.) I wouldn't worry about too many sessions in a given time period. So I don't think you need to back-off. (An exception would be if you develop any prostate soreness or other condition). And yes, sometimes a session can be a "dud". But there is no harm in going through the motions. You have described many elements on the pathway to a Super-O! You just have to "stay the course" and not expect too much.

I would suggest to you to learn to separate your ejaculatory orgasms (via intercourse) from prostate orgasms (via Aneros). This may take some time. The Wiki would be helpful to you, IMHO.

Is your wife understanding about your Aneros use? If she is, then you should be able to integrate your Aneros use with her cooperation. If not, you can develop your prostate orgasm potential on your own. Just remember, that Aneros massagers are not primarily masturbation aids although they can lead you to a great "Super-T" (ejaculation with Aneros) solo or with a partner.

Just make some "alone" time for your Aneros sessions and you should continue to make great progress! Good luck!

Sounds like the right kinds of things are happening to you! Those involuntary contractions can lead to prostate, hands-free orgasms. Also, they can lead to the Super-O you probably have read about a lot on this forum. @goldenboy knows his stuff!!

Before I start, what Aneros model do you have?

Yes just stay the course. You didn't say how long each of those sessions were. Whatever the amount of time, try to double it, see what happens. I know the involuntary contractions (or, autofucking) are amazing and are highly erotic and sexy feeling. But, you gotta hold off and keep your hands off your cock and let them keep going. Especially when they happen and then you're "waiting for them to happen again" and get frustrated because you're expecting movement immediately. That's the experience you have from what you do with your cock. When you're stimulating your cock with whatever (hands, toys, pussy, etc.) it's constant, consistent pleasurable feelings. You can probably touch one little spot on your cock and get a mountain of stimulation from it. Your ass doesn't work that way. Just because the toy is in constant contact with your prostate does not mean it's supposed to be as pleasurable as constant contact with your penis is. So, it can take time, but more contractions can and will happen. ESPECIALLY if you get contractions at all, that means your body is willing to let the toy move on its own, so if you give it time, you'll get more contractions.

It sounds like your wife is very cool with you using your Aneros. And, that she's happy to make you explode while having it in you!!! That's great man! But, her blowjob is just going to enhance your traditional orgasm while the toy is in you (the Super-T goldenboy mentions above) and keep you from feeling the hands-free prostate Os you seek. Here's what my wife does to me when she knows what I want while wearing an Aneros:

She'll touch me all over gently but NOT touch my cock at all. She touches my balls, ass, legs, under my knees (OMG), chest, stomach, nipples (OMG x2), etc. Everywhere but my cock. It drives me CRAZY! It feels so good. And all those signals and stimulation goes right to my ass and the contractions I experience are very strong and out of control. Sometimes she'll make me orgasm from just a few strokes in a few seconds. When you've had as many Os as you can stand, let her start working your cock. You'll become a faucet for cum 😉

Another thing she does that's stellar is a traditional Lingam massage. Its just three easy motions, but she has to be stern and not get carried away. Yes, it's stimulation of your penis. But the motions are designed to not really make your cock have an orgasm/ejaculation. So with Aneros in, you'll have orgasms that you can't experience through any other kind of stimulation or action that you currently know of (unless she does Lingam massage on you already, if so, throw that toy in your ass and have fun!!). There's lots of websites that describe Lingam massage.

Those are my suggestions for amplifying your already great sex life, for both you alone and with your partner. Once she's worked some tricks on you and you feel just how amazing the Aneros can be, when you're alone again you'll have new awareness of just what the toy can do to you. That knowledge works wonders for your solo sessions!