2 years with Aneros

However the contractions, while enjoyable, do not feel what I would describe as pleasureable in the sexual sense. It feels more like I was working out the muscle. Does anyone else have this problem and know how to get them to feel pleasureable?

While an exercise regime at the gym working out your muscles may be enjoyable on one level of consciousness for its health benefits, it may not be pleasurable especially when you think you may be sore as a result of the workout. I am wondering if this is the mindset you are currently experiencing. Pleasure from sensory input is largely a function of mental assignment and the line between pleasure and pain can be pretty thin and that line moves in response to our physical and emotional states. I get the feeling you may not be relaxing enough to surrender to your own body.

I must confess I have had vagina envy for all of my sexual life about this.

This may be a psychological obstacle you have erected for yourself and is worthy of some self reflection to understand the what, where, why and how of that envy.

In the past, my Aneros sessions would ultimately end in ejaculation. However I am able to get at least 3 rounds of the previously described contractions. Last night I did have what I felt was like a non-pleasureable male orgasm. What I mean to say is I did not get the penile pleasure, however I was able to feel the afterglow as if I had ejaculated, yet I was still hard and did not feel drained like in a normal ejaculation. So this may be a bit of a discovery here.

Prostate based orgasms (and Super-O's particularly) are qualitatively different from penile based ejaculatory orgasms, they quite naturally do not feel the same. Not triggering the ejaculatory reflex minimizes the release of prolactin the hormone mainly responsible for the male refractory and the sedative effect. The other two important neurotransmitters, oxytocin and dopamine are less affected, hence the "...afterglow..." may still be experienced.

Lastly, I notice that the sessions have been getting better over time the more often I use the Aneros. I suppose like any skill or body/mind training, this is to be expected. What I would like to ask is there any recommended number of days per week to practice?

There's no specific formula to determine your optimal frquency of use, everybody is different and numerous factors will govern here. I am an advocate of allowing at least one day of rest between sessions. I think this is particularly important for newbies who may be over eager and prone to pushing their progress. I think it allows time for a user to assimilate their learning on a subconscious level and give their prostate adequate recovery time to avoid fatigue or desensitization.
Good Vibes to You !

Thank you Rumel for your reply. It seems that everything about this is more or less opposite of a traditional male orgasm. Instead of working toward it, one allows it to happen. Instead of forcing, I need to surrender. Etc. Nonetheless I look forward to trying the new one when it arrives. One day of rest makes sense, like other muscles we work out. Undoing decades of bad habits won't happen over night.

It sound to me that you have rewired and your body is activating the correct muscle groups you are experiencing 3 limiters:

You muscles strength needs to be developed - that will happen over time and use
You need to relax and focus on whatever sensation your device delivers - it will develop
You need to use more lub inside ans less outside - your muscles are contracting but the friction between the device and your rectum is limiting the device's ability to move. Try to get as much lub up inside. Try not to have too much lube around your anus or around the P tab. Your sphincter muscles need to be able to grip the device shaft and drive it in and out.

@chestinut Thank you for your suggestion about using more lube. I tried this and it seemed to work better.