Can I LEARN how to achieve anal orgasm ?

Good question. I think it's possible — whilst I haven't experienced it myself, people seem to say that anal sex is better when it's at the right angle.
What they probably mean is it's pressing the prostate. Even though the Aneros is designed to make this easier and hands-free, it's logically possible with dildos if you angle it correctly and within the right amount of insertion

I am planning on buying my first Aneros toy in next couple of days, Helix Syn. Seems like a great all-round starting toy that gets most people to the Big O. I have been using number of big sex toys like dildos throughout the years so I am not a beginner in anal play but never reached hands-free anal orgasm and I wanna give this a try and I am very excited about it.
Now my question is, once I get there with Helix and I reach anal O, is there a way for me to learn how to control my body to achieve hands-free anal orgasm even when penetrated by dildo toy or an actual person ? Or is that something it can be achieved ONLY by this toy? I guess I wanna know if this toy can help me kick start that whole process for the future.

Thank you.

True. Those are my exact same thoughts. I used all kinds of dildos and sizes and I usually get tired or can't really relax and make it to where it would take me to the orgasm. I know it can be done but not sure how. Than I discovered ANEROS which is completely different concept so I figured (and I also think I read someone wrote about this) if I am able to build AWARENESS of where that spot IS and HOW it should feel when hit before build up maybe I can concentrate and make it happen even without ANEROS. Like manyt ANEROS users say it takes them months or years to achieve Big O but née they do every next one is easier until they can do it almost on a demand. That's what I am driving at, wondering if that is possible with any toy or partner once the awareness is kick started.