New to prostate play... some questions about depth

I often wonder if the massager is hitting the right spot and have a question about depth, when I I insert the massager, the last 1/2 in or so sticks out of my butt, it doesn’t bottom out. Is it supposed to?

NO, and this is explained in my introductory PM to you with some additional hints and tips to get you started here.

The last session I did, I tried inserting it in a squat, and felt a lot more pressure similar to being fingered by a partner, but without holding the toy there, it won’t stay in that deep, which I think I might need it to?

Perhaps and perhaps not, initial sensations from Aneros prostate massage can be very subtle. As you learn to to focus more intently on these sensations they will tend to grow and become more pronounced, eventually leading to orgasm. It is possible the depth is not quite right but more likely you aren't yet attuned to those initial subtle sensations.

I’ve thought about getting the progasm for its extra length. Thoughts?

While the Progasm will offer a little extra insertion depth over the Helix SYN model you will lose a lot of the agility inherent in the Helix model. You might consider the MGX Trident instead because of its design it will actually seat it self about 1/2" deeper into your rectum than the Helix SYN. it will almost match the Progasm depth but you will retain much more agility.
Good Vibes to You !

I've been through a number of different sensations in my, I guess, four month Aneros adventure. Session
to session things change and from my perspective get better.

Bigger is not necessarily better. Progasm is a BIG step up in size. Unless you've had more than a finger
or two up your ass you're probably going to find it uncomfortable.

Read what rumel sent you. Seems to be one of the gurus with lots of experience and wisdom to share. Be
patient and enjoy what comes. I feel like I cheated as I had awesome results within a week of buying my
Helix Trident. May be all those vibrators, dildos, butt plugs, and whatever else I had in my backside over
the years helped.

*

Have been using Aneros two years plus and just recently experienced the pleasure HelixSyn can give. Had the same problem early with Aneros not going in far enough. Once I got past that hurdle through breathing and controlled muscle movement, a new world of pleasure opened up! I now get awesome prostate pleasure along with lots of Os.

@Cptnwhacksparrow . Rumel's advice is sage. And do be patient. As far as the device not 'going in all the way': Since we are all here using and playing with our rectum and anus, I will allow myself to get to the 'nitty gritty' here: if you tend to be constipated, it is possible, but not likely, that you may have some stool that occupies the lower rectum and prevents insertion all the way. I am "against" aggressive preparations (though I know that many users do use enemas, etc) only because i think it irritates the inner lining and could theoretically lead to issues with normal eliminations--enema dependence. But if you tend to have hard stools and have to strain quite a bit, it might be worthwhile trying a stool softener and/or a gentle enema prep before inserting. (I still believe that less is more when it comes to prep). More likely is that you haven't learned how far in the device can go, if you are unfamiliar with the anatomy and the feelings associated with insertion. I would encourage you to have a look at a side view of the anus and rectum to understand the twists and turns that occur down there and which might require firm but gentle manipulation of the device (in a forward/backward direction) as you insert. Often, when you have inserted it "all the way" there is (especially with newbies) a sudden sensation of needing to pee. That is an indication that the device is well seated. Also, when it is, it feels like it is "well seated" and won't come out. And, of course, generous lube is a good idea.
One other maneuver that I have only recently learned (I've only been doing this for 6 years), is to elevate your butt a bit after insertion, draw the device in as high as it will come and move several times from side to side and do a few pelvic tilts. And then, relax and let things happen.
Wishing you good and better experiences in the very near future..It will happen and you'll love it.