making a little headway in my journey

...with that being said i do feel a bit relieved that i am making some sort of headway with this after 5 months or so.
Unfortunatly i will be living with my girlfriend in a week so my sessions will really be slowed down to possibly once a month (just because for me, the aneros is a me time sort of fun). with that being said will i lose any progress i make in my journey if it slows down too much?

It seems to me like you have gotten off to a pretty good start. It also seems a bit incongruous you feel it is unfortunate you are moving in with your girlfriend. I think this would typically be a reason to experience increased happiness to share time with a caring lover, am I wrong in thinking that way? It seems to me this would be an excellent opportunity to increase the level of intimacy between you two by including her in some your sessions and by including your Aneros use while focusing attention on her. In this way your continuing Aneros learning journey becomes a win-win for the both of you. There would be no reason to decrease your Aneros time if your girlfriend is included. Your level of progress can continue, in fact it might actually accelerate with the additional energy of a loving partner.

I invite you to look at the Women Too section of the Aneros WIKI. Expanding the range of intimate play between partners is a good, healthy thing to do. Even better, why not buy your girlfriend an EVI or the new Vivi for simultaneous Anerosessions with mutual caressing, kissing and fondling, PIV sex is wonderful but there are soooo many other ways to make love that you should try to explore them all. I'm pretty sure if Aneros had existed 1700 years ago it would have been referenced in the Kama Sutra.
Good Vibes to You !

Squeezing that muscle is how I learned how to have Aless orgasms. I probably wouldn't have figured it out if not for the postings of someone on the forums (thanks btw!). The suggestion was not to squeeze that muscle hard, but lightly. As light as you possibly can while still know you're doing it. You mentioned you have a hard time keeping it flexed, so maybe you're going at it too strongly and need to dial it down a notch. It's something that took me a while to fully appreciate that to escalate things, more aggression is counter productive. Sometimes it takes a little finesse.

Now, that part that I would have had a difficult time figuring out on my own was that once you start to feel strong sensations while flexing that muscle, back off completely and just relax every muscle in your body. I remember reading that advice with skepticism, but I shit you not it worked on my first ever attempt and blew me away. My body took complete control of the situation and gave me some nice waves followed by a hard prostate orgasm within about a minute. For whatever reason, this method only works for me without the Aneros inserted and only while sitting or lying on my side, so you may have to play around to see what works for you. It may not work at all, or may only work once you're further along with rewiring, but it's worth a shot right?

Moving in with your girlfriend might help your sessions more than you realize. I can have Aless sessions only "sometimes" when I'm by myself, but when I cuddle with my girlfriend I can have them every time. Just being in her proximity sexually charges me in ways I never realized before my prostate woke up. Next time you're spooning with her, do some kegels while thinking about how warm and close she is to you. Then listen to the tingles, flutters, or buzzing going on inside of you and see where they take you. It's kinda funny. A lot of guys complain when their girlfriends only want to cuddle instead of having sex, but I can cum my tits off just holding mine. Once I learn how to do it on long plane rides I'll be all set in life.

I can cum my tits off just holding mine

This is so true (and a great phrase!). I was with a fuck bud of mine yesterday and just cuddling/making out gave me some really intense aless. Plus, it turned him on immensely that he was helping me cum, so that just ramped it up even more.

I agree that there is no better opportunity to explore aneros than with a partner. It might not be the key to finding orgasmic bliss, but it definitely helps. A big part of aneros use is arousal. When you are in bed alone, arousal is harder to ramp up. But with a partner, the simplest thing like caressing or kissing can bring your arousal up very fast, and distractions (mind noise) are few.
.
Thus far my experience with partners and prostate massagers is two sided: A partner's presence makes really letting go to have minutes-long prostate based orgasms more difficult for me. BUT overall I am incredibly aroused and I have tons of dry orgasms, from rubbing my cock against my partners skin, from being caressed all over my body, even sometimes during sex (although I use condoms regularly so sensation is usually too dull for that).
.
The further down this rabbit-hole I go, the less I need toys to get these same effects during partner play. Vive le aless!
.
.
.
The "penis head muscle" is maybe the "levator prostate"?
.
I think @Mumbo is talking about this:
.
https://community.aneros.com/community/general-discussion/how-to-have-a-less-orgasms-almost-instantly-male-vagus-nerve-orgasms
.
And if not, this is the same idea. It works really well if you are sensitive already to the sensation caused by squeezing that "penis head muscle". Just follow the steps, and be relaxed. As usual less is more.
.
If you are getting exhausted, don't worry! I fatigued very quickly down there in the beginning of my journey, and thought I would never get stronger. Now I never notice any fatigue at all, after 9 months of regular use! I don't do kegels either, but I think 3 sessions a week plus aless is enough to get your pelvic bassin ready for the olympic games 🙂

As you go you learn that deft touches are often the best and don’t burn out the machinery. Try going so light your almost willing the muscle to move.
I would advise you knock the super T endings on the head so you can really learn to separate orgasm and ejaculation. There’s no point to it,I have my prostate orgasms and save the ejaculations for the wife. Hell if you have a partner,you shouldn’t jack off at all I say!!
.Tell your girlfriend to jump on the journey bandwagon,she’ll probably love it,my wife did admit to liking the fact that I haven’t done the journey/anal stuff with anyone else lol.