I actually went through a period where I thought this whole journey wasn't for me, and so I threw away my Aneros... sad days. Turns out all of this type of thing is deeply ingrained in me and a part of me. So I'll probably try the Aneros again at some point.

Did you consider any inner conflicts holding you back from enjoyment? “This whole journey wasn’t for me” sounds a bit like that and made me ask this question. You must not feel urged to answer this question here, but please think about it and take account of the following. Your subconsciousness is a mighty opponent meant in a good way, because it’s your protector, but thus it can become a severe obstacle. If you can’t convince your subconsciousness that you really want that prostate fun and that it will do yourself no harm, no matter if physically or perhaps concerning your mental health including your self-acceptance in your social environment, it will remain its watchdog behaviour and try to hinder you from further success with similar sublime techniques like your weaker self hinders you from doing more sports or from eating healthier food. 

I speak from experience, because my first encounters with my Aneros tool have been so overwhelming that I was frightened I could hurt myself or collapse or become insane. Only soothing my subconsciousness by telling it again and again “I will do myself no harm” helped me to finally let go and let my second brain - how I now name my gland - take over and give me all the joy that makes my days. 

Only my 2 cts here, never mind, only an idea that may be deliberated or not. 

Cheers, Mart

Are you on the prostate journey as well? I had much pleasure from my nipples and chest and neck for years, but it wasn’t until I discovered prostate orgasms that I understood the mechanisms that allowed me to have nipple orgasms. 

if you are on a prostate journey I have good advice. If you aren’t, my advice is to embark on your prostate journey. I still have other advice, but I think it is easier to rewire your nipples after or along with your prostate.

if people don’t give good answers as to what it feels like or their techniques it is because these orgasms are very personal and mysterious, just like prostate orgasms.

It would be helpful if someone who has made that journey could share it even just as encouragement.

When I stimulate my nipples, the first 5-10 minutes are very pleasurful, but that wanes after not reaching some sort of climax, but I do continue in hopes of having some sort of epiphany. I'm guessing if it happens once, it would shed light on how to get into that state. My wife will stimulate my nipples as sort of a foreplay before sex, and that gives me a very hard erection and a lot of precum, and a lot of pleasure, but haven't achieved a climax (with or without intent) without penile stimulation. Also feels great when she does it during sex.

The reoccurring theme from those that have demonstrated or claimed to have done it seems to be light touches and to just focus on and "enjoy the sensations." I do try to throw analysis out the door and do that, but I've still never gotten past a state of being highly aroused and some jerky contractions in the genital area that are slightly pleasureful, but brings on the component of frustration of them going on and on without a feeling of release. I'm not sure of those contractions are what people are describing as a "dry orgasm," or if that's a precursor to an orgasm, or I'm just different and they don't experience that.

The people that are able to do this do not seem to answer if semen retention and some abstaining for days is one of their keys. Also, there doesn't seem to be a kegeling theme as to what they are doing or at least they don't mention it. I'm not sure if doing so is a hindrance, or if you should go more into it in a completely muscular relaxed state. I haven't found someone who has tried and tried, and suddenly figured something out that got them over the top. Arousal I'm sure plays a major role, but I'm not sure if erotica, fantasy or if there's any other mental fuel going on from start to finish for those that can bring themselves to an orgasm and ejaculate.

Wuerstchen https://xhamster.com/users/wuerstchen seems to be the biggest nipple orgasm ambassador out there, and he has his own guide to try to help others figure out how to climax this way. I haven't found anyone that has reported using that guide and developing the ability to orgasm from it. He seems to have figured it out through serendipity and a lot of his writings are hard to completely relate to if you haven't experienced whatever it is that he is experiencing. He has a lot of videos demonstating his ability. He often talks about a connection to his prostate, and penis, but I'm not sure in what combination and what "sensations" that are contributing to his orgasm. He talks about a sensation he feels in his prostate when he touches his nipples, and often refers to it as a "throb", though that may not may not actually be a physical thing as in the prostate. He also rests his penis on leg, and somehow that frenulum to leg contact makes a contribution to the buildup of his handsfree nipple orgasm, although when asked, he plays that down that it's very minor. It is mentioned in his guide. He doesn't seem to be able to do it without that requirement though, and frequently readjusts the position of the penis as he leads up to orgasm, so I'm not sure what sensation he is following there. He also has a constant jerking / twitching in his body, and it appears that there is tension on his scrotum, so I'm not sure if that plays any role. He doesn't seem to think so when I've asked him. "Breast projection" and feeling the size of his breast seems to be arousing to him somehow. I'm not sure how to relate to that one. You will see various kegel like contractions during his sessions, but he hasn't seemed to voice that those are intentional or contribute to him reaching orgasm. He also talks about it being some sort of emotional thing, and I also have a hard time relating to what he's talking about with that. His description of what happens phyically during a nipple orgasm is that there is some persistent sensation that occurs in the nipples, his body tenses up, induces heavy breathing, and there may or may not be an ejaculation. It seems a mystery to him why there is ejaculation or not, but I have also seen him insinuate that it is something he can control. He does mention that he has gynecomastia which is an increased amount of breast tissue due to an imbalance of hormones. So there may be a small anatomical difference to those who can "easily" achieve an orgasm from nipple stimulation.

Another one I've found is zeitihrbereit https://www.pornhub.com/model/zeitihrbereit. I reached out to him to see if he had any guide or tips on how he does it. His reply, "Hi! Thank you! Sorry, I can't give you any tips. I did not read any guide or something, I just realized, that I like very much, if I touch my nipples. It gives me erection right away, my penis is pulsating. It's like some connection between my cock and my nipples. And it gives me orgasm that I never felt before. maybe try it again, and again."

One more that was incredible to watch was https://www.pornhub.com/users/eastworld2 although since he was not verified, Pornhub took his videos away as they did with all unverfied accounts. He ejaculated a gigantic amount of semen when he did through nipple stimulation. I do remember on one of his videos his response to when someone asked was just something like, "just enjoy every sensation."

From the female side, https://www.pornhub.com/model/clitsation is notable. Watching https://www.modelhub.com/video/ph5d594971445a5 does look like an orgasm. In the comments when asked how she does it, she says, "That can't be taught luv"

There is also the Aneros wiki which has a section on nipple stimulation http://wiki.malegspot.com/index.php?title=Advanced_Skills#Nipple_and_breast_stimulation That appears to be written by Darwin, not sure if that's just tips collected from nipple stimulation posts or if he can have a full orgasm and ejaculate from nipple stimulation.

If there's anyone out there that has the ability to orgasm from nipple stimulation, I would love to hear if any descriptions, mental approach, and techniques you might be able to provide. I always feel like I'm close to possibly doing it, which I see as a reoccurring theme in a lot of places where I've found people talking about it. It seems the people that can do it are very far and few, and even farther and fewer is people who can describe it.

Yea, I guess if you don't use it you lose it as they say. I have a helix trident now and some of the feelings have come back but its been tough getting to where I was. Before, I mostly used the mgx trident and that one seems to have worked the best for me.

I've definitely used those nipple techniques before, but I think my problem is not being relaxed enough i.e. over-thinking. Nipple stuff really gets me deeper while using the aneros, though.

      I know how you feel. I’ve been using Aneros products since the beginning. I’ll occasionally take a break, and when I resume using them I notice I’m not as wired as I was before I stopped. But after a few (or several) sessions, I notice the feelings come back, usually better than before. As for my nipples, I really work on general relaxing before I start, usually with meditation, soft  music and/or a good cup of Sleepytime tea ( at night ).  My nipple technique always starts the same way.  I start by  going VERY SLOWLY around the areolea of one or both breasts without touching the nipple. I feel them getting harder and more sensitive. After a minute or three I really get turned on and want more. I pinch the nipple between my thumb and one finger, which feels awesome!! Then I roll my nipple firmly between, then I pull it upwards away from my body. These 3 motions of various amounts of pressure and movements can take me to amazing heights to the point of many orgasms. Let me know or if you want any more tips. FYI, you don’t need the aneros inside you to have nipple orgasms. Butt they feel incredible together.

Thanks. It's encouraging to know I'm not the only one to have struggled with "dead nipple" syndrome. I try to branch out and and use the nipples more sparingly.

Kegels too, if I can remember to do them.

I'll do my best to try other parts than the nipples. I have to be patient I know. I know the nipples aren't all there is, it's just their the most accessible. I don't have a partner, so I'm alone in the caressing department.

That's funny you were the guy that gave the gain analogy. That's a good one.

There's so many paradoxes, faults, and hidden gems in sexual dynamics, it's good to consider how it works so one could liberate them self, in a sense.