Sisyphus

I'm in a similar boat, but looking back on the best experiences, a common theme was feeling like the rules that were supposed to be in place weren't applying, and maybe never really did. I think most of these experiences didn't give me much to work with in future sessions, aside from not being surprised/distracted by them.

One exception to this, and what I'll offer as my "tip" (if I can even explain it) is experiencing what I'll call micro-orgasms.
In traditional masturbation, it's all about one long pumping build-up to a single big orgasm. It's predictable enough that someone would model their aneros session on this. But I've discovered this isn't a real limitation, and I've been able to bring this into my sessions with interesting results.

I consider orgasm to have a rising and falling edge, maybe like a sine wave, with one kind of pleasure on the rising side, and a different kind of pleasure on the falling side. The rising side being a tense kind of pleasure, and the falling side being an outpouring of relief and satisfaction. And it's that relief side that I've never allowed myself to experience during a ride, because why would I? After all, I haven't reached orgasm yet, so this part isn't supposed to happen yet. It was that deeply-held expectation that kept relief off the menu. But it's not off the menu. To put a finer point on it, I consider the pumping I do during traditional masturbation to be like slowly climbing the rising edge, there are good feelings along the way, but the relief is for after I go over the top of the roller-coaster, and not before then.

You might have to practice calling upon it, and drawing it forth by imagining that feeling. That feeling of completion, that the job is done, all your muscles can go limp, and a cool relaxing liquid is washing out of them, while your body and mind are bathed in pure satisfaction. You might only get a tiny glimpse of this feeling, but it can become part of the rhythm of your session, occurring every few seconds. Where you have the same pleasure-building energy as before, but it has an extra phase. Like how a physical contraction tenses and releases, this is pleasure doing the same thing. So rather than denying relief until "the big orgasm", you allow a series of smaller orgasms to build and resolve over and over again. This creates a really nice momentum that can build, with the peaks of both getting amplified. And because there is a relief component, the whole thing is enjoyable for its own sake. The experience is that of having many micro-orgasms.

Of course this relies on you having the same mental block that I did, but it took me so unbelievably long to realize I was shaping my sessions this way, that I consider it worth mentioning.

Thankyou so much Clenchy, your response was exactly what i was looking for. I'm definitely going to try and imagine what it feels like and hopefully in time learn to make it real.

I know exactly how it feels like on the other side of the edge. I've been there a thousand times while masturbating, and the endless craving to go back never ever stops. Like you said, a different kind of pleasure, filled with satisfaction and release, and so very delicious. 

The Aneros experience, as amazing and wonderful as it may be with infinite amount of pleasure, is very lopsided. With only one side of the coin showing, and the other side forever out of reach makes it extremely frustrating sometimes.

Posted by: @brailleskin

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I'm definitely going to try and imagine what it feels like and hopefully in time learn to make it real.

Hope it helps. I'm not sure how I got there initially, I think it was during a session with THC (I don't smoke weed anymore, and do this in sober sessions) when I first found that the "relief phase" was already there waiting in the wings, and I just had to allow my body to feel it, and in a way to "become" it, to stop waiting for it. Not to be thrown into it by an overpowering orgasm, but to walk into it by choice. Imagine it, allow your body to recall it, how your arms and legs and chest feel, act like it's real, act like it's already happening and there's nothing left to wait for. You're not trying to create it, it's already happening, and it's just a tiny mental-shift away from you becoming it. It's already a natural counterpart of the rising edge pleasure. It can be a very small feeling, even only a gesture in that direction, but it feels right and complementary when it becomes a rhythm. It's especially good to try it in a rhythm or cycle, because you don't spend too long chasing anything. Maybe focus on deep relief for a few seconds when it feels right, then go right back to the other pleasure-building, yearning mindset. Then see if there's a natural pace to it.

It felt quite natural when I was doing it, almost to the point where I wondered if this is just how other people normally feel, but don't notice it, because they're not withholding relief.