TL;DR multiple_o wrote a great post about how to approach a super-o, this post is about how to get the toy into you and enjoy it, because that's step 1 in this crazy thrill ride.
First of all, I've always found that referring to aneros playtime as a journey was kind of corny. I assumed it was some jargon by the aneros marketing team or something, and discounted it…but damn! I couldn't have been more wrong and I couldn't be happier. After a long 10-year "getting to know you" with my ass and prostate, I can finally say that we are no longer in the intro phase and I'm onto some really great things.
From a young age, I've always known that there was more to this whole sex thing than just my cock. I remember getting hard-ons and never knowing what to do with them. Hard as steel accompanied by a faint "ache" from within my crotch. Sometimes it was a subtle ache but other times I could literally feel my pulse within my groin. I obviously didn't know it at the time, but I've been having A-less contractions since high school and it's taken me 10 years to fully understand It.
So why did it take so long for me to finally get a super-o if I started with a leg up? Maybe hearing my issues from the past will help those struggling in the present, and no one else will have to wade through 10 years of frustration.
My first problem was the cliche "anal is gay, what does that say about me?" Confounded with the fact that I am indeed bi and couldn't own it internally. It's crazy because it wasn't about being viewed as gay that bothered me, but being viewed as a bottom irritated the hell out of me. That was the true roadblock. I consider myself to be very masculine and proud of these characteristics. I look very clean cut and white collar and give off a complete "vanilla" vibe, and I like it this way, but from a very young age I convinced myself that "the type of person I am doesn't do butt stuff" which led to more harm than anything else.
How did I knock it off? By learning to enjoy myself, which is the next part.
I assumed that the prostate worked like a doorbell and all you have to do is press the button to get results. And boy, I couldn't have been more wrong. For the first couple of years, my protocol was to jam my finger up there and press up. Obviously this system will get you nowhere and is kind of laughable knowing what I know now. This does not work for me, and maybe it doesn't work for you. So what changed?
Well, I gave up like I typically did, putting the project on hold, but around 26 (currently 28) something clicked. I was with this girl who was very sexual and very directive who enjoyed anal. She would let me rub and finger her ass while fucking (typically doggy) and she taught me how to tease her hole, how to entice it, how to make her ass want more. As hot and amazing this period of my sex life was, I walked away learning a whole lot more about my ass than anything else: my ass needs to be teased, touched, played with and coerced before anything goes into it. It's kind of like driving a car in the sense that you need to go through first gear to get to second. If you wanna go 60 you gotta go through the motions.
Because I was still very shy about my anal play, I never shared this with her, and started playing during my own time. I bought some toys initially (the aneros being one of the first) but my cluelessness clumsiness always led me back to my fingers. And this is what I learned about my anal geography from said method:
In my opinion, the ass has three landmarks before the prostate which all feel amazing to touch in their own way. Playing with these spots further relaxes your hole AND gets your body sexually excited in a very different way than you get by stroking your dick. You will be surprised.
The first is the taint and outside of the hole. This is the starting point of your journey and is the most accessible without fears of cleanliness. The base of your cock runs through your taint and slightly protrudes out. Stroking the sides of your taint feels awesome, as does the skin that circles your hole (the area right before it turns pink) Playing gently with this area typically leads to your hole relaxing enough for the second landmark.
The rim of your hole can feel amazing to rub and gently finger (spit or lube is highly recommended). By fingering I'm talking about the tip of your finger, like as deep as your finger nail, and using the fleshy pad of your fingers to dip into your hole and wiggle around gently. Yes being gentle is key, because the minute you go to rough your ass will clamp shut. Depending on your ass' temperament, that could be the end of that session.
As this goes on your hole will naturally start "sucking" your finger in deeper until you reach the 3rd spot: end of hole and entrance to anal cavity. This is my favorite spot and is about 1 knuckle deep. I find it to be the most sensitive of the three and you are basically golden if you made it this far. If you break through this wall comfortably you can easily proceed deeper to the prostate and you can probably get the aneros in you and actually enjoy the process.
So I started doing this for fun without realizing that I was essentially practicing for my aneros journey. Fast forward to me returning to my aneros. I was getting a lot of fun out of shallow anal play but wanted my prostate to get a real anal orgasm. I also started smoking weed which helps I hear.
So I reunited with my aneros this past December and used a totally different approach: lots of forplay and no dick touching. When you get aroused blood collects in your cock (duh) but if you arouse yourself via anal play more blood than usual will collect in your prostate and internal organs, causing the good kind of swelling and increasing sensitivity. We like this.
The other thing I did was after putting in my toy, I would proceed by doing nothing. Yes, nothing. No squeezing my ass on the toy. No thrusting. Just laying on my back, legs spread and arched. I would just breath long deep breaths with my eyes closed, and focus on the feeling within my ass. For the next moments in time you are a taking a ride, experiencing the moment rather than controlling the moment. I think it is really important to keep this in mind in order to get results: go into it expecting nothing in particular while being open to everything (aka just go with the flow).
The toy causes pressure up against your g-spot and at first, while you're at your lowest level of arousal, it can be subtle. In my minds eye, I think about this pressure, mentally pinpoint it, and I kind of visualize the toy in me and how it looks poking my prostate. This pressure quickly turns into a low-level pleasure, which slowly (yeah this isn't a quickie type of JO) grows and intensifies.
From this point on I think multiple_o does a great job explaining how to go from insertion to orgasm. He had a great write up that explains this part of the journey better than I ever could. In fact his write up inspired me to write this just because you already have to be advanced in order to get to the starting point of his tutorial. You can't have a super-o if you can't even get it in!Source: http://www.reddit.com/r/aneros/comments/35miwa/its_been_a_long_journey_but_i_finally_see_my/