From the Guide to Prostate Sex, at:
http://ambigendered.blogspot.com/2013/10/stimulating-prostate-to-orgasm-i.html
In two previous posts, I talked about what prostate orgasms are and described my own long journey of discovering how to have them. In the next few posts, I'll describe different ways of stimulating the prostate so as to cause them.
Before we start, however, let me emphasize that one should not expect too much too soon. For many men,* and especially straight men, the sorts of sensations you will be experiencing when you start to stimulate your prostate will be unusual, and it will take time to learn what feels best to you, and what kinds of stimulation are most effective. If you're not used to being penetrated anally, just adjusting to that sensation can take a while. So be patient with yourself. There are a lot of enjoyable feelings to be had here, even short of prostate orgasms.
Second, if you are going to play with your butt, then you are eventually going to run into a bit of poop. Usually, it will be just a tiny bit, and it isn't that big a deal, but it's not the most pleasant aspect of anal sex. Still, if the very idea of running into a bit of poop freaks you out, then butt play is probably not for you. It will be difficult to relax and focus on what you are feeling.
I tend to confine my anal play to the afternoons or evenings, as my rectum tends to be cleaner then, and to avoid anal play on days when things aren't quite right down there. Very often, though not always, I'll clean myself out before I get to playing. It feels good, and it makes it easier for things to move around inside you if there's nothing blocking their way. Many people already have an appropriate device for this purpose. A lot of hot water bottles double as enema delivery systems. Most drugstores carry these if you don't have one, and there are several simpler devices available as well, often advertised as anal douches.
You will want to use plenty of lube, since the anus and rectum are not naturally lubricated in any way. How much you need will depend upon what sort of play you are engaged in. If it involves in-and-out, thrusting motions, then you need more than if it involves just putting something inside yourself and leaving it there. Either way, however, you want to lubricate yourself inside and outside. For the inside part, I have found that a small syringe works perfectly. (Without a needle, of course!) You can fill it with lube, and then squirt it inside yourself. But whatever you use (and do make sure that it is appropriate to any toy you may be using, e.g., don't use silicone lube with silicone toys), double check that it does not have any sharp edges. Ouch! And not in a good way, either.
You can't wish yourself into having orgasms, so when it's time to play and experiment, try to get yourself into a nice, relaxed, comfortable mood. Have a shower first, or a warm bath. You can massage your anus a bit, to start enjoying those sensations, while you get nice and clean. It'll make your skin extra-sensitive, as well. And when you do start playing, try not to go right for the prize. That will only frustrate you. You have to learn a new way of having an orgasm, and that means you have to unlearn a lot of what you think you know about your body.
Most men's sexuality is very centered on their penis. If you want to learn to have prostate orgasms, then one of the most important things you need to do is decouple your sexuality from your penis. You have to learn to let sensations from other parts of your body be the ones that drive you to orgasmic bliss. So stimulate your nipples. Stroke your stomach and the inside of your thighs. Massage the cheeks of your ass. Massage your anus. Delight in all of these sensations, just for what they are, and not for anything they might bring.
If you're used to watching porn while you masturbate, give that a rest. Watch porn beforehand, if you like, or read some erotica, or whatever. Once you start playing, you will need to give your full attention to the sensations you will be experiencing. Your body is a wondrous thing. You are learning something wonderfully new about it. Honor that.
You are probably used to having an erection when you are aroused. But you may not get one from prostate stimulation. Or you may have one before you start and then lose it once you do. It does not matter. Your penis is not part of this experience. Until you understand this, you will not be able to have prostate orgasms.
You are probably used to doing something to cum. You are probably accustomed, as you near orgasm, to moving faster, pushing harder. Give that a rest, too. If you try to do something here, you will fail. You have to relax and just let it happen. As your arousal grows, focus on the feelings emanating from deep inside your body. Ignore your penis. Instead, focus on your breath, as if you are meditating. This can be a great way to focus your mind on what is happening inside you. It is inside you where the action will be, which is very different from how most men (especially most straight men) are used to experiencing sexual pleasure. But remember to breathe, even if you do not do it mindfully.
And remember: All of our bodies are different. I can tell you what has worked for me. But your body is not my body. Your intimate anatomy is different from mine. Your prostate has a different shape. It lies at a different place inside you. It is more or less sensitive than mine. It will take time for you to learn how to have prostate orgasms. Or maybe your body doesn't work that way at all. Maybe your body orgasms in ways mine does not. It's all good. Everything is normal.
Manual Stimulation
The obvious way to start exploring your prostate is by inserting a finger or two into your anus. And, indeed, this is not a bad way to begin. There are all kinds of wonderful feelings to be had from this kind of play. The anus is full of nerve endings, especially right inside the anal ring, and penetrating yourself with your fingers is a good way to get used to how it feels to have something inside your ass.
You can also get an initial sense this way of where your prostate is, and what it feels like when it is stimulated. You'll find it on the front wall of the rectum. It feels much harder than the surrounding tissue, kind of like a walnut.
Once you've located your prostate, then what you want to do, basically, is massage it. Use a firm but gentle pressure, and experiment with up and down movements, side to side movements, circles, or maybe just tapping it. Don't be shy! It's sensitive, and delicate, but you are not likely to hurt it with your fingers. So do whatever comes to mind, but always start out slow, and stop if it hurts.
When you first start doing this, it will feel strange, and it may take some time before you figure out what feels best to you. Experiment, and keep an open mind. You may feel like you need to pee. This is normal. You probably don't need to pee, but your prostate is very near your bladder, and your urethra passes through your prostate. You are probably just confusing this new sensation with one familiar to you. But have a good pee before you start, if that will make you more comfortable.
If you have a partner with whom to engage in this kind of play, you may find manual stimulation to be quite effective. Honestly, though, I do not find this to be a very good way to achieve prostate orgasms on my own. I tend to treat it more as a very pleasurable sort of foreplay. (Did you know you can have foreplay while masturbating?) My fingers are not long enough to reach more than the very front of my prostate. Even getting my fingers far enough into my ass to stimulate the front portion of my prostate is somewhat uncomfortable. I usually try to roll my hips forward to make access easier, but I find that my wrist gets very sore very quickly. The most comfortable position is on my side, and I reach around behind myself and put my thumb into my ass. This allows me to stimulate the anterior part of my prostate quite firmly and effectively, but it is very much limited to that part of the prostate. I've only been able to orgasm from that kind of stimulation a few times, and usually only when I'd already have several other prostate orgasms.
Still, as I said, this kind of play can be very pleasurable, whether it leads to orgasm or not. Try using a latex or nitrile glove. I find that very sexy, and it is much smoother than a bare hand. It makes clean up easy, too.
So, manual stimulation isn't that effective for me. In the next post, then,, I'll talk about some other ways to stimulate the prostate that work better.
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* When I speak of "men" and "women" here, I generally mean anatomical males and females. This use of the terms is not meant to offend men and women whose bodies do not match the usual gender expectations. As I'll explain in other posts, I'm a gender-queer myself.