Either way, when you have a successful penetration and insertion into your derriere, that's when you want to allow yourself to have that orgasm you were fighting so hard to keep down. This is going to help your body learn that this is for pleasure and begin remolding its instincts about that part of itself. Then, pull out or continue according to what your own instinct says you can do, and then do whatever feels natural after that. Usually relaxing is a pretty good idea.
This process can be repeated as many times as you wish or need to, to really get the full pleasure and effect of this kind of play. Allowing your SO to watch you do this to yourself should also help him or her to learn how to give it to you.
Again, from this advice I've known some women who have taken a number of times to get this to be a success, while there have been others who have had success right from the start. I even know of one woman who was taking anal fisting within a week of taking my advice, and she was a complete anal virgin prior to my advice.
Once you've done this successfully, you will start becoming much more conscious of your muscles that make up the anus and you should be able to start controlling them rather than just forcing them to cooperate. Again, this control is something that may happen the first time you do this, it may not happen until a later session of exploration.
I've kept to some very simple basics of how to do this. I'd love to hear the experiences of others from either trying this or learning another way.
I by no means consider myself to be any kind of an expert in this area. I'm only writing this from my own experiences and the experiences of others that I've told these things to.
Sorry this was so long. Information like this can't be given in just one or two sentences.
Continuation from later in the same thread...
The biggest key with this pleasure, for the one that's doing the receiving, is that your pleasure and comfort have to be first priority over everything else that comes before during and right after the act. I've stopped sex on the drop of a dime because the woman I was with felt a tinge of discomfort. Then I slowly moved on to pleasuring her another way without "getting my cookies" at all because of my concern for her comfort.
In time this can become just another part of sex play, like with my wife and I, we get into anal sex almost as easily now as changing from missionary to doggy-style. You'll also be able to experiment with the various positions just like with vaginal sex. We enjoy it immensely when my wife is on her back and I'm entering her derriere from an upright position. I love seeing her cunni while I'm doing this, and this position also allows her easy access to masturbate while I'm in her bum. While in this position she's also inserted on of those small remote control eggs into her vagina and used another vibe on her clit. When I thrust into her bottom the egg presses snug against her G-Spot. The combination of the three pleasure points being stimulated all at once has sent her into some room-shaking orgasms.
I can't stress enough how important it is for the one receiving to explore this pleasure with her or himself FIRST! And a number of times afterward just to make sure. You cannot guide someone else through the motions to please you this way if both of you are equally lacking in the knowledge of how your body will receive this pleasure.
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