First remember that this is a journey of exploration so be patient and enjoy the journey. Always make sure that you are calm and relaxed before you begin and that you have at least 30-45 minutes.  I have found that it is good to get used to prostate massage by conducting several solo sessions before you engage in use with a partner.
For your first session take things very slow.  Don’t force it and just get used to the sensation of having this inserted.  I also recommend starting out with one of the smaller massagers to give your body time to adjust.

For hygienic purposes wash the prostate massager with warm, soapy water before and after each usage and make sure that you wash the anal region thoroughly before starting.

Lubricate, lubricate, lubricate! Apply adequate lubricant to the anal canal and to the entire massager.  This is very important especially for removal of the massager when you are done.

Dont’ rush. Slowly insert the massager, positioning the perineum tab (P-tab) to press against the area between the anus and the scrotum.

Experiment with positions that work best for you.  I have heard that many people have had success laying on their right side.  However I enjoy using the massager while sitting in a chair.  I position myself so that the massager hangs over the edge of the chair and I have easy access to tug on it lightly or to pull it out and replace with other massagers.

Relax (mentally and physically).  Allow your body to get used to the massager.  Practice deep breathing and release your tension.

Slowly begin to contract the sphincter muscles. The best way to explain this is to contract the muscles that you use to cut off the stream while urinating.  Increase frequency and intensity of the contractions at regular intervals.  I have also found that to intensify the sensations it helps to contract the anus tightly and then relax it but not fully.  Another technique that sometimes works is to do this while the massager is inserted about 3/4 of the way in.

Massages can either be used while stroking the penis or not.  I have heard that in order to achieve the Super O that you should not touch the penis but my best sessions have involved masturbating while the massager was inserted.

Like I said at the beginning, remember to be patient and enjoy the journey.  You are rewiring your brain and before you know it you will be experiencing mind-blowing orgasms that you never thought were possible.

Don’t be afraid to experiment and find out what works for your body.  I have found it very enjoyable to use several different massagers and butt plugs at increasingly larger sizes during the same session to achieve earth-shattering orgasms.  Right at the moment of climax try pulling or pushing out the massager or plug to take orgasm to another level.