Enemazed, the last person you probably want giving you advise on prostate massage is a female, but I'm going to give you my two cents worth. I think prostate massage is a must for any relationship to really flourish. It's so healthy for men to have this done. I'm also a nurse, and yes I give my husband a prostate massage on a regular basis. It's one of the most blissful, mind blowing sensations a man will ever experience, both physically and emotionally. First order of business for you is to relax. I know you're young and still trying things with your girlfriend, but consider yourself lucky you've been given a chance to have this done to you at such a young age. Since your girlfriend is a nurse, and if she's been trained like myself, she'll know how to perform a gentle digital insertion of the rectum. She'll use lubrication to minimize any discomfort. In med school, we were trained to place the pad of the index finger against the anus for several seconds before inserting into the patient's rectum. She'll likely do this for you, and will enter you only when you're ready. As for positioning, my husband seems to like the left sims position the best. It's also the best position for receiving enemas, as you'll probably want to have her give you one before anal play, for cleanliness. With the left sims position, you'll lie on your left side with the left leg almost straight to slightly flexed, and the right knee flexed forward, parallel with your hip. This will relax your pelvic floor, and will give your girlfriend easy access to your rectum and perineum. Other men prefer laying on their back with legs pulled toward their chest, or just bend over on the hands and knees usually works okay. Either one you use, you'll both want to be comfortable and give her full access to your body. When inserting her finger, the depth she puts it in will depend on your anatomy. Some men get intensely stimulated with just a fingertip inside the anus, while others require a fairly deep insertion to hit the right spot. My husband's "sweet spot" is about two inches in, about the second knuckle of my index and middle finger....I use two fingers. One of the biggest mistakes women make when massaging a man's prostate for the first time is what she does with the prostate when she first finds it. The greatest mistake is to accidentally poke him with the fingertip. That's going to hurt him, because he's sensitive there. The best technique is to use the pad of the finger to gently caress the prostate and start milking in a come hither movement. The pad of the finger is soft, but will feel amazing on all those thousands of nerve endings around the prostate and anal cavity. She needs to cover as much area of the gland as possible to create the most pleasure and get the best health/drainage benefit. As the milking becomes more vigorous, so will the pleasure increase, and there will be clear fluid coming out of your penis. It's prostatic fluid being drained out, and it's healthy for men who are less sexually active to get the gland drained periodically. You may indeed feel the sensation of having to pee at first, but it will pass. Stimulation of your penis will compound the pleasure until you have an intense orgasm. It's common for men to actually cry out in ecstasy, or get in a euphoric state, during a great prostate massage. So you have a lot to look forward to.