You will need a few basic items. If at all possible set aside at least an hour in a warm room that’s completely private. Turn off the phone and put your cell phone in another room. Wash you hands and make sure you have smooth clean fingernails.

1. For your genital examination you will want a make-up mirror that stands alone with at least an eight-inch mirror surface. Improvise: A mirror on a closet door.

2. A gooseneck desk lamp is the best or some light source that can be aimed between your legs. Improvise: Light coming through a window.

3. A bottle of massage oil such as almond, coconut, apricot or avocado.

4. A towel to sit on.

GENITAL EXAM: To learn about the form and function of your vulva, it’s essential to start off with a genital exam. Get a soft towel and put it on the floor or a bed with some kind of back support. Place the mirror so you have a view of your entire genital area. Aim a bright light between your legs. Oil your hands. Now spend a few minutes doing a genital massage while observing your vulva in the mirror. Enjoy the pleasurable feelings as you press, kneed and move your hands over the entire area.

1. Spread your outer lips apart to explore your vulva’s intricate internal design with its delicate folds.

2. Locate your clitoris at the top of your vulva just below where the pubic hair begins.

3. Identify the shaft and hood of the clitoris. Pull the hood back so you can see your clitoral glans.

4. With a well-oiled finger, touch the tip of your clitoral glans.

5. Next using different kinds of pressure from light to firm above, or on either side of the clitoris.

6. Spread your inner lips apart with both hands. See if you can locate your urethra, a tiny opening nestled somewhere below the clitoris and above the vaginal opening.

7. Locate your vaginal opening. It will appear as small folds that will part when you enter with your finger.

8. The hymen is a membrane that partially covers the vaginal opening. When we reach puberty, most hymens naturally open and separate so your vagina can be penetrated. If this membrane is unusually tough it might have to be surgically opened, but this is very rare. Many women like Carlin and myself never saw our hymens.

VAGINAL SELF PENETRATION: Make sure you have covered the area with plenty of oil. After spending several minutes doing clitoral stimulation, take a deep breath and as you exhale, press into your vaginal opening slowly using you finger pad not the tip. Stop if you feel any discomfort. Now take another breath and repeat. Each time go back to clitoral stimulation and focus on releasing your vaginal and anal muscles.

THE PELVIC FLOOR MUSCLE (or PC muscle): You’ve heard of women practicing their Kegel exercises. They are talking about the PC muscle that is like a sling that goes across the floor of your pelvis. It connects in front to the pubic bone and circles the anus. When a woman squeezes this muscle, she can feel it in her clitoris, vagina and anus. To locate this muscle simply stop the flow of urine several times and you’ll feel it.

Once you are comfortable having your finger inside your vagina, you will also feel the muscle when you tighten it. When I say squeeze, I mean lift the muscle up instead of bearing down as in straining during a bowel movement (which is not a good idea either). Getting in touch with this muscle will help you to relax the vaginal opening. By repeating squeeze/release repetitions for ten counts up to fifty and then resting, you can strengthen the muscle if it’s weak. If it’s chronically tense, then simply squating like women washing clothes on a river bank. Repeat while practicing finger penetration.

USING A DILDO: Once finger penetration feels comfortable, try using two fingers. Medical professionals use dilators. However, dilators or a good silicone dildo can be costly and easily replaced by an organic veggie like a zucchini or carrot. Using a vegetable peeler, simply peel off the outer layer and leave some skin at the bottom for a handle. You can adjust the size as you progress.

I always recommend clitoral stimulation to build sexual interest before any vaginal penetration takes place if you want penetration to feel good. Besides paying attention to what you are feeling, also focus your mind on some erotic image or idea to help the process along.

Happy Penetration!

The best resource for more on this subject is Scarletteen:
“Let’s Get Metaphysical: The Etiquette of Entry.”