Question: When I'm stimulating my partner with my tongue and I go near her clitoris, or what I believe is her clitoris, she says it hurts and tells me to go lower; to her inner labia. This is completely fine with me but it seems as though she doesn't want me to touch her there because of the pain. Part of the problem is that I don't think she knows where her clitoris is; she said she has never masturbated. I'm just wondering what I should do? Should I keep trying? She says it feels good when I'm down there, but I don't think she has reached orgasm with labial stimulation.
Answer: When girls and women do not learn to masturbate, they sometimes do not know what to expect during partnered sex, as far as the type and intensity of sensations. Everything is totally foreign to them, physically and mentally. If her clitoris is extremely sensitive, her brain may not know how to handle these intense sensations. Her brain may have no experience processing these strong nerve impulses. As a result, she may prevent anything that causes these feelings. She may also subconsciously see all sexual sensations as being bad and undesirable, having had no prior experience of them. This is why self-exploration and masturbation are so important to female sexual development.
The clitoris, especially the glans, can be exquisitely sensitive to touch. In addition, the line between pain and pleasure is often very narrow. There are many women who have a clitoris that cannot be directly stimulated, even during masturbation they must stimulate it indirectly. In this situation, there is simply no correct or pleasurable way of doing it. When a woman has a sensitive clitoris, and her partner keeps touching it, it usually just makes her mad, since it is painful, not pleasurable. You probably would not like it if someone kept hitting your thumb with a hammer, the same principle applies here.
I describe how to go about finding the clitoris here. Also look at the information in the Anatomy and Body Image sections.
Ask her for permission to look at and examine her vulva. If she consents, have her undress below the waist, and sit in a chair that reclines or sit up against the headboard of your bed. You will want to have a lubricant available. Also get a handheld mirror so she can watch what you are doing. This way you can explore together. Then very slowly and gently start exploring her vulva. Gently touch her pubic mound and outer labia. Do not poke or jab, use caressing motions. Maintain constant contact with her vulva, as much as possible. Ask her what feels good. Does she like what you are doing? Apply some lubricant and see how that changes the sensations she experiences. If her pubic hair is thick and obscures your view, you may want to ask her if you can trim it. Then part her outer labia and explore the inner structures. Apply more lubricant. Again, ask her what feels good. Avoid her clitoris at first. Gently caress both sides of her inner labia.
When she is comfortable with your touch and the sensations, apply lubricant to the hood of her clitoris, using generous quantities of lubrication. (Have her sit on a towel if you do not want the lubricant to get on the chair or bed.) If at any point she becomes uncomfortable with what you are doing, stop and repeat the exercise again, in a day or two; do not push or pressure her. Using a very light touch, explore her hood and clitoral body. Slide the hood back and forth. Move the hood in circles, and back and forth. Does this feel good to her? Spend some time doing this. Then gently slide her hood up towards her belly button, if you can. If you can see her clitoral glans, apply additional lubricant to it. Do not touch her clitoral glans with your dry finger; use saliva if nothing else.
See if there are ways to touch her clitoris that feels good to her. If really light strokes tickle or are painful try using a little more pressure, massage versus caress. If she experiences pain, simply stop. If this is true, she probably will not be able to tolerate direct clitoral stimulation. If she permits and seems to enjoy or is open to it, repeat the above exercise several times or consider making it a regular part of your sexual activities. Once you get some practice, try stimulating her to orgasm using the information you learn. Do not expect her to have an orgasm, only explore means of giving her pleasure. Try to set aside at least an hour for each session, do not have intercourse, and make her the center of attention. Explore her entire body, not just her vulva. The information given above is also presented in the article about Clitoral Massage
Once you have some idea as to the sensitivity of the different parts of her vulva, attempt oral stimulation again. If at any point prior to developing the above skills, she should specifically ask for oral stimulation of her vulva, do it in whatever manner she requests. As outlined above, slowly work your way towards her clitoris, starting on the outside slowly move in towards her clitoris. Give her mind and body time to become sexually aroused. Orally stimulate her entire body, start at her face working your way down to her feet, and then go back up toward her vulva. Bypass her vulva on the way down.
If manual and/or oral stimulation still causes discomfort, or doesn't result in orgasm, if she desires one, then read about outercourse.
Provide some positive encouragement for her to explore masturbation. If you know she has strong feeling against it then it is best to leave the subject alone. If this is the case, if she learns to enjoy your touch she may naturally be curious about her own. If she is comfortable having you touch her vulva, when doing the examination of her vulva, ask her if she would like to give it a try herself. Buy her a copy of Betty Dodson's book Sex for One: The Joy of Self-Loving or For Yourself: The Fulfillment of Female Sexuality by Lonnie Barbach. Buy her a nice quality vibrator a Hitachi Magic Wand or equivalent, though just about any vibrating device will do. If she is not interested or is resistant then do not pressure or pester her. She needs to want to learn. Sometimes it is just a matter of being given permission to masturbate, since her parents and society probably have not. You can also watch each other masturbate.
Do not be overly concerned about whether she has an orgasm. You must first learn to make her feel good, by giving her pleasure, and by developing her trust. Talk to her about your expectations and concerns, and listen to hers. Buy either of the above books and read it together. Show her this website, and discuss the information given, then explore other websites. Mainly, have fun.