Dinah answers: I understand the frustration of not being able to reach orgasm in some form with a partner. I would suggest that you experiment with other forms of stimulation, but that you do so alone at first to reduce the pressure; if and when you are able to experience other orgasms, you can then try introduce them into your couple’s sex. Even if you do not manage to reach orgasm with a partner during penetration (which most women do not), being able to orgasm from oral sex or mutual masturbation, or by masturbating for your partner, you’ll have brought a whole new world of experiences into your sex life. The main idea is to use a great deal of stimulation while positioning yourself differently, so that you break that age-old pattern with pillows. You could try stimulating your clitoris with a vibrator while lying on your stomach, and then try sometimes on your side and back. You can elicit fantasy, perhaps have a pillow in that fantasy, or whatever other material gets you really excited. Childhood masturbation techniques that have become entrenched are not uncommon, and they are difficult to overcome but not impossible.

Dinah answers: I don’t understand how you can get fed up with pleasure. Clitoral, or externally-stimulated orgasms are the only way that most women have orgasms. Sure, penetration is a pleasure of its own, but for most women, and you seem to be one of them, vaginal stimulation cannot provide the same intense feeling as direct clitoral stimulation. This will not necessarily change once you start having sex. If you would like to feel something different perhaps you could try a clitoral vibrator, which will provide a new kind of sensation. You can also try inserting a thin dildo while masturbating clitorally, and you may feel some subtle internal throbbing when you reach orgasm. By the way, there is no issue of underage for masturbation. Its legal and unstoppable everywhere!

Dinah answers: Sometimes during surgery in the pelvic floor area, the surgeon cuts nerve endings and this can effect your sensation. The second surgery would have tightened your vagina, which might add more sensation for your partner, but does not necessarily improve your feeling, especially if your orgasms were reached clitorally (as opposed to vaginally / from penetration). This doesn’t mean you should give up hope. The loss of sensation may be temporary, as you get used to feeling different things in your vaginal area. If the sensation does not slowly improve, you can try stimulating the area with a strong vibrator, both internally and externally. If you cannot feel a difference after a few sessions, try consulting with a Pelvic Floor Physiotherapist, who will be able to identify the problem and provide specific exercises.

Dinah answers: Maybe you are that good. But before you declare yourself a virtuoso, try doing it again when she hasn’t had alcohol. Try bring her to feel as uninhibited and as sexy when she is sober, and you’ll have learned something about being a good lover.

Obviously, some credit goes to your girlfriend, who not only knows how to let go and experience pleasure without restraint, but also is fortunate enough to have the physical ability to keep going for 2 hours. It is not unusual, a lot of woman can experience such multiple orgasms if they are given enough stimulation, but some women never make the effort to exploit this ability.

Dinah answers: If anything, it is believed that orgasm actually helps with conception. The spasms that result from orgasm probably draw the semen into the inner reproductive organs and the stress relief that it brings can only be helpful. So don’t stop.

Dinah answers: In order to learn to experience orgasm and to discover the individual style of your own orgasm, you should try reach orgasm by masturbation when you are alone and don’t feel pressure to perform. Read more about learning to reach orgasm here.

You can also read more about Female Ejaculation, which may or may not explain the feeling of needing to pee. You need to give yourself the opportunity to feel a proper orgasm to discover if this is at all relevant.

Dinah answers: Meds, such as pain killers might be involved in delaying your partner ejaculation and orgasm, or even preventing it altogether. Vicodin can drop a guy’s blood pressure, which basically reduces his sexual capacity. But meds do not necessarily explain what happened. The very obvious answer is that he was highly stressed on the first night that you were having sex, especially as you say, after such an extensive build-up. It is very common to have performance anxiety under such circumstances, and this is exactly the result, even if he really wants you and is turned on by you. In fact, it is probably BECAUSE he really wants you and is turned on by you. The answer lies in reducing the tension and his cause for embarassment. Sex for the first few times with a new partner is stressful, especially when the meds may or may not be making it a little bit tougher. He and you shouldn’t feel that the initial attempts represent what lies ahead. You need to take your attention away from orgasm, and just enjoy the pleasure ad sensation that these sex acts bring. Let him know that it is irrelevant whether he orgasms or not, and that you can enjoy the sexual behaviour without it. From there, I believe things will work themselves out.

Dinah answers: Not being able to orgasm just from penetration is the case of MOST women, possibly about 70%. So throwing in a hand, yours or your partners, or a toy, is a must if that is what you need.

Before you toss away the baby with the bathwater, consider what feelings you enjoy about intercourse, and consider if they are worthwhile even in the absence of orgasm.

Also consider that sex is a very wide range of activities; intercourse is just one of them. Whichever activities you choose to perform with your partner should be pleasurable, either because they give you sexual satisfaction, they give you the opportunity to share pleasure or they bring you closer.

Dinah answers: At your age a lot of women don’t yet experience orgasm. We don’t know if it is a function of body image, confidence, learning the right skills, or if something changes in your body overtime. In any case, don’t give up trying, because it will be realized; just don’t spend all your time obsessing over it.

Orgasm should be treated as “the cherry on the top”, and not the whole point of having sex. Enjoy the closeness and pleasure you feel, and don’t stop trying as a couple to give you pleasure.

The issue of abuse may or may not be relevant, but because it is vague and at such a young age, you may want to explore it in therapy when the time is right for you. Find a therapist who has expertise in sexual therapy, which a lot do not. In the meantime, keep trying to discover your pleasure levels, both with your boyfriend and alone, where you are under less pressure. Toys are great for creating strong stimulation for the clitoris, and once your body learns to orgasm, you will be able to experience it with greater ease.

Read more about Finding Your Orgasm

Dinah answers: What you may have is a recently discovered disorder known as “Persistent Sexual Arousal Syndrome”. It means that your body is constantly sending blood to the vulva area, something that usually happens when a female is feeling sexually stimulated. So even when your mind is not aroused, your body is. This can be very disturbing and even painful, because even orgasm does not give you complete relief. I suggest you speak with your gynecologist and mention the idea of Persistent Sexual Arousal Syndrome (PSAS). If she or he does not know about it, ask for a referral to someone who does.

Dinah answers: It would be nice if I could throw out a big round number that would just add to the motivation and pleasure. But it is sort of like asking how many vegetables you eat in one meal. Well, that depends on your supply, your taste, your effort, your appetite and whats on offer on the particular occasion.

Calorie burning depends on your weight, fitness and metabolism. Measuring orgasm is complicated even further. If you start counting from the workup to the orgasm, consider it to be at least as active as a brisk walk (4-5 calories a minute). When we reach the all powerful orgasm, the heart rate increases and various muscle groups begin contracting which makes for effective burn-off (probably as good as jogging – 6-10 calories a minute). Of course, the orgasm part can rarely be measured in terms of minutes.

On the exercise level, it would be advisable to be more active and make the sex last as long as possible. But when it comes to the overall value of the sex, you will probably be losing something when you start to regard it as sport. So stop looking at the clock and focus on a sexy body under / over / entangled in you.

Dinah answers: Your guy seems to have a bit of a problem with his sensitivity: either physical or emotional. If this has always been the case, he may have low sensitivity of his penis. There are some creams that can increase sensitivity, but before you try that, let’s see where else the problem could lie. It could be that he feels pressure to come after your orgasm and begins hard thrusting. This would not only leave you sore after a while, it actually reduces his own sensitivity and leaves him shooting himself in the foot (let’s leave the metaphor as is).

If the orgasm problem has developed over time and wasn’t always the case, it seems to be something related to his feelings toward himself or the relationship. This could be a reflection of his feelings of control, or lack thereof. Perhaps he has lots of thoughts and reflections going through his mind while he is at it, and is getting distracted and this is just adding extra pressure, which is feeding into the same cycle and making it harder for him to let go.

The idea here is to try and move him out of his security zone, and take the sex back to a place where it was new and exciting, naughty and unexpected. Surprise him with a new trigger, a naughty place or a sexy toy or piece of underwear. Do something that will reset the limits that have become old habits. When the sex is exciting and novel, you can stave away the background thoughts and reestablish the intimacy.

If he can orgasm by masturbation, include some good-old handwork in the routine. Move in and out between penetration and a hand-job, or work it with whatever you have until he’s close to orgasm and then try entering. But make it interesting, with some fancy timing or new texture. Lubricants generally add sensuality, so shop around for something with a liquid texture and not a jelly one. There are also great lubes with warming capabilities which can add a little punch to your party. If the problem continues, it would be wise to pop over to a sex therapist for a consultation, instead of leaving it to erode your sex lives and your relationship.