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Bill, LCSW, Consultant, Expert Witness
Category: Mental Health
Satisfied Customers: 3707
Experience:  35 years treating individuals, couples, families with mental health and substance abuse prob's
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My girlfriend has not been a relationship for 14 years. She

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My girlfriend has not been a relationship for 14 years. She masterbates regularly and achieve orgasm. Hand rubbing on clitoris and legs straight tensed. But she cannot at this moment achieve orgasm any other way. I am wondering if this is a form of conditioning, and the response can be reconditioned. If so perhaps in phases. It would be helpful if I could understand the broad phases that needs to give her greater flexibility in achieving orgasm

Bill :

Hello- Thank you for asking the question. I have over 30 years of experience working with individuals, couples and families & am happy to reply.

Bill :

I am sorry to hear about this problem in your sexual relationship. It is great to know that you have a desire to help your partner enhance her sexual experience so that she is able to enjoy orgasm in other ways besides masturbation.

Bill :

Foreplay is often the road to enhanced sexual experience for women who have issue with achieving orgasm. This involves less focus on the desired outcome of achieving orgasm and more focus on the process of relaxing and using a variety of techniques that will make for a mutually fulfilling sexual outcome.

Bill :

bove all else, emphasize the "play" in foreplay. It's shouldn't be rushed or treated like an obligatory task. In fact, foreplay can begin hours before sex actually occurs, and every minute of it will prepare her for an orgasm. Here are some tips for getting both of you in the mood:

  • Use your head. Remember that for women, mental stimulation is as important as emotional stimulation. A sexy love note, a flirtatious call at work, and other sorts of playful fun can get her thinking about your upcoming liaison. Candles, fresh flowers, and mood music can also create a loving and sensuous atmosphere.

  • Tenderness. Touching can create sexual tension even before you've started making love. Hug her, hold her hand, or touch her thigh. Female orgasm is more likely to happen if, when you're kissing a woman, you let your hands roam to more erotic regions of her body. (Another hint: Yes, the breasts are erogenous zones, but they're not the only one! Try stroking her back or her thighs, or sliding your fingers into her hair.)

  • Kissing. This is essential to good foreplay. Discovering new places to kiss that turn her on is both fun and rewarding. Try the back of her neck or her shoulders for starters.

  • Sweet nothings. Don't forget to talk to her during foreplay. Women tend to be more verbal, and hearing how good she's making you feel can help her feel freer to open up and have fun.

Female Orgasm: The Sweet Spots

There are two places on the body that are critical to female orgasm. You need to learn to stimulate these areas of the female anatomy if you want her to achieve orgasm.

  • The clitoris. This tiny organ contains a high concentration of nerve endings, and you can find it outside and at the top of the vagina. The clitoris is covered by a little bit of skin called the "clitoral hood," which keeps it from being stimulated all the time, so you may have to coax the clitoris out by touching or licking it. Once she's aroused, the hood will draw back and the clitoris will become slightly erect.

  • The "G" spot. This other orgasmic area is located inside the vagina. It's a bundle of nerve endings about two inches up from the pubic bone on the inner, upper wall of the vagina. To find the G-spot, gently slide your finger inside her vagina with your palm facing up, then curling your finger up in a "come hither" motion. Be warned — some women love having their G-spot directly stimulated, while others prefer less pressure on this sensitive area. Explore different techniques and ask your lady which she likes best.

Bill :

Female Orgasm: Sexual Positions That will enhance orgasm

Given what you've just learned, you can pretty much guess that the best sexual positions for female orgasm involve those which provide maximum stimulation to the clitoris or G-spot (or both!). These positions include:

  • Woman on top. This position provides some of the best stimulation of the G-spot, given the angle of the penis. She also can move her body in a way that stimulates her clitoris.

  • Rear entry. This position isn't so great for clitoral stimulation, but provides excellent penetration and stimulation of the G-spot. Either of you can reach under during sex to rub the clitoris.

  • Sitting.Having your lover sit on your lap allows for both deep penetration and good clitoral stimulation. It also provides plenty of intimacy.

    Notice that the so-called missionary position isn't on that list? It's difficult for the guy to stimulate the clitoris when he's on top, unless he really grinds his pelvis into his partner. The angle of penetration also is also all wrong for G-spot stimulation.

    Keep these ideas in mind — and don't be afraid to ask your partner for feedback! Achieving the female orgasm may require some trial and error, but don't forget to have fun while you're trying.

Bill :

Work on these techniques and I think you will find success. IF not, you may have to have some help with a trained Sex Therapist.

Bill :

If you have additional questions for me- feel free to ask- I am happy to help.

Bill :

Kindest regards, Bill

Customer: replied 4 years ago.

Hi Bill, thank you for your reply.


I need something more information.


You see, I am not a younger person and have had very good experiences with previous partners. They all have different ways to achieve orgasms. We work on it and we eventually get it right.


This GF, is probably my greatest challenge of them all.

Let me explain in more detail with reference to your suggestions.

Then, I would like to offer my thoughts, and possible action plan.


But as you know, you have had seen a lot more cases than my life experiences and I really need your best estimate of the situation and also your recommendations.



We had candle light dinner in the a beautiful resort in our room. Wine, cheese, fruit, rasin, nuts, conversation, little cuddles and hugs... Massage her feet, calves and thighs... shoulder and neck


It was just a nice easy romantic loving evening. We enjoyed it in itself. We enjoyed the company and conversation.





Long soft kisses... french kisses... ears, neck , breast...touches, feather touches...


Then she gets excited and hurries. She reaches her clitoris and stimulates it to try to achieve orgasm.


On later occassions... I whispered "slowly"..." wait"..."take deep breathes" ... and removes her hand...

and that restraints her for a little time...then back to impatience...and trying to make herself climax...


So much for trantric techniques... sigh



I have performed oral sex


1) wrote the whole alphabet on her virginal area in caps and lower casing


2) Pulled her hood back and licked her hard... This seems better but not as good as strong finger pressure... but still no orgasm via oral sex


3) Massage her labia - inner and outer


4) Massage her G spot simultaneousy...



Sweet spots:

She says that she can only achieve orgasm via clitoral stimulation and only if her legs were straight out tensed.


That G spot stimulation does nothing for her... I tried with my fingers and her arousal ebbed... I tried a rear position to stimulate her G spot ... and her arousal ebbed.


Asked her to stimulate her clitoris while having intercourse, she says the penetration was good but she cannot feel her clitoris when vaginally stimulated. Moreover, she says she cannot climax with virginal stimulation. Now that is a real challenge!


She straddled me too. Again good but not going to climax.



This is the history:


She is a very attractive and sexy woman of 48. She had not had sexual contact with a man for 14 years. She is not ready, her ex-hubby lives with her and children for the sake of her children... usual reasons...


But she has masturbated every morning to achieve multiple orgasm. To get rid of the sexual tension, have a shower, have breakfast, and go to work. This is a routine and very utilitarian. It is to get up, don't get distracted focus on work.



What I think:


I maybe wrong but I think she has created a pathway for orgasm over the years. It is a habit, it is a response she learnt.


If this is true, then I will have to work with her to achieve different pathways and different responses. I know this will take time... hey 14 years of masturbating in the same manner with the same purpose is a habit and response hard to rewire.


If this is true, I need to have an idea of the process, and the stages.


I have done this on the path to create new pathways:


1) I have requested that she masturbate in different position (of course she is reluctant.... but I will persist)


2) I have done mutual masturbation so that she can feel another hand, and another rhythm. I am glad to report that this is working, she can get multiple orgasm with my hand.



If reconditioning is the key to creating new pathways, how can this be done perhaps more systematically and in stages.



Here is my own issue


I often can only achieve orgasm after the woman achieve hers. It is a conditioning too, I like mutual orgasm and often work towards it. Most of the time in a new relationship, I don't climax until I can make my partner climax.


This situation creates a tension. She too like to have me climax. Hey she loves me as much as I do her... so no surprise here. She feels guilty if I don't, that is why we are doing mutual masturbation when penetrative sex does not get us to climax, or when she gets sore (she can't feel with lube, so it has to be her own bodily fluids and my sliva.)


I hope this gives you a clearer picture. And I hope it helps you formulate something to help me.


Hey, this is a very challenging problem for me. It will teach me more patience than I have ever exercised!!! But I still enjoy her companionship, her wit, her smarts, her sexiness, and her love.


It is only this department that needs greater expansion so to speak..


Thanks Bill for listening.

Hope to get some ideas on making things better.










HB- Thank you for the additional information.

Please allow me to consider what you have sent and I will respond to you later in the day.

Thanks, Bill
Very interesting to read your response:

A couple of issues are apparant that may be causing performance related issues:
1) Your GF is still living with her ex and regardless of the status of the relationship this could me a major stressor impacting your relationship.
2) You did not say if you are married or whether you have been married and if so- the nature of your sexual relationship with an ex wife.
3) If you are only together with your GF on an episodic basis, this can also add considerable performance related anxierty.

I am wondering if (as a couple) you would consider seeing a Sex Therapist?

Bio-Psycho-Social Therapeutic approaches are indicated in situations such as this and if you are open to it---there are Experts in these approcaches in Singapore,

The biopsychosocial approachsystematically considers biologicalpsychological, and social factors and their complex interactions. A biopsychosocial framework is a framework which recognises that biological (e.g. hormone levels), psychological (e.g. self esteem and body image) and sociocultural (e.g. the degree of social acceptance of women playing an active role in sexual encounters) factors all play a role in determining an individual's health, for example in relation to sexual functioning.

Yours is a complex situation and if there is mutal interest- seeing and expert is what I would suggest.

I look forward to your response.

Kindest regards,

Customer: replied 4 years ago.

Hi Bill thank you.


Yes there are stressors in her life.

So there is a lot of rushing and business...

It has probably become her lifestyle, yet I am working to help her slow down and calm down.


My partners are long term, my ex wife for 25 years is probably my best sexual partner. I don't have many sexual partners. I am usually with one person on a long term basis.


Yes, I would like us to see a sex therapist.

However, I am not sure if she will ... at least maybe she isn't ready yet.


Would you recommend one in Singapore?


Meanwhile, patience, slow her down, get her to just enjoy the experience...


Maybe I have to play retrain games... so she cannot finger herself...

Get her to learn to build more sexual tension and learn new responses.


Is this a reasonable approach?


Thanks again


Definitely, slower process is much better- less focus on orgasm.........less focus on outcome and it will take care of itself.

Here are some suggestions and tips to enhance your sex life:

I also recommend the following Book:

Woman's Orgasm: A Guide to Sexual Satisfaction by :

Georgia Kline-Graber R.N. and Benjamin Graber M.D. (Dec 25, 2011)

Product Details



For Sex Therapy Consultation in Singapore - Contact:

I trust these resources will help you and your GF and I wish you the very best.

Kindest regards,


Please Leave Positive Rating So that I receive Credit for My time.

Thank you.

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