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Sex Advice/Oral Sex/helping a guy with his self-image, inexperience with dating


Hi. I am 37 and recently began dating a man who is 42. We have been on a few dates so far and we like each other's company. However, he doesn't have a lot of self-confidence in general and he has not dated very much at all throughout his life. We kiss and cuddle, but I initiate kissing. Whenever I bring up previous relationships or anything having to do with sex, he gets very quiet and uncomfortable. I suspect that he may be a virgin. I have had self-confidence issues too, but have had sex and some relationships. I did have some therapy and it helped a great deal with my condition and my anxiety. Your whole world is different when you have much more self-confidence in yourself. Getting back to my situation: If we get to the point where sex is going to probably take place, and he is a virgin, how can I help him to be more self-confident and realize he is desirable and worthy?? I have some thoughts and ideas, but what are your thoughts on teaching him about sexual technique and skill?  I enjoy sex and have a healthy sex drive.  I want him to feel comfortable with it as well. And enjoy it. How can I encourage him to give me oral sex if he has never given it before?  One more thing: We are both bigger and pretty overweight.  I have not been with a big guy before, and I'm wondering what positions would be both comfortable as well as pleasurable?  Thank you so much for your advice and time!!

Hi Holly,

You are absolutely right, self confidence is a huge factor, especially in sex.  A few unsatisfactory attempts can scare one for life.  Talking about it is the key.  You want to make him feel special to you.  Even though you have had some sexual experience, he does not have to "measure up".  A good way to open up conversations is to have a book like Kama Sutra or Joy of Sex lying around.  Coffee table.  Look at it together and ask him what looks interesting to him.  Make sure you stop on an oral sex page.  Of course do that only when you are ready for sex in the relationship.  On my web site I have the Intimate Couple Store where you can find many books DVDs and accessories to help make sex better.  Those and other books can be found  there.  On my site you will also find a link to a hypnosis down load company with programs for people with self esteem issues and sex and relationship issues.  My site is

Good luck,  

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Tom Blair


Sexual Relationship Coaching. Publish author. I am comfortable answering questions dealing with most areas of sex.


Neural Linguistic Practitioner Hypnotherapist Sexual Relationship Coach Internationally read author. Retired Educator All relationships are based on having certain needs being met. Healthy relationships are ones where there is a mutual meeting of these needs. Respect, honesty, communication are just some of those needs When those needs and others are not being met, the relationship will fall into disrepair. Together we will identify those needs and work to correct the imbalance. It is not too late, love can be rekindled. And it can last a life time.

Neural Linguistic Practitioner Hypnotherapist Sexual Relationship Coach Internationally read author. Retired Educator

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