Betty Dodson with Carlin Ross

Better Orgasms. Better World.

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While this is all great advice so far, maybe we should also talk a little more about taking some of the pressure off of this poor guy when it comes to satisfying you. Instead of thinking about this as "hey, he didn't satisfy me!" Think about it as something you are doing together. When I'm with a new lover, I often have to take matters into my own hands in order to come. Men don't generally feel bad about that, in fact they love to watch how you do things so they can learn! Also, it doesn't really sound like it was such a bad experience overall to me. Maybe it wasn't a mind blowing, super multiple orgasm fest, but you had fun right? You felt some degree of pleasure? Sex doesn't have to be about achieving an orgasm every time, especially when you are first getting to know someone sexually. I would say to focus less on the goal and more on all the fun you can have getting there. Eventually, the orgasm will come naturally.

Well..most women need clitoral stimulation in order to orgasm...remind him of this.  There are certain positions which work very well to provide stimulation to the clit while penetrating...the coital alignment technique is a good one.

To nicely put it to him, you should say something like, "you know what REALLY gets me off, when you put pressure here", or something along those lines.  Get over the embarrasment of this conversation, and get into it...it will be beneficial to both of you.

I wrote about this topic in my blog today, regarding the importance of making a woman orgasm during sex, as well as the importance of communication.  Check it out:

Making a Woman Orgasm; doing what you have to as man in the sheets

First of all, much of what you say looks very positive and bodes well for the future: you enjoyed the foreplay, and you would like to have more sex with your new man. That suggests to me that although you didn't have an orgasm, it wasn't altogether terrible! And you obviously excite him, for him to be able to do it several times in one night...

Video Witness and eleni223 have both made very good (and highly practical) points. Maybe I can add a male perspective, with some experience of your situation.

You say that his stroking was both a bit painful and a bit pleasant (that latter sounds hopeful). Perhaps the painful aspect, even if not severe, was distracting you from your normal ability to enjoy the sex act and reach orgasm. Most men with long penises are very aware that their size can cause some women discomfort or pain, and will be more than happy to do things differently in order to suit their partners better. But without any feedback from you, he may have been unaware that his strokes were painful. Communication is essential to good sex; telling each other what you like is the simplest and surest way of getting it! Why not tell him, just as you did in your post here, that his erection is longer than you are used to -- and that for you to maximise the enjoyment that you get from it, which clearly you want to do, you both need to take a little time to experiment with different positions and angles and depth of penetration. Ask him to let you be his guide with respect to how deep he should go. You might even turn it into a game, where on entering you he starts by only putting the head of his penis inside, and you can tell him "a little bit more... a little bit more..." until it's just right. Try to have some fun!

You might be surprised by how well he reacts. I'm sure he wants you to love having joyful, painless sex with him, and will take the time and effort to explore what works best for both of you. And as eleni223 said, over time, you may "adjust" to fit -- what at first may have been longer than you were used to, simply becomes what you are used to.

Good luck, and why not keep us informed about how you get on?

dunedin at http://dodsonandross.com/art/celebrating-it-just-it

Seldom did I ever orgasm with a new lover on the first time.  With other lovers, did you orgasm the first time with them?  If you did, what did they do differently?  I ask, to rule out whether his size is the issue, although, it has been my experience that over time, we do "adjust" to fit.

Was there any clit stimulation, either by him or yourself?  Sometimes with a new lover, reaching down and playing with your clit is a bit uncomfortable, not that it should be, but it is.  Focus more on your orgasm, either by positioning yourself for better stimulation or taking control of it yourself.  As far as a larger cock, well, enjoy it, I do miss my 10" lover at times.....

Sometimes it's all about the position with either a smaller or larger guy. I'd say let him recline and you do the riding. That way you are in control of everything; level of penetration, speed, and angle which sometimes makes all the difference. You can even try putting your legs forward and sitting on his thighs rather than kneeling and then moving him in and out with your hips rather than up and down on him. This way he can still be looking at you and touching you. 

I would dispense with the "is it the best you ever had conversation" and instead talk about sexual exploration and positions because you are new to each other and want to find out what works to help you find that perfect fit as a couple to offer the most satisfaction to both of you.