Crystal,
Wow! Thank you so much for the response. When I was writing I was half embarrassed, and half nervous for never really sending off such a plea for advice before concerning sex. I had a suspicion that what I sent was too short and not enough detail to actually get my situation down right. So, as you requested so eloquently, here is more information.
Before this woman I have never been with a girl who A. enjoys giving as much as she does receiving and B. wanted me to cum in her mouth. As I stated in my first e-mail, our sexual chemistry is out of this world as well as our openness to each other about what we like, dislike, pushes our buttons, gets us off and so forth. It is for all tense and purposes all there… except for my problem.
I do think at times it is a mental block of some sort because as you pointed out most of the previous woman I have been with, (ex-wife, past girlfriends) never was interested in fellatio. Sure, I would at times get the occasional token blow job, but that was about it. I also think it is a mental situation where like you said, I know she wants me to release in her mouth and so the pressure is on and that is what I think about even though I try not to. I don’t ever recall her voicing a statement that it is taking too long during the act. Sure we have discussed it just like we discuss many aspects of our sex but it has always been more of a productive conversation between the both of us discussing what we liked about so and so, or what didn’t work, or what we could change with something that didn’t seem to work that time.
This is what I or should I say we, because we have discussed this together, don’t understand. She was able to do it once but we have never been able to reproduce the same results. Let me emphasize so you can clearly understand. There are several occasions where it actually feels like I am blowing my load. When I stated previously that my eyes felt like they were rolling back into my skull that was how awesome it felt. Yet when she stops, me feeling like I had released she would inform me that I didn’t and I am left for a brief moment dumbfounded. She says there are such things as dry ejaculations, but she doesn’t think that is it for the simple fact that she knows when I actually ejaculate by my physical change both in twitching/pulsating of my penis and my breath or shortness of it.
As far as insecurity wise of my penis possibly being the problem, I would have to say no. While I am average in length and girth I know for a fact it gets the job done especially with her. I know, that really sounded conceded but it is the truth. I have had girls before who faked orgasms with me and this girl can’t do that. She is a squirter so it is really hard to fake that. You also asked if I have ever had any problems like this before with other woman and the answer is again no. She is the very first woman to ever bring me over the top with fallatio, even if it has been just once and that is what is frustrating to both of us. She did it once but for what ever reason hasn’t been able to do it again.
Your point about desensitization may also be a valid point, yet I have to go back to the times it felt like I was even though I wasn’t. She changes her methods during her giving me fellatio and yes at times she does it at a time where I feel I am almost there or she stops to give her self a rest and uses her hands to keep me stimulated. But then there are other times like I stated where I feel as if that is all I am doing is cuming but she doesn’t stop because I haven’t.
I hope this either brings out more questions and or gives you a better insight to draw other conclusions to help.

Retta I'm so glad you got back to me!  You left me wringing my mind all night trying to think if there was something better I could have told you.  And although you have given me an abundance of information in your latest comment, I think I can only help brainstorm with you and not necessarily yelp out, "Eureka I've got it!"  So let me start by addressing things in the order you gave them in your comment.  First let me ask the dumb, obvious question, when you have intercourse and have an orgasm are you ejaculating or is it also dry?  I'm fighting with myself because you start to say that you have never been with a woman who has enjoyed giving you head and furthermore wanted you to ejaculate into her mouth.  That is normally a red flag for me to say mental block for sure.  In that situation I would assume you are insecure that for once, if you let go, your fears may be realized and she may show her aversion or distaste of your semen in her mouth.  But what makes that theory not stick for me is the fact that you are building up to some feeling of joy and euphoria where even you are fooled by the fact that there is no semen involved.  With a mental block you don't get those feelings.  This same point also rules out the prospect that maybe she's just not getting you off orally but it seems like you are really enjoying these moments with her and you guys have great communication.  Point being, I hate reading sites and books by people who say that they are there to give you sex advice but every time you ask them a question they tell you to make a doctor appointment.  I don't normally want to do that but I do know that there are what the layperson has termed "dry orgasm" that are caused by your ejaculate being pushed back into your bladder instead of out your urethra.  Though this act itself cannot harm your health, it can be caused by such things as diabetes or certain drugs that are used to treat prostate enlargement like alpha blockers.  And between you and I, if you were on a prescription for enlarged prostate I'm sure you would have mentioned it.  In conclusion, what I'm wondering here is what are you missing?  If you are having a great sex life and you are feeling like you are having an orgasm and you are healthy, I would say leave it alone.  I know that actually getting the shooting, spurting cum shot can be fun, but if you guys love each other and are pleasing each other every other way possible I'd say que sera, sera.

I'm always here for more brainstorming...keep me informed!

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