Dear SIMIC,
While I understand your desire to please, I'm wondering if it ever occurred to you that this "woman" did NOT have five orgasms and in fact she was acting the part so that you would eventually climax and end this "endurance" test?
One thing is certain, and that is that it is impossible for men and women to orgasm on command. That's why statements like "come for me" are ludicrous, hackneyed and mean absolutely nothing in the larger scope of things. People come when they come, period. Now, there may be things that are impeding you from orgasming - what these issues are, I have no idea, since your email is not descriptive to that extent.
Generally speaking, a man will orgasm and/or ejaculate when sufficiently stimulated. Hence, if the condom is reducing sensitivity, or if the person you're engaging with is not sexually stimulating to you, then yes, you will perhaps have difficulty orgasming. If this is situational, but, say, you orgasm with your wife/SO/girlfriend/someone else, then I'd say that you can't expect to climax so readily with someone you're not into 100%. Or, you could suffer from performance anxiety and clam up...there are zillions of issues why people don't have orgasms. But one thing is an absolute: NO ONE CAN HAVE AN ORGASM ON COMMAND. That's not how the brain works and we can't expect for it to happen.
The whole issue about "reciprocate" and "feel as if she was not special" should be laid to rest. Yes, of course it's nice to have a simultaneous orgasm, but then again, that's something promoted by Masters and Johnson and not really replicated statistically - or in biology either, for that matter. Honestly, if you really wanna cum - ignore her, ignore the world, disappear in your own erotic haze and focus on your own pleasure. Above all, forget about the "endurance" - please, no one thinks it's particularly cool and women DON'T LIKE IT. In fact, a guy who gets so into it that he comes after 2 minutes with a total smile on his face is preferable to someone who makes the sex act into a sweaty marathon just to get off. So my suggestion is to get into your own space and try to relax. If the condom is reducing sensitivity and you know it's going to be a problem, then get some hand-action or a BJ (bareback if you're risk tolerant) and then stick it in for the final curtain. No sense in tormenting yourself or the provider so that you'll have to hear that useless and cheesy phrase again..
Tricky dicky,
the Love Goddess
Lets start off by not assuming what most men would or would not be proud of. Sex is not an endurance contest. In it's best form it is an act of mutual satisfaction.
Every guy is different. What has been the easiest way for you to orgasm in the past? Are you getting older? Taking ED meds?
Nothing wrong with giving the lady an O or two...or five but you have to figure out a way that you can get to go along for the ride.
I only O through oral sex so my ATF and I have a pretty good routine that gets her off three to five times in a session and gives me one amazing orgasm...all I can manage in a two hour appointment. I get her off a couple of times, maybe three with my mouth, then she goes down on me. Sometimes we slide into sixty nine and I give her one while she is working on me, sometimes not. When I finally pop she slides up onto my face and I give her one last O before she collapses on the bed next to me. That's as close to "mutual" as it gets for us but neither of us is complaining.
