I have never been able to have an orgasm during sex, ever. However, I have been able to climax during hand jobs and personal gratification. During sex I am able to maintain an erection. During the initial act I'm enjoying myself but after any duration of time I mentally fade away. Are my partners holes not tight enough? Not sure what the deal is. Has this happened with anyone else?
I used to have this problem when I was younger. I think there were a number of factors at work:
1. I jacked off three times a day, every day (occasionally more) and almost never used lube. My dick was used to my hand and was probably somewhat desensitized. I never varied my technique, which also couldn't have helped.
2. Sex was a novelty and was maybe a little nerve-wracking and usually done in less than ideal circumstances.
3. It never occurred to me to have someone use a lube while jacking me off and I wasn't very good at saying "That's not quite it, could you try it this way?"
At an age when stereotype says I should have been shooting too soon, all my orgasms waited until I finally took over myself. It wasn't the end of the world, but I definitely wanted to be *made* to have an orgasm just to see what it was like.
It finally happened one night when a friend stayed over. He woke up around 5:00 in the morning and went to the bathroom, which woke me up. We started fooling around, but he didn't really seem to want me to do anything to him and instead just started orally concentrating on me. Didn't take long and it was *intense*. I think it finally happened because I was very relaxed at that hour, hadn't jacked off in a few hours and was being helped along by someone who really seemed to want to help me along.
It didn't happen again for something like four years and I can again think of how it was a special situation: It was a rare occasion where I had the apartment totally to myself without my straight roommate, the "date" had been set up several days in advance so I made a point *not* to masturbate after it had been set and, once things got under way, he asked me with what seemed like a totally sincere desire to get me off, "How would you like to come?"
It got easier after that and happened more often over the years, but it took time. Now I find I can kind of take or leave it (don't get me wrong, it's great when it happens, but as my nick implies, I *love* masturbating) and it's not such a big deal.
I don't know if any of that's helpful or not...I guess I mostly want you to know that you're not alone. I've also known guys who don't necessarily have a problem being brought to orgasm by someone else, but they swear they just enjoy it more when they do it themselves because they know exactly what they want. There was a time I found that kinda crazy, but I sorta get it now.
Probably the most important thing you can do is relax. And if it's something you really, really want to have happen, tell your partner. I don't think anyone is going to be upset by it and they may really get off on the challenge.