I somehow can't believe it has taken me so long to post here. But well, here it is, I am asking for your help and advice. Make sure you are seated next to wall, you might want to bang your head against it after reading this.
So what's the deal?
I have little to no feeling when I get an orgasm.
How did it happen?
I discovered masturbation early, like really early. Probably when i was about six i guess. I used to lay face down, press my hands against my penis which in turn pressed against my belly (its called prone masturbation) and moved by hips sideways. I had amazing orgasms, and i could do it a couple of times a day.
Then puberty struck, and my penis started growing. Now as you all know, the penis isn't perfectly round, its more of an oval shape because the expanding areas aren't evenly distributed. My penis was absolutely normal - but I didn't know it back then. I figured the oval shape was the result of my masturbation (I had somehow distorted it by lying on it) and I was too shy to talk to anyone about it.
So what i did was - I tried to make it round again. By Masturbating the "opposite" way - I would hold it left and right with a firm grip (opposed to the pressure from front and back as it used to be) - I was hoping to regain the original shape. Which of course didn't happen. I didn't hurt myself or anything, I just physically masturbated without psychically wanting to experience pleasure. I wanted to make it round again, i felt bad for what i had done to it, and i didn't want to feel pleasure while trying to "fix" it.
I stopped it only after i found the internet and discovered that other erect penises would look exactly like mine. By then I had done it for probably two years, i guess i was about thirteen. There was no physical damage to my penis, but over the course of those two years trying to fix it, the "good feeling" had gone away. (Head

I was hoping for the feeling to come back, but it didn't. I still kept on masturbating throughout my teenage years, sometimes once a day, sometimes once every 2 or 3. It was still fun somehow - but it was never the same again.
Now I'm in my mid-twenties, I have a great girlfriend, we have sex about every other day. The Sex is ok, in fact it's good most of the time. I enjoy the pleasure she has, and i am also able to enjoy the "whole thing" - getting aroused, foreplay, penetration, orgasm. Sometimes when i orgasm i feel very little, sometimes when my girlfriend masturbates me or in certain sex positions i feel a nice feeling in my head. I would say it is satisfying and I also would say it has no impact on my general happiness. but the feeling while we are / I am at it is just nothing compared to what it used to be. How do I know this?
Every once in a while, maybe once every 3 months, i suddenly get a glimpse in my head of what an orgasm used to be. As far is I know, there is no trigger, it just comes to my mind. I can't really hold on to the feeling, and I can't reproduce it when i want to. It just reminds me of what it used to be a long time ago...
What did I try to improve the situation:
-I talked to my doctor about it, he sent me to a neurologist. Who examined me, told me I'm perfectly healthy, and sent me away.
I once decided to visit a psychologist in order to get help - he was completely overwhelmed with the situation. he pretty much avoided the actual subject and advised me to do relaxation techniques. Which didn't get me anywhere, so I quit that pretty fast.
Additional information:
(not sure if this is useful, maybe it gives you some more insight)
-When i tried to have sex for the first time, the tip of my penis would hurt terribly, i couldn't penetrate her. I could masturbate just fine, but just touching the tip of my penis would give me immense pain back then. (I was about 17)
-It took about 2 years and various sexual partners until i could finally have sex without pain
-even today the tip of my penis sometimes still gets painful if i don't use lube (no matter masturbation or sex), but usually its fine.
-I stopped prone masturbation at the age of about 13 and switched to the "normal" version of it.
-i can maintain an erection for about an hour without a problem.
-I "orgasm" almost every time, my girlfriend usually once or twice a session.
-I never had erection problems, in fact even today i could erection wise easily go a second time, (i get a second erection easily) but the second time my penis always hurts, even when we/I use lube, so a second time practically never happens.
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looking forward to any sort of advice, help and comments on the subject!
Thanks.