sensitive head and erection problems

Ever since I started to have sex, my penis seems to go limp sooner than when I am ready to ejaculate. I have never been able to stay hard during oral, although I started out that way. In sex with my wife I am hard in the beginning but go soft too soon. When I masterbate with my hand and lubricant, when I start touching my head it goes soft, yet when I stroke the rest of the shaft prior, it stays hard. Not sure what this means other than a questionable ability to stay in the game. Any thoughts doc's? (when I was younger I masterbated with a pillow...do you think this had any affect on my challenge?)

I'm a 20yo, U/cir and I have been having this exact same issue! I have been looking around for answers everywhere! I have been told it's Phimosis, but my foreskin isn't tight. That it'll go away eventually... it's now been 7 years. Even that it's phychological and to start viagra/cialis. (Still doesnt address sensitivity). I've tried keeping my foreskin back to decrease sensitivity, it wont stay retracted, and it's not long, so I dont understand how that works. So I'm currently considering "Betamethasone Valerate Creme". It's a topical coricosteroid that should thin the glans skin (head) of the penis and reduce the sensitivity slightly, prescribed by my doctor.
I find this condition really distressing because when I was younger I could handle oral sex and masturbation with my foreskin fully retracted. Now I can barely stand it at all. I can't maintain an erection for very long (if at all), so I'm never fully rigid. And the main point of all, I can't enjoy sex as much as I used to, because orgasm is far from satisfactory if I even have one at all.

I'm having a lot of the same problems. I'm not able to stay hard when I'm trying to have sex, and often become too uncomfortable before becoming inserted in a girl causing me to go soft. As for the cream, I'm going to assume that you need to get a doctor to prescribe it?