My New Boyfriend is Unable to Ejaculate With Me But He Can While Masturbating!?
I've just started a new relationship....we're crazy about each other..and from my point of view..the problem could be lots worse..but is still frustrating...My boyfriend has delayed ejaculation...actually..he's unable to ejaculate with me at all.  He can if he masturbates..he's had this problem in the past..so I'm not taking it too personally...he's taking steroids.  Have any information on this or maybe where I can find some?  My boyfriend is 20 years younger then myself.
Dear Mrs. Robinson,
Your boy toy can shoot his wad when he jerks off but not with you. Hmmm. We could recite the often quoted list of possibilities for male orgasm dysfunction but first we'll just say " closet case" . Now before everyone starts jumping up and down accusing us of being gay hating homophobes, we'll just remind you of the many gay sexuality questions we've answered with equal respect and caring to the straight ones. What we do hate is when anyone feels the need to lie to themselves and thus others about their homosexual feelings.
Why are we jumping on this before the usually stated causes of male orgasmic dysfunction? You state you are between the ages of 41-50 so if your boyfriend is 20 years younger he would be somewhere between 21-30 and as you state able to ejaculate through masturbation. This means the plumbing is all working properly and that the 'steroids' he's taking aren't the problem. Your age differences, though not a bad thing, coupled with the non ejaculation push us in this direction as well (though we think every 21 year old male should have a 41 year old sexpert). If he is gay and unable to admit this to himself, there's not much you can do, short of suggesting a three-way with another male which if we are wrong (it's happened, once maybe) would really crush him.
So let's look at some other causes and solutions to male orgasmic dysfunction which is so lovingly referred to as 'delayed' ejaculation (even a damn plane is only delayed to a point, then it's canceled)! Things that could be clogging your boyfriends mental plumbing include fear of commitment, fear of getting you pregnant, fear of hurting you, guilt over sexual pleasure (with someone other than himself), or performance anxiety. Since he can jerk off to orgasm we suggest you have him do this to near orgasm then begin coitus. If this quick solution doesn't work, follow the more detailed instruction on the above linked page. Hope your flight leaves soon.