So apparently there is a name for what I have to deal with- Delayed Ejaculation.
To begin with, I was raised in a protestant household, and while it was not strictly religious aside from Sunday morning visits to a rather low-key protestant church, I personally embraced certain religious ideals (until I got older, took up serious study of holy texts and world history, and eventually rid myself of religion). I held vaginal sex up on some pedestal that, if experienced within the context of True Love would bring some profound understanding of life. So with the women I was involved with in high school, I did everything but actual vaginal penetration with my penis. We did all kinds of 'heavy petting' while in the nude, and the women even made a few even made rather clumsy attempts at oral sex.
Also, I never masturbated. I would read internet fiction about hardcore S and M, get erections, and even pretend to be older then I was for cybersex (before I had girlfriends), but never actually stroke myself off - although nobody ever told me that masturbation was 'bad' or 'forbidden,' I somehow came to believe it to be. This was back when the internet was green text on a grey screen, so I didn't have access to any pictures except for a copy of Penthouse that I bribed a schoolmate to steal from his dad for me.
It wasn't until I was 19, and had experienced a number of frustrating 'relationships' that I decided that I was becoming too old to be a virgin and for the 'true love' nonsense, and to just have it off with the next woman who offered.
While the coital sex itself was REALLY bad, she did give very good hand jobs and blow jobs. It was with her that I first came. It was also from her hand jobs that I learned to stroke myself off, and became quite addicted to the practice. She was the only woman to ever make me come from any kind of stimulation.
My life from that point was long periods of being single punctuated by a number of pretty strongly emotionally abusive relationships, usually with women who I'd say fit the profile of Borderline Personality Disorder (I've read a load of books on the same and on recovering from emotional abuse).
I should probably mention at some point that I have ADHD.
After a long period of time, I was able to break past negative emotional barriers, and this allowed me to keep myself up for as long as I used to in high school - and not ejaculating could often keep myself up for hours and bring a woman to climax repeatedly from multiple positions. I also became much more proficient at both oral and manual stimulation. I, however, never was able to cum with a woman (I tried to get into homosexuality- but could never get the slightest bit turned on by men) and would usually fake an orgasm and sometimes rely on the cum that oozes forth as I go soft - and subsequently collects inside of my condom, to let the woman assume I had came.
I'm with a woman that I really care about right now - the first person that I can really connect with intellectually, emotionally, etc. We have all kinds of fun together, things that most people dislike about her I adore (and visa versa) and we understand each other in ways that nobody else can. She's clearly becoming bothered, however, that while I'm quite competent at getting her off (and helping her explore the subversive sides of her sexual nature that she's been terrified to say the names of aloud until recently), she's been yet unable to get me off. I've masturbated frequently thinking of her, but I've been unable to successfully cum even if I masturbate while lying with her. My usual solutions of either causing a distraction or assuring my partner that I have indeed cum quite violently before receiving her oral stimulation are not working here.
Of course I'd really like to find a solution and tell her perhaps sometime down the road, but at this rate it looks like the best I can hope for is to get a solid handle on things and then somehow broach this topic while working with her on a solution?
Clearly I have a lot on my mind right now. Can anybody offer some words of advice?