30 and still not penetrated a woman - complete failure

I'm 30 now and although I've had relationships in the past with women, I'm still yet to successfully penetrate a woman. I've done other stuff like mutual masturbation, received handjobs, frottage (naked rubbing) but I have never gone all the way. This has caused me much distress and trauma. Without boring you with all the details my main concern right now is that I've noticed for a long time I cannot stay hard WITHOUT touching my penis for stimulation. In other words, I have to constantly touch my penis in order to stay excited and reasonably hard. Now this is all in reference to masturbation. I have not been with a woman in a physical sense since my last gf, the relationship which ended back earlier last year (it was horrific, she was a horrible person and treated me like utter crap, cheating on me and disrespecting me in so many ways and without getting into the details here I'm sure it is one reason why I failed to penetrate the few times we did try and have sex).

So, when I masturbate daily to porn (nearly always softcore only), I notice in order for me to stay reasonably hard I need to keep touching it whilst looking at some stimulating video/pictures. The moment I let go of my penis, it starts getting soft rather quickly. Why is this? I'm worried because I know this should not be happening, right? Should you need CONSTANT stimulation to stay hard? Surely a man like myself (I don't drink, smoke, take drugs, I'm in decent shape, no health issues) should be able to maintain an erection? I realise daily masturbation may not be helping but this is a habit I've had for many years now and so it's hard to suddenly stop. Earlier last month I did infact stop for 8 days (no masturbation and no porn), I noticed very little difference at all but maybe that's not long enough to really change things up.

I should have mentioned that I do notice sometimes getting erections without touching myself for example when I'm thinking of something in the past that turns me on. Also I do get morning erections (not everyday but have got them recently). So I don't know. However what bothers me is maintaining them. How are erections maintained? Do you need constant stimulation the entire time? Once you stop thinking sexual thoughts or seeing something that turns you on would your erection subside as a result? E.g say you're about to get it on with your partner and you're hard and ready to go but then she leaves the room to get some condoms...how would you remain hard in that situation? Should it be normal that you would remain hard without having to see or think about anything sexual? Earlier today for example, I got reasonably hard without really touching myself (I was thinking about something sexy) this went on for say about 2 minutes but then as I soon as I started watching CNN, I was soft again within like 30 seconds. So it seems like I constantly need sexual stimuli in order to stay physically hard down there. This is really worrying. Should it not have stayed hard for longer than 2 minutes once I got hard, EVEN if I ended up doing something non-sexual? That's what I'm confused about.

I did go and see the doctor about this back in April and they said they'll refer me to a specialist to which I insisted...never heard back. But that's typical, they don't give a crap about these sorts of issues. So I will go back on Monday and try again.

The larger issue in all of this is being a technical virgin at my age has really affected my self esteem now. Even though I am a decent looking guy who is outgoing and friendly, have had relationships where I have been physical, the fact remains I still haven't achieved penetration. I know this issue simply does not go away. I feel sorry for myself constantly and have no motivation to do anything else until this issue is resolved and extremely depressed to the point where I wish I was never born. The few times I did try, I failed. I feel like this has to be greatest failure of a man. Being unable to have sex because of outside factors is one thing but trying and then failing to have intercourse ... I can't think of anything worse in life.

You're better off, my friend. My goodness, how I only wish I could say that I never pentrated a woman. Did you know that I have never in my life, even once, had sex with a woman I wanted to have sex with? Yep. That is a fact. In fact, I've never even been looking for sex when I've had sex.

I always wanted a great wife and a couple of kids. By this time in life (37), I thought I would have a home, a family and a few cats or dogs. But no. Every last time I have ever had sex it has been completely unexpected. I would be like, 'What? Are you serious? Sex? With YOU? No way. And then sure enough, like a sheep led to slaughter, it would happen, and I would feel terrible.

Well, no longer. I always wanted a good Christian woman and have tried to do the right thing. I never meant to have sex. I know that sounds insane and unbelievable, but it's the truth. Most of these women I didn't even like. They've never been anywhere near what I wanted or hoped for in a wife or even a girlfriend. At this point I'm seeking castration so I will no longer even have to worry about the issue. I'll finally be free.

I think you're doing great bro. Keep up the good work. Two thumbs up.

Dude, stop masturbating daily to porn. Are you completely unaware of the damage that can do to some men? You get desensitized to "the real thing" if you're a porn addict (like it seems you are).

Stop masturbating daily, perhaps do it once or twice a week and try to do it without looking at porn. If you must look at porn, at least choose amateur videos, that are sometimes closer to reality.

The problem isn't physical (you have no problem getting an erection, which means that all the "machinery" works), it's psychological. Let go of your addiction and I'm sure things will get better.

As far as getting a new girlfriend, I think you need to work on your self-esteem before you attempt it. It's crazy that you associate your self-esteem with your sexual history. That's messed up, I think you should get some counselling for it.

The first line treatment for your condition is one of the ED meds such as Viagra, Cialis, or Levitra. You don't need to see a specialist. Your primary care doctor will ask you a couple of questions and give you a prescription. You may also be asked to get your blood pressure, testosterone, glucose, and lipid levels checked. You might need to try all three meds to determine which works best for you. They are each a little bit different. For example, Levitra and Viagra are stronger than Cialis, but Cialis will last 2-3 days, whereas the other two will only a few hours. Probably Cialis would be better for you since you are able to get a stiffy, but you just lose it easily. It would also help you tremendously to actually penetrate a woman. The boost in self-confidence cannot be underestimated. Also regular sexual relations with a real woman are important to maintaining sexual ability. The phrase "use it or lose it" is apt. If you know you are capable of properly servicing one woman, the confidence will spread to your interaction will all other women. This is one reason why some men can have multiple partners while others cannot get even one. Good luck to you.

dem, he has no trouble getting an erection, he has trouble maintaining one without the aid of his own manual stimulation and porn... he is addicted to masturbation to porn, that's why he has such a hard time keeping it hard (pardon the bad pun) in "real" sexual situations. The fact that he bases his self-worth on his ability to "penetrate a woman" just makes things worse, because it prevents him from building up confidence and self-respect and it makes him even more anxious and afraid when it comes to real sex.

I think medication might (might!) cure the symptoms, but the illness would remain. He needs counselling to regain his long-lost confidence, to realize that a person's worth has nothing to do with their sexual history. He also needs to become un-addicted to porn, which is once again a psychological problem.

Common sense would dictate he exclude all medical possibilities before attempting a psychiatric cure. While there is a very vocal cadre of people who express their dislike of porn and some correlation to ED for some men, there are many more millions of men who do partake of porn at what could be considered addictive levels and still are able to function in real life sexual situations.

Like I said and know from experience, nothing boosts confidence like success. At his level of dysfunction, I think it would benefit him more to experience a successful penetration, than to attempt a relationship which would likely result in failure and dissapointment to both parties.

I have never said that I dislike porn.

A guy that is unable to maintain an erection without manually stimulating himself while watching porn, AND that masturbates to porn every day, is almost certainly addicted to porn.

Of course he should get checked by a doctor, but as I said I'm pretty certain that his problem isn't physical. If it were, he wouldn't be able to get an erection at all. The fact that he only has trouble maintaining an erection without touching himself and watching porn, added to his daily consumption of porn+masturbation AND of his dysfunctional outlook on life, all point to the conclusion that his problem is psychological.

So, while I agree that it can't hurt to get checked by a doctor, he should not get medication for a problem that isn't there (unless his doctor says it's there, of course). He should definitely see another kind of doctor though, one that is able to help him with his lack of self-confidence and warped vision of the world that makes him think that a person's worth is based on their sexual history.

As far as beginning a relationship, I already said that he shouldn't attempt to do so until he figures out his issues. He can of course have casual sex with persons he doesn't care about (making sure they know that he isn't after anything serious). In fact, I would advice cutting off the fake porn entirely, limiting masturbation to once or twice a week, and having as much casual sex as he can.