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.

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).

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. I can barely even put on a condom. I've tried a few times just to test it out and can barely get it on and my penis kinda of goes soft anyway, it's a real struggle.
However I should mention that I am still getting morning erections, even after masturbating twice in a day. And I won't obviously need to touch it for it to remain hard, I wake up and it's already fairly hard.

This is all making me feel so pathetic and useless as a human being. Honestly I wish I had never been born. I mean, I'm 30 years old and I am an impotent virgin....tell me what is worse than that? Even though I am a decent looking guy who is outgoing and friendly, I know this issue simply does not go away. I am constantly plagued by the thought that I still have not penetrated a woman but even more to the point is this thought CAN I ACTUALLY PENETRATE A WOMAN??? This leaves me feeling extremely depressed to the point where I wish I didn't have to wake up for another day of this torture. I feel like this has to be greatest failure of a man. There is surely nothing worse than failing to even get it inside.

Don't tell me about going to see an escort or someone similar. You see I have waited all this time because of my Christian background which has taught me not to have sex before marriage. So this is what I've taken seriously for all my life despite going to other "bases." So you see my dilemma...I'm desperate to experience intercourse just to know I CAN actually do it and to a lesser extent know what it feels like etc. but at the same time I've waited all this time, who am I going to do with for the first time?? It can't just be anyone, it would be such a waste and so the wait will continue. Can you understand my dilemma?
With an escort, I mean I don't think I could actually even get hard because the guilt would overwhelm me. I'd be like "I've waited all these years to lose it to some prostitute ??