Dante,
I feel very sorry for you. Sex is hard to understand until you have done it and then it is hard to understand living without it. I wanted to have sex when I was 12. By the time I was 13 I was desperate but I only wanted to have sex with one man, my hubby and he refused because of my age so I had to stick to masturbation. I don't think there is a terrific different between a man and a woman except that a lot of women I know say that the first time was a real let down a "is that all there is to it" experience and I think men experience it a bit differently. But overall I don't think there is a huge different.
I think it is all down to experience. I was a slut and would do pretty much anything to get experience short of intercourse but here I think women have a huge advantage over men. If I went up to a 14 year old and suggested a blow job I don't think I would ever get turned down. Men on the other hand, experience rejection all the time. Oh, and by the way I'm talking about go up to a 14 year old when I was 13, not any underage activity involving an adult. But for men it seems to be confidence. The more experience you have the easier it is.
Hubby tells this story against himself about how he has never ever picked up a woman in a bar or a night club and he really is super experienced. He first hard sex at 11 and he hasn't been without a sexual partner pretty much any time in his life. But he was without a girlfriend for a short time and as 16 or 17 and saw this gorgeous woman in a bar and approached her, after getting up the courage for several minutes. He simply said high and was greeted with a very loud "Fuck off". He tells me that it had such an impact he has never ever attempted to do what he calls a cold pick up in his entire life.
I may not be the best to give advice in this area because I've only had one male sexual partner and I tricked him into having sex with me so even there I didn't have to "do the dance" or make any normal approach. I had known him for years and frankly the thought of attempting to seduce him in a normal way would be too terrifying for me to even contemplate. But from watching guys attempt to pick me up and that has happened a lot and guys that pick up girlfriends of mine I would have to say confidence seems to be the overwhelming key.
I hate to say this Dante, but because you've mentioned being a virgin a few times and obviously sex is important to you or you wouldn't be on this site, how about biting the bullet and just getting it over and done with, so you can concentrate on more important things such as being intimate with someone that really turns you on. Where we live prostitution is legal so it isn't a big problem. But I can only suggest you save your pennies and go and have sex with a professional. A sex therapist would be good if you can convince them that you have hangups because of it but a decent prostitute that is willing to spend a lot of time with you would be good enough. Don't forget the condoms and make sure the prostitute is happy to teach you and spend enough time with you, not get you off and leave the second you come. You probably will come straight away anyway and so you need to do it more than once, preferably several times over a how evening or night.
Then you will learn that the act itself is no big deal and can actually be a bit of a let down. Hubby says he'd rather masturbate than have sex with someone he really did not care about greatly. He doesn't think the act all that important without the right person. I agree with him. We have sex sometimes and it isn't very good. He is ill a lot and in pain so sometimes things go wrong. It doesn't matter. He's with me. He wants to be with me. He wants to be in me, hold me, kiss and fondle me. Really bad sex in those circumstances is still pretty darn good! But thankfully most of the time the sex is mindblowing. I hope you get the idea at what I am trying to say. The act is important so you know what you are doing but it is far more than that. For you, it sounds like the act is now terribly important because you haven't done it. So do it. Get it over with and then learn that there is a whole lot more to life and loving and sex than sticking your cock up some cunt or arsehole and pounding away.
Don't get me wrong. I rather like being pounded into when the mood takes me and hubby seems to enjoy it too but you need to learn enough so the fixation on being a virgin and therefore somehow lacking is no longer there so you can concentrate on what is important. As well as having the confidence to get to the point with the right woman, or man if that turns you on, where the actual sticking it in is only a tiny part of being together.
As I said I've only had one man but I did have sex with a woman when I was terribly frustrated like you and wanted to go "all the way" but couldn't bring my self to having a man do something that was reserved for who I loved. Some of it was fun. I learned a great deal but in the end it wasn't particularly enjoyable. But it did help me focus on what I realised was important to me and less than a week later I was no longer a virgin anywhere and never looked back.
When you think about it, it is just sex. Sticking your tongue in someone's mouth is just as intimate. Find someone willing to teach you so it is enjoyable and isn't a race to get you off in two minutes so they can go to work on someone else. Then maybe you will relax and finding someone that it will really matter with will be much easier.