I haven't lived your life, so I don't know how many chances you've lost. But even if it's subconscious, there's something sabotaging your love life, and that something is you.
To find the answer to that, you need to find the self-awareness to locate your lack of confidence and correct it, which I believe is possible. You just need access to a really good counselor/therapist.
(snip)
You have internalized your feelings of sexual inadequacy until they've carpet-bombed your feelings of self-worth. No matter what happened at some stage in your life, at this point, as an adult, you own it now. Eventually you'll need to deal with it or just remain lonely, which really are your two choices.
Hear, hear. Virginity is not something that, in and of itself, stands in the way of sex; it's only a hurdle if you choose to make it one. Just as everyone was once a kid, everyone was also once a virgin. It's just a technicality.
I spent some time a month or two ago chatting with a guy who was interested in me and who had never had sex before. He initially seemed like a cool guy, if a bit unsure of himself, so I made the effort to be as understanding, compassionate, supportive, reassuring, and positive as I could be, with the hope that I could gain his trust and build a great relationship. Unfortunately, he was so fixated on both his desire to have sex for the first time and his anxiety about it that once he got onto that subject, I was never able to lead the conversation anywhere else. It felt as though every time I reassured him that things were going to be just fine and that I liked him, those reassurances fell on deaf ears. I became very tired of and frustrated with playing psychotherapist and babysitter when I really wanted to be forming a solid friendship, and so I eventually called the whole thing off. He had spent so long fixating on the negative that I was unable to get him to see things in a positive light, and I didn't want to be caught up in that unbroken cycle of abject misery.
If you're anything like that guy, you may very well be sabotaging yourself. Even though misery loves company, that's generally not a good way to attract people you want to have positive, empowering, and beneficial relationships with.
As Bbucko says, you need to face and conquer the underlying fear that's driving your insecurities. Learn to trust yourself. Have confidence in the things that you do. Be in control of your life rather than letting yourself be helplessly railroaded down an unwanted path by factors beyond your control. A good therapist can do an amazing job of helping you discover what those fears and insecurities are, but you have to find the strength to conquer them yourself.