That time is probably never coming. Seriously. A dude like you, with low self-esteem is the worst. Your looks don't matter. Your dick is irrelevant. I've had male friends and acquaintances think they were going to make that transition with me, and I did my best never to lead them on once I sensed their attraction. However, once attraction became an agenda I dropped them like bad habits. There was one I really loved (as a friend). I valued him enough to maintain the friendship, especially since he was never deceptive or manipulative about his feelings, and because I was responsible for not knowing at first what I wanted from him. Once it was clear that he wasn't exactly a fan of himself, all I wanted was his friendship. I saw how good and beautiful he was, even though he did not. When he eventually asked me why we couldn't date, I was deeply offended. I said, "How dare you offer me something you don't even like? How little do you think of me to offer me something you don't think is good enough? If you wouldn't choose you, why should I?" That was the end of that. I don't believe he ever tried again. Eventually, he became ill and died. I still miss him, over a decade later. I still wouldn't date him, and I absolutely would never fuck him.
You think of women with experience as used up. Pussy is not a finite supply kind of item. It doesn't get used up. You don't deserve any until you think better of yourself, and of women. There is nothing wrong with your size. There is something wrong with YOU. Good news. You can fix that.
By the way. There is one guy I fuck every chance I get who is, objectively speaking, hideous by conventional standards. He's smoking hot to me though, and I was attracted to him the second he first walked into the same room I was in when we showed up to help his cousin move in with my close friend. My back was turned, and he didn't say anything. I felt an energy building as he climbed the stairs. When he entered the living room, it was like the Earth stopped spinning and I couldn't breathe. I turned, we lovked eyes, and immediately wanted each other. I have never had that kind of physical response to any other man. He hit on me for 7 years before I was available. I always just let him know the attraction was real, but I was not in a position to act on it. One day, after we had already began hooking up, we were at the same crowded bar. I overheard him telling a guy that he was very ugly but women really liked him. It's totally true. I've met women who wanted me out of the picture because they thought we had to compete for him. I've seen women try to get between him and his primary, a huge no-no he will not tolerate. For that guy, life is a sea of willing women. He's not good-looking, he's dirt poor, but he loves himself, handles his business, and therefore just oozes sex appeal.
Lastly, I don't know why I had you on ignore. I don't remember you. I mention this because I want you to know if you want to advance with women you mist be memorable in some way, and because I hope I won't regret un-ignoring you. I know my post has been worded bluntly. I know I may have hurt your feelings. I swear my intentions are pure, and I've only stated what I truly believe, and what I honestly believe is what you need to know.