I'm not sure what I'm hoping to achieve here but I'm hoping if I just start typing things will pour out and maybe someone can offer some insight for me. It may well be a jumbled mess, I'll try my best.
Background, I’m male, 30, decent height and build, do fairly well with women despite the fact I’m fairly introverted. This may well read a little misogynistic and some might even perceive it as boastful, but I genuinely believe I’m a nice, empathetic person, with a good moral compass.

I have a serious self-esteem problem that has been with me as long as I can remember, since being a teenager really. While I think the problem is bigger and multifaceted than this, the bulk of it is the huge cliché of penis size. I genuinely believe that so long as you’re within a normal range, you’re a decent person and you can satisfy your partner, 99% of women don’t really care about the size. I also know that statistically I should be happy with my size and that if I had to stick or twist I’d definitely stick!

But yet there is this part of me that desires to be the “big guy”, the one who girls talk about and want to experience. Like I’ll always be second best to one of her exes who was bigger than me. I know this perspective is completely skewered but yet it dominates my entire life. I get a sick feeling whenever anyone mentions big cocks and I’m hugely envious of people I know who have one. If I find out through chance or through my own stupid questions that a girlfriend’s ex was “massive” (as with the latest case) I feel absolutely crushed and cannot bear to be even naked around them. I try to pretend I’m not bothered but it’s all I think about from then on and sex becomes pretty much a non-starter as I can’t remain hard. This is always a battle anyway as I seem to lack naked confidence completely, my performances in the bedroom are very average unless I’m drunk and with someone I’ve very comfortable with, whereby my inhibitions drop almost completely and I can enjoy myself.

While this is a big part of it, I have other insecurities and it has manifested itself in quite an unhealthy way with relationships. I hate being in relationships and I’m kind of obsessed with being single and chasing women. I’m forever looking at attractive women, always hoping they might give me a smile or some reason to chat to them and try and get them in bed. I’m not shy per se, just introverted so I rarely approach them, and even then only places where it is acceptable, but when I do I’m nearly always taken well and in good humour and more often than not get a phone number or something. But as soon as the chase is over and I’ve slept with them, I’m looking for the next. There’s been times I’ve had multiple text conversations going on and more women agreeing to meet me than I can physically reach. I’ve slept with different women on the same day in a couple of instances. But I go through phases with this, I can have a “good” couple of months, then I seem to slink back into my default, sullen setting and not bother. I find some of this is linked with my mood and my feeling of myself. For example, if I’ve got back from holiday which I’ve gotten in shape for, tanned, nice haircut, new clothes, I have the confidence that radiates. As soon as any of those effects fade off, I regress again.

I think I have more to unload but I’m making myself unhappy so it’s time for bed!

Any comments welcome.