How do you ever get over wishing you had the courage to wear nappies earlier?

So I have been dealing with this for years and the regret never goes away. I keep looking back at my life when I was younger (early twenties now) at around 4 and 5 and remembering I had, had plenty of opportunities to wear but didn't. One time was taking diapers from the changing room at church or even just from my younger sister's box of nappies. I regret not taking those chances. I was too, for want of a better word...righteous? I couldn't bring myself to do it knowing they weren't my nappies it felt like I was stealing. Which maybe I was from church but from my own home? not so sure about that.

But anyway it's not just that, as a child I would say I had low self confidence as I would usually back away from confrontations. So after asking my parents a few times and leaving notes and catalogue cut outs of Huggies nappies around the house for them saying I wanted to wear them, came a point when it all stopped. My mum yelled at me about "writing notes about wanting to wear nappies" and so...I stopped and yeah that was it. I couldn't handle the confrontation/embarrassment anymore and so the desire itself left (or lay dormant more like it) for a few years. But as everyone says "it always comes back" and so it did come back at around 10 years old.

I regret not pushing it. I know now if I had just asked again and again, they would have bought me nappies. "what do you want for your birthday? Nappies. What do you want for Christmas? Nappies etc" and if I kept pestering they would of broke down and I would of had the chance to experience wearing baby nappies properly. *sigh* I mean what could they do to punish me? Grounded? For how long? Eventually they would have to relent. The punishment (if they thought it would work) seems so trivial now. It would of been worth it. Imagine if I went on for months or even a year. Eventually they would of conceded.

I know that would of worked because right now I am very open about a lot of things (except nappies) such as wearing woman's clothes and they don't care. My father actually says I should "always be myself" so if that wasn't proof I don't know what is.

It's not just nappies, it's girl clothes too. I wish I had the courage and confidence as a child to wear those cute clothes that now I so wish I could fit into. I wish I wasn't such a wimp when I was younger. I cared too much about what other people thought instead of looking inwards and being me. I keep beating myself over this.

TLDR: I know it seems silly to dwell on the past about what you could of done differently but I can't help it. I missed out on two things I will never get to experience again (young cute girls clothes and baby nappies) because of my lack of confidence and self-esteem and I can't stop kicking myself over how pathetic my worrying was when I was younger. I wish I could go back and change it.

You haven't missed much, because most of your life is ahead of you and you can still get 99% of the way to doing those things. It's just that the clothes you wear will cost a little more as they will be made to fit you, and the nappies will have slightly different designs on. You did yourself a favour by resisting the urge to steal nappies, which takes real determination because the urge can be so strong. You probably saved your parents a lot of angst, by showing your rational side and demonstrating to them that you could control the urge without relying on them disciplining you. That's not a lack of confidence, just being sensible and considerate. Give yourself a pat on the back and relish the thought that adulthood has brought a new dimension of freedom for you to do many things that were not acceptable or sensible for you to do a decade ago.

Thanks for the kind words Paxe but yeah I guess so but it's not really about finding an adult version of it. I mean for example working in retail I've seen many kids come through wearing things like princess dresses and little tutus. Like I as an adult can't just go do my shopping wearing a princess dress or tutu, everyone would stare at me and think I were some creep. That's what I mean. I'm restricted from doing those things and to only doing them in my own home which sucks. Because I can't think of really a time where I would get to wear my princess dress outside that of a non-existent Halloween party I don't go to.

As for the nappies it's more just a childhood thing. I know there are adult nappies quite like that of ones I used to wear (SDK) but I didn't get to wear actually baby nappies that would of fitted me if I had got my way at like 4 or 5 years old. That's what's so saddening by it. I think we all (or most at least) wish we could fit into baby nappies again and I had a chance to when I was younger but blew it.

I still think it was lack of confidence though. If this were about being gay would your response be the same? I was being kind and considerate to shut myself into the closet? I was being respectful to allow them to tell me who I should be? I hate looking back and seeing myself all shy and shut up. I love the past few years that I have finally been set free, after nearly going insane because it was trapped inside for so long with no one to talk to about it and yes that's true I was seriously considering to do some pretty crazy stuff to get nappies like walking down to a petrol station by myself at 4 AM.

I wasn't sensible or considerate just weak, I should of had the courage to push for what I wanted and to stand up for myself and be me. Not let others push me around and mould me into what they "think" I should be.

Thanks for trying sorry I just get so angry all the time thinking about it.

Yup, it's all because a lack of personal confidence (well, maybe not "all"). If you're too worried about what others think, and you want to "fit in" or conform with general society, then, you'll always be at odd with resolving to be true to yourself.