Because we're trained not to wet ourselves from a very early age, with the potential consequences including social exclusion, being mocked, bullied and other terrible things. This is no small thing as the humiliation of getting caught could be truly devastating.
Even if you have no trouble using your diaper in some situations, others can be tricky. Some commonly cited "problem" settings include peeing while sitting in bed, riding in/driving a car, talking to someone IRL or in busy public settings like stores or a classroom. You likely have a subconscious fear of the diaper leaking and being caught wetting your pants, which can be a legit fear if you choose the wrong diaper. You may also find that mechanical factors play a role, such as which way your urethral opening is pointed. (Men often find it harder to wet while sitting down, likely because they're used to peeing while standing in everyday life).
Whatever the reasons for your urinary reluctance, it can be overcome with enough time and effort.
Some Things to Try
Try spreading your legs for a more "open" urethra.
The best remedy for this is
practice. First, make sure you really need to urinate. You can achieve this by filling your bladder with plain water or water plus a diuretic like caffeine. In the beginning it's okay to give a little "push" or bear down slightly to get your stream started. You shouldn't do this often as it's bad for your urinary tract, but once or twice won't hurt. As you get more comfortable wetting in your challenging setting, replace this tactic with deep rhythmic breathing and/or closing your eyes and envisioning a babbling brook/stream. (If your setting is in private, put on an actual audio recording of water running,
someone peeing or similar. Or listen through headphones if possible). Spread your legs if possible as this tends to help mechanically, and if you're a male, make sure your penis is not squished under your body or in a too-tight diaper.
As I've stated before, the pudendal nerve can help trigger urinary release for some people. To stimulate it, gently run your fingernails or fingers over that indented spot at the top of your butt crack. If it works, you'll find yourself needing to pee much more urgently. If you're at home and have the privacy, watching Omorashi or wetting videos can greatly help you get in that headspace.
Quietly giving yourself "permission" to wet your diaper can also help. If you had an overbearing parent or teacher, pretend to be that person & tell yourself from their POV that
"It's okay, just let go. That's what diapers are for" or similar. You may also find
diaper-wetting hypnotism recordings helpful. Listen to these in your chosen setting or while falling asleep at night to gradually help your mind relax.
Some Things to Avoid
Oops! The fear of THIS happening is a big mental barrier for many diaper wearers.Try not to get frustrated, as this only makes it harder to achieve the necessary relaxation level. Instead, turn it into a game or a fun challenge. (Like, yay! Another excuse to wet my diaper). Rather than focusing on what's going on in your pants, try distracting yourself with other things like mentally singing "100 Bottles of Beer" or playing "I Spy". Or maybe try & think of as many yellow objects as possible. Scroll around on your phone, do some homework or whatever will help you take your mind off the goal of pissing yourself. Eventually if you don't go to the toilet you'll
have to let go in your diaper, so resolve not to get up to go to the bathroom to pee.
No matter where your challenging setting is located, practice wetting your chosen diaper brand & design at home in private before venturing out in public. Wear it all day and see how much pee it'll hold by using it over and over until it leaks. (For those worried about diaper rash: You only have to do this
once if you take good notes). This will either expose flaws with your diaper choice or give you the extra confidence to let go in any scenario. Trying on different pants/bottoms with your diaper can also increase confidence, as it will let you know whether it's visible from the outside or causes a noticeable "pooch."
The goal should be getting totally comfortable wearing & using a diaper, which means you'll need to do it as often as possible--preferably 24/7 for a while--so it doesn't feel as alien. After you've achieved your goal, don't stop there--plan to try & wet in that setting again soon or somewhere even more challenging. This will ensure you don't lose the "skills" you've acquired.
Above all, just know that it's perfectly normal not to be able to wet your diaper everywhere right away. Potty training took a long time, and so will undoing the mental & physical conditioning that came with it.
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