You’re not being rude at all! If anything I’m probably the one being rude for trying to give so much unsolicited advice. I’m sorry to hear that there’s pain regardless. Discomfort (and even pain if you’re not careful) is to be expected with toys above a certain length due to the rectal bend, which could be part of it maybe?

In that case, for starters I’d recommend positions where you don’t have to flex any muscles to hold yourself up. The mental part of relaxing is definitely the biggest hurdle, so it helps to eliminate everything else so that’s the only thing you have to spend effort on. Then you work to eliminate all of the mental blocks and stresses.

As part of the preparations, put on some music or white noise, focus on breathing for a bit, any exercises that help you get into an almost meditative state. Then, tease yourself, don’t even insert anything right away but touch yourself on the outer rim of your opening. Go in circles, make your anus comfortable with the non penetrative contact. You’ll eventually get to a point where your body is PHYSICALLY craving more, but that is very unlikely to happen if you rush it.

When your body begs you to put something inside of it, start with something smaller first (well-manicured fingers, smaller “training” toys) and then work your way up once you feel like you can comfortably go up in size. Make sure it’s what your body wants and not what your brain thinks would be hot to make your body do. Stretch yourself a bit, little by little with the smaller objects; this is where fingers do a marvelous job if you’re ok putting them down there.

It usually takes a fair bit of time the first couple of sessions to get your body comfortable with the sensations from anal play.

I hope this helps! My first few times were pretty rough and advice like this is what helped me make the experience more enjoyable.

Remember with kinks: consent should include anyone involved in your scenario, even people just walking by! I’m not gonna say you can’t be risque in public, but definitely be careful. There are ways to do what you describe ethically but make sure you minimize the risk of subjecting others to a kink they did not consent to.

Going out bottomless in a skirt seems harmless enough assuming the skirt is long enough to fully cover your bits plus some.

Going into a forest and stripping down can be risky, not to say you can’t do it but try and make sure you’re well off the beaten path and do your best to make sure random people don’t actually stumble upon you. They’re just trying to enjoy their hike/walk more likely than not, and running into a naked person in the woods doesn’t exactly help.

It’s a tricky balance especially when the thrill is in the possibility of being seen/caught, but it’s important to be able to separate the fantasy of the situation from the reality. People just going about their day shouldn’t have to deal with the surprise of running into someone expressing their kinks in a public space.

Depending on where you live, be careful in outdoor areas with tall grass because there could be ticks! Of course you could get ticks even clothed but if you’re stripped down you’re practically inviting them into the crevices they prefer. I’m unfortunately speaking from experience here (luckily they weren’t a species that feeds on people but eww I’ll never fully forget that crawling feeling all over and not knowing if I got the last one off 😰).

It shouldn’t! Make sure you use enough lube (you can never have too much), try to relax as much as possible, and be very slow and patient with yourself. If you’re not already, try using your muscles to “push it out”, which counterintuitively helps it go in easier since it forces you to open up.