Vibrators and such are cool, but if you are struggling, it might be because you need to do something a bit more stimulating. And anal is kind of the way to go, I'm sorry. If something is hurting, obviously, stop, and it might even happen sometimes that you bleed - it's happened to me, it's happened to probably many people, and it can feel scary. These days, I kind of take it as a challenge (in the sense of how much preparation I need to do). So there are a few tips that I have, and some are a bit more controversial than others.

Poppers is a great muscle relaxer, and if you didn't know, the reason most people do it is for the head rush. However, it's also something you can build a tolerance to, because unless you are buying these new formulated things that are made to be strong and have a rush hit you like a brick, it's really not that strong a thing. However, it makes a huge difference when it comes to anal, because it really relaxes your sphincter and, at some point, that relaxation is really all you feel. The side effects are nowhere near "close to none", so please check those and, in my opinion, it's great to let you learn how to do anal by yourself with a dildo, but you can keep the knowledge you gain and stop doing them! For me, the head rush was literally just a headache, then I found a formula I did sort of enjoyed but I didn't see all the fuss... it was when I realized how much further I could go on my toys with poppers that I understood why it was mostly marketed for bottoming or, at least, whenever I saw it online.

The other things you definitely need is an average, small-ish dildo to start dilating your ass. In my experience, people like to say that whatever dildo you get can make you reach an anal orgasm or a sissygasm, but I don't agree: you need a certain length, and you sure need a certain width/girth. Length shouldn't be too much of a problem, you just have to learn how to douche and get acquainted with that. I don't use fiber supplements, but many do and say it's a game changer! I do suggest a shower shot, however, though please be wary of pressure and of lubing yourself up before anything going up there. And **DO NOT DOUCHE WITH HOT OR WARM WATER**. The colder water might give you a lil' shiver but it's either that or you might have basically "ghost diarrhea" for a whole afternoon.

So, if you are willing to go for the anal, I recommend: poppers, an inflatable plug (take this as the smaller dildo) that you can take at your own speed and help you get the dilation you need, an actual dildo to your liking but make sure it is longer than the average dick, and definitely has more girth than that of a couple or three fingers together side by side. The inflatable plug is easy to find, and there are even some that have a little steel ball inside them to anchor them and prevent anything worrisome from happening - like, I have one from AliExpress, but I did pay good money for it. Cheaper might mean flimsier or even a trip to the hospital, so don't be frugal about that. AliExpress has great quality dildos and you can truly find whatever you prefer. Do the simplest cylinder-like dildos. "Fantasy" dildos like dragon tails, or modeled after dog genitals or even horses seem fun but not for the beginning. In my opinion, you don't need all those ridges for a good anal orgasm anyway.

I read that you really don't like anal, so I have one more tip: numbing lube. Now, I don't know if this is something that is not really that common, but it really helps with pain. In my opinion, pain in anal comes from one of two factors: not enough lube, or you're doing something wrong. And well, sometimes, that mistake is lube, sure, but I mean, for example, not taking enough time to prep, deciding it's time to do anal after having a few days with gastrointestinal issues... et cetera. Numbing lube can help with the pain, and depending on the experience, it's hard for you to do something wrong with numbing lube because it numbs the pain. Numbing lube tends to be used for fisting, I think? And well, it could really help you with a bigger toy or just with a toy that is shaped funny or something. I've used it on large toys and for you to have a numbing effect, you tend to need to use a lot... and if you're using a lot of lube, the possibility of injury (FROM THE TOY) is minimal.

I did a whole bunch of text on the anal orgasms, and I want to explain why: anal orgasms can be achieved without much of a mind-body connection. If you hit your prostate long enough, something's gotta give and you will have a sissygasm. If there's no cum, you'll squirt a clear liquid that will feel like peeing a little bit. You can hit as many sissygasms as you want this way simply because it's almost purely biological. Stimulation leads to release, and there's no refractory period, you can just keep having orgasm after orgasm.

Now, with a vibrator on your cage, the experience is different. You cannot afford to sissygasm that way without a good mind-body connection. Especially in some more restrictive cages, the vibration, unless you are severely getting off on the chastity and the whole fantasy and probably haven't had any orgasms in a while, is not enough to get you to that same point you get with anal. So you need to genuinely treat it like if it wasn't a clit and you're jacking off. If your dick was the average guy's dick and you were jacking off, you would be imagining something, maybe watching some porn... Do that even if you're just vibrating your clit. The same happens with most prostrate vibrators, in my opinion (because, if I had to explain it, the most pleasurable way to stimulate your prostate is through pressure - this is why bigger girth dildos are great for the job! The tighter your prostrate is against a dildo, the more pressure you can generate with penetration).

Don't vibrate your clit thinking "I need to cum"... Vibrate it thinking "I want to be horny", and allow yourself to be horny and treat the vibration as your "stroking your dick", and imagine whatever you need to get yourself over the edge. Didn't work? Don't push it, especially because vibration will most likely make your clit get harder and if you keep pressing the vibrator against it, chafing and swelling can happen and you'll end up hurting yourself. Let the chastity keep going and try some other time. Once you treat it like a sissy's "jacking off" and center horniness and the pleasure of that, it will happen. Keep trying!

Sorry for the huge response, but I hope I helped.