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Baby steps: read everything written by Lou Paget. Read Come As You Are by Emily N (amazon link) Start reading anatomy charts of the human nervous system and your partners particular reactions- using light touch, wartenberg wheel, and nails. Learn what the neurological exams doctors perform and WHY they do the things they do (I get old, cheap textbooks for things like this).

Reading a lot about the sexual response cycle and learning how to hack it- there is a normal cycle of getting more excited and less excited during sex (the technical term for it is arousal but that gets confusing). If you know what these cycles are, why they exist, and how to tweak them... you basically become a sex magician and an make other people's bodies do things and experience pleasure they've never felt before, and in my case, it makes me feel like a Sex God.

I have a few techniques that I have developed,

Some areas of the body have nerves further apart but at high sensitivity- like the sides of the ribs, down to the hipbones. So I'll do a light, random touch up and down the sides until my happy victim is purring, That means they've reached a level of neurological excitement and sort of plateaued there. Then you rake your nails down and it makes their entire body shake, and that ramps up the neurological excitement to another level- and you can then ramp up/let people cool down to get the effect you want.

Orgasm is a trained response. Nerves the fire together, wire together. So you have to train the nervous system to be able to orgasm in the first place, and then manage the neurological stimulation and excitement until the brain gets used to having multiple orgasms. Then if you do it repeatedly with high intensity of neurological activation (i.e, you have to make them come HARD- bondage helps because if your muscles are tensed beyond the normal activation point for movement it helps send the signal to the nervous system that This Is Serious and We Should Pay Attention, plus having someone begging not to come again and fighting to run away from you but BONDAGE and then give them an orgasm!) actually makes it easier to reach multiple orgasms in the future.

I also enjoy making non-genital places on people's bodies into a zone that they have been neurologically conditioned to respond to touch there as a sex thing. For instance. I have several people where I've turned the inside of their elbow into a place where they can come from me playing with it. Which means I can be out in public with them and sneakily rub that spot, it makes them all blushy and breathing hard and turned on, halfway to coming, but to anyone watching us at dinner... don't realize that I've got them halfway to having an orgasm and I'm tormenting them in public. Muahahaha.

How you do that is easy. You spend 10-15 minutes on genital stimulation. Then you go and work on the target spot (I like boobs for this) and play with them for the same amount of time. And then back and forth again. No orgasm for a long time, and keep this up. The end result is a lovely sexy trans wife who can come or gets close to cumming from me playing with her boobs.

TL;DR- mad scientist neurohacking for perverted reasons.

If your looking at cuffs is recommend something like this instead of traditional metal cuffs: https://www.amazon.com/dp/B07SWVH3BM/ref=cm_sw_r_cp_apa_i_UStpDb37FN321

Or if your feeling adventurous this:
https://www.amazon.com/dp/B07VQYTS82/ref=cm_sw_r_cp_apa_i_IVtpDbJKBXXCM

They're easier on your wrists if you want to struggle against them and it takes a little effort but you can usually remove them yourself so you won't accidentally get yourself stuck tied up to something if you drop your keys or something.

For plugs I've actually really been enjoying this one: https://www.amazon.com/dp/B008V6R2WE/ref=cm_sw_r_cp_apa_i_6YtpDbHNDTKGN

Unless you drop it on a hard surface it's pretty resilient, easy to clean, works with any kind of lube and it might be the most comfortable plug I've had.

The other stuff is hard to recommend for because a lot of cheap stuff had questionable origins and might be made with stuff that's hot healthy to expose your body to.

I will recommend that if you have the money you get a magic wand, they're very nice and it's quickly become one of my favorite toys.

I started with this four piece set, and really enjoyed them before giving them to my gf. They're a nice place to start, and then you can use that to base what you want from there.
I personally found that those are pretty firm, and I prefer much softer toys, but the best way to know what works best for you is to try.

Taking one entirely could be a bit rough for me at first. I found that when I was having trouble taking the entirety of one, starting on the next size would make it a lot easier to go back to the one I was struggling with.

As mentioned, make sure to use a lot of lube! Getting started, you can't really use too much. Also, if you ever do need more lube, make sure you use water-based lubes when using silicon toys.

Clean yourself up, get a bottle of nice lube, this thing, then slowly start with the wider end and don't stop until it starts feeling good (or you feel sharp pain, which means you overdid it and should stop for the next 3-ish days). It's also a good idea to get yourself very aroused using your penis first and then focusing only on your butt.

If you're hitting the prostate right then it should feel like you're going to pee. If you start moving the toy more intensly then that "feeling" will instead become real pee coming out so you have to clench your butt muscles while going faster and harder. This has the added benefit of making it feel better, so you should honestly keep flexing and unflexing the muscles all the time even if you don't need to keep them flexed at all times.

You can try listening to a metronome audio like this on youtube to keep rythm for the strokes.

Sorry, wanted to add something, then just ended up collating information I'd read years ago. Leaving this comment so I can find it later anyway.

Oh Joy Sex Toy did a comic about anal cleanliness, but I think it's not great advice. Most medical sources will recommend against doing full enemas like that. This vice article summarises and mentions the medical recommendation: a small amount of water. Good LGBT resources sometimes recommend using the ear bulb syringes you can buy for blocked ears. Although, different people will recommend either doing nothing or taking the head off a shower hose and putting it two inches up your butt, because that's just how sex education works I guess?

It normally gives a bit of pain when going in but once it is in it can be great.
This is the one i use. You just do the standard masturbation and it moves the butt plug giving both stimulations at once.

you can, but you'd have to make a housing for it. Or you could just buy the wand/regulator set off amazon.

no link cause It was a gift to me. nvm

https://www.amazon.com/Magic-Wand-Massager-Essentials-Controller/dp/B0089175GE/ref=pd_lpo_sbs_121_t_2?_encoding=UTF8&refRID=JPYQBSC0XS6D86WPCSGQ&th=1

basiclly it'll look like that. That's not the one I have but it's basically it

https://www.amazon.com/Womens-Bikini-Panties-Underwear-Bamboo/dp/B07DPK2W4J/

Sexy, comfortable and haven't had issues with stuff falling out.

ProTip for taking a dildo eventually, use a [lube launcher](Cleanstream XL Lubricant Launcher https://www.amazon.com/dp/B008ASBIU0/ref=cm_sw_r_cp_apa_i_LljqDb928BT66) to squirt lube inside while smothering lube outside like normal. Sometimes when going deeper you have enough at the entrance but not inside and this helps s lot.

Have fun!

https://www.amazon.com/gp/aw/d/B07K565KYB/ref=ya_aw_od_pi?ie=UTF8&psc=1

Before you buy it though, be aware that it took a bit longer for me to orgasm with a wand, but it feels so much nicer and satisfying so it's worth it imo.

here just use these and you don’t have to fuck with enemas and cleaning out

I take 3 a day and that’s usually enough to keep it clean down there for me ☺️

This is the one I got

https://www.amazon.com/dp/B00PP0E3JY?ref=ppx_pop_mob_ap_share

This made me think of Jagannath by Karin Tidbeck. Blimp and steam engine erotica ensue in the first few chapters.

https://www.amazon.com/dp/B01I6KHHKQ/ref=cm_sw_r_cp_api_i_IqIlDb5HD0BZ9

I see, so it gets a little bit easier every time... I still don't like the idea of trying again though... I mean it's the next day and my ass still hurts, not so much that I can't ignore it though.

Do you think it would be better to get a smaller vibrator instead of the glass thing that I have now?

For reference this is what went inside me last night: Prisms Devi Glass Anal Plug https://www.amazon.ca/dp/B008V6R2WE/ref=cm_sw_r_cp_apa_i_xhLsDbDHP9BTZ

This. Shit. Right. Here. Learn it. Know it. Love it. Swear by it. This shit lasted me 8 hours in the hottest, sweatiest pride parade I've ever been in. It is goddamn sticky magic.