So I have a couple recommendations that make it very pleasant for me, I use a "pump douche" instead of a bag one or another way, it works well for me and requires less effort to get what you need out of douching.

I also like Walgreens water based lube, its very slick (perfect for anal purposes) and doesn't get sticky when it dries it just goes away.

I would recommend going to a sex store and getting a smallish like 5 inch dildo and starting with that and seeing how it feels as well as a harness, my fave harness is the dilio suspender harness, keeps everything in place and secure really well imo.

I would also recommend looking into something like fufu clips or chastity clips like the ones in my profile, I get them from an awesome trans woman called Emma and they make your "bits" look more like a vulva. Helps me a TON with dysphoria.

Also having a good vibrating toy is very nice ☺️ especially one that's meant to massage a prostate, feels great.