Like peeing immediately after sex to avoid a UTI, it's good to go to the bathroom right after you're done. I'd do it again as a "special occasion" thing, like on our anniversary, or Flag Day. Necessity is the mother of invention.
Keep It Clean! Silicone-based lubricants are a great choice for anal play, as they will stay slick and not dry out like water based lubricants.
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If you hate it, you hate it, and that is fine.
Changing gloves is easy anytime you want to switch between touching the anus and then genitals or return to full body touch. Some people like to shave, wax or otherwise remove hair around their anus. You can tear your anus if you use a certain position that allows for more penetration before you're ready, and Taormino points out that the missionary position allows for the least clitoral stimulation and suggests receiver-on-top for beginners.
External and internal anal massage can be highly arousing, without a moment of discomfort. If all these things are good to go, and you just don't like the sensation, you'll know pretty fast.
The thing about every single roller roaster ride I've been on so far is that I've loved them all. You can use nitrile or latex gloves for quick and easy clean-up, so your hands can keep moving without a break to wash your hands. Throw other stimulation into the mix.
Never use an enema with vinegar or other harsh ingredients. They're not farts, no matter what anyone says. The thing about every single roller roaster ride I've been on so far is that I've loved them all.