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Butt plug for sure.
For starters, maybe an hour before you try butt stuff, go and take a poop. Your body self cleans down there after some time.
1. Start with something small, like fingers, than a but small butt plug (you can buy a training kit, smaller to bigger) and from there you can get bigger, longer ones.
2. You can never have too much lube. If you thing you used enough, put more.
3. Sanitary wipes are good to have around. You are playing with your butt, shit happens.
4. Again, shit happens, lay down a towel or small blanket under. Makes life easier in case something falls out or a small accident.
5. Go slow and communicate if you feel pinch or pain. Do not pull back if there is any pain. Just stop and wait, if you feel OK moving forward do so but do not force things.
6. Any object you use should have a flange or edge to prevent it from going up and getting lost. You do not want to know how often my nurse friends tell me stories of what they “find” up there.
Optional rule. Putting a condom over a plug or object makes for easy clean up and if not an official butt toy will prevent many issues.
7. Aftercare. Once everything is done it can be an emotional experience for you both. Lay back hold each other and talk about how you both felt, what was good, bad and what you want to try or not.
I am sure I am missing something. Consider reading the section on anal at badgirlsbible.com
The key is to relax your muscles while it’s doing it. If she tightens/squeeze her asshole, it hurt. If she smokes, then I suggest hitting the 🍃 beforehand to relax. Lube will also be your best friend, makes it wet wet. So, relax them muscles and continue with the lube. Also, like they stated above she can start off with butt plugs till she gets comfortable.
Get her wet go in slow and rub her front while you doing it