Hi guys - i’m bi (and a guy haha) and i’m looking to have anal sex for the first time. Any suggestions on what I can do to prepare myself? Any toys I could try that will help me prepare? FYI - i’ve tried it before and it hurt pretty bad and I stopped. That was several years ago.
Thanks for your help! - Will
What you can do is buy a buttplug training kit and a good quality lube.
Start put a nice amount of lube on your finger and on your bum. First finger yourself slowly making circles to relax anus, when you are relax try to add another finger or try the smallest plug, go really slow if it hurts it means your going to fast.
When the smallest plug fits easily try the next size until your on the desired size.
Always go slow and use enough lube, If you think your using enough lube add a little more 
Dont be in a rush. Take it really slow. I like a finger or small butt plug first. Im female so my experience will be slightly different obviously but i tend to play with my clit especially during entry so maybe masturbating at this point would be good for you.
Number one rule above all of this is lube, lube and more lube and when you think theres enough, add a bit more for good measure!!
Go to the loo before you do any anal play. Some people douch as well.
Defintly google anal training and get your self some butt plugs of incremental sizes. You can buy a set, but sometimes the size differences between the plugs might be really big. 1” circumference more when going up is really max (i went up in 0.5” as it was more comfy for me). 3.5” circumference is a good size to start with.
The sizes you want to be reading on the toy listings are the circumference and the length. Both effect how intense a toy will feel. As does the material (start with silicone).
Get a good quality anal lube and dont be afraid to use it. (I like sliquid sassy). Wetter is definitely better.
If you havent tried anal before, theres a ton of good info on here if you have a search. (Search bar is top right.) heres one that might help.
Most anal toys would be useful in warming up before intercourse especially if you try them out an hour before hand to get loosened up. Buttplugs, dildos, massagers… lovehoney even has some anal starter kits too!
On the lube side of things, you wanna make sure to have plenty for a smooth entry and there are some specialist brands what can help relax the muscles down there too, such as ‘Backdoor’ lube.
I’m sure you already know about the cleaning out side of things so won’t go into that 
Personal I bought a starter kit and found it not a challenge, I would suggest the lovehoney beginners butt plug and see how that goes.
I find a good start Is to make sure your nice and relaxed. Get yourself into a comfy position and get yourself aroused through porn or your imagination if doing it solo.
Then pick a small butt plug and apply lots of lube. I think lube is the key, you want a good thick lube that doesn’t dry up easy. Once you can comfortably use a small butt plug then pick a next size up or a different material plug. You could adventure out a bit and try anal beads or a small dildo. If you experience pain, slow down or stop.
When I have anal sex with my partner because he is on the larger side I have to repeat them steps every time. Well I get him to do it for me as that makes me much more aroused. With previous partners around average length, I have never needed to. don’t feel like you can’t ask the person your engaging anal sex with to warm you up before hand as it definitely can ease the pain and it makes great foreplay 
I personally don’t douche before hand as I don’t like it but I make sure I go to the toilet and have a good shower to make sure I’m all fresh and clean. Accidents will happen though and if your playing around with anal then it’s expected at times so nothing to be embarrassed about there.
Good luck and enjoy!