I would say start with some small tapered plugs and play by yourself to get used to it and of course, use plenty of lube (make sure it’s the appropriate kind!). Work your way up to a dildo before the real thing. I used to feel like you and now there’s nothing more I love than doing DP with my partner and an anal toy! I still have reservations about the real thing like you (with mess etc) but working up to it!
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I have only recently started to get back into anal after traumatic experiences in my past put me off it for years. I started very very slowly with a small butt plug. It took me a week to get myself fully relaxed to get it inserted. Use lots of lube and relax and take it slow. Try it on your own for the first few times until you feel more comfortable and dont push yourself too hard too quick. I would also advise to try and insert even a very small butt plug every few days just so that your training doesnt go to waste. Hope this is of some help to you
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Fingers and tongues feel really nice
I have found that the real thing is easier to take than the over estimated sized toys I tend to pick out. My grandparents had the phrase that my eyes were bigger than my belly. I think that has since changed to my eyes are bigger than my bung hole. As everyone has already stated, go slow and lots of lube. What wasn’t mentioned is push out while being inserted.
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What does pushing out do? I’m guessing it helps to naturally open up?
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I always thought pushing out meant your muscles tightened up and forced things out rather than let anything in! 
so that’s pretty interesting to hear, we just make sure we have a clean up session before (go to the loo etc!) and then use plenty of lube and build up with a small toy, plug or finger.
Taking things slow and using a good thick lube is key to success with anal! It’s definitely not a race to the finish
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That is correct. It counters the spinters tendency to contract making things tigher than they need to be. Not an issue if things fit comfortably but if one needs to work on penetration it does help.