So im hoping to get some help on this! Iv tryed this a few times and its always painful but iv heard from many people it can be really enjoyable!
I suppose im always concern that where it is i dont want to do damage and equally i dont want to shit myself either so i can never fully relax
any help and advise would be great please and thank you!
Start off small, use lots of lubrication and practice.
It takes time and patience to stretch the sphincter muscles so that anal penetration is easy and comfortable.
Also it may take a few times to learn to relax . Everybody finds their own system of making the experience less messy . I generally wait until after evacuation . I tried anal douche and found it actually made things messier . Even though I have been into anal play for many years , I almost always start off with a basic tee plug and use plenty of water based lube . They are very tapered and go in easy and pre lube before larger toys .
Start off with a small butt plug and plenty of lube. Relax and don’t put pressure on yourself to get it in. Gently push it in. Stop if it starts to hurt, pull out and lube up again. You can never have enough lube. Once you have it in relax and stand up, walk about , hold it in place if you need to or just lie down and have a moment. Now gently pull it out a bit and then push it back in. Try this a few times and get used to the feeling of movement in your bum. If you have got this far then you are well on the way to enjoying anal.
Once you are comfortably taking this small butt plug go up a size. And repeat the above.
Prep is always a good start! Douche yourself out beforehand and then let settle for 30mins-1hour before play 
Then during play, plenty of lube, start off small and then work up. Some people find sniffing poppers helps them to relax better, others have a warm bath or shower.
My wife and I have been working our way up to this for a long time. She is also very hesitant about anal and says she’s not interested. But in the heat of the moment her body language says different. She loves her ass eaten and I can tell then how relaxed she is. I’ll begin to rub her opening with a finger and some lube and I really let her be in a position where she can press down on my finger to allow her to control the pressure. I always let her know how hot she is and how good it feels during. This is as far as we are but I’ve seen signs that she’s interested in trying my dick soon!
@The_lady_in_pink
Anal can be very enjoyable but also painful if you do not get it right
Start with small thin toys and relax - never force push the toy and if you are using the real thing (a man) ask him to take it slow and as others say lube is essential
It takes ages to get real pleasure- and you need patience- but it’s worth it in the end
As others have said, it needs to be taken slowly and copious amounts of lube are needed.
If you are not relaxed then the chances are it will be painful, and not very fulfilling.
Start either with fingers or a small butt plug and build up, do not try to force it in, but relax and slowly ease it in, it shouldn’t feel unpleasant or uncomfortable, if it does, then stop.
I am sure with patience you will get there.
You should really be exploring yourself with fingers anal beads plugs and dildos before you let anyone else, helps you find out what you like. Plenty of Lube start off small relax and enjoy. Few times by yourself and you will be hungry to try it again.