My wife and I have a good sex life. We are fairly adventurous, but have stayed away from toys for the most part. During oral we both enjoy receiving and giving rim jobs and this has peaked my interest about toys and anal play. I ordered the fun factory bootie ring and would like to expand into anal play for both of us using plugs.
We tried anal a while ago young and dumb quick and no lube and it has scarred her from trying again. Any advice for getting her into anal play with me?
I hope this isn’t too blunt, but if you put her in a lot of pain in the past (anal with no lube sounds horrendous to me) it may be that you need to work on getting her to trust you again in that area. I don’t know how you handled the aftermath of that incident of course, but what I would recommend is talking through it, reassuring her again (and again) that you are genuinely sorry for the pain you caused her back then. Make sure she knows that you care about her safety, that you have learned and matured since then, and that something like that will never happen again. You can also show her these things in daily life. A general high level of trust and comfort between you will help foster the confidence to try new things (although I assume it’s already quite good since you say you have a good and adventurous sex life).
Of course don’t pressure her. If she doesn’t want to, she doesn’t want to. However, if she’s interested but scared, start easy. Try the plug on yourself first so she can see it’s not that bad. Get the smallest plug you can for her, or maybe let her pick out the one she thinks is prettiest to excite her. Get her warmed up and aroused before you start suggesting things. Make sure she feels safe and relaxed. And if/when she’s ready, use tons of lube, more than necessary at first, to give her an easy start.
Another thing you can do to build up is to just slip a finger in (if she agrees of course). Make sure your nails are trimmed and smooth, and use a disposable glove (glides easier and a good way to check if it’s clean), of course with lube. It will start loosening up there and make it easy to slip in a lubed up plug, and eventually maybe even bigger things. Although one thing at a time. If she’s genuinely scarred, stick to baby steps, go slow, and constantly reassure her that you’re looking after her (and do so of course). Good luck.
I approached it by using plugs on myself first and when she saw that it was not painful or messy she was happy to try (initially) a small vibrating plug. She found that she quite enjoyed the feeling and it enhanced her orgasms significantly so she became comfortable with the idea of anal play and , eventually, full anal sex.
If she’s been scared off from an unpleasant experience then the best way to try encourage her is for now focus on your own joys of anal play and in time from seeing how much fun your having, she may be more intrigued to try it on herself again 
@Mr_and_Mrs_new_2_toys myself and Mr John had a similar no prep go at anal in the beginning of our relationship @nordgirl I never blamed him for “hurting me” it hurt but was 100% consensual, we just didn’t know what prep was needed. My mistake as much as his.
Having said that when we tried again years later he did lots of research into how to achieve anal that we BOTH wanted. That made me relax
Thank you for the advice. It was 12 years ago when we were dating and when she said no we shut it completely down. She has been to toy parties where they talk it up and has been very shy at trying it again. I ordered a toy for me and plan on using it like you said, letting her play with me first and see how things progressed. Thank you for you honesty and advice.
@Mrs.John thank you! This makes me feel better as this really is our situation. I have been doing more research and even playing with myself to see how to work up to it. I want her to be a part of my pleasure and at the same time hope she will open back up to giving it another go.
@Mr_and_Mrs_new_2_toys I’m glad my sharing our experience has helped. I’d be truly devastated if I thought my Husband blamed himself in any way.
When you are young and full of hormones you don’t always do your homework is the way I look at it.
I first tried with an ex with no prep… ow. But as @Mrs.John said, I never blamed him for it (it was probably my idea!)
Hubby was told about this, and when he raised he’d like to try I was apprehensive, but we did SO MUCH reading around the subject it put me at ease and made us so much more prepared. The first time we successfully had anal I wished I’d tried it again earlier!
So I’d carry on testing on yourself, and talk talk talk with her and read everything you can get your hands on!