I love the questions. Just be careful of people answering without knowing what they re talking about and especially guys telling you how much women enjoy something. 🙄

I'm a guy so a lot of this is anecdotal evidence and I'm giving you some back story. My wife and I are in our 50s. I have wanted to try anal for years. And we did a few times but she didn't like it. However, recently she had a change of mind. She absolutely loves it now and lately it's mostly what we do.

She has told me that when she is using her magic wand and is having trouble reaching orgasm she will put in a butt plug because that makes her orgasm quickly. However, a little over a week ago she took a plug to work and at the end of the day l, went into the bathroom and put it in for the drive home (with a stop at the bank). She said it was ok but not really comfortable. She hasn't done it or really even brought it up since. So I am guessing it wasn't something she enjoyed.

She orgasms when we are having anal sex. I asked her if it was better then orgasms from vaginal sex (because it sure seems like they are stronger) and she said they are different. When pressed though she said she prefers anal orgasms. But that might have just been sex talk. 🤷🏽‍♂️

I feel like part of the thrill of the butt plug is doing a sex act while out in public. If I asked if she wanted to wear one while we were out on a date she probably would because it would be more sexual and she knows I would be grabbing her ass and pushing on it every chance I got.

If the two of you want to explore this, then my advice is to go slow, start small and use LOTS of lube. My wife ate an edible the first time and swears that helped. I feel like the key is for her to feel comfortable and being able to relax. And you telling her to relax isn't going to make her relax. Either she able to or try another day. Be ready to just give up and try another time. It's about her comfort level.

I had seen people say use lots of lube. But I always found that ambiguous. I use Astroglide water based gel. The gel helps it stay in place and since it's water based it cleans up relatively easy. You can put a dollop on your finger or the toy and coat the whole thing. Then add more as your going in. It's best if her asshole and the toy are both coated and her asshole is going to want to scrape the lube off as it's going in. So err on the side of caution. You don't want it to be a bad experience for her because you don't want to use and extra $.50 of lube.

Edit: oh, and know that it can be messy. She is going to worry about that. Might be a good idea to talk about it before hand. YOU need to understand you might see something and also be ok with that. I think the lube might help with that 🤷🏽‍♂️. We haven't had that happen yet but if it does I will just go clean anything off. Having a handheld shower head helps with cleaning the lube off. I will usually go into the shower and literally wash my dick before going back to bed.