Yes it was hard to get my wife to use toys for me anally. I started by getting some small glass toys that were non-phallic. They are 'non threatening' and didn't suggest that I may be gay. Once she experienced how explosive my orgasms are with anal stimulation - it got easier - because she always felt a little guilty about how many orgasms she had vs. my one-and-done. This gave her a chance to 'reciprocate' in a way.
Once we got started it got easier to introduce new and larger toys. She did eventually try pegging - but doesn't like the idea - so no more of that.
For what it's worth - when my wife was in her 30s, I doubt I would have had any success. Even she refers to her 30s as 'the drought' - she blames it on the kids. Whatever - at least once she reached her 40s, things have gotten much better.