@carzy: replying here as I’m sincerely trying to do better at not derailing threads 
We have actually played & she used a plug in me. It got awkward because I wasn’t as experienced as I thought I was and it got painful.
She was feeling kinda nervous about it anyway and it kinda crashed. Not to the point of “never gonna try this again” but at least for that session.
That was a few years ago. Since then I’ve gotten a lot more into self anal play and ordered several toys in the past few months.
Bought a beginner pegging strap on set that was on sale for valentine’s day.
Been practicing with the larger of the two dildos both anally & orally (if she decides to get super kinky)
Can take the toy pretty decently if I do a warm up session before hand. Orally I can proudly deep throat it all the way. My first oral success and it was just a few weeks ago. Nowhere near able to take thrusting orally though. But I imagine an awkward look on her face when I’m the one showing her how to deep throat 
Since we’re done anal play before, and she didn’t exit the room screaming, I’m thinking I can approach the subject again and maybe eventually get pegging on her ‘ok’ list.
Currently it’s not on either her yes or no list