Long winded first post: The [M/F] wife and I have had many conversations over the years regarding anal play of both sides. My question is a double edged sword kind of...

Part 1: She has kinda been wishy-washy when it comes to anal on her end. I've performed foreplay as well as had sex (mainly doggy) and included a finger or a thumb a few times in her rear. She has moaned and groaned hard and even cum harder than typical. During straight up conversations she's said she has no interest in exploring anal (poo factor, I've pieced together), we have straight up tried one time very long ago(to tight, not enough lube?) however a while back we made a bet if she wins she gets to choose, if I win I get an honest try at anal.(@ her suggestion) (Damned if I didn't lose) I've jokingly brought the contest up but haven't made any headway.

I have expressed my interest in anal play on myself and even bought toys. I've been playing around with prostate play for quite a while (to her knowledge). She has given me head and slipped a finger in (been a long time, I think even before prostate play was brought up) and given me an incredible orgasm of a lifetime 2 times in a decade. We've spoke about pegging(interest shown), even bought a harness but never acted upon. I've included a plug a few times while soft playing (hj and once during BJ) and during sex a couple of times (x2?).

I'm wondering if anyone has any suggestions on either topic on how to move forward with either side? We have had many discussions, including past experiences/fantasies/hot wife she has opened up but, is definitely a one man band so to speak.

5/23 - updates, & progress

We have continued conversations as mentioned above previously. I have lightly poked at the idea of trying anal again a few times periodically. She has not completely come out and said yes let do it but has hinted she was more open-minded recently.

During recent foreplay and a couple oral sessions, I lightly rubbed on her and asked her if it was OK to which she excitedly moaned um hmm. The second one I included tip of finger penetration and asked again if it was OK, she again moaned her approval. I also have included rubbing a thumb while in doggy again asking for approval and receiving the ok!

She definitely reacted to each time and seemed to have orgasmed harder than typical. When brought up afterwards I asked if she enjoyed it and she said yes but she thinks she was overwhelmed by vaginal care that she didn't really notice it?

We have not yet included actual full penetration of any kind.

Last week we were conversing and she had to go somewhere. I said something about wanting her ass (not litterally) and just as she was getting ready to walk out she said "you know I should have said something the other day, because I was kinda in the mood". :-o I was stunned and couldn't say anything because of her leaving also. I waited until the next day and asked what she meant, as I was under the impression that, that was a no-go-zone. She said no but I have to be in the right mood (totally get it), and I was the other night.

She couldn't recall the night (too bad for me because I'd be trying everything foreplay wise I did leading up to lol) But she had a brief moment where she got turned on thinking about it but she was just too shy to say it. I told her next time to let me know, even if we don't go all the way we can still play and try other things so see how you react to it. It's not something that happens instantaneously and can be worked up to. So we have some progress here!!

She has also initiated toy insertion (prostate massager) on me a few times now as well!

Thought I'd post an update for all!