How I helped my wife overcome her insecurities so she could follow through with being shared

So when I first met my wife, ex-wife now, she was a bit insecure.
She had trust issues from past relationships.

So when we started talking about having a three way she was exited.
She even picked which friend of ours she felt fit us better.

She was ok with how I intended to slowly break it to him by putting naked pictures of her on the desktop of my computer and letting the screen saver turn on, then later that night while he and I were in the computer room I would get something from the shelf over the computer and bump the mouse turning off the screen saver revealing her naked. I made sure I stayed preoccupied with my shelf quest long enough for him to study the pictures thoroughly. Then when I pretended to notice my mistake it opened the door to look at all my collection. Well a lot because I had tons of naughty pictures of her from years earlier to present.

That became a regular thing from then on, even though for a while I pretended she knew nothing about me showing her pictures.
I even started letting him make copies of his favorite pictures to take home.
She not only was aware of all this stuff we would actually plan it ahead of time.

After we had done the picture reveal and even went as far as to flash him her boobs in person and even asked him of his interest in having a three way, which he was very into, it seemed to still stall out consistently right at the start line.
I thought I was covering all the bases but we just couldn't quit get it to actually happen.

After a few months of confusing missed opportunities my wife revealed to me she was the reason we couldn't get it started. She then opened up about not wanting to do it because she was afraid I would want to use her experience to turn around and have a valid reason to be with another woman.

Not that I had ever done anything to ever make her think I would ever be unfaithful but she needed extra reassurance.
So, after hours of deliberation by myself, at the kitchen table, I realized what may do it for her.
My intention wasn't to just get her to go through with it. I truly wanted her to feel comfortable enough to embrace the experience that we were not only going to do for the first time but make it a regular thing right out of the gate.

Now I know that last line may have been a curve ball.
So when we first started talking about doing a three way with our friend, she said she would try it.
I told her that I didn't want to try it I wanted to start doing it. If it was a hot fantasy then it would be an even better reality so there was no sense in trying it without commitment to it. Our history was on my side with that.
So while she slept, I got some paper and wrote her a permission slip.
It started out just a few lines detailing our adventure and that I in no way would ever attempt to use her participation in this as a lever to attempt to make it ok for me to be with another woman.
As I wrote I found that it was getting crazy hot writing her a permission slip for naughty sex.
So I would start again only adding more details to specifically cover what acts she was allowed to explore during our new sex life.

I hate that part about her being "allowed", it was never my intention to have any say in what she could do. I just am wanting to get this out and couldn't think of a better way to say it.

So by the time she woke up the next morning I had drafted a very detailed, legal looking, permission slip for her to engage in a threesome with our friend and that it was all my idea and some examples of acts she was encouraged to do and so very much more.

I really found a lot of pleasure in writing that for her. I actually found a bunch of reasons for, probably the first year, to write her more and more permission slips each becoming more detailed in the freedom she was to feel as things escalated.

It ended up being the thing she needed to allow her to follow through with the three way and later so very much more.