she tells me that the reason we cannot be intimate is because of the reminder of that day. It was the day that I broke her.
This was a quote from your first post. So, I think it is in very, very bad taste for you to make sexual "jokes" to her about having something stiff. Do you not understand that whenever you make sexual jokes that it brings everything back about that time for her?
I may be wasting my breath, I hope not. For years I tried to tell my H something he was doing sexually that I did not appreciate. It turned me off, but he just kept on doing it. Just b/c he liked it and couldn't understand why I wouldn't like it....did not change the reality that I DIDN'T LIKE IT.
So, please take heed and stop with the sexual funnies b/c it is not funny to her. I suspect anything sexual where you are concerned would not be funny for a long time. Does it mean you have no future based on your past actions? Maybe. Other behaviors in the past can change the future, but I strongly encourage you to stop with the vulgar comments to her.
It is not about what you feel should work in your M. It is about doing the work that gets the right results. Do what works!