Help.

[restricted]

Hmmm. I don't kow what section to put this in so I thought I would start here.
I am going out with a woman who lost her husband three years agio. (I lost my wife six years ago). We have met a few times although mostly it is via the internet. I have taken her to the hospital as she has got breast cancer. I also look after her while I stay at her place in seperate rooms. We get on extremely well.

She loves my cross dressing and we have joked that she should get some fluffy handcuffs. I would like to share her bed even just for the warmth of another body. However, I have fiound a chastity cage that covers all the genitalia and is fastened with two locks.

I am thinking of getting one and letting her cross dress me from naked except for the chastity cage. That way she would have the fun of dressing me to her standards and knowing she has me locked away for her safety until she thinks it. What would you do? Go for it, or drop it?

[Kinbaku]

Go for it, or drop it?

As I understand it, you understand each other well.
Then you may be able to take the next step, but first discuss it with each other so that you know each other's limits of what is possible and what is not possible.

It is better to have everything clear in advance than to notice afterwards that one of the two does not like it anymore.

[Lotharjulz]

...

[Riddle]

I am also confused about what help we can provide. Given the circumstances as I understand them, I would ask her what she would like and what conditions she needs for it to happen. I would also suggest that fuzzy handcuffs are a hard limit for me and discuss other options that are within my comfort zone.

Hoping things go well for you.

[restricted]

Thank you. I will take my time and let her laugh at me trying to be presentable as a female and let her suggest she gives me a makeover to improve the look.