Dear Auntie Helga,
My wife's mother passed away a couple of years ago so my wife kept most of her clothes in the spare room in the basement. I remember when she was alive and I used to help her clean up after cooking or baking. My mother in law always insisted I wear one of her many aprons while helping so it was a normal thing for me. Since my mother in law passed I miss her in so many ways but one is the time we spent in the kitchen together joking around. One day I went into the spare room to get one of her aprons. My wife caught me with it on but it was no big deal. In fact she told me if I wanted to wear it more to help myself as her mom would have loved it. I also tried on a few of her dresses one afternoon and most fit me.
My question for you Auntie Helga is there a difference between a sissy wife and a sissy maid? I don't care for the pink sissy dresses I see on the internet but I would wear my mother in laws dresses and aprons if my wife approved. Is it possible for me to be my wife's wife in that I would only wear dresses and high heels like my mother in law?
If you think it's possible do you think my wife would be angry if I wanted to wear her mother's dresses? Would you be offended since that is not what I want to do? Sooner or later my wife will give all the clothes from her mother to Goodwill so I want to keep them instead.
What are your thoughts?
Thank you for your letter Randy. Condolences to you both for your loss, but I would tread very carefully here, not that there's anything wrong with being her sissy wife or sissy maid, but that you would be wearing her mother's clothes, she may be fine with it, but be delicate and sensitive on this aspect. Like most situations of this nature, delicate... honest conversation is the best way to proceed, I assume you know when during the day when she is most receptive to talking. I suppose wearing your mother in law's clothes could be considered a way to honor her memory.