Well I am glad my conversation with Jim is over at least for now. Jim and I have not had a serious conversation in years with our relationship having gone so well. He had not seen the serious side of me in quite some time so he knew something was up. When we left the dinner table I had already said I wanted to talk to him in the spare bedroom setting the tone.
As you recall Helga Jim's boxes were in basement so in his mind there was nothing serious about our spare bedroom until he saw the boxes on the bed. I asked Jim if he wanted to tell me about the boxes or did he want me to show him what was in the boxes. Jim started to apologize for what he had done when I was looking for the apology on the fact he was doing something behind my back. The clothes in the boxes were not the big deal to me.
He finally figured out apologizing about the wearing of the clothes wasn't my issue which is when he told me he had deceived me and violated my trust. I let him stew on on for a few minutes so as not to let him off the hook so easy in case he ever tried something behind my back again. I told Jim to sit beside when I took his hand to comfort him for getting caught and hiding something behind my back. It was then I talked to Jim about accepting him buying and wearing women's clothing to his surprise. I wasn't finished when I told Jim I not only was going to accept him wearing his lovely clothes but I was going ensure he wore them all the time.
Jim looked at me when I said to him he would start calling me his Mistress and I would call him my sissymaid. He wasn't sure what all that meant until I spelled it out and insisted he model some of of clothes for me right then and there. The begging started to go along with a few tears however I wanted to see Jim look pretty for me not just the walls in the basement. I made him stand up and take off his clothes telling him I wanted to see how pretty he can be. Jim tried to stall hoping I was not serious however after watching the video of him oh yes I wanted to see him live in his little dress.
Jim finally showed me his other side with me applauding his appearance surprising him. Helga I do think Jim was scared I was going kick him out and scream and yell at him. I took his hand as we walked to the family room then sat down to talk with me checking him out. Without me being an expert on the subject I began to tell Jim as my sissymaid I expected him to wear his pretty clothes every day including some I hadn't purchased yet. I showed Jim a few sissymaids on my laptop letting him know he too was going be wearing sissy dresses just like the pictures.
Jim didn't fight me on anything I said probably due to my tone and his fear or what else I might do. I told Jim how much I loved him and how much I wanted help him with becoming more feminine. Playing Mr Dress up once a week just didn't make sense when he was going to be able to dress pretty for me every day. Oh he tried to talk me out of it letting me know he only dressed up once in a while etc. Helga I am no fool so why would he try giving me a BS line when I caught him.
I remained calm talking to Jim about how life was going to change and how he would become my live in maid. The real work was going to start tomorrow since I was tired of talking. I sent Jim to model his new nighties for me so I could pick one and get him used to me telling him what to wear.
Helga I am alright with how it went down and yes maybe I should have said something else to Jim. We have the rest of our lives to work in mine and his new roles. What do sense from what went down?
Thank you for your letter Andrea. I am so happy for you to have this resolved, we discussed your shock and surprise at the discoveries and now you have turned his fetish to your advantage, really well done.
Thank you as well for the details of your conversation, I really enjoyed reading it. I think you pretty well covered the options for him and now he can relax and be himself. As you said, you have your lives to live these new roles, as he becomes more submissive you become more dominant, its only a natural response, you become the Mistress, and frankly, its pretty easy to get used to be waited on hand and foot by your sissymaid husband. I suggest you take some time and read through some of the letters at my site to get some ideas. I am also here to help if need be or you just want to talk.