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It was 15 years into our marriage before Glen confided into me his desire to become a sissy. At first I was horrified. How could he keep a secret from me all those years! My first thought was that maybe Glen was gay and had been living a lie all these years. I was really angry and thought it spelt the end of our marriage. I told him to get out of the house immediately. That night I visited my dearest girlfriend Amy and confided in her the whole story. Over a bottle of wine Amy managed to convince me that perhaps this was the best thing that could ever happen to our marriage. Rather than dump Glen she convinced me it would be simple to use his fantasy to enslave him totally. She said men fantasise about this sort of thing and it would be easy to get him to agree to a set of conditions that he could never get out of it. If he wanted humiliation let him have it and pay the consequences! Think of the advantages. I could enforce chastity on him and having him begging for the slightest sexual favours while at the same time I could take on a lover if I so chose. I would never have to do any housework again. I could be sure he would never cheat on me, never go out with the boys and never be a lazy slob ever again. I would become the centre of his universe and he would be eager to do my bidding in all things. He would hand control of his bank account to me and I could make all purchase decisions. I could put him on an allowance and how much he would get would be at my discretion. I could get him to sign the house and the share portfolio over to me. This really was a much better outcome. Amy’s prediction of how easy it would be was spot on. In fact I expected some resistance but was pleasantly surprised.
On returning home that night I sat down and penned the following email to Glen:
You have hurt me greatly with your admission that you want to be a sissy. I feel that you have betrayed me by hiding this aspect of your personality to me for all these years. My initial thought was to divorce you but I have thought about it and would like to make an offer to you that will keep our relationship in tact, albeit in a vastly different form. You will be here at precisely 7pm next Thursday night, dressed in your best business suit if you want to hear my offer. This will be a one time only offer and if you do not show up I will take it you are not interested and proceed with filing for divorce. Do not try to make excuses as I will not accept any.
I knew Thursday night was his tennis night and he would have to cancel, it was the first test in seeing how much he was willing to give up to make his fantasy come true. I had over a week to prepare the necessary documents and purchased a CB-3000 chastity belt that Amy had recommended. I did not know such things existed and had to do some quick research. The more I learnt the more I was attracted to the idea.
The following Thursday Glen arrived right on time. I made him wait at the door for a couple of minutes before opening the door. I was dressed in business clothes, a well cut grey jacket, white blouse, matching skirt that covered my knees and stiletto’s. I had my hair tied back severely and looked my professional best. I addressed him in a formal tone and had a look of seriousness on my face
“Good evening Glen, I am pleased you have come to listen to my one time only offer. Wait for me in the study in the chair nearest the door.”
The study used to be Glen’s special place. The main desk chair was quite grand, an extravagance that I disapproved of at the time but let him get away with. The chair nearest the door was much more modest. It was part of the plan that I would take the main chair of the room that used to be his. Again I made him wait, this time ten minutes or more before I entered. I was surprised that he stood up as I entered the room. That was a good sign I thought. I sat in the main chair and motioned to him to sit down.
“Right Glen, I have considered your deceit in keeping this secret from me all theses years and rather than divorce you and have nothing more to do you, and believe me I was very close to doing just that, I have decided out of the goodness of my heart that I will give you the chance to indulge your sissy maid fantasy and keep you here but only under certain conditions.”
The look on his face was worth a million dollars, the smile was huge, the sense of relief was evident and he began to gush with thanks.
“Oh Ellen, I can’t believe it, I am so grateful, I thought your proposal may have been to give me a chance to stay if I rejected my sissy ways, I can’t believe you are willing to indulge me, thank you, thank you so much”
“Wait a minute Glen, I have not outlined my conditions yet.”
“Of course Ellen, I will accept anything, please continue”
“Well the first condition Glen is you will NEVER call me Ellen again unless I give you permission. From now on it is Mistress.”
I looked down and could see the bulge in his trousers, I had him in the palm of my hand and wrapped around my little finger. Soon I would have him by the balls as well.
“The next condition is that you vow TOTAL obedience to me and I mean TOTAL. No questioning just pure simple obedience.”
“Of course Mistress.”
His eagerness to respond was puppy like, I was sure he didn’t realise what he was getting into.
“The next thing is to hand control of all finances over to me. I want you to go on line now and change the banking details on your company’s website so that your salary is now paid into this account”
I handed him a note with my banking details of a new account I had set up solely in my name. I could see the first sign of hesitation
“But what if my boss asks why I am not being paid into my own account”
“Just tell him it is better for tax reasons, besides it’s none of his business and I am sure he will not even look, it’s all computerised.”
With some trepidation he brought up the Human Resources page and found the form to change banking details and typed in the account details I had given him. I felt a warm feeling deep inside as I saw him hit the “Su
Next I have some documents from my solicitor which you will sign. It is transferring the house and the share portfolio into my name.
He gave me a very concerned look, his face looked shocked to say the least, he was about to open his mouth to say something but I quickly said,
“Uh Uh, no arguing, you take my offer or leave now!”
He took a deep breath and with some resignation signed the documents. I was feeling more excited now, this feeling of power was becoming quite arousing.
“Now before I issue you with your sissy uniform there is one more item to take care of. Stand to attention with hands on head!”
He was quick to obey which was most pleasing. I then undid his belt and pulled his trousers to his knees. There was a massive bulge in his underwear. I would have to do something about that I thought.
“Wait there and do not move.”
I went to the kitchen and returned with two ice packs. I pulled his underpants down and sandwiched his genitals between them. He let out a whimper and in a matter of moments shrinkage had occurred.
I then produced a CB- 6000 which had arrived in the mail just the day before.
“What is that?” he asked
I gave him a ferocious stare,
“How dare you speak to me before asking for permission, there will be punishment for that later!”
I refrained from answering his question and first locked the rings around behind his testicles. I then used a little lubricant to slide the cage into place and with a little fanfare locked the chastity cage in place
“I think I should call you Sister Glenda, you have now taken your vows of chastity, obedience and poverty.”
With that I had a good laugh. The look on his face was priceless. He looked most concerned and had pleading puppy dog eyes but he dare not say anything.
I am yet to get your sissy maid uniform but for now you can wear this tartan skirt, white blouse, apron stockings and heels. You can start by cleaning the kitchen. Dismissed!
That was the starts of Sissy Glenda’s life as a sissy maid. It was all just too easy. Life has been grand ever since. I am free from the burden of housework, I have massages, baths and breakfast in bed whenever I want. I have even started dating a handsome young stud. I have more money as the costs of keeping Glenda have greatly reduced. I know she cannot cheat on me and the longer I keep her chaste the more devoted she has come. He rushes straight home from work changes into his sissy maid clothes and starts on his chores. It is really the best thing that could have happened to me. I will share more of our life in another article.
TO BE CONTINUED???