My wife Jill and I lived in a four bedroom house located in a good neighborhood. Both of us had good jobs, she being the office manager in a large corporation and I worked as a loan officer in a major bank. We had a big house mortgage, schooling loans, along with other bills. We where making ends meet until the financial crash of 2008 which took our house, my job, two of the three vehicles, and most of our savings and dignity. My wife lost her job due to down sizing a year later and we ended up with mostly nothing but bills. We basically had to start all over again but had nothing to our name. My parents passed away nine years ago as did her father Dan several years back. Her father was well off and retired when he was in his early fifties due to some very good investments in his day. Her mother Dawn lived well in a very large six bedroom home. We ended up moving in with her until we could get back on our feet again. Jill landed a secretary job at an auto repair shop a few weeks later.
When we arrived Dawn was happy to see us and everything seemed to be fine. Two weeks later I heard Dawn and Jill talking in the kitchen. They did not know I had come down stairs and was in the next room. I over heard Dawn say to Jill that she should have never married me. Sound like her mother wanted Jill to married someone named Brad. Saying that I was never going to amount to a hill of beans. I could hardly believe my ears since Dawn had always treated me good and seemed to like me. I made some noise by coughing before entering the kitchen. I walked in and they where quiet not saying a word as I said good morning to them in passing. Helping myself to a cup of coffee I said it looks to be another nice day as I was going job hunting again. Jill said maybe you should stay home today and help mom, she has a few projects she needs done. I looked at both of them and said, I could do that but I thing looking for a job was more priority right now. Jill said her mother gave her a lead on a better job and was going to go check on it shortly. Dawn told me I needed to take a brake after all I had been job hunting every day since we had moved in. I said I could do that and asked Dawn what she needed done. After giving me a peck on the cheek Jill turned to her mother and said, good luck then walked out of the kitchen and headed out the door .
Dawn informed me that her washing machine was not draining properly and wanted me to take a look at it. I told her I had no mechanical skills and that it was out of my league. Well then I need the patio washed off and the pool cleaned and filters changed. Then I want to move some furniture around and flip the mattress on my bed she told me. I did the patio and pool first then went in to cool down a bit before doing the furniture and mattress. When Dawn came down the step she asked what was I doing as she had been waiting for me. Then she seen my shirt was all sweaty and told me to go shower before we continued, so I did. While in the shower I thought the door had opened to the bathroom but did not here any one so I just kept showering. When I finished and opened the shower door to get a towel, their stood her mother looking at me. With her hands on her hips she shook her head saying, oh my aren’t we a small little fella as I quickly grabbed a towel to cover up. What are you doing I asked as I fumbled with securing the towel around my waist. Just checking to see what kind of a man you are, she said as she stood looking at me. Do you mind, I am trying to dry off here I told her. No I don’t mind as she stood with a smile on her face, then said you really don’t have any cock or balls do you? Then she said meet me in my bedroom when your done, then turned and walked out.
I finished drying off and getting dressed then went to her room. She was sitting on the edge of the bed and told me to sit beside her. I did as she asked and she told me what she was going to say would hurt my feelings but I needed to know the truth. Some what puzzled I asked her what was it? Well I don’t know how to tell you this other than just say it. Jill is not happy with your small cock, she confided in me and told me your no man in bed. She is not checking on a job but out seeing an old boyfriend, he is a real man. I know because I saw him once when Jill was still living here. He has a cock on him and Jill needs that right now. I looked at the floor in disbelief and thinking that she was making this all up to turn me away from Jill. She put a hand on my leg and said, it’s not your fault you have such a small cock. Some guys are born to be sissies while real men with a real cock take care of girls like Jill. I know because my Dan had a small cock and I always had a real man fulfill my needs and still do. Dan accepted the fact that I needed a big cock and he could not full fill his duties in bed. This is not your fault but you need to accept what you are and what Jill’s needs are.
Stunned I just sat their thinking this was not happening, Jill would never step out on me would she? I know our love making has been less and less but I figured it was because of our situation and all the pressure. I thought she always enjoyed the sex we shared between the two of us. Dawn had walked over to the closet and retrieved something as she was walking back she said. Here this should fit you, your about the same size as Dan was as she handed me some kind of clothing that was black and white with lace and ruffles. I looked up at her as she stood over me, go on Dan wore it and you will too. Then she grabbed it and held it up in front of me, it was a maids dress! I am not wearing that I said in a pissed off voice, then Dawn slapped my face so hard I could feel each finger sting on my cheek. YOU ARE AND YOU WILL she hissed back at me with a pissed off look. Then continued to say, Dan was as sissy and so are you with that little cocklit you have. You get your sissy ass up off that bed and strip right now! With the next slap coming my way I ducked but she cough the top of my head then grabbed my ear and twisted it. You get your ass up and put this on NOW she yelled at me.
I knew I had pushed her to the limit and stood up and started slowly to take my shirt off. My eyes now had tears in them and I felt like a little kid standing their. I dropped my shirt to the floor and then undone my shorts letting them fall to the floor. Dawn told me to drop those undies, you will be wearing panties from now on if your going to be living under my roof. She handed me the short maids dress uniform and told me to get it on and don’t tear it as she walked back to the closet. She returned with panties, garter belt and nylon socks saying to put these on also. Then she retrieved a pair of shoes that had a low heel, I was to put them on after she instructed me how to put on the lingerie. For some unknown reason I got and erection putting on the lingerie. Dawn noticed it and said I see you are a natural sissy as I thought. It seems you all get erections when in lingerie, Dan was the same way. The shoes where big but not so big I couldn’t walk in them. I felt like a fool and looked worse as she pointed to the mirror telling me to get used to it because this is your new roll around here.
That is pretty much how it all happened and now I am both their full time maid servant wearing the appropriate clothing and all. When my wife came back that evening and she saw me she could not help but laugh at me. I felt like a beat down dog by now with nothing left, thinking Jill would now put a stop to her mothers bull shit. I was wrong, instead she asked her mother if I resisted any? She said not really all sissies know their place once you lay down the law. My wife Jill told her she was pleased she had broke me so soon or she was going to have to divorce my ass. I was shocked to here this and wondered how long this plan had been hatching. Then I heard more devastating news as Dawn asked Jill how Brad was. Looking into my tear filled eyes she said, he still has the big cock he always had. I am happy to here that since this one is so puny, I will get this one trained in no time. Mean while you can move your things into the bedroom across from him. That way he will be able to hear how a real man can fuck you when he visits.
Like I said, I am their full time sissy maid. It took some time to adjust but the choice they left me with, I would have ended up with nothing and in the streets. Thinking it over I decided to try it until I was ready to leave on my own. However that time never seemed to ever come and I settled into the roll of sissy maid. I have been taught the proper way to apply my makeup and I do a good job if I say so myself. Looking back this was probably what I was always meant to be. I have everything I need and don’t mind the job however I do miss sex and being in chastity don’t help.
Thank you, The Maid.
“SM” Sissy Maker