I am an older widow living alone on a quiet court where there are only three other homes. After my husband died I thought of selling the house however didn't like what was out there and wasn't interested in a condo. My house has a basement apartment that we rented out years ago to help pay the bills. Living alone at my age which is as they call the golden years I thought it would be nice to have someone live downstairs. One day while at the grocery store Todd, the young fellow who carries my groceries to the car, asked about apartments or houses to rent. Long story short I thought Todd was the perfect young man to live downstairs.
He moved in and for the most part things were going just fine until one day the smoke detector went off in the basement when Todd wasn't home. It scared me and there was no time to call Todd so I went to have a look. It was a false alarm that had happened before which caused me to think about buying a new one. While I was there it made sense to have a quick look just to be sure Todd wasn't making a mess on me. Things looked pretty good until I saw something on the table which I had not seen in years.
Young Todd had himself a couple of chastity devices so I thought he must have been into kinky things. You are probably wondering how I knew about those things at my age. Well Helga I wasn't always an old lady you know. There was a time when my husband wore a chastity device and he, like some of the men on your website, was my house maid. That was a long time ago in the fun days as I call them.
Anyways I didn't see Todd for a few days until Saturday when I asked if he would change the smoke detector for me. I explained the old one had gone off when he was at work and I was sorry to have gone in to the apartment but if there was a real fire my house could have gone up in smoke. Young Todd was alright about me going in until he remembered leaving his chastity devices in plain view. He blushed some which led me know he knew what I knew. Smiling at young Todd I mentioned pretty nice chastity devices you have there. I went on to let him know if he ever wanted me to be a key holder for him all he had to do was ask me since I had been one before.
The poor young fellow looked at me with a strange confused look so I confessed to being a key holder for my husband for many years. It was maybe a week later when I heard a knock at the door opening it to find young Todd. I asked him to come in while I was just having dinner then asked if he had dinner yet. Young Todd joined me for dinner while we chatted about his thing for chastity devices. By the end of dinner I agreed to be his key holder with Todd passing me four keys for both devices. I asked if he was wearing one which he was as I smiled letting him know good to see. We chatted about what his goals were about wearing the chastity device and when he wanted to get released and for how long. I thought to myself why not help him to help me if you know what I mean Helga.
It was a few days later when Todd asked for the key just for one night which I agreed to give him. The next time it was four days and I agreed once again for one night only. The night when Todd knocked on my door last weekend I didn't answer the door so he phoned me. Playing sick in bed I suggested he try to live another day because I was in bed. I wanted to see if he was angry or submissive by his tone. As I thought Todd was more submissive which was just what I wanted to hear.
The following night after work Todd was at my door to get the key which I agreed to give him. As you can see I was working toward holding off giving Todd the key however wanted to gain his trust first. The next morning Todd dropped off the key and I could see the chastity device was in place. As I took the key I asked him to make a goal of keeping the chastity device on for one week. He asked out loud "one week" when I replied it was a long time and something to work toward. Reluctantly young Todd agreed to try for me then off he went. While Todd went to work I went shopping as the time had come to prepare him for a little surprise.
Helga it was only three days later when Todd knocked at my door looking for the key when we agreed one week. I invited him in to talk about it just to see why he was not able to hang on and go over his goals again. Somehow I sensed he wanted more to beg me than actually have the key so I played the game. Todd had asked me about being a key holder for my husband a couple of times with me giving him tidbits of information. In his own words he thought it was cool my husband was kept in chastity. The time was right so I let Todd know he had what it takes to do what my husband did but did he have the nerve.
Saying that to a young guy is guaranteed to have him take the challenge which worked with Todd. We shook hands on Todd trying something new which involved chastity. I asked him to wait there while I went to get things ready then called him into the back room. He couldn't see behind the door so I asked him to take off his pants and underwear so I could ensure the chastity device was on properly. Todd was asking you mean right here and now so I said "well yes right now let's go". Boy that got him to pay attention as he dropped his pants and underwear to show me his penis packed in the chastity device. He did a good job buying the chastity device as it fit him properly with no room to move. I complimented him on his choice of devices then quickly pointed out the pubic hair had to go. Once again it was "you mean" as I let him know "yes shave it all off".
I had Todd's attention so I handed him a pair of pink nylon panties which he put on thanks to my look at him. I bought two bras for Todd not quite sure what his size was as I tried each of them on asking for comments on which one felt the best for him. Young Todd wanted to know if my husband wore ladies stuff as I confirmed for over twenty years. He wanted to know why and what the ladies stuff had to do with chastity. Helga both you and I know young Todd was trying to pretend he didn't know about sissymaids. I didn't answer all his questions but instead continued passing things to him to put on which included a pretty French maid costume. For the time being Todd can wear a cheap costume while I wait for a proper sissy dress to be made by a friend. I tried a couple of pairs of heels on him with one fitting just fine. You would almost think I had done that before, wink wink.
By the time young Todd was dressed I sat with him to explain how it will work. Remembering how I trained my late husband years ago we talked about chores, appearance and the number of nights and weekends. Surprising young Todd was accepting of his fate as though he wanted it or dreamed about it. Well it's been a month now with Todd coming here to cook, clean and look after all my laundry just like my husband did years ago. There is talk Todd might be laid off at work so I assured him if it happens he will have a fulltime job as my sissymaid and it will be rent free.
Helga I am having fun again going out with my friends for lunch and tea. They are all jealous knowing about my late husband and having a new much younger sissymaid in training. I haven't started punishing Todd yet or has he started any personal serving however he will. My hopes are he loses his job and becomes my fulltime sissymaid or he ends up quitting because he enjoys life as my sissymaid. In time I would like to feminize Todd to ensure he stays put.
Thank you so much for reading about my new sissymaid trainee.
Thank you for your letter Tonya. You obviously know what you're doing when it comes to training sissies, the 'wait' for the chastity device was perfect. Then straight into pink panties and a uniform, really well done Tonya.
You seem to have things well in hand though we would love to be involved going forward and look forward to seeing this project to fruition.