from Julie

Dear Helga,

Please don't think I am crazy when I'm really a fun girl. I have been looking at your website for a few months now with the thought of sissifying my son in law while my daughter is in Australia on a 3 month contract. My daughter and son in law are having their home renovated and have been staying with me for a few months now. With my daughter in Australia I have been getting my son in law to help around the house. I have got him wearing an apron when we do the dishes and even wearing my fuzzy slippers at night because he can't find his. Last week while talking to my daughter I let her know Roy was learning to be domesticated since she left. Now she was thrilled that I was able to do something she hasn't had the same luck with. I let her know about the apron and my fuzzy slippers too.

While were talking I asked her what she thought of me sissifying her husband while she was away. We both looked at your website Auntie Helga having a few chuckles along the way. The conversation ended with me getting Judy's approval to try sissifying her husband before she gets back here in March. I bought a few things for Roy that weekend without his knowledge. One night while he was in the shower I left a nightgown a pair or panties and my fuzzy slippers on the bed for him. He never put them on but did wear my slippers. Roy didn't say anything about seeing the nightgown and panties either. The next night same thing I left them on the bed except this time when he walked in the bedroom I asked him to wear them for me. Roy asked where were his pajamas when I said sorry hun they were in the wash. Within a few minutes Roy walked in the room wearing his new nightgown and my fuzzy slippers. I whistled at him letting him know it looked nice on him and fit well too.

Roy asked that I not say anything to Judy so I agreed it was our secret. A few nights went by with me leaving Roy a nightgown and clean panties after his shower. One night he asked where his pajamas were when I admitted I like him in a nightgown better. I could see him looking at me but I wasn't going to give in or say anything else. Roy was helping me with most of the housework now and wearing a nightgown at night. I started to call him my helper then my maid without not much coming back from him. I bought Roy a few more pairs of panties, a bra and a pair of stay up thigh high stockings. One night Judy called to talk with Roy then I spoke to her afterwards. Judy asked me how our bet was working out when I let her know just fine. Roy went to the bathroom when I mentioned to Judy so far panties and nightgown. She in Judy style said no way mom when I let her know oh yes. I asked Judy if that was alright when she laughed telling me go for it if I can. Roy walked back in the room asking me quietly if I said anything to Judy with me shaking my head no while Roy stood there in his nightgown.

The next day looking at the internet to get an idea about sissymaid dresses I went shopping leaving Roy to vacuum the house. I didn't have any luck until I went to an adult store off the main street. The lady told me all they had was French maid which were more like a costume to wear a few times. She asked if I wanted this for a sissymaid or a one time event. I did tell her it was for a sissymaid when she gave me a couple of websites then suggested I look at the uniform shop on the other side of town. She said most sissymaids start off wearing a maid uniform until their sissymaid dresses are made.

I thought that was a good idea so I went there and found a nice maid uniform that would fit Roy. I found a pair of shoes for him there too. That night Roy put on his nightgown again without anything said by me. Men are simple creatures and far more trainable than they think. The next morning at breakfast I asked Roy what he thought about being my maid since he was getting good at helping me. Roy asked what did I mean by my maid so I let him know like wearing a maid uniform while we did the housework. Roy laughed saying if I wore one he would too as a joke. I looked at Roy then told him I already bought his uniform though asking if he wanted to see it. Roy laughed with a nice try comment thinking I was joking but I was serious.

Roy looked at me now wondering what was going on in his mother in laws head. I said come on please try it on for me taking his hand. He looked at me asking if I was kidding when I took it out of the bag to show him. I asked Roy to take his nightgown off which I had to help with before taking out the bra. I moved toward him as he backed up away from me. It's only a bra Roy it won't bite as I put it on him adjusting the straps. I helped Roy with the stockings and then over his head went the uniform and finally the shoes. Looking at Roy I said see that wasn't too bad and it fits nicely doesn't it? I stuffed his bra then stood back admiring him. Roy asked why was I doing this to him when I let him know just for fun.

We worked away all day together with Roy asking a few questions and a few comments. He wasn't loving it that was for sure but on the other hand what guy would. That night he was happy to take it off and put on his nightgown. The next morning I was right there to ask if he needed my help putting on his maid uniform. Roy didn't want to wear it figuring he had tried it for me the day before. I told Roy he should wear the uniform every day from now on and if he was good I would buy him another instead of washing the same one each day.

Roy has been wearing his uniform for a week now while I wait for his sissymaid dress to arrive. Helga I would like to put Roy into chastity before his sissymaid dress arrives. What do you think about the use of chastity on sissymaids? Do the devices work like do they stop the sissymaid from taking them off? I would like to have Roy partially trained as a sissymaid before Judy comes home. She doesn't know how much progress I have made to date as I want that to be a surprise. Also if I can ask another question. Do you like heels on a sissymaid? I see all kinds of pictures of sissymaids in heels but I wasn't sure if men can wear heels or not.

Thank you for reading my son in law story


Thank you for your letter Julie. So glad to hear the website has been informative. You seem off to a great start and by taking a strict approach is the way forward. I fully approve of and recommend chastity for sissymaids, shave him first, the good ones stay in place and are difficult if not impossible to remove. I also approve of heels, not too high as it makes for a clumsy maid, but a 3-4 is about right.


Return to Index
Letter 6