Pat did agree to be my sissymaid and that was time for a hug that couldn't be done on the phone earlier. It was a promise by him to be a good sissymaid with me also promising to be a good Mistress, in time.
We started to get into details with me asking more about how it used to be. Pat admitted that his mother was Mistress at all times so I adopted the same. Pat used to look after and for the most part from what I could see the housework, laundry and all that fun stuff. To practice my part it was easy to confirm I wanted that to continue until I found other things Pat could do for me. Pat was to be clean shaven and in chastity at all times which I agreed while he went to get the chastity device. That was my first time seeing one of those things made of steel with the small padlock on it. Right away I wanted to put it on Pat so he walked me through sliding the tube into his penis pee hole with lots of gel on on it. Hearing the lock click gave me a sense of power right away Helga. Pat showed me the vibrator his mother used to milk him a few days a week. He explained when sexually active it wasn't as necessary but if I kept him locked up for longer milking would be important.
Pat talked about bathing and pleasuring as part of his role as a sissymaid. He also let me know his familiarity with blow drying hair and applying makeup to himself and his mother when she was alive. I basically let Pat know that he should continue where he left off while I fine tuned my own role and his. He asked me about going out like we do which I decided he should be prepared to go out dressed as a woman next time other than moving days. Pat responded OK Mistress for the first time. I made it clear he should always be in his sissymaid dresses and to move his male clothing to the basement for now.
I wanted to know more about the bottle of pills in the cedar chest I saw last night. Pat explained they were two types of hormones one taken daily and the other ten days a month when a woman would normally have her period. He explained that breast growth happens in two ways which is why the two medications taken on their own schedule. I asked him to go get them to show me they were prescribed to him which they were just as he said. Pat let me know he took them for about a year with no problems but he did feel nipple sensitivity and some growth. The bottles showed there were over a years worth of refills approved. I didn't want to tell Pat to take them without asking him first.
I know Mistresses don't ask however in this case it was important to be sure. Pat asked me if I wanted him to start taking them again to help his breasts grow and help feminize him more. I smiled letting him know that would be very nice if he would become more feminine for me. Pat agreed to start the program again. He was telling me last time his skin was softer and he felt different which his mother said was just the feminine side of his brain letting him know it was working. I asked Pat if the prescriptions affected his penis at all which he said sometimes it wouldn't be hard in the morning. He asked me if that was going to be a problem when I said no, that is fine.
Now with my reading I learned Mistresses use dildos for training which I talked to Pat about. Apparently his mother only used the vibrator around and in his bum for milking. I took a big step letting Pat know I will want to explore using a proper strapon as his Mistress. He didn't refuse or have any comments other than OK Mistress. I asked Pat if his mother was forceful, mean and demanding. When he answered with forceful I agreed to be the same which might be what he was used to before and easier for me too.
To show Pat I want to be a Mistress I ordered him to take off all his clothes for me. While standing there I ordered him to bend over and spread his cheeks so I could see his bum hole which he did for me. I sent him to get his favorite nightie short or long didn't matter with matching panties. Within a minute Pat returned just as I told him, I told him to put them on for me. I asked him where his slippers were even though I didn't ask for them before which he went to get for me.
Looking at Pat I wanted to know if he liked being a sissymaid which I then asked. He confirmed very much Mistress which was a good answer. I asked him if he liked the idea of me being his new Mistress which was another very much Mistress. Pat let me know he was looking forward to serving me for a long time to come. Normally I would think of having Pat between my legs unless I had just showered however a sissymaid has to be prepared at all times. I instructed Pat to remove my jeans and then panties. Taking his head I forced him between my legs holding him there until I came.
Pat stood up as I pulled his panties down to see his poor penis straining to get out. I sent Pat to get the keys for the device just so I had them. Pat did tell me his mother never took it off if she saw any kind of an erection. I thought that was a very good idea which I confirmed to do for Pat. Sending Pat out of the room I hid a key in one of the books on the bookshelf then attached the other to my necklace. Before I left Pat was made aware that if there was an emergency all he had to do was call me for the key location. I had been to the bathroom and his room before letting him know that so he had no idea where it was hidden. A good sissymaid wouldn't look which I think Pat will be or already is a good sissymaid.
Thank you for your letter Tania. What a wonderful and productive evening, he is going to make a perfect sissymaid for you and though there will be some surprises and a bit of a learning curve, you are going to be a great Mistress. He does sound as though his mother trained him very well.
I loved how comfortable you made him, after all, you're his friend. I am pretty sure you're right about his need to become a sissymaid again, at some point in the past he came to love this lifestyle and yearns to start again, my guess, he is jumping for joy at the possibility, so please do let us know.