from Joanne

Dear Helga,

We had an interesting day today or should I say Paulina did with mine just having fun. Today while shopping I spotted this cute summer dress that would look perfect on Paulina so I bought it. Now a girl has to have new shoes with a new dress doesn't she? Well Paulina should have a pair of heels for the summer preferably a sandal which took me to the shoe section. I found a cute pair in her size with a nice heel so into the cart they went.

When I arrived at home Paulina helped with the bags only this time I let her know the bags should go in her room. I followed her in giving the word to strip down to her panties and bra. She tried on the dress then the sandals with a puzzled look on her face. The good thing is they fit while looking vert nice on her as I patted myself on the back. Of course Paulina wanted to know why the purchases when I let her know she should have other women's clothes for laser and hair appointments. I can't have her going to appointments in her sissy dress or maid uniforms or can I?... just kidding Helga. Paulina wanted to know if her uncle went out to appointments too when I replied of course. No more was said as that was enough to know that her uncle did it so in her mind she can too.

It was not long after that when the doorbell rang with Paulina ironing I asked her to get the door. She walked in the kitchen when I said go ahead answer the door. Paulina opened the door to find it was my long time girlfriend who knew all about my late husband and she went to school with him. Paulina knows her very well just not as she was dressed today. Karen walked in giving Paulina a hug then letting Paulina know how pretty looked. We sat down while Paulina looked after getting us a glass of wine.

Karen looked at me whispering OMG that is amazing Joanne. Of course she was asking questions which I answered with the last one being chastity too? I replied of course right from day one. Paulina returned with the wine asking if we would like cheese and crackers so we said yes. Karen went back to asking questions which basically boiled down to Paulina was fulltime and was in the same training as my late husband. She wanted to know how Paulina was dealing with all of the changes so far when I said great. I shared that Paulina after the initial shock on day one has accepted the fact she is my sissymaid to do anything I wish.

As a small test I asked Paulina to show Karen her little penis so Paulina pulled her panties to her knees then lifted her dress. Karen said OMG Paulina that is wonderful that Mistress Joanne's penis is safely locked up so no more playing with it. Paulina politely replied yes Karen it is wonderful smiling. Karen went on to talk to Paulina about what an honor it was for her to give up her manhood for Mistress Joanne after all these years as your aunt. Paulina thanked Karen letting her know the honor was all Paulina's as Mistress Joanne deserved Paulina as her sissymaid more than anyone. Karen mentioned that like me, Paulina had large breasts asking if they were real with a smile. Paulina said no Karen they are silicone. Karen replied back well maybe some day Paulina would have her own like her uncle. I sent Paulina back to ironing while Karen and I chatted.

Karen didn't stay too long but the minute she left I gave Paulina the word then she met me in the bathroom. Helga the best thing about Paulina acting as my toilet after I am finished is she is right there. When I was finished I just sat down so she could give me an afternoon orgasm. The wine even though only one glass relaxed me enough to want Paulina to work her magic. On the floor in my bathroom with me sitting on Paulina's face she began licking my vagina. With me being a huge water drinker poor Paulina is consuming my water and her own now which has her in the bathroom more often now. I asked her if she enjoyed drinking my juices as much as her uncle did at one time. Pauline replied yes Mistress Joanne when I said that is good because I love sharing it with her.

Even after 20 some odd years with my sissymaid husband I wondered if some day he would stop responding to me telling me he had enough. It never happened thankfully so I guess I did a good job or reprogramming his brain as a sissymaid. Have you heard or seen sissymaids one day revert back to the men they once used to be Helga? With Paulina a younger sissymaid it keeps me on my guard for any signs. In just a few days I have put Paulina through more than the average guy would go through in a year. Paulina continues to obey me without a challenge. Sure she has questions and rightly so with this all being very new to her. In a few days when I think she is ready I will start dildo training her into a deeper submissive state. I believe she will accept the dildo knowing it is all part of her training. It is the positive reinforcements and reference to her uncle that I believe will she will be a wonderful sissymaid.

While Paulina was bathing me I talked to her about how proud I am of her knowing that this process isn't easy yet she continues to accept it with open arms. I let her know I loved her very much and that everything she has done for me is very much appreciated. I explained that in our relationship I am the dominant one and she the submissive so I need her as much as she needs me. Paulina shared that she understood there can only be one Mistress and one sissymaid with her preferring to be the sissymaid. We both laughed knowing that was the way it was going to be too.

I let her know that as he training progresses there will be times when she may not like some of it however it is all necessary for her to be a sissymaid. Again she understood that I make all the decisions now and in the future. I let her know pointing to her that body is no longer hers so I can do anything I want to it. Paulina asked does that mean I will have boobs some day. I let her know yes she would have boobs some day like her uncle did when he was my sissymaid. Paulina said she understood and would do everything I asked of her. I kissed her on the cheek. As the water was draining and he was drying me off she asked one more question so I agreed. Paulina wanted to know if she could keep her penis even in the cage was alright. I said there was no plan to remove her penis for now although if I wanted to some day it could happen. Helga I want her to see I own her now.

A while later at bedtime Paulina followed me to my bedroom removing my nightgown as I laid on my bed. I could sense a bit of stress after the talk about her body is mine so I told her to lie down beside me. I took her right hand placing it on my boob telling her to go ahead while I watch her fingers play with my nipple. As she played I made a remark that she really likes my boobs doesn't she. Paulina admitted very much which I thought she would say Helga.

I asked Paulina if touching my boobs and servicing my vagina were part of the reason that she will do anything for me. Slow to answer she admitted it was part of why she loved to be my sissymaid so much now. I let her know I felt she would say that to me although there might be times when I will not allow her to service me at all. Paulina just said that is alright with her too knowing that her life is ever changing now. Paulina looked at me letting me know she would always do everything to make me happy as it was her number one goal.

I took her hand guiding her fingers into my vagina while she sucked on my nipples. All this talk and her playing was starting to get me horny again. I reached down massaging her balls while she fingered me and sucked on my boobs. I could feel her penis trying to get an erection against the steel cage with no success. Then I told Paulina to lick her fingers and all of my juices which she did while it made me horny to watch. It was time so I got on top of her with her face in my vagina as I licked and sucked her balls biting them off and on. Paulina continued to lick my vagina knowing now I like it. I kept sucking her balls as she moaned in pain from the cage. I pulled on her balls and began to masturbate her with the cage on which amounted to a lot of motion and nothing else. I orgasmed on top of Paulina driving my vagina into her face pumping back and forth.

I notice her penis had a drop of cum on it so I got up to prepare to milk her for the first time. Slipping on a glove and getting my small dildo I ordered Paulina to the floor then on all fours. With my glove lubricated I entered her working her prostate as she moaned. After working it for a few minutes I slipped in the dildo working it against the prostate and no further. During this I was talking to Paulina letting her know I was milking her to get rid of that cum. It took a while but she did start draining and quite a bit too. Normally I would have my sissymaid drink her cum afterwards but I forgot the cup. When I was finished I wipe he off then pulled her face down on my vagina again. Before long I orgasmed again driving my vagina into Paulina's face. She wiped my vagina and her face then one more trip to the bathroom for a pee. Paulina returned to my bedroom where she spent the night on floor beside me at my request.


Thank you for your letter Joanne. I know how much you must miss your late sissymaid husband though now you have this wonderful opportunity to share your life with your nephew as your sissymaid, just fantastic. With your extensive experience her training should be a breeze and great fun. Of course I approve of the methods and practices you outlined above and I know our readers could learn so much from you.


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Letter 2