MY INTRODUCTION - PART TWO (Introducing Sissy Paulina)
from Joanne

Dear Helga,

My husband wanted to be my sissymaid making it easier for me to handle. With my nephew Paul it will be a new challenge yet one I can handle.

Arriving home today Paul and I walked through the house with me wearing a navy blue suite and heels while he was dressed like my sissy. Helga it is good to be back while I felt that power once again towering over Paul as he bent over to show me that he cleaned in the corners. I walked in a way that he could see and I knew he felt my presence. All that was missing was a cane or yard stick in my hand. Helga even after one day I can sense Paul submitting in a small way but I can see it. He was polite while he seemed proud of his first attempt. To be honest he did quite well although I made sure I had something to say about each room that could be done better next time.

During dinner Paul asked more about his uncle as my sissymaid which was good that he was showing an interest. Paul wanted to know all the things that his uncle did to help make my life a better one. I shared everything right down to the oral sex he did almost every night while he was my sissymaid. It was the perfect time to let Paul know he would be doing the same in time as well.

The wheels were turning however Paul didn't say anything to my surprise. I was very descriptive answering Paul with examples of dressing me, undressing, bathing me, looking after my nails and learning how to do my hair. I also asked Paul how he was making out with his new clothes and his chastity device. For the most part he is adapting alright with concern over his penis locked up. He wanted to know more about his uncle wearing the device and for how long. I shared with Paul that his uncle wore a device every day for over 20 years with it coming off the 1st Sunday of every month unless he was being punished.

Paul asked if I was kidding to which I replied no 30 days wasn't so bad when some Mistresses kept their sissymaids locked up for 3 and 6 months at a time. Paul repeated 3 and 6 months when I let him know that was true too. I let Paul know we could start with removing it on the 1st Sunday of each month as long as he did well with his training. Helga when I let Paul know 3 to 6 months his jaw dropped however he didn't say anything with the 1st Sunday of each month. To me he had just accepted it even though he has no choice. I do look for confirmation and acceptance signs.

After dinner with Paul having a better understanding of what I would be expecting I gave him the hint I wanted to get changed just to see his reaction. It took a few minutes before it clicked with him so I didn't have to hint again. Paul stood up asking me if I wanted him to help me change so I let him know well done.

He took my jacket off hanging it up then my heels putting them on my shoe rack. Paul started to unbutton my blouse as I could see him shaking somewhat. He set my blouse aside to be cleaned then Paul unzipped my skirt not knowing the zipper was on the back at first. So far he was doing alright yet stumped at how to remove pantyhose and not my panties then he got it.

I told him the top I wanted to wear and the shorts so he started with the top having troubles rolling over my boobs. Paul was so scared he would touch them and I would freak on him. Little did he know he would be touching them sooner that he thought. Finally I was dressed with Paul relaxing from such a stressful first time.

Paul followed me out to the deck without thinking of how he was dressed. When he figured it out I told him to sit down and not worry about it. My backyard is closed in so he had nothing to worry about. I talked about Paul's first day as my sissy with areas of improvement that I would be looking for as we moved on. With an old checklist I used with my husband we began to go over my expectations with Paul asking some good questions. He also wanted to know how long the training would take which depend solely on him. On my checklist were things related to Paul's feminization that he wasn't too excited about hearing.

I let Paul know he had nothing to worry about as it was my job to help him with the training so that he could as soon as possible become my sissymaid. Paul did notice I took all his male clothes from his closet wondering why. I let him know that from now on he was to only wear women's or sissymaid clothes however in the event of an emergency his old clothes we locked up in the basement. Paul said to me with a tear it was all starting to sink in. I took his hand reassuring him it was going to be alright as I had done the same thing with his uncle.

Paul asked me what he should wear when his dress needed cleaning proving once again he was thinking about this more. Part of me wants to allow Paul to have some input to his clothes just as my husband did when he was alive. He had 3 sissy dresses and a few maid uniforms with his name on them.

So I asked Paul what he would like to wear advising it would have to be in the theme of a sissymaid. Paul mentioned I guess another sissy dress, what else was there. I let him know if he wanted a real maids uniform I would buy him a couple as long as they were pink. Paul thought they might be good for days when his workload involved heavier tasks.

I agreed to buy Paul a couple maid uniforms however they would want to know the name to be embroidered on them. That stumped Paul so I just said without thinking much how about Pauline or Paulette or Paulina. He asked if he had to have a female name when I let him know yes it was coming any ways.

Paul knew a Lina so he chose Paulina which was a nice choice. I let him know that while we were on the topic of names from now on he would be referred to as a she which seemed alright. Next from now on Paulina was instructed to address me as Mistress Joanne only. She said it out loud before I let him know that punishment would be issued when she forgot. Paulina asked why punishment so I let her know that not calling a Mistress by her full name was a punishable offense for any sissy or sissymaid. Paulina's response was she thought I was taking this very seriously so I let her know she was right.

Paulina has gone to unload the dryer and now it is time to teach her how to use an iron. I will leave this email here then come back it it later on... Well Helga ironing is going to take longer than I thought. Paulina sure hasn't done any ironing on her own before now. It is going to take a while to train this sissy into a sissymaid but that is fine. Maybe I will teach Paulina some personal service tasks tonight so that by the end of her training she will understand it all. It has been years since I relaxed in the tub having someone else bath me so Paulina tonight is your night.

Well Helga I asked Paulina if she thought she was ready to bath me tonight. She looked at me with those wide open eyes followed by I guess so Mistress Joanne. I took her hand letting her know she was going to be doing this next week any ways so why not start tonight. Paulina asked if she wanted me to take her clothes off now or later so I let her know go ahead. She didn't know if my top should come off first or my shorts poor thing. Paulina was extremely nervous Helga. She took my top off carefully trying not to hit my boobs. Then all of a sudden she asked bra too Mistress Joanne while I let her know to take it all off. Finally I was nude with Paulina having real troubles paying attention. I asked her if she had ever seen a nude woman before when she replied not with such large breasts. Ok I do have larger boobs than some women but Paulina was in shock once again as I walked with her to the bathroom. She filled the tub with my direction checking the temperature then I stepped in with her holding my hand. I asked her to let me soak for a while then I would call her.

After soaking I called Paulina who looked to be having troubles with her chastity squeezing her penis from seeing me nude. I could see it in Paulina's face she was in some pain when she all of a sudden looked down at her penis. I just love that device Helga, so effective. Paulina began to wash me then stopped when she got to my boobs asking if I wanted them washed too. Silly Paulina of course I wanted my my boobs washed so she carefully washed them like they were made of crystal or something.

When she worked her way to my vagina again she asked as I opened my legs to answer her question. It has been a long time since anyone had their hands down there Helga. I let Paulina know how to wash a vagina then told her she needed to learn how to wash it nice and clean for when I wanted her to service me. Poor Paulina was in shock again although she replied yes Mistress Joanne it is better nice and clean. I asked Paulina to pull the plug when she was finished then I stood. Paulina started to dry me off trying to keep clear of my boobs and vagina although I told her to dry them too.

I lifted her dress while she was drying me off letting her know I wanted to see her penis so she pulled her panties down so I could see that her penis was trying to get out. Commenting to her that it looked like her penis likes my body with a smile. Paulina let me know her penis liked my body very much so I let her know too bad her penis can't have any. Paulina let out a yes Mistress Joanne too bad for my penis. She pulled her panties back up then helped me with my nightie and robe.

I let Paulina know I was proud of her today for her attempts at the tasks I left for her and bathing me tonight. Then I asked her if she was starting to understand that being my sissymaid was a good thing for her as well. Paulina looked at me letting me know it was ok so far but she wasn't sure about all of it. We talked so I could hear where her concerns were and oddly enough servicing me orally was one of them. I asked her why was I not attractive enough for her.

She let me know it didn't seem right with me being her aunt. I let her know that I was her Mistress now and it was going to be perfectly alright as I was very much looking forward to teaching her how to orally please me. Paulina asked really when I let her know she would be servicing me at least once a day. I explained her uncle used to service me a couple of times a day 3 to 4 days a week. Paulina looking confused so I asked her if she liked providing oral to women so she admitted yes she did like to do it.

Paulina admitted she never did that everyday though so I jumped in lettering her know that soon she will be for the rest of her life servicing my vagina. Paulina being very careful with her words asked if she could touch my boobs when she services me orally.

I thought for a minute thinking why not so I let her know yes she would be allowed to touch my boobs only when providing oral to me. Paulina quite mannerly said thank you Mistress Joanne. Helga all this talk of oral and touching was starting to get my juices flowing so without further thought I asked Paulina if she was ready to start oral servicing training tonight. Paulina's jaw dropped while she slowly answered I guess so Mistress Joanne.

It is getting later so I sent her to put on her nightie. Helga she is going to be the perfect sissymaid in time. There is just something about her that I never saw before getting her into a pair or panties. The chastity is also working while she continues to follow my direction without any verbal abuse.

When Paulina returned I let her know she looked so cute in her nightie then asked her if she liked it too. I like testing her to get a feel how she is accepting everything in such a short time. Paulina admitted she was starting to like her nightie and panties.

Now panties was a key word she just used so once again I asked if she liked panties now. Paulina admitted as stupid as it might sound she liked them all of a sudden. I let her know it wasn't stupid at all it was just the sissy coming out in her. Paulina asked if that was good or bad when I let her know was fantastic that she was accepting her new life so soon. I always knew she would sooner or later Helga, most do.

I am finding tonight Paulina is smiling more than last night and earlier today. It could be that she bathed me or will be learning oral in a while. It might also be that the thinking she did all day just caused confusion where now she has some answers.

I think most sissies go through this phase of the unknown along with fear of having lost control. My plan is to be honest with Paulina so when she asks a question she gets the answer and not necessarily what she wants to hear.

We are heading to bed now so I will update this in the morning...

Good morning Helga. I sure hope you don't mind me writing to you along with maybe too much detail. Please let me know when to stop. With the loss of my husband it was years I looked and read about others while being alone. Now that Paulina is here I feel a new spark in life...

Let me share last night with you ... If you don't want to read all the sexy details please do not read past this line


When we got all ready for bed I let Paulina take off my robe then my nightie as I laid on my bed. She stood there in her nightie wondering if she should take hers off too so I instructed her to leave he nightie on for now. With me lying there in the nude I had her get down on her knees while I explained what I wanted this time and every time she was there to provide oral.

Paulina seemed to understand so I wanted to see what she did in the past just in case she had a few tricks. She gently parted my lips with her hand then started to lick my vagina slowly. Paulina started playing with my clit rolling her tongue around it which was starting to feel really good. I let her know it was ok to feel my boobs so she reached for them then started feeling them all over. Even though she was playing with my boobs her tongue stayed very busy getting me extremely horny. I started to pump her face hold her head so she wouldn't get away. Paulina had done this before and was better at this than ironing. She began playing with my nipples an my clit together sending me into my first orgasm.

OMG I forgot how good that felt having someone between my legs. I needed some time to cool down so I asked Paulina to lick my vagina without touching my clit as that felt so nice. She continued to play with my boobs so I asked her if she wanted to suck on them a little. Paulina straddled me leaning over to suck on my boobs gently until I was ready for her to lick my vagina again.

Paulina was very gentle and before long she was licking my vagina again. I let her know what to do and she did it on command until I grabbed her head as I orgasmed once again holding her there. Paulina had licked me from top to bottom with little input from me. I let her know that was very good and I had enough for one night. She stood up passing me my nightie after wiping my vagina and her face.

Paulina asked in a very submissive way if she was able to perform oral in an acceptable way. Helga I wanted to kiss her as she was quite good for a first time. I remained calm remembering I was the Mistress and did not want her to think she wouldn't need some training.

I asked her if she was horny or is that how she performs oral on a woman. Paulina admitted she was very horny so I let her know that was good she felt something too. I told her to show Mistress her penis so she pulled her panties to her knees lifting her nightie. Helga he penis was pink from trying to get out which was so wonderful to see.

Once again I asked her if she understood why I wanted a sissymaid so she replied yes Mistress Joanne I see now. I asked her if she still like my boobs now that she felt them and sucked my nipples. Paulina let me know she always like boobs and mine too. I asked her is they were too big so she said no Mistress Joanne they are perfect like the rest of you. Just a thought went through my head so I asked if she would like to have her own boobs some day.

Guess what she did next Helga? You guessed it looked at me with her mouth wide open again in shock. How can that happen when I am a guy she said to me. I corrected her letting her know she is now a sissy not a guy. Then I asked how about some nice breast forms for now so she can till out her bras.

Paulina has a thing for boobs alright as she asked if she can have the same size as me. I thought to myself why not she is going to be wearing a bra for a very long time so why not have her like what she wears. I will take her other bras back tomorrow then get her something with a larger cup so she can feel more feminine.

Helga it was a risk buying Paulina a sissy dress with all the extras however now I couldn't be happier about my decision.

What do you think about using a dildo to train a sissy or sissymaid? I used one on my husband quite often finding it really helped him with submission. Based on what you think of it I may look for one to help train Paulina. The chastity is a great start showing signs of working already. I just think a dildo will help Paulina totally submitted to me.

I look forward to your reply at some point. Now I must leave for work.


Thank you for your letter Joanne. I must say right off, very well done! This is like watching an artist at work, you know, usually I am advising novices on how to train and what to expect from their new sissymaid, so I can really appreciate your expertise. I look forward to a long and fruitful correspondence, I hope you feel the same way.

What an amazing start, I loved how you kept a running conversation to distract her a bit while creating your masterpiece, much like watching a magician performing the trick with the right hand while the audience is watching the shiny item in the left, really Joanne, that was inspired.

The introduction of her device, she is well and truly into it now. I must say, other than some expected confusion, she does seem to be adjusting pretty well and the fact that she already knows what a vagina is and how to treat you properly is a real plus, at least it seems so to me.


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