ADVANCED TRAINING - PART ONE
from Jill

Dear Helga,

When Daisy arrived at home we chatted about her day along with now wearing panties and a camisole. According to Daisy it went well with the camisole straps not getting in the way more than a couple of times. While we enjoyed our chat with a glass of wine I talked a little more about Tara just to ensure Daisy was going to be alright with meeting Tara as my sissymaid. Daisy explained it did shock for a moment as it wasn't expected so like a few of the other items related to her new role it took her some time to digest it. The good thing Helga now Daisy is putting the puzzle together where as in the beginning she was just confused.

I asked Daisy would she still feel embarrassed to be seen by Tara when she replied not now that Tara is supportive of Daisy's new role. Helga I think we are making progress with Daisy while she thinks it out before she speaks.

In the bedroom after Daisy had her shower I introduced the butt plugs purchased today. Daisy didn't seem to be terrified yet her eyes showed concern so I explained to her. I asked if she remembered Auntie Helga letting her know that the dildo was all part of the training which she replied yes. I also mentioned that neither Auntie Helga or me primary's purpose was to cause pain although some would be part of training. Daisy understood what I was talking about as I described the purpose of the butt plugs was to train her anus to release and not be so tight as that was what would cause the pain.

I let Daisy know we would start off the training with the small one to see how that would be for her first. Daisy asked if we had to do this part of the training when I looked at her replying yes it was all part of the training for all sissymaids. With that I slipped on a rubber glove lubing up the small butt plug then asked Daisy to lean over the bed. I promised to be gentle and stop if it hurt her so Daisy obeyed as I slid the butt plug in place. Helga it looked so amazing in there.

Daisy didn't say a word so I know it didn't cause any pain. She stood up as I asked her if she was going to be alright with her replying she thought so Jill. Next I plucked a few more eyebrow hairs with things looking much better than when we began. I asked Daisy if she wanted to try mascara again and possibly some lipstick this time to which she agreed. Helga I actually like Daisy with some makeup on now. Then Daisy dressed in one of her hotel maid uniforms for a change with me just watching. Within a few minutes we walked to the kitchen with Daisy taking much smaller steps Helga. You know the butt plug might be a good teaching tool for walking in heels.

After dinner Daisy went about her chores just like last night with cleaning the bathrooms first. Every so often I asked her how the butt plug felt with her funny answer feeling like she had to use the toilet. We laughed together about it then I took her into the laundry room. Tonight she was going to start hand washing our panties as the pile was getting up there. I showed her how to soak them then wash each one gently with love and care, not so male like. Helga what a sight seeing her bent over hand washing panties, priceless. I left her there for about an hour when I looked in to see how she was making out.

Helga every day I am so thankful for having Daisy and for all your help developing her for me. She thinks the world of you Helga with always good things to say and never anything bad. With introducing her to being my sissymaid I think that says something about you, me and Daisy. I look forward to spending the rest of my life with Daisy as my sissymaid. She has taken this much better than I had ever thought she would not to say in time should would have had no choice.

Daisy is such a caring person with her blossoming more now. Oh, you had asked for a wedding date at one point Helga. We talked about next year although I haven't seen a ring yet. I do know she bought one a few weeks ago thanks to a deposit receipt found in her pocket. Knowing Daisy as I do she is probably moving money around preparing to pick it up soon. To be honest after finding the slip I wasn't sure about moving forward with petticoating her. Then I thought waiting for an engagement ring just so I could petticoat Daisy was wrong. I felt she should know who she is marrying and the life she can expect as a sissymaid. Now I am glad I did it this way with her loving me just as much or more even though she is being feminized daily.

We spent the rest of the night watching some TV with Daisy sitting beside me in her maid uniform. The house is getting easier every day to keep clean and I love it.

I am going to surprise Daisy with some oral sex later for she has been performing well as a new sissymaid. When we first started her shaving and sleeping in a nightie the reward was sex. Now that she has submitted I will still keep her happy unless you don't agree Helga. If Daisy was refusing and giving me a hard time I would lock her penis up in a cage to get her attention. With her agreeing to everything I demand there is no reason to lock her up right now like some mistresses have done.

We will still play with chastity though with me being kinky I want to try everything at least once.

Jill


Thank you for your letter Jill. I'm sure that many readers would agree that a plug can be very helpful in preparing the sissy for the strapon, one of the many steps involved in creating a sissymaid. Not only getting her used to all the pretty clothes she will come to enjoy but altering her body both to feminize her and to allow her to experience the feeling of being penetrated without undo pain, a kindness some Mistresses allow as you have.

I do have more from this wonderful contributor that I will be sharing over the coming months, not only does Daisy get penetrated (often) she becomes an exemplary sissymaid with ever stricter training.

Helga

Return to Index
Letter 2