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Mistress Feminizes Reluctant Sissy

Your reluctant feminization

Mistress Olivia reluctant sissy training

At the beginning of your feminization, you have the best time!  You love the clothes and cute fashions.  I decide that I want you even more femme, more girly.  I even decide you’re going to be my sissy bride.

Enjoy the free sissy feminization audio of this Experienced Mistress blog post.

Chastity makes the sissy

Then I notice something troubling: even though the wedding planning is going smoothly, I see you slowing down in your feminization.  Your femme training begins to stagnate. This is unacceptable and something must be done to kick start the process.  I think it’s time for sissy chastity to solidify the feminization process!

Strict Mistress feminizes struggling sissy

I wake you early one morning. As you open your eyes, you see the dress hanging on your door.  Today I am a strict Mistress:  dressed in black leather pants with 4″ black patent heels, with a black leather jacket over a black tank top. My hair is piled high showing the diamond stud earrings in my ears.

Busy day for my girly girl

Mistress says, “Get up missy, we have a busy day.”  You look over and realize your lingerie is set out.  You spot that huge, fluffy petticoat from your closet.  I am very stern as I say, “This is punishment day.  I suspect you will enjoy every minute.”

Punishment and training for your feminization

First we head to the salon.  You will have a very …. FULL … day.  I say, “Remember this punishment is for your own good.  You can struggle, sissy, but you know that Mistress always gets her way.”

Your Experienced Mistress,

Ms. Olivia


6 comments to Mistress Feminizes Reluctant Sissy

  • yvonne

    I know just the dress you have in mind 🙂


  • mike

    this might sound remarkable but one of the very most powerful experiences of my life was the first time
    a girl told me I had to put on a slip for her. It was not describable and has stuck with me for a long time. She “just” handed it to me and told me she wanted me to put it on. I was reluctant as per your title but she insisted quite firmly and said I had to do it. I had not had a girl quite that strong with me before and it just did something to me. It was like she was stronger than me – by a long shot. I did as asked and she had me stand in her apartment and laughed at me. I felt like I was her little helpless toy. I will never ever forget it.

  • Petey cream puff

    This is happening to me for real Ms Olivia! I came out to my massuse and she fitted me for bra and wanted to see how I looked. She adjusted it for me. She had same bra but in black color. She sold me coach purse called me purse boy. I showed her my dresses and she said I have great taste and wants to barrow my dresses. She wants me to use same foundation she uses and I asked her if it was ok to go shopping with her and her gf & she said yes. I’m going to wear bra/panty to massages now that she knows and ask her about lipsticks she uses and have her pick out shade for me. I have done and hope she like sit and puts it in me. Now that she knows I don’t dare upset her nor be late for waxings/massages as she can use this against me. She has her nails dug into me with no intention of letting me go. I’m her cream puff purse girlie boy toy.

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