Sissy Annie Humiliation

A few days ago, sissy annie sent me the attached photo and said there was a humiliating story to it. I asked for details, and she sent a one-sentence follow-up. Ms.Holly told her that was not sufficient and she should tell the whole tale, no matter how embarrassing and humiliating it is. She complied with the following:

It was a Saturday morning and I was going to a meetup with the other girls about noon or so. Mommy had a morning breakfast meeting that she could not miss. So Ms Hayes was to get me ready for the day. I guess I understood that she was going to dress me and help me with my makeup and hair. Mommy gave me breakfast and Ms Hayes arrived about that time. Mommy told her that all my clothes, accessories, etc. were all laid out on my bed and in the bathroom.

Mommy gave me a hug and kiss and told me to be a good girl for Ms Hayes. I was still in my Frozen nightgown.

Ms Hayes told me to finish my breakfast. She was going to make me a bubble-bath. I was a little surprised because Mommy had given me a bath last night, but that was ok. She told me to come to the bathroom as soon as I finished my breakfast. Maybe ten minutes or so later I walked upstairs to the bathroom. She saw me and told me to take off my pajamas and step into the bathtub. I loved the bubbles but also asked for my bath toys. Ms Hayes said that there was no time for playing today. She scrubbed my face and all the rest of me. She had me stand up to get to all of me. She washed my privates with a wet washcloth and my bottom too. I was a little nervous, but she was very gentle with me. When she was finished she washed away any remaining bubbles and had me stand up on the bathmat so she could dry me.

Then she had me stand straight up so she could look at me. I put my hands in front of me to cover up my privates. She immediately unlocked my fingers and told me to hold my hands behind my back. Then she saw that my peepee was stiff. She laughed and told me how unacceptable that was and also made a comment about how small it was. She asked me if I knew how to make it squirt. I said that I did. She laughed and said, "of course you know". She told me to "wank" (that was the word she used) until I squirted, and it was soft again. It was so humiliating to do that in front of her. I was crying until she told me that if I did not stop crying she would paddle me too. It was not long before I squirted. She had me lick my hand and swallow it all. Then she had me clean my peepee with my hand and swallow the rest. Finally she cleaned me up and took me to the bedroom. I did not expect what she did next.

She took the pink chastity from the drawer and put it on my peepee. I had to stand there with my hands behind my back as she took some pictures of me. Then she explained to me what a bad sissy I am. She said that she would recommend to mommy to keep me locked so I would not be a disgusting wanking sissy! Then she took me back to the bathroom. She put sweet smelling body lotion all over me, deodorant and body spray. She put on pretty sissy panties on me and a bra. She took more pictures.

Then she sat me at the vanity and did my makeup. I loved watching her make me pretty. Eyelashes, eye shadow, eyeliner, mascara, concealer, liquid makeup, blush and my pink lipstick. All of my makeup was very pink which is almost always my color! Then she put on my knee socks and shoes. Finally she put my dress on over my head and adjusted it. Lastly, my two pretty petticoats. Then Ms Hayes sat me down to put on my wig and style it. She added a pink hair bow. When she was done she put on my earrings, necklace, rings and bracelets. Then a spray of my Pink Sugar perfume! She took me to the living room and had me pose for pictures. She told me that I was a darling and delicate little sissy! I gave her a deep curtsy and thanked her!

We still had time, so she gave me a lesson in feminine deportment, walking with mincing steps, sitting like a lady, and how to eat and drink in the most delicate manner. She also explained to me that little sissies are seen and not heard unless spoken to. Then we left and she drove us to the lovely restaurant.

We had a lovely time. Everyone was so pretty! I love being a beautiful sissy!

When Ms. Hayes saw this, she added an addendum:

Annie said in an earlier email that "It was the most humiliating and embarrassing thing ever. " The fact was that she loved the entire process of being properly sissified, feminized and humiliated.

One can disagree about how much sissies need or desire to be humiliated. But it is a fact that it is in their DNA to need sexual release. Most sissies masturbate to give themselves release. In a few days or so the craving returns. Those sissies who are not allowed release (by chastity or self-control (LOL) or strict domination) crave humiliation.

When I saw her "stiffy" I knew I had to calm her down in order to get her ready for the meetup. Just details but it varies a bit from her story. I had her wank by stroking through her silky panties. Then I had her lick her fingers and also take off the panties and lick the cum from them. I cleaned her up with a washcloth and put a new silky pair of panties on her. She mentions that she only "wanked" once. It was actually twice. I had her beg for a third time, but I decided twice was enough.

She really wanted it again. She could not have faked her desire. I did lock her in chastity.