Mother's Pretty Little Sissy Daughter -- Part 2 -- Getting Ready for a Sissy Day

*** This is a continuation of a story from 2012.  To find Part 1, click on the "Sissy Jessica" Label in the right margin of the blog.  Enjoy! ***                                                                             As you already know, I have been pushing my son, Jesse, to embrace his feminine side.  In fact, I want him to become my daughter, Jessica, full-time.  Jesse is much too pretty to be a boy I think. And I tell him that almost every day.

I encourage my little Jesse to dress up as Jessica every chance he gets.  I do everything I can to get Jesse to think of himself as a girl.  I want him to let go of being a boy and to embrace a completely and permanent feminine existence.

Jesse still goes to school as a boy, but he spends all his time at home as a girl.  He has been living this way for almost six months.  He has become so naturally feminine that it has become unbearably painful for me when he reverts to being a boy.  And over that time, Jesse's hair has started to grow out long and beautiful and his body is slender and pretty as a result of the strict diet I keep him on.

As soon as he gets home from school and throughout the weekends, there is no sign of Jesse, only Jessica.

And because he spends so much time as Jessica, he has become very girlish and feminine. And he very talented at doing his hair and make-up.  Here are some photos I took of Jesse getting ready to spend a Saturday with me as mother and daughter.  He starts his day with a warm bubble bath, soaking in a tub where fragrant oils soften his skin. The experience relaxes and prepares his body and mind for a day of feminine fun.

After his bath he applies lotions to his skin before he begins to do his hair and make-up. Since he has been doing his own hair and make-up almost every day for several months, he has become a true expert at making himself look beautiful.   

I have a fun and exciting day planned for the two of us.  First, we will go to the big shopping mall that is about 20 minutes away.   We'll shop for dresses and lingerie at the big department stores.  Jessica always gets so nervous when I push him into a ladies dressing room to try on things.  Then we"ll head downtown for lunch at a restaurant we like. 

 I haven't told Jessica this yet, but there is a huge car show going on downtown.  The streets will be crowded with people and we'll probably have to park far away.  And of course the car show attracts men -- and teenage boys -- by the thousands.  So Jessica will get plenty of attention and admiring looks -- and comments, I expect -- from the men and boys we will be walking past.

Doesn't that sound like fun?

Now hurry along and finish getting ready, Jessica.  We have a busy day planned!

Mother's Pretty Little Sissy Daughter -- Part 1

The day I caught my son crossdressing was the happiest day of my life.

I had come home early from work and found my son, Jesse, sitting at my vanity, putting on make-up.  He was wearing one of my cocktail dresses -- and my stockings, my high heeled sandals and, it appeared, my lingerie.  He hadn't heard me come in, so I just stood silently in the doorway watching him put on mascara, blush and lipstick.  He was completely mesmerized by his own ladylike reflection, completely entranced by the girl in the mirror. He did a very good job with his make-up; clearly he had done this many times before.

Of course, Jesse was very upset and embarrassed when I announced my presence after enjoying the show for several minutes.  He started spewing all sorts of pathetic explanations and denials.  I tried to calm him by saying that it was OK.  He settled down enough that he even let me help him finish doing his make-up.   I encouraged him to stay dressed while we ate dinner.  I treated him like a girl throughout the evening and he seemed to enjoy the experience.

So why was that the happiest day of my life?  Because I had always wanted a a daughter -- and now I had one!

That was two months ago.  Ever since that fateful afternoon, I have been working day and night to convince my little Jesse that he is too pretty to be a boy and that he was always meant to be a girl.  When he is dressed as a boy, I treat him mostly with indifference and I react harshly to any little mistake he makes.  But when he is dressed as a girl, I shower him with the affection he craves and I lavishly praise his every girlish accomplishment.  In this way I have lured him -- trapped him -- into more fully embracing his feminine side, using my love and affection as bait. 

He is now in the habit of changing out of his boy clothes as soon as he gets home from school.  My son Jesse becomes my daughter Jessica for the evening.  And all through the weekends.  He has become proficient doing his own make-up.  And with my coaching, his mannerisms and his voice have become delightfully feminine as well.  He now has a closet full of his very own dresses and his drawers are overflowing with his own bras and panties and stockings.

Recently, I have started taking my daughter Jessica out of the house at night.  We've started going to restaurants and movies together.  Tonight we are going to the ballet!   I even bought him a pretty new dress to wear.  He's very excited.  Here's a photo of Jessica doing his make-up for our big evening out.  Doesn't he look sweet?

I can't stand the idea of not having my daughter Jessica with me all the time.  I have all sorts of ideas for how we can spend more mother/daughter time together.  I'm hoping that by spending more time as Jessica that Jesse will more fully embrace life as my beautiful, sweet little sissy daughter.    

I think he will learn to love his new life as Jessica.  Don't you?