Mommy's Pajama Sissy - Part 2

When Tommy returned home from school the next afternoon, the first words out of his mouth were, "Mommy, can I dress up in your pretty pajamas?"

I will admit that I was surprised by how anxious and excited Tommy appeared to be to repeat last night's experience.

I told Tommy I would let him wear my pretty pjs as soon as he was done with his homework. Well, Tommy tore into his homework with a vigor I had never seen before.  After about an hour and a half, he announced that he was done.  I took him up to my bedroom where we picked out a light blue floral print set for him to wear.  I again sat him down at my vanity and fixed his hair and put a little make-up and perfume on him.  "There," I announced when I was done.  "Now you look and smell pretty."  He beamed when I said that.

He moved from the vanity to my full-length mirror, where for stood for nearly ten minutes, as he turned and struck various poses, mesmerized by his own girlish reflection.

I changed into my pajamas and we ate dinner together.  He chatted happily about his day -- something that he hadn't done with me for ages. Afterwards he helped me do the dishes without even being asked.  We watched tv together and generally had a wonderful time.

Our pajama fun continued every night. Each evening I would pick out a set of my pretty pajamas for Tommy and each evening he would race through his homework so that he change out of his boy clothes and into my ladies pajamas.  Over the course of that first week, I let him wear a pretty white set with red flowers, a black set with pick flowers, and a very sweet powder blue set.

Of course I knew this was a bit unusual, but it seemed to make him so happy.  And it also brought us much closer together.  He was so engaged and affectionate when he was wearing my pretty pajamas. I soon realized I was enjoying Tommy's unusual fixation with looking and feeling feminine as much as he was.

Mommy's Pajama Sissy -- Part 1

Last fall, shortly before Halloween, the weather turned suddenly very cold.  Our house is rather drafty so I wanted to be sure that my teenage son Tommy stayed warm.  But I then discovered that, over the summer, he had outgrown all of his winter pajamas.  Since Tommy and I were about the same size, I suggested to Tommy that he borrow a pair of my flannel pjs.  I handed Tommy a set that was white with a pale blue floral print.  I thought he might protest, but he didn't.

When Tommy emerged from his room wearing my pajamas, I could tell that his mood had brightened.  He went into my bedroom and stood in front of the big mirror, admiring his reflection. "Do you like those pjs, Tommy?"  I asked.

"Oh yes, Mommy.  I do.  I think they are very pretty," he said.  "Mommy," he continued hesitantly, "Do you think I'm pretty?"

"Pretty?" I responded with surprise.  "Well, I never thought about it, but yes, I suppose you are pretty."

He smiled.  "I want to be pretty.  Pretty like you," he said, still gazing at his reflection.

I was puzzled but also very touched by what he said.  "Well, maybe I can help you to be even prettier," I suggested.  I sat Tommy down at my vanity and started to brush out his hair.  His curly, dirty blonde hair hung down nearly to his shoulders.  As a boy, his long hair gave him a wild, surfer dude look.  But as I brushed it I realized just how pretty his hair was.  I gathered up some of his hair and pinned it up in back.  I brushed out a few tendrils and let them fall to the sides of his face.  I dabbed some pink gloss on his lips and brushed a little blush on his cheeks.  When I asked him if he wanted me to spritz him with a little cologne, he said, "Yes please, Mommy."

Tommy and I proceeded to spend a delightful evening together, both of us wearing pretty flannel pjs.  We snuggled up together under a blanket on the couch and watched tv together, something we hadn't done since Tommy was just a little boy.

That night, I even tucked Tommy into his bed.  He did indeed look very pretty, with his lips and cheeks pinked with my make-up and his brushed out hair falling across the pillows.  I kissed him good night on the forehead and he said, "Thank you Mommy."

As I turned off his light and closed the door to his bedroom, I wondered if this was going to prove to be a one-time event.  I suspected it would not be.

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!

Don't look so sad, little Sissy!

Don't look so sad, my little Sissy Princess!  After taking a long break, I have decided to come back and add some more delicious Sissy fantasy stories!  Isn't that wonderful news?                                                          There are a few stories that I started writing down a few years ago that I will finish up and get posted.  Some are sweet and soft and romantic stories that will make all you little Sissies swoon with pleasure.  Some are a little bit rougher and scarier.  These stories will make you little Sissies squirm with fear -- and envy.                                                                                      So turn that frown upside down, little Sissy!  Mistress Trainer is back with more stories for you.                                                                                Now get on your knees and open that mouth nice and wide because I have some gentlemen friends in the next room that are dying to meet you!