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?

750,000 Page Views!!!

Hello all you little Sissies and Sissy Owners and Trainers!

My blog has now had over three quarters of a million page views!  Isn't that exciting!!!

This tells me that there a great many Sissies in need of strict training, manipulation, captivity and humiliation.  And there are many Sissy Owners (and men and women who wish they had a Sissy of their very own) who are very interested in learning more about the art of forcibly transforming a male into a Sissy plaything.  I am delighted to see how large -- and how global -- our community is!

But listen up, all you pathetic little Sissies.  If you are a Sissy and you are visiting my site, I am INSTRUCTING you to leave Comments.  I am very pleased with the Sissies (and Masters/Mistresses) who have been leaving Comments.  But I am VERY disappointed in you Sissies who are visiting this site in secret.  That is not permitted!  Part of your Sissy journey REQUIRES you to put your Sissiness on display for all to see.  Express yourself to your community of Sissy sisters and superior Masters and Mistresses by commenting on the stories and pictures posted.  Share your Sissy feelings about the stories, your Sissy dreams, your Sissy fears.

The little Sissy in the picture is being punished for being disobedient by his cruel and demanding Mistress.  Ouch! You too will be punished if you continue to disappoint me.

After School Sissy -- Part 3

Last Friday afternoon, when I came home from school, I went straight to my mother's room to do my make-up and put on one of her dresses like I do everyday.  As soon as I was satisfied that I looked pretty and girlish enough, I got busy on my chores before it was time to start making Stepfather's dinner.  As I was dusting upstairs, I went into my bedroom and discovered that my bed was gone.  When Stepfather came home I asked him what happened to my bed.

"Oh, I decided that you wouldn't be needing that old bed any more," he said.  I didn't understand what that meant, but I know he doesn't like it when I ask a lot of questions, so I let go.

After dinner, we went to the den and I climbed onto Stepfather's lap like usual to watch TV.  He wrapped his big arms around me, and started stroking me through the satiny dress I was wearing.  But after just a few minutes he let out a big yawn and announced that he was tired and wanted to go to bed.  "Come with me," he said.  "I have something to show you."

He took my hand and led me up the stairs to his bedroom.  I noticed that one of my mother's nightgowns was laid out on his big bed. 

"I want you to put that on," he said.  I knew better than to argue, so I picked up the silky nightie. 

"Okay," I said.  "I'll take this to my room and I'll try it on."

"No," he replied.  "You can change right here."

So I unzipped my dress (I mean mother's dress) and let it fall to the floor.  Stepfather seemed to enjoy watching me as I did this.  I unlaced my corset and pulled off my stockings.  I was about to take off my bra, but Stepfather said to keep it on.   While I was undressing, Stepfather started rubbing the front of his pants with his hand and was breathing hard.

I carefully pulled the silky nightie over my head, being careful not to mess up my wig or make-up.  The nightie was extremely feminine and sweet.   It had little ruffly cap sleeves and was trimmed with several ribbons and bows.   "Walk around," Stepfather instructed.   "Yeah, that's nice," he said as I paraded around the room. 

After a few minutes he handed me another one of mother's nighties.  "Here," he said.  "Try this one on."  I did as he instructed.  I modeled several nightgowns for him that evening.  He decided that he liked the one I tried on last the best.  It was soft pink with white applique flowers trimming the neckline. 

"Yes," he said.  "Keep that one on."  He kept staring at me, his hand still rubbing his erection through his pants.  I felt so exposed just standing there in th sheer nightie.  I held onto the back of the chair while he continued to stare at me. 

After a few minutes, he came out of his trance.  He said that he was going to go to the bathroom, and that when he came out, he wanted the lights dimmed and the candles lit.  I didn't like where this was going but I didn't argue.

I prepared the room the way he asked and after a few minutes he emerged from the bathroom.  He was completely naked!  He ran at me and literally pushed onto his bed.  He fell on top of me, all of his weight -- and his erection -- pressing down on me.

"This is the way things are going to be from now on, Lydia," he stated, calling me by my mother's name.  "Now spread your legs."

After School Sissy -- Part 2

Stepfather arranged for a lady to come the house to help me look the way he wanted me to.  She was waiting for me at the front door when I got home from school.  We went inside and she had me take off all my clothes.  With her help, I put on a pair of mother's panties and one of her bras.  She gave me a set of breast forms that filled out the cups of mother's bra and she laced me into a tight corset to give me a "prettier shape."    She sat me down at mother's vanity and for the next two hours she gave me a thorough lesson in putting on make-up.   I was taught how to do everything: putting on foundation, plucking my eye brows, putting on fake eye lashes, mascara, eye liner, blush -- everything!.    Here's a photo she took of me while I was practicing putting on lipstick.

When she was satisfied with my make-up, she had me put on a silky flowery dress and a pair of strappy high heels that she picked out from my mother's closet.  And lastly she pinned a long wavy blonde wig that was styled to look like my mother's hair.  When the lady was done with me, I didn't just look like a girl, I sort of looked like my mother!

But she wasn't done yet.  She stayed for another hour, giving me lessons on walking and sitting and even talking like a girl.

By the time the lady left, it was almost 6:00, so I had to hurry to get Stepfather's dinner ready before he got home.  It felt funny being being dressed up like a woman but I was in a rush and I didn't really have time to think about.  It was a little hard to move quickly wearing my mother's high heels.  I also tried to be careful not to spill anything on mother's pretty dress.

When Stepfather came home and saw me with my new look, including my glamourous make-up, my big boobs, and my nipped waist, I could tell he was very happy.  He was very friendly and relaxed during dinner.  After dinner, he invited me into the living room to watch TV with him. He had never done that before!  He insisted that I sit really close to him on the couch.  He even put his arm around me.  That seemed kind of strange, but it sure was better than being beaten with his belt!

That night was two months ago.  Since then, I've been dressing up in mother's clothes and doing my make-up, just as the lady taught me, every day after school.  I do my chores and make Stepfather's dinner.  And even though I don't like dressing up like a lady everyday, Stepfather is very nice to me all the time, so I guess I don't mind too much.

But recently, when we watch TV together after dinner, he's been making me sit on his lap.  He wraps his arms around me and I have to lay my head on his shoulder.  Sometimes he kisses my neck which feels really weird.

  

After School Sissy -- Part 1

Everything changed after my mother died.

When we got back home after her funeral, my stepfather told me to make him dinner. He said that now that my mother was gone, that I would have to start "taking her place." I made his dinner without arguing, because he is a very big man with a bad temper.

Over the next few days, I would learn that "taking her place" also meant that I had to do all the chores around the house, including all the cleaning, doing his laundry, mending his clothes, cooking his meals, everything.   I did my best to do these things well, but my stepfather was never satisfied. He beat me several times when he was displeased because I hadn't ironed his shirts as well as my mother had or because his coffee didn't taste the way it had when my mother had made it.

One night while he was beating me with his belt for over-cooking the roast, he said, "Maybe you would be able to do your chores more like your mother if tried dressing like her." So the next day when I got home from school, I went into my mother's closet to look for something to wear.  I pulled out a pink dress that I knew had been one of her favorites.  I took off the jeans and tee shirt I had worn to school and slipped the pink dress on over my head.  I struggled with the zipper in back, but was able to pull it up most of the way.  It felt strange wearning my mother's dress, but I really didn't have time to think about it because my stepfather told me that he wanted to whole house vacuumed before he got home.  So I just got busy with my chores. 

When my stepfather got home and saw me wearing mother's dress, he smiled. That evening he was much nicer to me and didn't complain about any problems with how I performed my chores.  As I finished putting away the dishes, my stepfather said that tomorrow he wanted to see me wearing mother's stockings and high heels with my dress. And he wanted me to wear some make-up too. I had no idea how any of this was supposed to help me do chores better -- but I wasn't going to argue, especially since he was being so much nicer to me.

But I did tell him that I had no idea how to put on make-up.  I was afraid if I tried to do myself and I looked bad, he would just get angry with me again.

"Don't worry," he said.  "I'll have someone come over here to work with you after school to show you how to do it."

A Sissy Learns his Lesson

Master pressed his Sissy hard against his muscular chest.  His massive arms wrapped tightly around his Sissy's head.

"There, there," Master said softly.  "It's over.  Now stop crying."  Master had just finished administering a severe spanking to his Sissy -- 50 of his hardest hits against his Sissy's bare bottom.  Master was very angry that Sissy had been two minutes late serving him his breakfast in bed this morning.
Sissy forced himself to stop crying as his Master had commanded, even though his bottom still burned from the brutal beating.  His tear dampened cheek now rested against his Master's chest.  Sissy felt so safe and so protected when Master held him like this.  Sissy relaxed as he inhaled deeply, savoring his Master's rich, masculine scent.  Sissy even managed a little smile as he felt his Master's massive cock stirring, stiffening.

"Have you learned your lesson, Sissy?" Master asked.

"Oh yes, Master.  I have.  I am very sorry that I disappointed you.  It will never happen again.  I promise."

Master smiled seeing his Sissy's complete subservience.  "Good," Master said.  "Now get on your knees and suck my dick."