Sunday, May 6, 2012

Mother's Pretty Little Sissy Daughter

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 haven't told him this yet, but as soon as school is done next spring, we're going to move closer to the city.  Only Jesse isn't coming with us.  Just my daughter Jessica and me.  I'm planning to enrolled "her" in a private girls school for the fall. 

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


  1. This was me i love this

  2. What a lovely story. Janey is so lucky.

    I was caught when I was fourteen, but not by my mother. Although I did wear my mothers undies and dresses whenever possible. I had a neighbor ten years my senior who had a summer home on a lake. His parents and my parents were friends and he would take me to the lake house for weekends of water skiing, wakeboarding and fishing. Sometimes his mom and dad and sister would be there other times just he and I. His sister was seventeen and kept clothes and bathing suits, undies and dresses for church on Sunday at the lake house. Whenever Ken would be off doing something and I had the chance, I would put on Pat's undies and a dress, or a bathing suit, or something. One Saturday Ken went into town and was going to be gone for a couple hours. I took the opportunity to dress in Pat's panties, bra, pantyhose, sundress, and shoes. I felt wonderfully girly. I was vaccuming the living room and never heard Ken's car pull up or Ken enter the house. I don't know how long he watched me, but when I turned to go vaccum another room there he stood smiling at me and taking photos. I was mortified, I am sure I stared back at him with the deer in the headlights look on my face.

    I said, "I can explain."

    He replies, "No need, you look lovely."

    I said, " I will go change out of these. I am sorry."

    "Don't be sorry." he said, and please don't change. I like you dressed like as a sissy. Come here and sit on the sofa with me."

    I sat next to him and he put his arm around me. We just sat there like that for awhile. It felt comforting. He told me how cute I looked and that since I liked dressing like a girl he would help me do so.

    He said, "Whenever we are up here, just the two of us, you will be my sissy girlfriend. And with that will come certain things that you will have to do for me."

    I am sure you can guess what those things were.

  3. Dearest Miss Trainer:
    He's back to get excited with his story. It is very sweet and delicate. That good feeling has this sissy with her mom.
    Anyway my favorite stories are what add something of domination and morbidity.
    His whore always Gwendolin

  4. Very lovely story Miss Trainer, Janey is such a lucky girl to have a mother who knows what is best for her.

  5. Oh,yes indeed. Janey is one lucky lad, and this story, most definitely, is after my heart.

  6. My mom caught me wearing panties and a bra when I was in my last year of high school. She thought I was having a break down and sent me to a shrink. I kept my desires hidden from then. Janet is very lucky.

  7. My son at a very early age would wear my shoes and sweaters while playing house. One day I caught him in my bedroom drawers. Asking him what he was looking for his answer was something that you wear that would make me feel like a mommy. I gave him a basic white panty. He put in on over his own pants and continued playing. I thought it was so cute that he could want to play a female role while palying with his friends. In later years he began to wear panties instead of male oriented underclothes. As he turned 25 he came to me and told me that he was gay. Being a single parent most of my life I was so happy for him and knew he would happy with the way he led his life. He is now in his 50's and dresses as a female. I must say he looks wonderful and I am not saying that because he is my son but he always had female features and he looks great. I am very proud of him and the life that he lives with his partner.

  8. Dearest Miss Trainer, love the short story. I so wished my mother would have been so understanding, especially being she didn't have a daughter. I so loved playing dress up in my mother's clothing when I was like 5 yo until my teen years..

  9. Miss Trainer...This is so Delightful to hear. more mothers Need to allow their sons to experience their Femininity. The Future will consist of Independent Women with Feminine Males as their Partners...This is Awesome. You are a Great Mother!

  10. I remember mom coming into my room finding me in one one of my sisters dresses experimenting with makeup. Needless to say I was petrified when I turned and saw her staring but in reptrospect it turned out to be a postive thing. Finally though scared I was forced to talk to someone about my fascination with crossdressing and we in turn bonded as she helped me with my hair and makeup and taught me a bit about dressing and being a woman.