Boy to Girl

Boys dressed as Girls by Mother

Boy dressed as girl by mother

In many occasions, mothers have dressed their sons as girls, mostly for Halloween, School plays & functions or simply for fun. It is also a complete new experience for boys to find out how its like to be a girl & wear a pretty dress.

Many boys have said they enjoyed dressing up and it was a fun experience. Here are some lovely photos of boys dressed as girls by their mother in cute dresses & makeover.

Boys dressed as Girls by their Mother

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  1. Great photos. This brings back great memories of the times my mom and I would play mother and daughter. We used to dress up every weekend and go out. Then I started to dress everyday after school. I would run home and then become Miriam. I have been a life long cd and it has always been the best times of my life. I love looking and acting as a girl. I only hope it will go on forever. My motto is, ( Heels forever, flats never)

    1. It is so nice to have a understanding mother that likes having a son dress in her clothes. I have purged all of my male underwear and now wear only bras and panties. Also enjoy garter belts. I too hope it never ends!
      l love to hear from you!


      1. I can understand. My mother also liked that I put on stockings and a bodice

      2. Hallo Patricia mein Name ist Ilona. Mein Mutter nannte mich Ilona. Dann durfte ich ein strumpfhalter und nylons tragen.und einen bh.und Röcke und Kleider.und das trage ich heute noch.

  2. we are girl girl

  3. They all look so cute! And they all look so happy and excited. Im sure some of them will continue to be interested in dressing again. My mother got me started by hanging a few nightgowns in my closet to see if I would secretly try them on and i did! Then she said that i didn’t have to hide in my room while wearing them.

  4. It is so nice to have a understanding mother that likes having a son dress in her clothes. I have purged all of my male underwear and now wear only bras and panties. Also enjoy garter belts. I too hope it never ends!
    l love to hear from you!


  5. Omg yes isn’t it wonderful to Wear the same clothes our mothers wear I JUST LOVE WEARING A BRA AND GOURGOUS PANTIES AND BEAUTIFUL DRESSES she caught me fully dressed and wasn’t taken back buy it she just said I looked very pretty after dinner we disgust how I feel in women’s clothes and makeup on I just said to her I just love it very very much on my 18 birthday she said to me we are going To another town over night and buy me my new wardrobe we got up the next day showered and she did my hair and makeup and my nails that was the beginning of me becoming ambermaria today I still love to dress and hopefully this year I can finally trastion to be the woman I always felt and wanted to be

  6. Ich habe auch strumpfhalter und mieder angezogen. Meine Mutter hat mir geholfen die strumpfhalter festzustellen

    1. Legal gostei….

  7. Meine Mutter hat mich damals Ilona genannt und ich habe ihr geholfen ihren mieder anzuziehen und die strümpfe zu befästigen dann sagte ich wenn ich Ilona bin dann möchte ich auch mieder und strümpfe und einen BH und Rock und blusen tragen. Und so wurde ich ein Mädchen. Was ich auch heute noch bin.

  8. i can you do it to me

  9. can i wear a bra

    1. Te puedo meter mi verga

      1. can you come get me i live at 402 6th st north winsted mn?

    2. I love to wear my bras and have several pairs of stockings garter belts dresses and heels ! Love to feel like a wonderful ! Love to.hear from others .

      1. so you will adopt me

  10. I have a feminine side, have no male under wear, love my new panty girdles and panty corseletts, also wear granny knickers and school knickers

  11. I was dressed as a junior Bridesmaid for one of my mom’s sister’s daughters. I really and thoroughly enjoyed that summer day of myself wearing a bridesmaids dress, panties and heels. Mom asked me and many of my relatives, how did I enjoy being a bridesmaid? I just honestly told them, that I wish I could have turned into a girl on that day. After that day, my mom and my two sisters would have me dressed as a girl after school and at weekends. Well I had worn a nightdress to bed since I was in diapers, as mom never bought me a pair of pajamas not even girl’s pajamas, always a nightie. So wearing a dress was just like a nightdress for the day. Then when my sisters got married and moved out, so it was just mom and myself at home. What fun we had. Mom treated me as a girl, her daughter. Thank you mom, for making me so happy in life.

  12. My mum introduced me to the joys of wearing her clothes, starting with knickers, bras and dresses. Then I got my own. Mum and I still dress together and share clothes, especially half slips and stockings. To all of the girls who commented, it is so liberating being the femme person we like to be.

  13. Starting at age 8, my mom would put me in just girls underwear after getting home from school and she’d keep me and my sister like that.

  14. i need a dress

  15. I love your story. My aunt dressed me when I was 4 and it carried on until I was 15. I love dressing completely to this day, doing my makeup 💄💋 and wearing my heels 👠. Always looking for a friend to chat with, janie

  16. My Mother and I had wonderful dress up times together, it started about age 5 or 6 and lasted until I was 13 or so, I always loved girl things and she indulged me, it was embarrassing at first but with a Mother’s love it became very natural overtime, sissy.

    1. Hi Janie,

      Funny we kinda had the same experiences, aren’t loving women in our lives wonderful.


  17. I loved it, I love wearing panties, maybe the next one will wear a little dress.

  18. When I was young, my Austrian relatives often brought several cardboard clothes. They put them at our place. That’s why I had time to choose and try it on. My mother caught me once. It wasn’t good, but then it was forgotten. I’ve been dressing ever since. At a New Year’s Eve party, my aunt, a friend of hers, and a friend dressed me up and did a little make-up. I was like that all night. It was a wonderful feeling. It’s been many, many years, but I still like to dress up today.

  19. The stories brought such amazing feelings back when I was dressing in my mums bras and panties. Her night gowns and nylons/garterbelts.

  20. Mom raised me in my older sisters left over clothes until I started to school at age 6. I don’t remember much before about age 4 but from 4 to 6 I remember wearing dresses and going places. I remember playing outside in them. I remember wearing one when we went to my uncles one afternoon. After I started to school I continued to wear her clothes after school and on weekends, especially during the summer when it was hot and school was out. Nothing fancy just plain cotton simple ones. The sundress type. i remember when I was 8 or 9 having a couple of skirts I liked. I wore them with t shirt tops. I wore a lot of her shorts. Usually if we went somewhere I wore her shorts. I always liked them and wore them all the way into high school. I liked they way I looked in them and started shaving my legs when I started getting peach fuzz on them. No body ever really said anything because I never had any hair on them. I liked the look of smooth and brown tanned legs.

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