Page 1 of 2 12 LastLast
Results 1 to 10 of 12

Thread: how did you start wearing dresses?

  1. #1

    Question how did you start wearing dresses?


    I kind off never come hear. Part from being a horrible little boy, and telling you lot that lipstick has fish scales in it.

    But something happened to day.

    I work as a support worker and one of my clients needed to buy a present for his 5 year old niece.

    So I had to help him choose a dress for a 5 year old girl.

    Now I really enjoy looking around the boys section choosing what I like. Then trying to match it in the adult clothes section. Which is a challenge.

    But in the girl section they had some pretty summer dresses. And they had similar in the women's section.

    Now this is the scary bit for me, I actually found myself wondering. What's it would feel like to wear on at these summer dresses.

    I have worn a dress before. But that was to a party and before I had embrace my toddlerism.

    So my Question is how did you start wearing dresses?

    Pluss my son Would probably fit a lid if you saw me dressed as a little girl.

    Really not sour if I really won't to go down this road.


  2. #2



    You shouldn't be afraid to try new things, Life is short, and experiences are out there for the making. However to answer your question, I haven't worn a dress (yet), but I'm a sissy because it helps me connect with another side of me. Maybe you should try and find that side?

  3. #3


    Hi Sisi,

    I don't wear dresses or feminine clothing anymore and have not for quite a few years. My first memories of being a dress were back from when I was four or five in the early 1970's. I was still in diapers and my mother put me in my sister's old dresses for two reasons, to make it easier for diaper changes and to try and shame me into potty-training. At that time here in the United States, it was not viewed as child abuse (it wasn't until several years later that they even started pushing for reporting of physical abuse of children).

    It wasn't until I was 13 that I started dressing again, I asked my mother one night what it was like to be a girl and her thinking was that the only way I could know was to try it firsthand. When she found that I enjoyed it and was willing to dress more, she bought me my own things and I dressed on and off quite a bit until I moved out at 18. There's a lot of stories behind that, I won't go into depth right now.

  4. #4


    I dressed up as a girl when I was a young boy. My mom had a bag of all kinds of dresses, etc. I had gone trick or treating as a girl one Halloween as well. It was one of those early childhood experiences where I felt some sort of early sexual sensation, just like wearing diapers. It does make a case for sexual imprinting.

    Now, the residual is that I enjoy wearing girl Goodnites, and pink print Baby Pants training pants. At the same time I also have blue printed training pants. You can always try wearing a dress, woman panties, etc. and see what happens. It doesn't mean you don't go back to being a boy. I'm a boy most of the time.

  5. #5


    I don't know why but sometime around the age of 10(?) I started to sneak through my mother's bureau and tried on various pieces of underwear and also some dresses and shoes. I never went outside and I never wore at Halloween (I was not and am not a fan of Halloween).

    I had a younger sister but all of her things were too small for me (except for one one-piece bathing suit which I wore several times).

  6. #6


    As a newborn I was dressed in doll clothes from my grandmother's vast doll collection. I don't remember it obviously but I do believe it contributed to my crossdressing desires later. My first actual memory, I was 4 and had climbed into my Mom's bed while she was showering to get ready for work. She had her clothes laid out on the bed and I curled up on her slip. I fell asleep. When I woke up she had left for work and left me asleep on the bed (my grandmother baby sat me when she worked). I was covered with and in the slip. I still remember how wonderful it felt and the smell of her perfume in the air. Not exactly a dress but close enough to the form of a dress. I wear full slips today under my dresses and skirts.

    When I was eight I was diaper disciplined for babyish behavior a few times which also probably led to my diaper and plastic pants wearing today.

  7. #7


    I vaguely recall wanting to wear a dress growing up. However, knowing that it wasn't "okay" (roll of eyes) for a boy to wear a dress, I never tried to wear one as a child. As an adult, I started wearing them privately about a 1 - 1.5 years ago.

  8. #8


    When I was younger my dad was always at work so I was often home with just my mother and sister. My sister used to like to dress me up like a girl for fun and paint my nails and all of that stuff. I think that's what contributes to me being trans today. I never really did hang out with any guys or have any sort of guy hobbies. I was always a girly boy growing up. Quite often would my sister make me wear girly clothes. After a few years I started getting curious and would find the bags of old clothes from when my sister was my age (skirts and dresses) which there wasn't a lot of since she was kinda a tomboyish girl. I kind of wish I had realized sooner that I wanted to be a girl instead of a boy, probably would have led to less issues in my life, but that's a different topic all together.

  9. #9


    It was when I was younger going through moms dresses and sorts and finding that they are wonderful feeling to me dresses are just fun and functional all around ( makes changing a Diaper, or panties much easier )

  10. #10


    I started wearing dresses when I was a latchkey kid during my junior high and high school years. I had realized in elementary school (if not earlier, but I can't remember farther back than elementary school) that girls could wear dresses and skirts but boys could not; I had also started thinking girls were lucky because they have many more choices in clothing they can wear.

    Once I realized that being a latchkey kid gave me the freedom to actively pursue new interests without fear of being discovered by anyone, as well as the ability to easily pursue wearing dresses and skirts at the home I shared with my parents - and it didn't take me long to realize all this - I started going through my mom's closet on most school-days once I got home from school, picking out one of her dresses (or one of her skirts & one of her shirts or blouses) that I thought looked pretty, and changing from the boy's clothes that I wore in public that day to that dress (or that skirt & that shirt/blouse) of my mom's. I didn't change back until just before the regular time that my step-dad would arrive home with my younger sister.

    I never left the comfort zone of my parents' house (out of fear of being embarrassed and seen by someone) while I was dressed up like this. So I very much enjoyed this time alone pretending I was a teenage girl or a young woman.

    My advice to sisi would be to truly pursue these feelings you had when you were helping that customer choose a dress for his 5-year-old niece. If you fear being discovered, sisi, then do this when you have some time alone.

    I think Step # 1 for any man or teenage boy who is just starting to pursue wearing women's (or girl's) clothes should be to do a little research into how clothing for females is sized. This is because clothing for males is sized in a pretty intuitive/easy-to-understand way; but clothing for females is not. One way to do this is to go to the website of any clothing store for females and look for their sizing charts (virtually all such web-stores have a page devoted to this). Another way to do this is to go to a brick-and-mortar store that sells clothing for females, find a customer service (or sales or something like that) employee there, and ask her about how to figure out your size in women's (or girls a.k.a. juniors) clothing. I have found that virtually all of them will be happy to help you.

    Then Step # 2 would be to browse through that store's selection of dresses (and skirts, if you're also interested in those). Find one of those in a design that you like/a design that you think looks pretty. Once you've found this, look through that store's selection of clothes in that design, checking the size of each one, until you've found one in your size (which was determined in Step # 1 above). Finally, take this article of clothing to the store's register/check-out location. Again, I have found that virtually any employee that you get at the location to pay for the article(s) of clothing that you have selected will be happy to assist you.

    That last paragraph was for a brick-and-mortar store. The equivalent process for a web-store should be easy to figure out.

Similar Threads

  1. wearing lolita dresses
    By mistysummers in forum Sissy / Girls
    Replies: 32
    Last Post: 03-Sep-2013, 06:05
  2. going to start wearing diapers to bed
    By Trev156 in forum Diaper Talk
    Replies: 14
    Last Post: 19-Jul-2013, 20:12
  3. Should I start wearing 24/7
    By kennyrallen in forum Diaper Talk
    Replies: 16
    Last Post: 22-Jun-2013, 15:14
  4. Husband says I have to start wearing pants again
    By Calico in forum Diaper Talk
    Replies: 57
    Last Post: 04-Dec-2011, 22:29
  5. whant to start wearing 24/7
    By babyjhonny in forum Diaper Talk
    Replies: 75
    Last Post: 07-Apr-2010, 05:00

Posting Permissions

  • You may not post new threads
  • You may not post replies
  • You may not post attachments
  • You may not edit your posts
  • - the Adult Baby / Diaper Lover / Incontinence Support Community. is designed to be viewed in Firefox, with a resolution of at least 1280 x 1024.