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Time spent in dresses
It's been quite a few years since I would dress as a girl. I wrote about my beginnings on the old Voy forum, and figured I would revisit them here.

My first memory of being in a dress was when I was four. I was still in diapers (much to my mother's chagrin) and my mother was frustrated with me not potty training easily like my sister. There are several things I didn't know or understand at the time, like the fact my mother wanted a second girl, and that my sister was the last girl born out of all my cousins, so my mother had no one to send her hand-me-downs to. My mother used disposable diapers with me, she was hooked on a lot of the new convenience products that were being introduced and certainly wasn't happy that I still needed regular diaper changes. She had hit upon the idea of using my sister's old dresses on me to make it easier to change my diapers when we were out and about. I finally toilet trained around my fifth birthday.

On top of this, there were a few occasions after my mother and father divorced before she started dating again where she had me in some of my sister's old clothes to save money (she helped justify this to me based on how much she had to spend on night diapers for me since I wet the bed nightly). Once she started dating again, she stopped with it since she wasn't sure how it might be viewed by the men she was bringing into her life.

Mom remarried when I was eight, and the stress of changing schools mid-year together with moving, new stepfather and stepsisters, and all of the upset that went along with it put me back to daytime toilet troubles and sent me back to daytime diapers for a couple months. Mom certainly wasn't happy about it, and neither was the school. The principal wanted to send me to a special ed class since I needed diapers, fortunately the teacher recognized I was one of the smarter kids in the class and just had the control issues and refused to let it happen.

I didn't start dressing again until I was 13 and I asked my mother one night what it was like to be a girl. Her response was that it was something you just do and couldn't really say anything more than that. Later she asked if I still wanted to know and then told me to follow her to her room, explaining as we went that since I wanted to know the best way was for me to experience it myself. She had me strip completely and gave me a pair of panties, a bra, and one of her dresses to wear. Back downstairs, she asked me my thoughts, and pointed out I would make a convincing girl with hair and makeup done. I asked about doing that, and she said there was no time that night, but if I wanted to dress again the next day she would help me with it. She also asked if the clothes were available if I would wear them regularly. I said I would, and not much more was said from there. When bedtime came around later, she brought me one of her nightgowns to wear to bed, telling me to keep the dress for wearing the next day.

I was surprised the next day when I got up and she wanted to go shopping, I didn't want to dress as a girl in public, but I should have done it. She took me out and bought me my own clothes so I could dress and wear them when I wanted and on the occasions that she and stepfather might like to have me look nice. I was bought a sundress for the summer, a skirt and blouse combination, plenty of panties, three bras, a couple nightgowns, and a girl's one piece bathing suit. The most embarrassing part of all of it was having to try things on in the store!

When we got home, mom had me bathe and showed me how to shave my legs. She got me panty liners to use to avoid 'skid marks' that I tended to have a problem with in my regular underwear. She then did my hair and makeup, showing me what to do myself as I would have to learn. She took me downstairs and gave me nail polish, then spent quite a while teaching me how to walk and sit properly as a girl. I spent the next several days dressing constantly (at her suggestion) to get used to the clothes and get good with acting feminine and doing my own hair, makeup, and nails.

My stepfather liked having me as a girl, so mom bought me more outfits, my sister and stepsisters didn't care, their only complaint was I didn't have to deal with a period which they didn't think was fair. My mom felt they had a point, so she gave me the full 'talk' and started me on a cycle to match the rest of the girls in the house. She gave me both thicker pads and tampons to try the first time, telling me to let her know which I preferred using. She personally liked tampons and recommended them for all of the girls in the house, and that included me. She commented that a thick pad often felt too bulky, almost like wearing a diaper. After trying it, I understood her point, and she seemed happy to know I preferred tampons.

I kept up a monthly cycle and dressed on a regular basis until I moved out at 18, and then it slowly dwindled away. If you want to hear more or want details, let me know.
That's a lovely story. You're very lucky having such an understanding family.

How old were your sisters and step-sisters? Did you borrow their clothes too, or just stick to your own?
I too was dressed as a girl. From about age 11. My mother wanted two boys and two girls but got three boys and 1 girl. Mom decided that i would become her second daughter. Momdressed me completely as a girl, even the dresses with the attached petticoats (late 1950s-early 1960s). I even had play dresses and was allowed outside to play in them.
My oldest stepsister is three years older than me, my sister is two years older, and last stepsister is a year younger. I know all of them had started periods by the time I was dressing again at 13, all of the feminine hygiene products for them were kept in our bathroom under the counter together. Mine joined them when I started dressing, which mortified me because it meant that all the girls would know about that as well.

I didn't borrow their clothes, they didn't even borrow each other's clothes, mom and stepdad both told me that was a lot of the reason I was bought all my own things, that there was so little borrowing of clothes done in our family. To a little extent, I know mom and stepdad used the fact that they spent money buying me those clothes as leverage to get me to wear them as often as possible. "We paid a lot of money for you to have such pretty things, you need to wear them more." It also meant that it could be used as an excuse to not get me certain boy's clothing; when my swim trunks were too small for me that summer I first started dressing, mom refused to get me new ones since I had a brand new one-piece bathing suit to wear.
That's unusual for sisters not to borrow each others' clothes. And unusual too for your step-father to want to have you dressed as a girl.

My Dad was long gone before Mum started dressing me. I had to wear my little sister's clothes most of the time I was made to dress. She's two years younger than me, so not only wear they often a bit small, but they were too young for me too. I think that's why I ended up enjoying dressing as a younger girl.
I understand that sisters often borrow each other's clothes, I think there was enough of a difference in the attitudes and style tastes of each one that they didn't share, or there was enough age/size difference that it didn't happen.

With my stepfather, I think a lot of it was that I wasn't a typical 'boy' that was rough-and-tumble or into sports. Being the only boy in the family of four also meant that there was a lot of friction between the girls and I just due to gender differences. Once he saw me dressed as a girl, he commented how I looked much better as a girl than a boy (I was very slender and not muscular). After that, when he saw that the girls and I got along better, he was a big proponent of me dressing just to have the household more peaceful. It also was a big thing that mom was the dominant one in their relationship--whatever she wanted, he always let her have.
It must have been nice having so many sisters too. Were they kind to you when you were dressed as a girl? Did you go shopping together and stuff?
(06-02-2016, 09:09 PM)Ali Wrote: It must have been nice having so many sisters too. Were they kind to you when you were dressed as a girl? Did you go shopping together and stuff?

They were fairly kind to me when I was dressed as a girl, much more inclusive of me on things. Of course, my mom put her foot down when they first found out about my dressing that any teasing or other unkind words/actions would bring down her wrath on them. Mom knew that they might tease me or tell others about it that might make my life difficult, that had happened before with my nighttime diaper needs.

There was some shopping together, my mother and stepfather seemed to enjoy taking all of us girls out to dinner on a regular basis. My sister and I were closer than with our stepsisters, there was enough time away from each other due to the divorce decision for my stepfather versus the one that came down with my mother and father.
Oh wow - diapers too?! I got put into diapers, or nappies as we call them.

What did your sisters think about that?
(06-02-2016, 11:14 PM)Ali Wrote: Oh wow - diapers too?! I got put into diapers, or nappies as we call them.

What did your sisters think about that?

My sisters used to tease me quite a bit about my diapers, and they told more than one person at school about them. Mom had no qualms about that because she thought the embarrassment would give me some motivation to stay dry. I had nighttime diapers every night because I wet the bed, and there were only a few occasions where I wore them during the day because I had accidents (one major spell when I was eight and mom had just married my stepfather, we had moved, and I was in a third different school in six months). The night diapers went on until I was almost ten, at which time I had outgrown the infant disposable diapers so mom stopped diapering me nightly. The bedwetting hadn't stopped, but there weren't good diapers for kids my size available.

Mom would still harass me when I had wet sheets, asking me if I needed to go back to diapers. When I was 16 and we moved across the state, I got frustrated after a few days of her asking me that and finally told her I probably did. She stopped asking me about it, and took me to the doctor a few days later to get me checked and discuss my bedwetting with him. The doctor dismissed it, saying there were a lot of boys my age still having trouble and the recent stress together with puberty had brought it on. Mom asked if there were anything we could do and was told I would eventually outgrow it. She then asked if diapers would be appropriate, and the doctor said they wouldn't help or hurt, just keep the sheets dry.

Mom took me to the local drug store and bought me a large package of adult diapers after we left the doctor (Depends had just arrived on the market) and made me start wearing them to bed, diapering me the first night and then slowly teaching me how to do it myself and checking how well I had done.

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