Amber_Fountaine's blog post - Chapter One - Born to be a Sissy

When I tell people that I began cross-dressing before I was born, I get a mixture of reactions but none of them are belief. Yet it’s true. Even before I was born I had a full layette of baby girl’s clothing and accessories, all in pretty pink.
How it happened is that my mom was fully convinced, by tea leaves or a witch doctor or just a hunch, that I would be born a girl. She insisted that all her baby shower items be for a little girl so from the moment of birth, I was wrapped in pink. That might account for it being my favorite color today.
For the first eight years of my life my dad traveled extensively so my mom had a free hand to continue to treat me like her baby girl while my dad was gone. In my toddler years I always slept in a nightie because it made changing my diaper easier and when it was time to potty train me, I was trained not to have messy diapers but wet ones were allowed and possibly encouraged. That would come back to haunt me at various times in my life.
I was four when my sister Gwen was born and my mom finally had the little girl she’d wanted. I was kicked out of the nest and sent out to play with the neighbor kids and they were all girls. There were no boys anywhere close to my age but I didn’t mind – I felt more like one of them anyway. After years of hearing how I should have been a girl and how pretty I was and how cute I looked in play dresses, I really didn’t want to play with the boys and in a way, it got even better after I started school.
I had to go to school dressed as a boy but was allowed to put on a dress after school and because of my ‘wetting’ problem, I wore panties in the daytime and diapers at night. My wetting problem is almost a story in itself and was never a real problem.
When my sister was born my mom told me I had to stop wearing diapers, that I’d be starting school soon and they wouldn’t take me if I was still in diapers. I’d grown to love my wet diapers and according to family friends and relatives, I used to hide from my mom so she wouldn’t change my wet diapers. I went along with it until one night a few months after I was considered fully potty trained, I accidently wet the bed and my mom made a huge mistake. She told me if it happened again I’d be put back in diapers. I was hoping that was a promise but acted otherwise.
A few nights later, as soon as I was in bed, I wet myself because I wanted to be wet when my mom woke me. I think it took two or three more times before she made good on her threat, but only partly. She concluded that I was way too big to be diapered, but since it seemed like I needed them, I was also old enough to diaper myself. She was right. A six-year-old boy is fully capable of folding a cloth diaper and pinning himself into it. And if he happens to like his diapers thick and wet he can use extra diapers and make them that way. I think she thought I was doing it on purpose to get her attention, since she spent all her time with my sister. When I agreed to diaper myself, she figured I must really need the diapers.
So for the next 2-3 years, I’d wet my diaper a few times a week as soon as I was in bed. If I didn’t wet it then and fell asleep before it was wet, it would be dry in the morning. What I really loved was weekends when I could get up on my own, still in a wet diaper and nightgown, wet it some more, and go play with the girls.
That bedwetting ruse worked so well I came up with another one. I’d gone from diapers to training pants to tighty-whities in just a few months, almost without an accident. Then one day after school, I’d forgotten to use the boys’ room before heading home and wet my pants. Carol and Ann, my two playmates, had gotten pretty panties as part of their new school clothes and I’d campaigned for some, especially the colorful nylon ones that Carol wore, but my mom wasn’t buying it. So I tried a new track.
I told her the jockey shorts felt just like a cloth diaper or training pants and if I could have nylon panties like Carol wore it would remind me not to wet myself. It’s hard for me to believe she was so gullible as to fall for that, but the bottom line was me getting pretty panties that became my underwear for the next couple of years.
At school, I was made to play with the boys and hated it. At home I could change into a play dress and play with the girls and loved it. Then we moved to Texas.
These boys were awesome! They were just as rough and tumble as the boys I’d previously encountered and probably more so. But they weren’t mean or nasty. It was a country school and one of my classmates rode a horse to school at least once a week. Suddenly I wanted to be one of the boys. No more panties. No more diapers or nightgowns or play dresses. I wanted boots and blue-jeans and t-shirts.
It was tough, and I got a lot of teasing because it was really hard to hide my sissy beginnings, but I was managing okay, mostly because of the help of a new boy in the neighborhood that was almost two years older but in the same grade. His dad was in the Air Force and an ill timed move plus a school in Germany being behind the local curriculum had put Bobby and I in the same grade and same class. He took me under his wing and taught me how to play baseball, football, and do ‘boy’ things like ride a bike. I was well on my way to being a regular young man, entering puberty, and looking at girls in a whole new way, when a couple of seemingly harmless events, a Christmas gift and a school carnival, changed my life.
The gift wasn’t for me though I wound up being the ultimate beneficiary. One of my aunts sent my sister a package of panties for Christmas and she didn’t want them. For one thing, they were nylon and my sister hated nylon anything. In discussions years later we concluded it was because of a nylon nightgown and a wool blanket earlier in her childhood and getting shocked every time she touched something until my mom gave her a cotton gown to wear. In addition, the panties were too big for her.
However, I loved them! It wasn’t because they were panties – I didn’t wear panties any more. And while I did admire all the beautiful colors with lace edges – so much prettier than my all white jockey shorts, there were seven in the package and each had a day of the week embroidered on them.
I’ve never been a neat freak but great at organizing things and having a different pair of underwear for every day of the week made incredible sense to me. I was well on my way to being OCD about some things so I decided I was going to take seven of my underwear and write the name of each day on one of them with a fountain pen. Had I been successful and my mom hadn’t noticed, you can imagine what might have happened to the white laundry and things like my mom’s white blouses and my dad’s white dress shirts. Fortunately she caught on to what I was about to do and I explained myself.
After thinking it over, my mom said she knew I didn’t wear panties any more, but that my sister would never wear them, that they would fit me, and at least they’d go to some good use and she’d buy my sister some cotton panties, something she planned to do anyway. So after three years of being all boy, I was wearing panties again and wondering why that made my little boy pecker get hard.
Then five months later, on the last day of school before summer break, I became a full- fledged girl for the day and that’s a story in itself so I’ll save that for the next chapter.