With comfort comes confidence

This must have been the summer after my senior year of high school, I think. I was home alone for a night, maybe a weekend or so. My parents would occasionally travel for a few days to see old college friends and at this point, my sister that had been living at home had now moved out. Of course, I was slick enough to hold on to some key garments of my sister’s that would stick with me for a few years: bra and panties and a pair of bike shorts.

As time had past from my early experiences with dressing, porn, and masturbation, I had grown to be more comfortable wearing a bra and panties around the house while home alone. A big bonus was that my senior year of high school, I was able to leave school as early as something like 115pm because I had study halls scheduled at the end of the day. So back in those days, I was able to dress with panties and a “stuffed” bra for at least a few hours before my parents would arrive home from work.

As was the case with most high-schoolers in the mid 1990s, most of my clothes were probably too big for me. I did however have some t-shirts that I didn’t wear too often because they were smaller than I would want them to be. So this one summer night while I was home alone and dressed for most of the day, I had been lounging around in a pair of Champion basketball shorts and a small t-shirt that helped show off my bust more than my normal t-shirts. With the shorts, I had rolled them up over the waistband a few times to make them seem a bit shorter, like girls used to do with those types of boys’ shorts.

As night fell, I continued to watch TV and surf some of the adult-oriented chat rooms on America Online (I tell you more about this some other time). The next thing I knew, it had gotten past midnight and I was getting bored, but not quite ready for bed. Despite how comfortable I felt now wearing a bra and panties, the chat rooms helped me develop more confidence as my feminine self, and it was that confidence and comfort that had me thinking that I was ready to go out for a drive…

Getting creative

When I started crossdressing, as I’ve mentioned in the past, it was always with something I pulled out of my sister’s room. As time went by and I continued to dress while home alone, I became much more comfortable wearing women’s panties and bras. This is kind of funny and a little bit embarassing, but I remember trying to think of how to create, as realistic as possible, a respectable chest and hips.

Both of my sisters have very small chests; actually, they are both probably the most petite women that I have ever met, both about five feet tall and weighing in around 100 pounds… tiny. If I remember correctly, my sister that was living at home for a short time when I was in high school was a 32B. Nothing special there. It did work out well for me though because as a 14 year old, I still hadn’t grown as much as I would by the time I was in college.

So, back to the embarassing part, I used to go to the kitchen and take some plastic sandwich bags, fill them with water and tie them off with some twine. After some trial and error, I was able to fill them both to the same size and keep them from leaking for quite a while. Into the bra they would go, and all of a sudden I had breasts that for all I knew, moved and looked like real ones!

As for a pair of hips, I had found some bike shorts in my sister’s room; you know, the short, tight, spandex shorts that girls wear jogging or riding a bike. She had a pair that fit me perfectly, and when I pulled them up to my waist, they extended down just below my butt. I tried a bunch of different “fillers,” and eventually settled on using two washcloths from the bathroom. Again, after some trial and error, I had found just the right way to fold them and push them into the shorts, and the spandex material would smooth over the wrinkles and folds and give a nice contoured look.

So there you have it… I had created my own breasts and hips! My mind would immediately turn to the dresses and skirts in my sister’s room, and since I now had some girly curves, I spent plenty of time trying to find one that fit me right.