Video non-sequitor

I stumbled across this series of videos which, according to the description on the blog upon which I found them, seems to be rather intriguing. I’ve only watched the first one (of seven, I think?) and it might seem to move a bit slow at first, but it takes a rather interesting turn nearly halfway through. I’m definitely curious to see where they go from here!

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…

Teenage influences

So now I had begun to dress more often and more realistically (perhaps?) with the breasts and hips I had created and access to my sister’s wardrobe. Keep in mind, I was still rather young and nervous, but curious. At that point, there was no way that I was going to go shopping for myself, dress to pass in public, or anything else that might expose my secret hobby. I wasn’t even sure if dressing was something I wanted to continue to do or if it was just a phase. However, I knew that when I was dressed, at home, alone, my mind would race with different thoughts and fantasies.

Looking back to that time of my life, it’s a bit easier for me to identify a few factors which definitely influenced, increased, and encouraged my desire to crossdress and explore further. As a young teenager my friends and I had discovered porn, I was still a virgin and would remain so until I was 19 years old, and I was going to an all-boys high school. Having an older sister living at home facilitated crossdressing rather nicely as well, providing a wardrobe through which I would search for outfits and inspiration.

As my libido grew through high school, I struggled a bit with the fact that I never really had much interaction with girls. There was a “sister school” that we would have mixers with and they provided cheerleaders for our sports teams, but I was often more concerned with doing well in school and working in my spare time rather than chasing girls. Masturbation is just a part of life for teenage boys, but watching porn on occasion allowed me to calm my desires and sort of refocus until the urge came again.

I had gotten my hands on a porn video that I kept at home and that’s when things started to turn in a different direction for me, I think. I had a TV/VCR combination in my room and was able to watch it whenever I wanted after my family went to bed (my parents and sister’s bedrooms were well away from my own). Now, I was able to dress and watch porn at the same time, so that after I’d get my fill of the video I would slip into the bathroom to masturbate. It’s sounds so crude, I know.

As time went by, I became fascinated with the different roles that the man and woman had in the videos. One of the things you observe early on in run-of-the-mill porn is how the strapping guy would pound away at his woman, leaving her wasted but satisfied, sometimes hungry for more. Or, conversely, the woman diligently works on her man, sucking his cock, riding on top of him, or offering herself from behind. Her overall goal, often, is to bring her man to cum, either inside of her, somewhere on her body, or in her mouth. Remember, this is a basic assessment at best; certainly not applicable to all types of porn, merely what I was exposed to early on.

I could have masturbated all I wanted, but at that point in my life, I was never going to know what it would be like to be that man, to fuck a girl. While most teenage boys would watch and masturbate to the fantasy of indeed being that man, I would often fantasize about what it was like to be the woman. The women often derived so much pleasure that I became intensely curious about what it would be like and feel like to have a cock deep inside of me, to have my lips and my tongue all over his cock, or to accept his cum as a gift, a reward to me for my work.

Though I have never been attracted to a man in any way, a lack of exposure to and interaction with girls and crossdressing during all of these fantasies surely heightened my curiosity and desire to know what it felt like to be that woman.

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.

Do I even remember how it started?

That’s a good question. I don’t think about this all too often, but I’ve been thinking about it more lately because this is a post I have been wanting to write sooner than later.

Well, my best guess is that I started when I was about 13 or 14 years old. At that point, my older brother had left home for college, and my oldest sister was back living at home after college (I’m quite the junior in my family).

Since I was in middle and high school, I was getting home much earlier than either my parents or my sister after their days at work. This is around the time I started snooping around my sister’s room and the laundry room (our family had a habit of cleaning clothes, but letting them sit in the laundry room for a few days) for something, anything. I remember some pretty basic floral cotton panties that belonged to my sister and a one-piece bathing suit that she got from her high school swim team.

I know I didn’t do much at that age… I’d slip on a pair of panties, wear them under my normal clothes for an hour or so, and that’s about it. Time was always an issue back then, and it’s something, of course, I didn’t want my parents or sister to find out about.

It’s funny to think how much things have changed in the last 15 years!