A late night drive, finally

(continued from my last post…)

It was nice and warm out, so I ran to my room and threw on a pair of sneakers, grabbed my car keys, and headed for the door. You can’t imagine my nervousness!!! I hesitated and waited at the door, worried sick that my nosy neighbor across the street or the state police trooper that lived next door would see me and either approach me or tell my parents. We lived on a quiet side street, only a dozen houses or so, where cars very rarely passed, so I thought that someone would surely notice my hatchback lighting up and pulling away well after midnight!

But after a few minutes, I dismissed my jitters, surveyed the street to see if any lights were on in the houses or if any cars were coming, and ran out the door to my car. Butterflies took me over as I started the car and as quickly as I could, shifted into first and sped up the street. After a few turns, I was finally out of my neighborhood and started to calm down. I drove back into a few neighborhoods were I knew there wouldn’t be much traffic until I had almost forgotten about the two bumps I had in my t-shirt.

After about half an hour, I decided that I would head back home, but instead of taking neighborhood streets, I would take the main drag, Route 1. Looking back, I must have been crazy! There are cars and trucks on that road all night, and being a few miles from home, I had a ton of traffic lights to stop through. But I did it anyway…

I did have to stop at a few red lights, but not once did another car pull up next to me. I got really nervous when I saw a big 18 wheeler come up next to me, thinking that the driver would be able to see down from his cab into my car, right at my crossdressed chest! But as he pulled up on my left, I realized he wouldn’t be able to see me. A few minutes later, I had arrived back into my neighborhood and took a lap around the block just to make sure no one was out and about. I pulled up to my house, in neutral so I was as quiet as possible, shut off the car, and sprinted back inside.

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…