Most Memorable Upskirt
Between my junior and senior years in high school I took a five week tour through Europe. The tour was designed for late teens, and there were small groups from all over the USA. The promoters must have picked a target school in each area, because the kids from any specific area seemed to know each other and their chaperon was also a current or former teacher.
I became close friends with a beautiful girl from Oklahoma. She had a boyfriend back home, and I my steady back home had recently relieved me of my virginity. So neither of us were looking to hook up, although there was a definite sexual tension between us.
She was tall and thin, with great legs that went on forever, and cute little B-cup boobs. (I got a few shallow down blouse looks, but never close to a nipple and never even a pokie.) Her brunette hair was straight and reached about half way between her shoulders and her fabulous ass.
Part of the experience was an overnight train ride. She invited me to join her in her "cabin", which was just two benches with sliding doors. We rode with her best friend (not so good looking) and an ex-teacher who was her chaperon. We talked for a couple of hours, then I nodded off, leaning my head against against the wall of our compartment.
I woke up after a couple of hours and glanced over to see that she had also fallen asleep. But she was reclined, with her left leg on her chaperon's lap and the right leg on the floor. Her navy blue knee-length skirt had ridden up to mid-thigh, and her cute little white panties were there for the looking.
Since I was eighteen, I woke up with a hard on as usual, but looking at that beautiful pantied pussy kept me rock solid as I stared at her. Those panties were like none I had ever seen. I had plenty of experience by then with white cottons and nylons/rayons, but these were something else. The fabric was shiny and opaque, not revealing any telltale hint of bush show-through that common fabrics allow. She did have a few pubes sticking out the side, but nothing you would notice unless you had time to stare, as I did. She had a very prominent mons, and i spent the next two hours imagining the different looks it might have when uncovered. When I noticed her stirring I feigned sleep until she started talking to her friend. I pretended to wake up, stood and stretched, with my still-hard dick making the very best tent I could make in my sweatpants. We all pretended not to notice for a minute, then I left the compartment to find the bathroom.
When I got to the bathroom I rubbed one out quickly, recalling every detail in a mental fast-forward. I then brushed my teeth, took a leak, got rearranged and went back to the compartment. We chatted about the upcoming sights for about an hour until we rolled into Strasbourg, but I knew that I had already done the best sightseeing that I would do that day.
We were supposed to return into Newark, but for some reason we flew back into Philly. Not a big deal, since most of us were making connections the next day anyway. But her dad was already in Philly on business and met us at the plane. After introductions were made he invited us to join him for a Phillies game that night. That was my first ride in a limo - turns out that her dad was an oil company executive and she had grown up rich. As she was getting into the limo I got another quick pantie shot and then it hit me - I was looking at silk! I wanted to ask her, and had figured out a way to do so without incriminating myself. I was going to ask if she was so well off that she wore silk undies, but I was never alone with her after that long enough to ask.
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