Some upskirt views require good planning or being in the right place at the right time, which requires good anticipation.
With experience one gets better and the results are commensurately improved.
We all have memories of seeing
upskirts at school. Usually they consisted on seeing up girls skirts when they were going up the stairs or catching a glimpse if they were sitting in an unladylike manner.
I always had much more excitement and my pulse would be set racing if I caught a cute view up one of my teachers’ skirts. This was definitely more of a thrill as it was so much rarer and required more risk.
I have generally enjoyed the risk and taking chances, it lends a thrill to what you are doing. Now don’t get me wrong, I am not reckless and don’t go looking for trouble needlessly. When I take a risk it is usually calculated, and I like my chances to be in my favour.
I remember an instance that this would definitely apply to.
The bell had just rung at the end of the fourth period and the lunch break. There would be a mad rush as not only students would be rushing in all directions to stack books in lockers and head for the cafeteria, but there would be teachers also hurrying to the staff common room or anywhere else they wanted to spend the lunch hour.
I joined the crowds of people heading for the main stairway. As I made my way toward it I noticed Miss Carole H, a very fetching and pretty brunette, lovely body and stupendous legs. She just happened to be wearing a pretty grey skirt coming to just above the knee. This already got me interested, but with so many people climbing the stairs it would be extremely difficult to get a view up her skirt. Furthermore, remaining at the bottom of the stairwell would probably not provide a clear view either.
As we are making our way closer to the stairs Miss H notices a colleague and they momentarily stop to say hello and then continue to the main staircase.
Miss H has met up with Mrs Hilary D who teaches History. She’s a bit taller than Miss H and a few years older but she has maintained herself in good shape and still draws eyes, especially of us adolescent boys. She is also wearing a dress to the knee.
Now my interest is really piqued. Who should I pursue, where do my chances have the biggest probability of success? Is it to be Miss H, who I spotted first or the taller Mrs D?
In the end the decision is made for me. I manage to get directly behind them as they start climbing the stairs with Miss H on the left and Miss D on the right.
I should point out that there are actually two staircases, one for going up and one for descending.
We are going up and in the mass of people we are towards the right near the bannisters. I should add that to achieve my goal I enlist the aid of a little mirror from a lady’s compact that I can conceal in the palm of my hand. I figure that if I try to see up Mrs D’s dress it will be more obvious to anyone watching from below as there would be only the bannister to obstruct their view. Much better to try to catch a glimpse up Miss H’s skirt, which is also a little shorter, as the view would be more obstructed to anyone from below. So with my decision made up I stalk my quarry.
I remove the mirror from my pocket and position it comfortably in my left palm. As unobtrusively as possible I extend my arm to reach just below the hem of Miss H’s skirt. If I’m caught it could mean dismissal or at the very least suspension and possibly even criminal charges. But fortunately in those days it was looked upon as a boys’ thing that they’ll grow out of.
People are all round me, but they are all in their own world, or busy talking to someone not to notice the antics of a student like me set on looking up his teacher’s skirt. The two teachers ahead of me are equally occupied and in the throng of people hardly expect anyone to do what I am about to.
So, easing my hand into position I check to see what I can catch a glimpse of.
It is to be my lucky day, Miss H is not wearing pantihose or tights and so any view won’t be inhibited or reduced by their existence. When I do position the mirror just right and adjusting for the jostling of the crowd I see she is wearing white panties but they are not just plain. Thy have a certain pattern or design on them. Very fancy and arousing, No a thong, perhaps a bikini or hi-cut brief.
I maintain the position for the ten seconds or so that it takes to reach the top of the stairs. Time seems to go slower I am in my own little world where all that exists is Miss H and the view of her panties, and me. I notice the perfume she is wearing, it is deceptively arousing, feminine and very sexy. This all conspires to make the view all the more wonderful and erotic. We reach the top of the stairs it is time to end the escapade and so just as unobtrusively as I brought it out I reconceal the mirror back in my pocket the dastardly deed done!
No camera to record the event, and also stand as incriminating evidence, no, just my memories of the event, of Miss H’s sexy white panties and the thrill I have received to get it. Was it worth it? Definitely! I didn’t get caught, no one was hurt, and none the wiser, as they say:
‘what you don’t know won’t hurt you!’