Doc Sherwood
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Petticoat Peril
In the summer term, we boys had the option of wearing just a light petticoat under our skirts as girls did, instead of underpants. No boy I knew had ever tried it, because we were all frightened our bits and pieces would drive us up the wall if went around with them unsupported by underwear-elastic! I was well aware mine were sure to do just that if I tried it, but after yesterday I'd had it with stockings and pants. They so weren't meant for a boy my age! Anything seemed a better choice than that, so I decided to give our pantless petticoat option a try.
By Doc Sherwood3 years ago in Filthy
Jenny's Asking For It
Somehow, I knew. From the minute I saw that Jenny was wearing her too-tight long pants in the grey plaid, I knew. Those things always made me catch in my throat. They way they stretched and strained to cover the awesome broadness of her butt still had the same effect on me, and likewise the way they made the most of her triangle. That was to say, the little space of daylight framed by Jenny's inner thighs where they came together at the top, and above them the horizontal of her crotch. It made the neatest and sweetest perfect little upside-down delta of emptiness, right at the part of Jenny in which I was most interested, and nothing showed it off as well as her tight grey plaid. Jenny was proud of her triangle, with some justification I thought. Chubbier girl-thighs squeezed snugly together at the top, but that sly little space of Jenny's was special.
By Doc Sherwood3 years ago in Filthy
First Steps
She'd seemed perfect for me at the nightclub. Not just her big glasses and her tight colourful tee, but most of all that absurdly short denim mini-skirt with pleats. Oh, I so hoped those were coming back! Now I trotted after her up the stairs to her room, my toes tingling, feeling weak and shy all over. She must have known my eyes were pinned to her pleats, because she teased me, pulling out the skirt as far as it would go to one side.
By Doc Sherwood3 years ago in Filthy
Shopping Spree
That quite pretty girl with the ponytail had remembered to put on her white dress with black dots, but apparently not everything else! I was following her up the hill and so I knew her bum was bare. I didn't even know if she realised I could see! But I could glimpse quite a bit just under her hem, and when the breeze lifted that skirt, much more.
By Doc Sherwood3 years ago in Fiction
Interschool Day, Part Three
Next time I saw that blonde-haired girl from off the bus was at the stadium, and she'd changed into her gym kit. That was when I guessed I'd be playing her later, since she looked around my age. Gazing at her pleated short gym skirt I didn't even know if she had pants on.
By Doc Sherwood3 years ago in Fiction
Interschool Day, Part Two
Anna finished dabbing her slightly pink face, and stuffed her sports towel into her bag as we walked down the corridor together after practice. My pants were still in a massive twist over how badly it had gone. We'd both changed back into our blazers and our pleated school skirts.
By Doc Sherwood3 years ago in Fiction
Interschool Day, Part One
That tantalizing cheer-routine...! My mind was spinning with Anna's marble-white legs, several shades lighter than those of any other girl, not to mention her vivid red hair or her vivid red underwear, both of which took your breath away. The cheerleader who was happy to flaunt like that never quite seemed to sit alongside that other Anna, the one who made every boy know she was waiting. It made the waiting worse for us, when we had to see so much of what we wanted. That was why I was sometimes sure she did it on purpose.
By Doc Sherwood3 years ago in Fiction











