The train pulls out of the station, just as it does every day. I look out the window at the same passing scenery, just as I do every day. I long for the demure redhead who sits three rows away, just as she does every day. The train rumbles along the tracks, stirring my passion with each bump. Every day.
I can’t remember when I first noticed her. But I know it was the hair that caught my eye. She always wears it pulled back, in a neat ponytail down her back. In the winter, she wears a dark coat pulled up around her ears. In the summer, on really hot days, spaghetti straps. I actually can’t see much more of her. Like most commuters she’s a creature of habit and sits in the same seat every day. Of course, I’m too shy to approach her. Because I’m only 19 and she’s probably twice my age.
Age has never been a concern or interest of mine, probably because I’ve only dated girls my age. But from the moment I saw her, I could tell she was older and I could tell I wanted her. Most of the time she reads so I can just peek at her beautiful face. Every once in a while she’ll look up, look out the window and sigh.
I want to make her sigh. And moan. And cum. My cock strains at the thought.
The particular ride home is a bit unusual. Today is a rare holiday Friday and it seems most people have taken the afternoon off work. The train has only a few poor souls who didn’t plan ahead. Me being one of them, she another.
She usually departs the train one stop before me. I get my whole trip to fantasize about her. Today she seems entirely disinterested in her book. She looks up frequently, and on a couple of occasions, catches me gazing at her. The first time she notices me, she smiles. The second time, she looks angry. With that, I fear upsetting her and switch seats so that my back is to her. This way I won’t creep her out.
Because our train car has only a couple of other people on it, imagine my surprise when I feel a hand on my knee. I’d been looking at the window and bang my head on the glass. She settles into the seat across from me.
She’s wearing a skirt. Mid-length. And black stockings. I’d always wondered…
“I don’t mind you looking at me,” she starts, her voice soft and comforting, “but I don’t want to catch you watching me again.”
The second part of her statement is harsh and firm. She stares me right in the eyes. The hand she startled me with still rests on my knee. She gives it a squeeze and pushes my legs open. She does the same to the other knee.
“Do you know what I’m going to do if I catch you staring at me so blatantly again?” Now her tone is both playful and sinister. With those words, she places her high-heeled foot between my legs. The hard sole of her shoe rests on my rigid penis.
With increasing pressure, she continues.
“I’m sure you can guess. Now, what do you say?”
I’m dumbstruck and confused. Does she want me to apologize? That seems the right thing to do, but how can I think with her sexy foot pressing against my dick?
“I’m... sorry?” I stammer and question at the same time.
“You don’t sound so sure, boy. You need to be taught this lesson now.”
She pushes her foot right against my pelvis, squishing my cock and making me gasp. It is both painful and amazing at the same time. As the train hurtles down the track, jostling and bumping, small changes create tremendous sensations.
I am on the verge of orgasm when she eases up. My eyes fixate on her and I quickly blurt “I’m sorry. Very sorry.”
“Good boy,” she purrs, and replaces her foot in my lap. Her stop is approaching and so is my explosion. Just as the conductor announces her station, she wriggles her foot back and forth and my penis explodes in my pants. Waves of cum fill my underpants and I buckle with pleasure.
The doors open and she gets up. She leans down and whispers in my ear, “I’ll see you Monday... but you won’t see me, right?”