Train Dating


It's an important day for you. The convention in New York is the chance you need right now to meet some of your regular lines, make some sales, and also to make connections for that next job move. You're taking the Amtrak up from Washington, an early morning train, filled with the regular commuters. Business types, absorbed in their cell phones and newspapers.

You're dressed and ready, professional but just a bit dangerous. Your charcoal gray dress shows just enough of your ample 38D breasts to draw a man's eyes down, wondering how much he can see. And when he does look down, you'll catch his eye, smile coyly, and start talking about the price of kitchen sink units. A smooth guy could keep up the conversation about sinks, but he'd also be looking lower, down towards your legs, shapely, stepping out in sexy heels, but most importantly, he'd be checking out those incredible stockings. He could see the sheer fabric covering your thighs, knees, calves, a thin black seam. He wouldn't know, but you would, that these are thigh highs, with only a thin skirt above. Your pussy hairs could feel the warmth of the air in the train. You find a seat on the train, and lay your bag down on the seat next to it, trying to signal that it's taken.

It's an important day for me. I've been trying to set up this meeting with this company in New York for months. Finally I got a date. It's all casual -- I'm just "happening" to be in town for other business, "why don't we get together for lunch and I can tell you about our program?" Hell, this is a big deal, I would have flown across the country on a moment's notice for this lunch. But I've gotta play it cool, confident, like the big league is my backyard playground. I'm hyped. The adrenaline flow makes me feel alive. It also has a tendency to make my cock hard.

I get on the train in Baltimore. Early morning. I look like the other guys on the train, business suit, briefcase, shiny black shoes, pressed white shirt. Confident bullshit grin, but they know they haven't had sex in a year and today is another make it or break it deal. But my smile this morning is more subtle. I'm looking for a friend. One I don't know. Except I know her intimately. Except we really are not supposed to know each other. The arrangements are complicated, but it's really quite simple.

I find her three cars deep in the train. She's sitting in a seat on the aisle, having given up her other seat to a middle aged woman who is now deep into her New Yorker magazine. She sees me as I enter the car, but looks away. My eyes are full of her, but no one could tell. The car is full. Many people are standing, particularly the men who have given up their seats to the women, and who are now either playing with their cell phones, or are trying to look down the blouses of the seated women.

Unfortunately the woman I'm interested in has drawn a bit of attention. She's the kind of woman a guy notices when she walks in the room. It's not just her pretty face and curves, it's the sexual energy she gives off. Any guy who is half alive can feel it. Those who are fully alive are drawn in like moths to a flame. She knows this, and enjoys the attention.

I'm going to have to work at this. Two guys are already standing next to her, quietly watching as her breasts rise and fall. I approach where she is seated. Just as I get there I stumble, my briefcase opens, and papers cascade to the floor. Both guys drop back, surprised, and I quickly crouch to the floor, picking up papers. What a vantage point: the papers are all around the sexy shoes of this lady. I'm picking up papers, but making sure to "accidentally" brush her ankles and calves with my fingers.

She is stifling a laugh, seeing the game I'm at, enjoying it immensely. While I'm stumbling around on the floor, she bends over to help me. Our hands brush each other. I look up slowly, and see that she has parted her legs and is giving me the most incredible view of her pussy. I don't know whether to laugh out loud at the outrageous audacity of this lady, or to dive tongue first into those soft folds I know so well. But I behave myself. I gather my papers, put them back in my briefcase, and with a quick thank you, stand up next to her.

Mission accomplished. The other guys have backed off and I'm standing in the best position. My lady is now amused and aroused. I've got a hard on like no one's business. I'm laughing internally but my balls are starting to hurt. I look down. She's smiling, her blue gray eyes twinkling. She's also beginning to get naughty. Her hand is on her blouse. I don't think anyone can see it, but she's slowly pulling the gray business dress down. Now I see why. She's not wearing a bra. She's wearing a black cut out that may look like underwear to the casual observer, but no. There is nothing there. Nothing except a very erect red nipple. Exposed only for someone who can look directly down from above. For me. She's touching her nipple, just a bit, making it harder. I know that nipple wants my lips.

This is becoming more painful. She knows I'm watching her. She can see my hard on in my pants, practically next to her face. She can probably feel the heat coming out of my dress pants. She knows that as much as I like the tease, I can't stand it for long. I lean down and whisper quickly to her, then stand up and walk towards the next train car.

A discrete time later, she rises, smoothing down her skirt, smiling mischievously at the guys who have been watching her, and wander towards the back of the train. It's not hard to find me. I'm standing two cars back just inside one of the doors. There is a luggage compartment with a sliding door. As she passes me, I slide the door open, step in, and without anyone seeing, she steps in beside me.

Now we're not fooling around anymore. She pulls her dress open as I'm diving into her breasts, squeezing, biting those aching red nipples. My hand is under her dress in a flash, up her thighs, to her very wet pussy. She's been ready for way too long. I've got a finger in, then two. She's not good at waiting.

I'm too much taller than her to fuck her standing up, but she knows what to do. She slides her butt up onto a huge suitcase, spreads her legs, and reaches down for my cock, just as I'm dropping my pants. She guides me in, but my cock knows where to go -- where it is very wet, deep and oh so hot. She covers her mouth with her fist to stifle her screams. I'm crazed as I thrust into her, again and again, as deep as I can. I can feel her cervix as I bottom out in her pussy, I know it is hurting a bit but in a good way I can tell. She always says my cock fits her pussy like Cinderella's slipper. Her pussy gushes as she cums. I gush as I cum in her. It's hard to say who is producing more fluid at the moment, but it's good, very good. Very very very good. We are shaking and drenched. I pull out, but I'm kissing your neck and feeling the blood rush through your veins.

Two hours later I'm sitting in a nice New York restaurant, wondering if the corporate official I am meeting with can smell pussy juices on me. If she can, she doesn't seem to mind. I'm wondering if the guys trying to buy your kitchen units have any sense of what a sensual woman they are meeting with, and how wet her pussy still is.

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