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Third of the “Deb’s Tails” series. There are more in the works; Deb has told me several others, I just need to find the time to write them down.

My wife, Deborah, often tells me “bedtime stories” of her sexual adventures. Some of them I know are true, either because I was there, or because she has corroborative evidence. Some of them, I’m sure, are fictional. Others, I’m just not sure about.

I don’t know about the truth of this one. It sounds like the kind of thing she’d do if she were in the right mood, but since I wasn’t there, I can’t vouch for it.

If you’ve ever heard anything about the New York subways, you probably think you know what they’re like. Noisy, obnoxious, and crowded. Most of the time that’s true, but as any New Yorker will tell you — once you get past his pride in living in the least livable city in the country — that some trains can be practically empty if you pick the right times and routes. Many evenings, around 10 or 11, even the busiest routes start emptying out, and by midnight it’s sometimes possible to have a car to yourself.

In all fairness to New York, though, it does have it’s good points. The Circle Line is one of them. It’s a mini-cruise around Manhattan (it is an island, you know!) Any place that’s got a decent-sized body of water has something similar. Seattle has trips around Puget Sound, New Orleans has riverboats running along the river. The Circle Line cruise is really beautiful at night with the city all lit up, but in the middle of winter, you can — and probably will — freeze your ass off.

Deb and I often have separate social lives — an inevitable reaction to work-related gatherings where people sit around and talk shop. What usually happened in New York was that I’d stay home and play with my techie-toys while she was out partying with her colleagues, or she’d stay home with a book while I was out cheering for the Mets. Naturally, that meant a few solo subway rides for both of us, often at somewhat odd hours.

This is the story of one of those trips as Deb told it to me (albeit, with my title).

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“Let Your Fingers Do the Riding”

I never did tell you about the aftermath of that party last month did I? The one that ended up in a ride on the Circle Line? Yeah, that’s the one, when I didn’t get home until around two. I was so pissed at you about that. Going to bed before I got home wasn’t nice. I’d been hoping you’d still be up so I could fuck your brains out, and there you were, sound asleep in bed with MST3K blaring away on the TV. Why was I so horny? That’s what I was going to tell you about.

When the boat got back to the dock, we were pretty much partied out, and I, at least, was frozen stiff. We all went our separate ways, which for Gary and me meant heading straight for the uptown number 1 train. It turned out that he was frozen too, so once the train showed up we decided to try a little hypothermia treatment. We had one of the sideways sets of seats next to the car door to ourselves — in fact we damn near had the car to ourselves. He sat down right next to the barrier between the seats and the door, and I sat in his lap, with his coat buttoned around both of us.

Once I started to warm up a bit, I realized that Gary’s lap was not the most comfortable place I’d ever sat — somehow you never realize just how bony someone’s legs are until you sit on them — and I started to squirm around, trying to find a position that didn’t include a bone poking me. Not surprisingly, this had something of an effect on him. I suppose you could say that I warmed him up a bit. The net result, though, was to make his lap even worse as a chair. If he wasn’t poking me, I was squashing him, and all-in-all, I think we were both a bit relieved that Gary had to get off the train at Times Square and head for the E out to Queens.

Losing my butt-warmer did have a few advantages besides easing my seat. Most notably, I could sit sideways on the seats, lean my back up against the barrier, and try to make my knees a little more comfortable by straightening them out in front of me. On the other hand, I did miss the warmth he had been providing, so I did what any normal person would do: I pulled my arms out of the sleeves of my jacket and hugged myself inside it. By 50th Street I was warm enough to realize how frustrated I had been with a hard cock against my ass and no time or opportunity to do anything about it.

Without even thinking about it, I reached down, slipping my hand inside the waistband of my skirt, and began to rub my pussy through my panties. I was already wet, and after just a moment or so of rubbing, I knew that wasn’t going to be enough. I was about to slip my hand into my panties, figuring to get a finger or two into my pussy, when I realized where I was. I took a quick look around, and was a little surprised to see that there was only one other person in the car: a guy sitting all the way down at the far end, his nose buried in a book. I only hesitated a second before I lifted my butt and slipped my panties off. I had my arms back into the sleeves of my jacket, my feet on the floor, and my panties in my jacket pocket seconds before the train stopped at 59th.

As soon as the doors closed, I turned sideways in the seat again, putting my back towards the guy at the other end of the car, lifted the front of my skirt to my waist, and buried a finger in my pussy. Ahhh, heaven. My eyes closed involuntarily as I began to slide the finger in and out, rubbing the palm of my hand across my clit. I was rapidly approaching orgasm, when something made me open my eyes. A man was standing in the aisle about ten feet away, his eyes riveted on my crotch, the bulge in his pants clearly showing just what he thought of my little show.

I froze, my on-coming orgasm evaporating. Not that I have any objections to showing off, quite the contrary, in fact. It was just the unexpectedness of it; thinking I was alone, and then discovering I had an audience. Seeing that I had stopped, he looked up from my pussy and our eyes met. Neither of us even breathed for several seconds, until, finally, he broke the silence.

“Sorry to disturb you,” he said, in the most incredibly gentle voice I’ve ever heard. He sounded for all the world just like someone trying to lure a strange kitten into coming over to be patted. “I saw what you were doing from the next car, and I just couldn’t resist coming over to this one for a better look.”

What can you do when you’re faced with a gentlemanly apology like that? Especially in New York! I did the ladylike thing. “Why don’t you have a seat?” I said, pointing to the seat beyond my feet. Since I was sitting sideways, that seat was maybe five feet from my head, no more than two feet beyond the tips of my toes, directly in line with my pussy; sort of the pornographic equivalent of first row seats right behind the goal at a hockey game. “Perhaps you’d like to open your pants and do likewise?”

“Thanks. I think I will,” he said, with a sudden smile.

The train was pulling out of the 79th Street station as he settled himself in the seat and opened his fly. He winced a couple of times as he worked his rock-solid cock out of the opening. They aren’t the most maneuverable things, are they? Especially when you’ve got those silly jockeys to deal with.

“Very nice,” I told him, quite honestly, when he had it out and comfortably nestled in his hand. As he began to stroke it up and down, I resumed finger-fucking myself, thinking how silly I must have looked, carrying on a conversation on the subway, with a complete stranger, all the while with a finger deep in my pussy. After a minute or two, I switched to a masturbation style better suited to showing off, spreading my pussy lips open with my left hand, and rubbing my clit with the fingertips of my right.

“Yours is very nice too,” he said, his hand moving faster on his shaft. “You don’t suppose we could…” His voice trailed off, as he tried to think of a good way to suggest that we stop fooling around with this masturbation stuff, and start fucking.

I hesitated for a moment, wanting a cock inside me, and tempted by the drop of pre-cum that was just beginning to run down the underside of his cock head. “Probably not a good idea,” I finally replied, regretfully.

He shook his head sadly. “Damn. I’d love to sink my dick into that hot cunt of yours.” His hand moved faster and faster (and so did mine!), and his breathing got rougher and more ragged. “Hot and wet,” he moaned. “Shit, I’d love to eat you, you look so good!”

I closed my eyes again for a moment, imagining my fingers were his tongue, sliding back and forth over my clit, and then that they were his cock, as I plunged my index and middle fingers as far into my pussy as they could go, and then began to finger-fuck myself frantically.

My eyes flew open as I heard him cry “Oh, shit, YES!”. I was just in time to see the first spray of his cum shoot up into the air. I watched it rise and fall in a perfect parabola, seeming as if it were in slow motion. As it reached the peak of its arc, I knew what was going to happen, and happen it did. His load came down directly on my lower leg, splashing hot and wet, and then running down to my ankle and onto the seat. The feel of his cum was the final straw for me, and I cried out as my own orgasm washed over me.

I began to come down from my peak just as the train started to slow for the next station. “All that between 79th and 86th?” I thought, just as the conductor announced “Hunnerd ‘n’ Tenth Street. Next stop Hunnerd ‘n’ Sixteenth.” We had made four stops, and I hadn’t even noticed!

“Hundred and Tenth!” my partner exclaimed. “Oh, shit! My stop was 96th!” Simultaneously, he leaped to his feet, stuffed his cock — still dripping with cum — back into his pants, threw a quick “Thanks a lot, Lady” over his shoulder to me, and leaped out the door just before it closed.

I waved to him out the window as the train started up again, and then started thinking about how much fun I was going to have with you when I got home. One more stop, a couple of blocks walk, and then I was going to tell you the whole story, and then fuck you silly.

I nearly froze my pussy walking home from the subway stop, because I was in too much of a hurry even to put my panties on; I didn’t want to have to waste time taking them off when I got home. I gave the doorman one hell of a show when I slipped and fell on the wet marble in the lobby, nearly killed myself when I slipped again getting out of the elevator, got inside, and then discovered you were asleep! Fink!!

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Deb and I hope you’ve enjoyed reading this story as much as we enjoyed writing it — not to mention doing the research! If you have questions, kudos, or complaints, I can be reached:
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by Solo Polyphony