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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).

(click to read entire story…)

It had been months since I had seen him. Three months to be exact, three months of loneliness and frustration of the emotional and sexual kind. The intensely sexual kind. Three months of becoming literally a mistress of the art of masturbation and self-pleasuring. Three months of experience which I couldn’t wait to share with Brian.

These were the thoughts that filtered through the sleepiness of my jet-lagged brain as I stared out the tiny fiberglass window of the plane. Not that there was anything to see but the fluffy whiteness of clouds, so there was no view to distract me from my contemplation. And considering the reunion soon to be at hand, I could think of little else but finally ending three months worth of grueling celibacy.

I checked my watch again. Still an hour and a half remaining in the flight. With a sigh I lowered the window shade and nestled my head against the pillow I had stuffed between the seat and the wall of the airplane. My gritty eyelids inexorably lowered, and I dozed…

He stroked my face and gazed into my eyes as I squirmed underneath him. I gazed back earnestly, all of the need and desire mirrored blatantly there for him to see. But still he teased me. Lifting his hips, he probed my pussy with just his cock head, and in my sensitized condition, could almost feel the slit slide like a custom-made groove over my clit. I arched against him further, seeking to suck him inside of me, needing the penetration so badly I thought I would die.

Although I knew he wanted it almost as badly as I did, he still withheld. “Just a second,” he said, “Need to make sure you’re wet enough.” Then his mouth was on mine, his tongue plunging into my mouth aggressively. My eyes were closed, my head swam, but still I could feel his hand snake down between our two sweating bodies, inch into my damp muff, and slide a finger slowly over my clit and down between the cleft of my slick pussy lips. He pushed his finger inside of me, up to his bottom knuckle, and wiggled it around, testing the waters, as his knuckles continued to grind into my hot mound.

“Oh God…” I moaned shakily, “Please…” His hand left my soaking cunt, and slithered up between our torsos, leaving a slimy trail up my abdomen. He stopped to cup one heavy breast, and roughly pinched my nipple. I gasped.

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I hated this feeling. I can can tell exactly where he is standing: over to the side and back a bit. Around the corner of the bar and moving into the hallway. To the bathrooms? Sigh. I am feeling, well, heh, warmed up.

Mmm. If I take a deep breath [BJ breaths in], I can feel the my top tighten against my breasts. As there is no bra tonight, I can feel my nipples rub across the knit fabric. A thick yarn. Rub, rub. My legs too; movement, or squeezing is good. There is that slippery sensation and a bit of dampness on my panties. Arrgh!

What would he be like? I’d love to run my hands through his hair; to feel his hair tickling my fingers. To trace a finger down his chest. What would the hair be like on his legs? Soft and fuzzy like some forest animal? Or strong, tickling my hands as they rubbed his inner thighs? To kiss his neck. He has a beautiful neck. I love to kiss necks; a sloppy sucking kind of a kiss. His ears too. Then to move down to his chest. Maybe nibble a nipple? Wonder what he likes. Across his stomach, which I imagine as a washboard. And then, oh! I should stop thinking like this! Dam it, I’m married!

I open my eyes. Hey — where did Jamie go? Oh, there out slithering with that guy she met on the dance floor. They look like they are having fun. If anything Jamie says is true, boy is he in for a treat tonight! Wish someone would do that sort of thing to me!

Wait. Here he comes again. I can feel that tugging in between my legs. I try to squeeze it way, but it is still there. And stronger. It must be really wet. Mmmm. Oh! He’s coming closer. Checking me out. Ah yes, the usual male scan. Rests a while on my breasts — I push them out and feel my sweater rub across my nipples. Wonder if he saw the expression on my face. Moves down to my legs. I’m wearing a short mini-skirt so he should get an eyeful.

Yikes! Eye contact. I’m locked. I can feel a flood of heat into my face. Good thing the strobe lights, etc. don’t show anything. He looks around at the dance floor. At Jamie. Why did he do that? Back at me. Oh my! He’s coming over. He’s asking me to dance!

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When I met Jon he was just past chubby, melted down into a lithe boy who was starting to show signs of man. He was a young man the way a colt is part gangly animal and part magical apparition. He wore his awkwardness like a beetle wears its shell, to cover up the soft inside.

He was my highschool friend. He sometimes flirted with me, just to practice. I watched him hesitating on the cusp of growing up. If he had been more self-assured I would have been smitten, and if I had been any more self-assured I’d have taken him — easy, the way his hormones were trembling and threatening to spill over, like water from a glass. But I was not the one he chose for his first affair.

Mr. White had just been hired to teach at the highschool. He was on a three-year contract, and that was all the longer he would stay, because teachers like him are never hired back. He must have interviewed in his one regular suit — he’d never have gotten the job dressed the way he usually did, in old, old clothes, antique three-piece suits and wire-rimmed glasses and a watch and chain. He was hired to teach drama, of course — that’s probably why they let him slip by — and English.

He looked English, actually, like a headmaster at a shabby third cousin of Eton. He had bright, lavishly-lashed eyes and a mustache that curled. No one in our remote little town had never seen anything like him. He was like a time traveler who had taken a very wrong stop. He could not have been expected to have anything in common with a bunch of ranchers’ sons and daughters. Nevertheless a few of us had determined that we were not going to be hicks. We were over him like flies on honey.

Jon was skittish around Mr. White from the start, manic even. For about a week he joined the other boys, raving about what a fruit and a faggot the new teacher was. But by the end of the second week of school he had arranged to join three extracurricular clubs — the Thespians, the school paper, and a modern novel study group — so he could be near him.

On any given day Jon could be found before class, after class, and often at lunch in Mr.White’s room. I knew that because I was in the habit of dropping by at those times myself. Of all the students who clustered around the new teacher, I was the closest to understanding just why he seemed so odd. He was so completely different from any other man I’d ever known, in his eccentricity so sweet and strange, that of course I began cruising him almost right away. I was just learning that having sex with a person could teach me things about them and about myself, and I was sure Mr. White was a wealth of things I wanted to know.

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She was humming as she changed the sheets from the smooth percale she liked to the fuzzy flannel he preferred. She imagined what she would do to him tonight, and her humming grew quieter until finally it ceased.

First she would undress him, slowly, slowly, kissing him softly as each bit of flesh became visible. “To keep it from getting cold,” she would say teasingly. They’d done this before — he would say, “No fear of that!” and they would laugh together as she began to stroke his skin with her warm hands.

Then she would push him slowly back until he fell onto the bed and she would take his penis into her hand. By now he would be fully erect, and it would jump as she touched it. They would laugh again at this familiar occurrence.

Next she would begin to lick him with little, teasing cat-laps at his skin, all over him, from his collarbones to his toes, but avoiding his crotch. She would roll him over and lap at his back, covering every inch of his skin, and then she would suck at his toes…

The phone rang, shattering the intimate silence. She picked it up. “Hello? Oh, hi! I was just thinking about you! When are you getting here? Oh. Oh, I see. Yes. Yes. Bye, then.” He wasn’t coming after all. Again. She was momentarily disappointed, but then she began to get angry.

“Who needs you anyway?” she demanded of the walls in a quiet but intense voice. “Damn you!” She was already wet and wanting from her imaginings.

She went downstairs to put away the wine she had gotten out for him. She seldom drank wine herself; she disliked the taste. She paused, looking at the bottle. It was almost empty. “Am I sex-starved, or what?” she asked herself, as she noted the phallic shape of the bottle’s neck. She picked up the bottle and one of her two crystal wineglasses and took them up to her bedroom and set them on the nightstand.

(click to read entire story…)