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February 6, 2007

older woman fucking young coworker

The summer after I turned 18, before I went to college, my parents decided that it would be better if I got a job, instead of spending the summer “loafing” (their version) and “hanging out” (my version). When I proved less than enthusiastic in my pursuit of this goal, my parents managed to find a job for me—in the business office of my father’s law practice. And, while I thought I’d hate it (I never had any intention of going into law, or business), it turned out to be one of the best experiences of my life. That had nothing to do with the work; in fact, there wasn’t much for me to do, except file and make copies. But I sure learned a lot from my fellow employees.

They were all really nice to me; not that they had much of an alternative—I’m quite sure that my father didn’t ask them what they thought of the idea, and then put it to a vote among the staff; that just wasn’t his style. Still, they accepted me with good grace. There were four of them in the business office: Jean, the receptionist; Arlene and Sally, the secretaries; and Deborah (not Debbie!), the office manager. They were of various ages (being young and utterly self-absorbed, I had no ability to distinguish the ages of anyone above 30), with Sally being the youngest (early 20s) and Jean the oldest (my inner child still sees her as 80, but in truth she couldn’t have been more than 50 or so). They were a fast-talking, wisecracking bunch; jokes flew around the room constantly, and a lot of the humor was decidedly on the salty side. For a gangly 18-year-old, who had never been on a date, or spent any time in the company of women—apart from his mother and grandmothers—it was an education.

I immediately developed a crush on Sally. She was the closest to my own age and, although even then I knew that she wasn’t really pretty, she had an ease, and a grace, and a sense of her own sexuality that, even though I could not have articulated it then, impressed me with the sense that she was a woman in the ways that the girls I knew were still only trying to be. She was married—as were all of the women, except for Deborah, who was divorced—and, even if she hadn’t been, I’m sure I would never have seriously entertained the hope that she would ever do anything more than smile at me (which she did, readily enough). Still, in my fantasies, I imagined her begging me to fuck her, which I would then do, over and over and over again. The others came in for bit parts, too, on occasion: Arlene, who had the biggest breasts, and a pair of thick, black plastic framed glasses that made her perfect for the role of what I would only later—when I discovered video porn—realize was the naughty librarian (no matter how hard I fucked her, she never took the glasses off); Jean, I suppose, for a bit of variety, although I never had much interest in her; and Deborah, almost as rarely. Not because she wasn’t sexy—she was: she had the best ass and legs of the group, and knew how to dress to show off everything to the best advantage—but because her air of authority made her seem off-limits, and a bit intimidating. She was the only one in my fantasies who, when I fucked her, stayed in control.

Although I would have vigorously denied it at the time, I was enjoying my working summer vacation. I was learning that women were not the mysterious, decorative creatures my limited contact with the species had led me to believe that they were. I learned that women could be capable and hard working; that they could be at least as willing as men to talk about sex, and even more willing to have a sense of humor about it; and that, even if they weren’t above enjoying the occasional joke at my expense, they were not, as my school experiences had taught me, conspiring to take turns alternately humiliating and ignoring me.

One morning, about a month after I started, Deborah approached me and suggested that we go to lunch together, because she had something she wanted to discuss with me. This wasn’t especially unusual; going out to lunch was routine at the office, and people usually went out in groups of two or three (it was necessary, of course, to leave at least one person to answer the phone). The prospect of a tête-à-tête with Deborah was simultaneously worrisome (I knew I hadn’t seriously fucked up, but there was always the possibility that I was in for some criticism) and exciting (I was having lunch with an attractive woman, just like the man I knew I had it in me to be). At noon, we walked out together into the July sunshine, to her car (I rode to work with my Dad). Inside it was steaming, but, more than anything, I was struck by the smell: pure Deborah, a mixture of her perfume, with a faintly musky odor that I unconsciously recognized as sexy. She drove, confidently and efficiently, to a Mexican restaurant across town. Inside, it was dark and cool, and almost empty; we were led to a booth in the back, and left alone to look over the menus.

After we ordered, and the waitress had disappeared, Deborah got down to business. “You’ve got a crush on Sally,” she said, “and that’s natural, I suppose, and, ordinarily, harmless. But it’s beginning to disrupt the atmosphere in the office, and that makes it my problem.”

I began a feeble protest, but she cut me off. “I don’t blame you,” she said, a bit more gently, “as I said, it’s only natural, especially for someone your age. You must be a seething mass of hormones, and you don’t seem like you know what to do about it yet. I don’t suppose you have a girlfriend?”

“No,” I replied, now thoroughly miserable.

“Look, it’s OK. Girls your age can be difficult, I know. They don’t know how to make themselves available for what they want, any more than you do. But Sally knows, all right. Not that she really wants you, mind—but believe me, she gets a charge out of turning you on. Yeah,” she nodded at me, noting my surprise at that, “you should know that. Flirting with you makes her just as hot as it makes you. But she’s never gonna let you pull those damp little panties down; at least, not as long as she can lead you around by the nose the way she’s doing. And it’s creating some resentment. Yes, I know they’re all married. But we’re not talking about marriage here; we’re talking about sex. And, as the only man in a group of women, you are unsettling the balance. You are giving all of your overtly sexual attention to one woman. Even if none of these women actually want to have sex with you—and maybe you shouldn’t jump to that conclusion too quickly—they don’t want to be made to feel that they are utterly uninteresting to you, compared with Sally.”

“So what do I do?” I asked, finally. My mind was still clinging to the image of sweet Sally pulling down her damp panties.

“You have to stop it, obviously. I don’t mean stop flirting with Sally altogether; that would just make her upset, and make everything worse. But tone it down. Be aware of what you’re doing, so you don’t walk around with your tongue hanging out. And try flirting with the others. If nothing else, it’s good practice. Believe me, a man who knows how to flirt will never have to settle for a strong right hand.”

I must have looked pretty embarrassed at that. “There’s nothing wrong with it,” she laughed. “Women do it too, did you know that? Not the same way, obviously. But it’s just as much fun.” She looked me straight in the eye, and winked. She murmured, more to herself than to me, I think, “It’s too bad nobody teaches kids these things. Still, I suppose there are some things you have to find out for yourself.” Then our food came.

After we started eating, she changed the subject, asking me a lot of questions about myself: what subjects I liked in school, what I did with my friends, where I wanted to go to college, what I wanted to do when I “grew up”; pretty standard conversational fare between an adult and a teenager, which put me back into familiar territory. She even told me a little about herself: that she had divorced her husband nearly ten years ago, after only a year of marriage, but not before she became pregnant with her son, who was now the center of her life; that the men she met were either uninteresting and unimaginative, or else too controlling, and unwilling to allow her the kind of freedom she had become accustomed to.

“I have a lot of one-night stands,” she said, matter-of-factly. “I like sex—need it, even. But I have to separate it from what’s really important to me: raising Nick, and living life on my own terms. You must think I’m a terrible person,” she added, almost shyly.

“I think you’re terrific,” I objected. “In fact, at the moment I can’t think of anyone I admire more.” I felt my face flushing; not, this time, with embarrassment, but with determination.

“Not even your own mother?” she asked, with a smile.

“I love my mother,” I said, “and I appreciate what she’d done for my family, and for me. But sometimes I feel a little sorry for her. I think maybe she gave up too much to get what she has.”

“You keep thinking that way,” she said, after a brief pause, “and you’re going to make some woman very happy, someday.” Then, glancing at her watch, she became suddenly businesslike again. “It’s time to get back to work. Remember what I said: be aware of yourself; flirt, but do it on your own terms; and remember to spread it around. You do it my way, and you’ll be cock of the walk by the end of the month—guaranteed.”

Dropping some cash on the table with the check (I had made a feeble attempt to grab it, which she had briskly ignored), she whisked us both out of the restaurant and back again to work.
I was a bit nervous about going back to work after my lunch with Deborah; her admonition to be more self-possessed, and to flirt, but to be sure to “spread it around” among all the women in the office—well, it sounded like good advice, but I wasn’t sure that I could pull it off. I wanted to please her, though; she had done me the rare favor of speaking to me as a fellow human being, and not just some kid who was too green or too stupid to grasp what she was talking about.

I began by complimenting everyone, and I was careful not to start with Sally (on whom I’d developed the crush that prompted Deborah to advise me, in the first place). I noticed that Arlene had on a brightly-colored summer skirt that came to just below her knees, showing off a pair of smooth, solid legs.

“Wow, Arlene . . . that skirt’s a knockout! Are you going dancing after work?”

Arlene cocked her head at me, not sure whether she was being complimented or insulted; this was the first time that I had ever commented on what she wore, or suggested that she even had a life outside of the workplace.

I persisted, sweating a little, but determined not to blow it so soon. “You should be careful about showing off those lovely legs.”

“Hmph!” she grunted, still not sure how to respond. “Never you mind my legs, young man.” But when I cast a sidelong glance at her a few moments later, I saw that she was smiling to herself. Maybe this wasn’t going to be so hard, after all.

Jean was next. This wasn’t going to be quite so easy; she was obviously overweight, but it was impossible to tell much more than that about what she looked like, because she always wore large blouses, buttoned at the neck, over wide-legged slacks, a combination that gave no hint about what was underneath, except that it was generally round from beneath her collarbone to below her waist. Today, however, she was wearing a very colorful scarf. I took a shot.

“Jean, that scarf really brings out the blue in your eyes. Got a hot date tonight?”

She looked down at her collar, tripling her chin. “This? Why . . . thank you. But my eyes are hazel, you know.”

“Not any more they’re not. From where I’m sitting, they’re as blue as the Adriatic in August.” Even as this came out of my mouth, I was terrified. No one was going to let me get away with this kind of bullshit.

Jean tried to frown at me, but failed miserably, then let her mouth spread into a grin. “You’re sweet, even if you are a lousy liar,” she said. I just grinned back at her.

I stayed as far away as possible from Sally for most of the day—not easy, in the small space of the office. She was looking good, too: she had on a nice tight sundress, with spaghetti straps that showed off brown shoulders, dusted with slightly darker freckles, and the silky fabric only accentuated the two deliciously apple-sized breasts that I had been longing, all summer, to taste. Finally, though, she cornered me at the copier.

“Aren’t you the busy little worker bee today,” she observed. “Usually you’re buzzing around my desk, but today you seem to be looking for flowers somewhere else.”

“Maybe I was beginning to think you weren’t going to share your nectar, after all,” I replied, letting my gaze drop to her chest.

“I’m very careful about my nectar.”

“You should be,” I said, now looking her in the eyes. “From what I can see, it’s worth some effort. But even a drone needs a little taste of honey, now and then, just to keep his strength up.”

She didn’t say anything for a moment, and I guessed that I had gone too far. But then she dropped her eyes, and suddenly I felt her hand brush mine, quickly, and so gently I wasn’t entirely sure whether I had felt it or just imagined it. Then she spun around on the ball of one foot, so fast that the hem of her dress flared up, and marched straight back to her desk. When I came to myself, I looked around to see Deborah smiling at me. She held my glance for just a second, but for that time I felt the ground fall away from beneath my feet, as if there were nothing holding me up anymore.

In the days after that, I started noticing details about all the women: not just their clothes, but their hair, their makeup, the jewelry they wore, their perfumes. I felt, sometimes, like an anthropologist, studying an undiscovered race of people; undiscovered, at any rate, by me. It was hard to be sure, since I had no data to compare with from before I began my experiment in flirtation, but it seemed to me that as I noticed, and complimented, the women began taking more care with their appearances. Arlene especially seemed to blossom: necklines crept down, until fully half of her pale, fleshy melons was exposed; at the same time, hemlines crept up, above the knee, and she seemed to sense it when I couldn’t help but look, wiggling her delightfully painted little toes in the stiletto sandals she had begun to wear. I couldn’t tell if Jean was losing weight, but she began wearing dresses that showed off an ample bosom, securely anchored in tasteful support bras. Her hair, which had always struck me as rather nondescript, changed, too: fuller, wavier, blonder, and, without a doubt, sexier. Sally, who had been, from the start, the sexiest dresser, didn’t have too much room to work with when it came to upping the ante (while remaining professional enough not to attract the attention of my father, who would not have approved); still, I noticed that she occasionally defied decorum and came to work without a bra—not that she needed one; those luscious tits were still clearly pointing up.

And me? I was in heaven. It didn’t take long to realize that Deborah was right: these women liked flirting with me; they made it easy for me. They encouraged me. My fantasies grew wilder. I imagined them in all sorts of combinations; in my favorite, I fucked all four in the office after work. First Jean would kneel before me, begging me to suck my dick. Dropping my pants, I would lean back against a desk while she sucked and slobbered over my cock. The other women would gather around, licking their lips, and awaiting their turns. When I was ready to cum, I would motion to Arlene, and grunt, “Take out her tits.” Arlene would kneel behind Jean, unzip the dress from behind, then unlatch the bra, and shake it free from Jean’s monstrous mammaries. Each a foot long, they’d sag to the top of her thighs as she knelt. As I felt myself lose control, I would shove her back, her mouth still hanging open in lust and surprise, then, grasping my spasming dick by the hilt, I would come in thick ropes on her fat titties, watching the cum ooze thickly down towards her saucer-sized nipples, until she scooped it up with her fingers, and greedily slurped it down.

Arlene would shove Jean aside and, kneeling in her place, begin sucking my cock back to life. Knowing what I wanted, as soon as she had me hard she’d peel off her top and bra and encase my rigid fuckstick with her soft, white globes. When she could tell that I couldn’t take any more, she would stand up, sweep everything off of the closest desk, and unzip her skirt. Stepping out of skirt and panties in one smooth motion, she’d turn her back to me, setting her feet wide apart (still in those stiletto heels, hiking her ass way up), and bend over the desk. “Fuck me,” she’d beg, and I’d oblige, stepping up behind her to shove my fat dick into her hot cunt. I’d pound her furiously, as she hung onto the edge of the desk. As I’d feel the cum boiling up from my balls, I’d release a roaring grunt, then I’d coat her insides with my sticky seed.

Arlene, fucked to exhaustion, remained bent over the desk while I stepped back and slid my lovebone from the viscous soup in her gaping slit. I’d turn, and there would be Sally: panting, wanting it so bad her knees were shaking. Meekly she’d unzip her tight dress and pull it down, the sheer fabric snagging on her nipples, the size of fat, red gumdrops. “Please, please,” she’d moan. Hungrily, I’d reach for her, grabbing her by her narrow hips, pulling her to me. Bending over her, I’d devour her perky udders, biting and nipping and pinching and licking, while she threw her head back and groaned with ecstasy. Soon enough I’d be stiff again; feeling me poking into her flat little tummy, she’d grasp my scummy rod in one hand, and hoist herself up by my shoulders with the other. Grasping her ass, digging my fingers deep into her crack, I’d lift her up, while her legs sought a purchase around my hips. With my proud manhood still in one hand, she’d find her slit and sink her weight down on it, as we both would heave sighs of pleasure. Both arms around my neck now, her head lolling back and to one side, she would surrender to the feeling, as I’d raise and lower her along the length of my shaft. All too soon, I’d pass the point of no return, erupting up inside her as she’d scream, “Yes, yes!” My balls drained and my arms heavy, I’d let her slip to the floor, where she’d lie, unconscious, in a heap.

Now panting with exertion, I’d wipe my brow, and drop into the nearest chair. A hand on my shoulder; I’d look around, up into the hungry eyes of Deborah. “Didn’t forget about me, did you?” she’d ask, with a pretty pout. “You aren’t finished yet. Get up!”

She’d be naked, having prepared herself while waiting her turn. Deborah was only about 5’2”, almost a full foot shorter than I, even at age 16. Her tits were larger than Sally’s, and their weight pulled them downward; but the nipples, with their firm, tight, pink areolae, pointed straight out at me. I’d bend toward them, salivating.

But Deborah would have other ideas. “No, no,” she’d croon, pulling down on my shoulders with a light but insistent pressure. “That’s not what I want.”

Understanding, I’d kneel before her, my nose at a level with her sweet little innie bellybutton, perched in the middle of an ever-so-softly swelling belly. Clearing off another desk with a sweep of her arm, she’d hop onto the top, mashing the two perfect globes of her ass onto its surface. As she spread her legs, I’d see a shadowy triangle of dark, curly hair, and suddenly I could smell, again, the wonderful smell of her sex—the same funky sweetness I’d first breathed in her car. Unable to restrain myself, I’d bury my face between her thighs, rooting with my nose and tongue, grasping her hips to pull her more tightly against me. How much time passed before she bid me, “Stop,” I couldn’t tell; but I’d again be ready for action. Rising to my feet, I’d approach her; again, she’d stop me. “Wait,” she’d say, “I have something special for you.” Turning away, she’d bend, like Arlene, over the desk. “In my ass,” she’d demand, “stick it in my ass. Hurry!” Lining it up, I’d sink my dick into her asshole. “Give it to me! All of it!” she’d roar. And I would—sawing back and forth, I’d fuck her with my last burst of energy, and fill her breathtaking butt with the final few drops of my immortal sperm.

Like I said, heaven. Lying on my bed, surrounded by clumps of semen-soaked tissues, I’d gently caress my chafed and shrunken penis, and dream of the day when I would become—in more than just my adolescent fantasies—the cock of the walk.

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