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My Shy Boss

I’m living with a great guy and finishing up my master--but sometimes when I’m going past some building I worked at on a weekday I get a hint of those strange times.

It was bad enough dealing with the crazy bosses who acted as if the world was going to end because the presentation folders were not ready in time. More deadly was the boredom, the hours I spent on hold for the travel agent who handled the company’s account or tending a photocopier. I probably would have gone crazy myself if I hadn’t slipped into the restroom now and then to masturbate. At least it brought some excitement to the day.

What I remember best, though, was walking down the bustling streets at noon, engulfed in a wave of men in business suits. Their heads always looked blurred and faded, as if they’d been rubbed out with an eraser. It was the suits that seemed to take command as they marched purposefully toward some unknown battle of commerce. However, at least once on every block, one man’s face would suddenly shift into focus, and his eyes would leap out at me with such longing, my pulse would falter. I suppose it might have been mere lust for any passing flesh that was young and female. This gaze felt different, though, as if the man in question were sending a coded message from deep inside his woolen prison— Hey, I’m alive in here.

The weirdest thing was that I felt the urge to help the poor guy. In my daydreams, I did. I reached out and pulled away his stiff wrapper like the peel of a fruit and pressed my fingers to his warm, secret core as I whispered—Yes, I see you.

Of course in the next instant, my momentary soul mate would be swept along in the tide, but I let myself believe that something important had happened between us. It made my own prison sentence go faster.

I never imagined that by the end of my Year, my dream would actually come true.

It was ironic that Steve was the man I finally did penetrate, among other X-rated activities we enjoyed in his plush office. As bosses go, he was one of the best. It was just the two of us, with me sitting watch at the receptionist’s desk. Most of the time he left me alone to email my friends, surf the net and race through the day’s novel, which I usually finished on the way home. Plus, he always brought me coffee or Juice when he popped down to the cafe on the corner and he always got it right.

Now that’s a good boss.

I’d guess he was in his mid-forties, but he had a pretty good body from workouts at a health club. Steve was shy, as you might expect of a tax accountant, although he was clearly bringing in the bucks. I sensed, though, that the constraint went deeper, that he was somehow shackled inside, even more than the typical suit rushing along the sidewalk at lunchtime. Of course maybe I had it wrong and he’d found his heart’s desire in a smooth, reliable life. Except if that’s really how he wanted things to go, during the weeks I worked for him, Steve made three serious mistakes.

The first thing he did wrong was to catch me playing with myself in the  restroom. Okay, so I didn’t lock the door, but he’d just left for a meeting and I wasn’t expecting any clients for quite some time. He didn’t even knock either, he just pushed the door open and there I was, standing in front of the mirror by the sink, my panties pushed down around my thighs, my blouse open, and my hands doing the usual coffee-break-quickie cha-cha with my clit and my nipples.

I let out a cry and covered myself as best I could. Without a word, he stepped straight back through the door, like a movie playing in reverse, but he’d seen me, there was no question about that.

My heart was pounding as I straightened my clothes and dabbed my sweaty face with a wet paper towel. I was in big trouble. How could it be otherwise? Steve would fire me and everyone in the city would know I jerked off in the restroom during my breaks and I’d never find another job and I’d starve and….

The face in the mirror broke into a giggle.

If the word got out about my activities, I’d probably get even more work. And, really, if he did kick my ass out on the street, he’d be doing me a favor. I might finally have to get myself a real life.

Still, the prospect of facing him after our little encounter was too daunting even in my new what-the-fuck mood.

When I stumbled back into the office, he opened his door and asked to speak with me for a moment. It was pretty obvious he’d been waiting for me.

He motioned for me to sit down on the sofa and perched himself on the edge of his desk—a good choice to project benevolent authority, which seemed to be the way he’d decided to spin it. He was blushing, though, as he told me in a kind, measured voice, that it wasn’t his business what I did during my breaks, but he hoped in future that I would keep the door locked in case a client wandered in.

 “Thanks,” I said with a touch of insolence. “That’s very cool of you to be so understanding of your employee’s needs.”

It was then he made his next mistake, an attempt to joke with me. “Yes, well, maybe you’d better tell your boyfriend to be more attentive to those needs.”

“I don’t happen to have a ‘boyfriend’ right now,” I shot back. It was the silly high school word that bothered me, because I did have a couple of fuck-buddies handy for when the urge struck, but of course, good old Steve misunderstood.

“I’m sure that’s only temporary,” he said gallantly.

“Temporary. Yes, well, that’s me. And don’t worry, I’ll, um, be more careful in the future.” But as I headed for the door, I very carelessly staggered into him. It wasn’t on purpose exactly, but I didn’t pull away when he caught my arm.

“Megan, are you okay?”

I stared at his hand resting on my bare flesh. It was a very warm, sturdy hand and I couldn’t help imagining his fingers at work where mine had been earlier that day. I glanced up at his lips, which looked much softer and fuller up close. My eyes dropped lower — and I’m not sure if this counts as another one of his mistakes — but you couldn’t miss that tent pole poking up under the trousers.

Cut the concerned authority figure crap, Steve. You want it as much as I do, so why don’t we just go ahead and fuck right here?

I didn’t actually say that out loud, or maybe I did, because suddenly we were kissing and I was running my hands all over that fine gray suit. I’d been right all along, there really was a living body inside, warm and soft in some places, hard in others. And that body did have secret hungers — in this case to perform a variety of adults-only activities with mine. Steve guided me back to the sofa, peeled off my pants and asked me, with beguiling urgency, if he could eat my pussy and help finish the job he’d so rudely interrupted.

“Sure, why the hell not?” I answered, lounging back and spreading my legs. I did have an unresolved ache down there. And, after all, who could turn down such an offer?

Steve made sure to lock the door, but then he dove right in without any preliminaries, still wearing his jacket and tie. He was pretty good with his tongue, but the best part was watching him kneeling between my legs, face buried between my thighs, lips moving as if in prayer. Which is exactly what I’d dreamed about day after day on my lunchtime walks.

I was getting pretty hot from his attentions, so I asked him—more like ordered him really--to play with my tits, too. Not long after I finally did reach the climax he’d snatched from me two hours before. As he pulled away, he unconsciously fished one of my hairs out of his mouth, which could have been an awkward moment, but we both laughed.

“I don’t mind returning the favor,” I said.

“Well, I would like to make love to you, but I’m afraid I don’t have any protection,” he said, not quite meeting my eyes.

“Make love”? “Protection”? Was this guy quaint or what? But by that time I was curious to see what he had in his pants so I confessed that I carried condoms in my purse.

As he started to undress, my heart sank. Not that his body wasn’t fit—I’d guessed right about the benefits of the health club—but I missed the suit. Apparently I wasn’t quite ready for the “uncovering his warm, secret core” part of my fantasy.

So I knelt on the carpet, stuck out my ass and told him to take me doggy-style. Then I closed my eyes and imagined he was still fully dressed with just his cock poking out of his fly, and his nice trousers were getting all stained with my pussy juice. This, along with the thrusting of his cock against my sensitive, post-come sweet spot, almost brought me to a second orgasm. Almost, but not quite.

Still I left work that day in a much better mood. Yes, he’d caught me masturbating. I, however, had good evidence he’d cheated on his wife. Or maybe she was a girlfriend, but I’d taken note of the picture of a handsome, assured-looking man smiling from the bookshelf behind his desk. Steve would surely realize that he and I were equals in crime and treat me accordingly.

That was my mistake.

The next morning he called me into his office as soon as I arrived. This time his blush was deeper. With much throat clearing he told me he’d enjoyed the day before, but he wasn’t in a position to be pursuing a relationship right now. He hoped I would stay until the end of my short contract, but he’d understand if I didn’t feel comfortable….

I wasn’t the least bit drunk, but the honest me immediately took exception to his terms. “Hey, all we did was fuck on the carpet in front of your desk,” I interrupted. “That’s not a relationship. It’s a way to make a very boring afternoon go a little faster.”

His head snapped back. He clearly hadn’t planned for this response from docile little me. But I was suddenly tired to death of that pretense.

“Too bad I spent a good ten minutes in the shower this morning shaving so I could sit on your desk and have you lick my smooth twat without any worries about stray short-and-curlies in your teeth.”

I pulled up my skirt to show him my bare slit. He stared, eyes wide.

“Listen, I like this job, so I’m staying. I’ll be sitting out there with my shaved pussy all day, so if you’re interested in taking care of my needs, the job’s yours. But please, oh, please, don’t ever think I’m expecting a relationship.” I spit out the last word with a sneer and headed for the door.

It was then he made his third mistake, in a voice so low, I could barely hear it.

“Megan,” he said. “Wait.”

So, just as I’d imagined in the shower that morning, Steve did lift me onto his desk, and pull my skirt up to my waist, and glide my green panties over my legs. Then, licking his lips, he started to take off his jacket.

“Stop,” I said.

He looked at me, confused.

“Don’t take off your clothes. I really get off on watching a guy in a business suit eat me.”

His eyes twinkled. “Whatever you say, boss.”

The oral sex was even better the second time, and I came with shuddering gasps, knocking pens and paper clips all over the floor. There were some wet spots on his tie, but he didn’t seem to care. He did ask, politely, to borrow another one of my condoms, but his faintly taunting use of the word “boss” still stung a little.

“I think you should buy your own, don’t you?” I jumped off the desk and smoothed my skirt. “So, you know, just give me a buzz when you’re, um, protected.”

I winked and walked out the door, leaving my panties behind.

Steve got the condoms at lunch, but I made him eat me again before I let him fuck me. It’s funny how quickly we settled into our roles. He seemed to like it when I bossed him around and made him “earn” his orgasm. Once I ordered him to lick his lunch from my body—cucumber and tomato slices from my breasts and hummus from my shaven mons. Another time I told him I wanted him to make me come just by tonguing my pussy without fucking. It took a long time, but with some auxiliary clit action, he finally got his work done.

I sucked him just once, when he was on the phone with a client, and as a reward for keeping his voice normal, I stuck my finger up his ass and did the little come-hither wiggle until he shot in my mouth with a soft groan. Most of the time I made him keep all his clothes on, and I’m sure he had lots of extra dry cleaning bills, but he never complained.

I know why I liked it—it was fun to be a spoiled bitch who pushed the limits and made the rules for a change—but I wondered about him. Was it a sort of Oval Office approach to infidelity? If it’s not intercourse, it’s not sex? If I don’t come, it’s not sex? Except Steve and I were having intercourse and he was coming, so maybe for him it was more like, if she orders me to do it, it’s not sex? Or, who knows, maybe I really was nourishing something starved and withered inside him?

Eventually, however, we came up against an insurmountable limit to doing it in his office: carpet burns. I’d spent the lunch break riding him on the floor—me naked, him with his trousers pushed just halfway down his thighs. Afterwards I stroked the angry marks on my knees and said, “Wouldn’t it be nice to do this on a bed?”

Again he misunderstood, as he always seemed to do when we actually talked. “I’m sorry. I believe I mentioned back at the beginning I can’t take you to my place.”

I snorted. “Would you stop it already? I meant a hotel. With a big, soft, four-poster bed so I can tie you up and have my way with you.”

He smiled. “You’re already having your way with me.”

“I think I can do much better. In the right environment.”

He definitely looked intrigued. “Okay, how about tomorrow afternoon? You bring an overnight bag to throw them off when we check in.”

He knew who was in charge.

The first thing I did when we got to our anonymous hotel room with the four-poster bed was order Steve around;

“Well, it looks like we have a lot of work to do. Why don’t you get undressed?”

“You want me to take all my clothes off?” he asked warily.

“Different place, different rules. Go ahead, give me a little strip tease.”

He smiled sarcastically, but his face was flushed with embarrassment.

I sat on the bed and watched as Steve took off his jacket and draped it over the chair. Next came the tie and shirt, then the trousers. He kept his eyes fixed on some spot on the carpet the whole time, submissive rather than seductive, but by the time he was done he had quite a bulge in his boxers.

“Take off the underwear, too. I want to watch you touch yourself. You know, just so we’re even.”

He began to caress his hard-on rather self-consciously. In the meantime, I pulled off my own clothes, leaving them in a pile, then walked over and snatched his jacket from the chair.

It was still warm when I slipped it on. And it was like armor, stiff and boxy, but oddly sensual, too. The faint smell of male sweat made me dizzy, and I soon discovered that every time I moved, the lapels chafed my nipples, sending shivery jolts of pleasure to my cunt.

I handed him his tie. “I want to wear this, too, and I’d like you to knot it for me.”

A quick smile played over his lips, but he complied. Halfway through the attempt, he tilted his head and frowned. “May I try this in front of the mirror? I’m not used to doing it for someone else.”

We stood in front of the dresser, Steve behind me.

“Would you like it snug or loose?”

“Fairly tight,” I said, thinking the constriction might be a turn-on, but I regretted it. It was more like a slave collar, which might be the simplest explanation why those legions of businessmen looked so unhappy.

When he was done, we both studied my costume in the mirror. The shoulders of the jacket were all out of proportion and the sleeves hung to the middle knuckles of my fingers. Plus, the tie hanging between my breasts made it all the more obvious I was naked underneath and the friction of the wool on my nipples was really getting distracting. Far from appropriating the symbols of male power, I looked like exactly what I was--a girl playing dress-up.

Steve seemed to think so, too. His face, hovering over my shoulder in the mirror, showed an indulgent, almost tender, smile.

Fortunately, even a “cute” dominatrix could regain the upper hand when she shackled her slave to the bed. When I tied his knees together with my pantyhose, he was no longer smiling, and his cock was standing at respectful attention.

“I think we’re ready to get started on today’s project.” I straddled him and began to rub my swollen pussy against the coarse hairs of his belly. “We’ll skip the blindfold today because I want you to be able to watch what’s going on.”

Did I detect disappointment in his face? Well, I was running the show and I had other things on the agenda, things I’d been thinking about long before I met him.

“I’m going to tell you something I’ve learned about your jacket. He seems to have a mind of his own,” I said in a low voice. “He’s rubbing up against my breasts and making me wet. But maybe that part’s not such a secret?” Indeed, I’m sure we could both hear the soft smacking sounds of my arousal as I skated over him. “But he’s getting a little rough with my poor nipples and I know it would feel so good to soothe them in a warm, soft mouth. Too bad you’re all tied up and can’t manage it right now.”

Steve stared as I opened the jacket. The nipples did look sore, as if they’d been bitten.

“And my poor cunt, it’s so hungry and there’s a hard, thick cock that’s so close I can feel it knocking up against my coochie, but I can’t sit on it because it’s not protected.”

Steve sighed, arching up against me. “If this is how you planned to torture me, it’s working.”

I looked down at him, smiling sweetly. “Maybe that little cock over there will please the client? We must always do our best to please the client.” I got up on my knees and buried my fingers in my vagina. I fucked myself with them for a few strokes, then held the glistening fingers in front of his face. “Oh, I forgot, this is supposed to go in someone’s butt. How about yours? I know how much you like having something up your ass when you shoot.”

Steve flinched, but he didn’t deny it.

I straddled his belly again. He gazed into my face, his eyes glowing with something like fear, except it was somehow sweeter, softer.

“Steve,” I said, “You’ve got it all wrong. I’m not doing this to torture you. I don’t even like seeing you tied up like this. I want you to be free. Can you try to get free for me?”

At first he looked confused, but then seemed to understand it was part of my game.

“Try,” I said softly. “When you’re free you can do anything you want. You can suck my nipples and fuck me and come inside my hot, hungry cunt.”

Take his cue, Steve obediently pulled on the tethers and tensed his legs. The effort made his whole body shake, like a big vibrator between my thighs. It was another unexpected benefit for me.

“I can’t do it,” he said.

“Try,” I urged. “I like it when you try.”

He struggled against his bonds again and grunted, with arousal or exertion I wasn’t sure. After a few more times, I was skidding all over his belly on my juices as I rode him like a bucking horse. With our shouts and cries and the screaming bedsprings we probably were as noisy as a disco. Finally I took advantage of one of his earnest, but futile, attempts at release, to settle myself on the saddle of his cock.

He gasped, a low, velvet sound of longing fulfilled.

“Fuck me. Come inside me,” I said, riding him in a different way now.

It was a redundant command if there ever was one, because that’s what he was doing, thrusting up into me with bellowing groans. He’d never made those sounds before—in the office he was as quiet as a mouse. This time he came with a yell so raw and shattering, it did sound as if something inside him was breaking free.

After I untied him, he took me in his arms and squeezed me so hard it hurt.

“That was good, Megan,” he whispered. “So good. Thank you.”

Suddenly I was aware of the choking grip of his tie, still wrapped around my neck. I reached between us and pulled it off. But even then, the tightness still lingered in my throat.

I barely recognized my shy tax accountant at work the next day. He actually bounced off to get our lattes, announcing with a wink that he didn’t have any clients that afternoon.

I gave him a big smile in return, but once he was gone, I buried my face in my hands. Our offsite meeting had been a success, but I was worried about the troubling twist my thoughts had taken since. But my wayward mind was intent on probing darker and more dangerous taboos—holding his hand in public, long talks about our feelings, Sunday mornings curled up together with scones and the paper. In short, a real relationship.

I felt like one sick pervert. Not to mention a liar.

Just then the phone rang and I answered, half-hoping it would be a request for Steve’s more public services this afternoon so I’d have time to pull myself together.

“Hello, Cynthia?” It was a woman’s voice.

“Cynthia’s on maternity leave until the end of the month. I’m Megan.”

“Oh, yes, that’s right.” The woman actually sniffed. “Well, Megan, I’ve been trying to get in touch with Steve all morning but he must have turned his cell phone off. Is he there?”

“No, he stepped out for a moment.”

“Damn him, just when I really need to get a hold of him. Well, could you please tell him we finished the project early and I’ll be home Friday. He should call me as soon as he gets back.”

She hung up before I could reply.

Here was a woman was clearly used to being obeyed.

I allowed myself one brief moment to smile.

Then I quickly gathered my things from the desk drawers—it wasn’t much—grabbed the call memo pad and wrote out my last order to him: “Call your wife.”

I had a good ten minutes to make my get-away before Steve came back. The alternative—the guilty apologies, the assurances he did care for me in his own way, the bittersweet goodbye sex on his desk—was all just too dreary.

I knew it would be best for both of us to tie it up with the girl disappearing into thin air, leaving a faint, sweet soreness in his wrists and ass to remind him she really did exist once, even if she was only temporary.

I never saw him again, so I don’t know if he was totally on board. But it was obvious I had to be the one to come up with our strategic approach and execute the plan.

After all, I was the boss.

 

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