With Interest Ch. 2

Continued from part one, this is part two of five.

Bill, a fast-moving, loud-talking, big spending businessman from the interior, had come in late morning and insisted on taking me out for a 'working lunch.' It had, interestingly enough, been very productive, and while he consumed copious amounts of expensive booze, we both stayed reasonably sober and got a hell of a lot accomplished in the restaurant. Consequently, on our return to the office all I had to do was clean up the copy and reprint it.

"Ms. Lord, will you ensure that Mr. Shields is absolutely comfortable while I finish this up?"

Putting down her pen and standing swiftly erect by her desk, Penelope answered, "Of course, Mr. Jackson." Her steely gaze and bold poise held Bill's attention as she led him to the couch, and offered him a drink. She had serviced several clients since her first time, with Jock, yet, I never failed to enjoy the show. My final copy always took a little longer than expected, what with the distraction across the office.

Bill, knowing his limits, or perhaps anticipating something, declined a drink. He watched in rapt fascination as my assistant sank to the couch beside him and immediately reached for his crotch. Stroking his entrapped manhood with one hand and toying with his zipper tab with the other, she said softly, "Can I make you more comfortable, sir?"

"I believe you could," he replied, still motionless, but tense with expectancy.

I watched this exchange from my desk, delighting in the interplay. Penelope did this so well – played it so straight – although I puzzled about how much of it was play. Nonetheless, I thought I caught a trace of smile before she turned her attention to releasing his monster. And monster it was. Bill was huge and getting huger. He must have been nine or ten inches already and he wasn't yet stiff. Caressing it to full stature with deliberately slow strokes, Penelope looked like she was considering how to approach a new problem. I saw her subtly lick her lips just as she lowered her face to his cock. However, she'd barely covered the helmet when he lifted her head and plunged his hand beneath her skirt, into her crotch. "Let's not beat around the bush, as it were."

I didn't catch all that was said, but, abruptly Penelope had swung around on the couch and was lying on her back, legs wide open, waiting as Bill removed his clothing. He caught my eye, smiled and winked; I attempted to focus on my computer. Penelope watched him intently with a curious look of interest as he undressed. His erection bobbled out in front as he climbed between her legs. "Here he comes," Bill announced plunging in unceremoniously.

Penelope's legs shot straight up; her hands clasped his shoulders and her eyes clamped shut as she expelled a whooshing grunt. Bill began to move in long, slow strokes, stopping once to peel my assistant's blouse from her wonderfully stiff boobs. Taking up his rhythm again, he pumped faster and faster, watching steadily as Penelope's breath puffed audibly and her head, eyes shut tight, began to shake back and forth. They sounded like a pair of locomotives playing chicken. Bill's huffing, her whimpering – his hips slapping her buttocks, the tempo increasing to a frenzy; Penelope's head snapping left and right, her legs across his back, pulling him tight – it was a marvelous sight.

Just as I was sure Penelope was going to climax, Bill let go an eerie howl and stiffened, holding his massive meat, deep inside her. I could see his hips twitch as he shot volley after volley of come into her.

"Kee-rist!" Bill rolled off her, unclasping her legs, then sat with a thump on the floor. "Wow! Dan! You gotta have some of this," he called, adding, as an aside to himself, "like I'd believe you don't, anyway." Rousting himself off the floor, he yelled, "Haven't you finished the fuckin' contract, yet?" He stomped his foot. "Get your ass over here!" The whole time, Penelope had just laid there, almost catatonic, her breasts heaving, glistening as they parted the front of her open blouse. Bill turned to her, grabbed her hand and pulled her to sitting. "Now then, little lady," he coaxed, pulling at her blouse, "let's get you naked." She let him finish peeling it off then, smoothing it down again, unzipped her skirt and stepped out of it. "You may as well leave your stockings on, don't you think?"

"Okay," she murmured, straightening the tops.

Turning to me, as I approached the lewd scene, he said in a conspiratorial stage whisper, "Quick, Dan. Double team! Get out of those duds." With that, he guided Penelope onto the couch, positioning her on all fours, then, with amazing stamina, stabbed his once-again-rigid member into her slick, blossoming vagina, doggy-style. Moving to her head, with one knee on the couch in front of her, I presented my luscious assistant with my own now raging hard-on.

Grasping it with one hand, she guided it to her lips then hesitated for a moment. I waited – but not for long. With Bill's next stroke, Penelope rounded her lips and allowed herself to be pushed onto my ready rod. Bill set the rhythm, but that was fine by me. "The customer is always right," I said to myself, as I luxuriated in Penelope's expert oral ministrations. Bill was accelerating and Penelope was puffing through her nose and around me with in a growing frenzy. As for me, my cock was throbbing against her tongue – quivering at the feel of her inner cheeks – trembling as it was drawn in and out, through the perfectly warm and soft opening of her lips.

Our mutual cadence was becoming frantic. I knew we were, all three, approaching crises. With a cry of anguish, Penelope suddenly pulled off me and dropped her head to the couch between her elbows. She continued to hold me, squeezing, and subtly stroking as she gasped short, sharp breaths, her shoulders heaving under the constant pounding behind her. It all happened in an instant, her cry of woe mingled with Bill's bellow of triumph as he threw his head back and rammed his full weight into her folds. Her pitiful defeat, supplicating before his victory, whilst her little hand continued to hold onto my enflamed sword – it was all too much for me, and I jerked and pumped strings of semen all over her hair and onto her neck.

We were all still for a moment, a silent dénouement to a battle well fought. I felt a pang of – I don't know – not guilt – but disappointment, for her – that she had got so close but had not come. Yet, it was amazing to me that she could actually have not come. So it goes.

Penelope collapsed, panting, onto the couch when Bill and I stepped away. As we gathered our clothing and put them on, she rose like a wraith and slipped into the washroom. We were in to final process of completing our contract when she re-emerged, hair damp but otherwise all straightened up, and returned to her desk.

Signing the papers and putting all the documents into envelopes, Bill kept exclaiming, "I can't believe it," and, "Danny-boy, you dirty old shit," and the like. Penelope was back at work as if nothing had happened.

Bill shook my hand and, as he turned to leave, he stepped over to Penelope's desk and said, "It was very nice to meet you, Ms. Lord."

She looked up at him and replied in a friendly business-like voice, "My pleasure, Mr. Shields."

I'm sure it was that hint of wild frightened innocence in her eyes that I still often see that did it. "How about one for the road, my sweet?" he asked, his voice dripping just a little, and his hands already unzipping his fly-front. Penelope swiveled her chair, extricating his still turgid, still damp cock without a word and leaning forward to engulf him. I just stood and stared. There was no need for pretense now. Holding one hand on his hip and the other at the base, deep in his pubic hair, Penelope utilized her wheeled chair to facilitate a fast, deep blowjob. Bill's hands went to her ears, as he followed her measured bobbing, her lips stretching and welcoming his slick meat. Showing no signs of fatigue, Bill's erection grew once again to its massive proportions. Nonetheless, Penelope was eminently effective. Suddenly jerking and moaning and pulling her lips hard against her own hand, Bill stiffened yet again, unloading his liqueur into her throat. Despite it being his third round, it must have been substantial as Penelope, gagged and coughed. As she sat back in her chair, a string of semen fell from the corner of her mouth and landed on her skirt.

Bill rearranged himself quickly, picked up his case and headed for the door, with a casual wave. "'Bye folks," he called, "Catch you later."

"Well," I muttered, returning to my desk, "that was a fine bit of business," although I'm not really sure what I meant by that.

Penelope dabbed at her skirt with a tissue before turning her attention back to her computer screen.

Before she left that afternoon, I called her over to my computer to show her an accounting spreadsheet. "I just wanted you to see your bonuses for today. Fourteen hundred's not too bad, eh?" She just nodded looking closely at the screen, so I explained my reckonings. "You gave me a hand job – I know I spent a lot of time in your mouth, but I actually ejaculated in your hand. Okay?" Once more she nodded without removing her eyes from the screen. "And Mr. Shields came in you twice, as well as a blowjob. Randy old bugger, isn't he?"

Penelope rose from peering at the computer and turned to me. "Mr. Jackson," she said, with an almost unnatural serenity, "please don't share these details with me anymore. I trust you to be honest in your accounting. But to see it like that," she nodded towards the screen, "makes me feel… I don't know, makes me feel very hollow – very empty. It's a feeling I don't like. Okay?" She looked hopefully into my face.

"Okay," I assented.

"Thank you, sir," she whispered, giving my shoulder a very slight squeeze before heading back to her desk. "I'll go now, if that's okay."

I glanced at the clock. It was five to four. "Sure. Good night." It turned back to the offending file and saved it back to its locked and hidden folder. I mused about what she'd said. I guess I could sort of understand it. It was sort of, 'if I don't face it, it doesn't really exist.' I suspect we all like to leave our heads in the sand at times.

–– o ––

Some while later I was musing about the fact that Penelope seemed to get so close, right at the edge, in fact, but she hadn't yet climaxed. I thought about my 'faking it' clause in her bonus schedule, as I observed her pretty features, focused and intent at her terminal. "Bit of a non-concern, that one." An image of her lying on the couch, head thrashing, limbs vibrating, voice keening, ran across my mind. She'd been so close. I really would love to see her come. I'd love to make her come. I could picture myself, crouched between her thighs, laving her in long strokes, my tongue parting her puffy, trembling labia as she bucked and heaved and leaked against my face. Oh, wouldn't that be nice?

Yet, that image didn't quite work. Although I would dearly have liked to go down on her – have her come against my tongue, there was something about our arrangement, something unwritten and unspoken, something silently understood that forbade me from giving her the cunnilingal orgasm she desperately needed. I believe she understood that, too, for she never tried, even subtly, to tempt me to go down on her, even when she was left hanging on the very edge – vibrating like a tuning fork.

And it worried me that, through all of this, Penelope hardly ever smiled. It's not that she looked unhappy, or even indifferent, but she didn't smile. Finally, as we sat for a moment in the sweaty afterglow of another great afternoon fuck, I asked, "What's the matter?" She gave me a puzzled look in response. "Are you so unhappy here?"

She heaved a sigh, as she straightened her rumpled skirt and blouse. "No," she said, most matter-of-factly, "I like the job well enough, it's just that – I don't know – maybe I just don't deserve to smile."

"What the hell do you mean by that?"

"Well," she explained, sounding rather forlorn, "I foolishly trusted a bastard who left me half a million dollars in debt, and whoring to pay it off. I mean, how much worse could I have fucked-up my life?"

"Oh, please. Whoring is such a crude term. I mean, really, it's not nearly that bad."

Her look said loud and clear, "Oh, yeah?" but she just muttered, "That's easy for you to say."

"Okay," I went on, "I'll concede you're basically indentured until you – uh – pay off – or at least facilitate repayment of this debt, but 'don't deserve to smile'? Give me a break!" She glanced at me with a peculiar sort of interest. I started pulling my trousers on, taking a moment to formulate my argument. "I mean, listen," I turned to her and grasped her shoulders, turning her to face me. She was virtually limp. "Look at me, will ya?" Her eyes slowly rose to meet mine. I paused for a bit, holding her gaze, then I launched my lecture. "It was foolishness – your foolishness that got you into this situation in the first place. You made a poor choice – perhaps a very poor choice. But it was just a simple mistake – a simple and genuine mistake; everybody makes mistakes from time to time: but mistakes don't endure, they just pass." I gave her shoulders a little shake for emphasis. "That mistake has long passed. For Christ's sake, stop dwelling on it. Let it go." I let go of her arms, but she didn't slump. Her eyes held mine. "Jesus, stop beating yourself up about it. Just accept what you've got and go with it." I cupped her cheeks and as I added, "You might even try to enjoy it, eh?" She nodded, looking sort of like this was a novel idea. "Smile, already!" I shouted as I stood, buckling my belt. "What else is there?"

Amazingly, it worked. She smiled as she stood and shook her head, whispering, "Yeah, what else is there?" It was virtually the first full smile I had ever seen from her.

"My god woman, you're absolutely radiant when you smile!" She shook her head again, her blonde locks swinging softly, still a little damp from exertion, and allowed a barely audible chuckle, before returning her attention to her computer screen.

–– o ––

Fully ensconced within her delicious snatch, I pounded frantically the last couple of strokes before raising my head to bellowing my arrival out loud. It had been a busy morning, and our noon quickie was a welcome respite. My office couch was beginning to show evidence of horizontal activity in its undulating seat cushioning. Pushing myself up on my arms, I savoured her echoing pulses against my slowly diminishing cock. Penelope had stopped, once again, just shy of an orgasm. Her sweaty breasts rose and fell, as she regained her breath – her eyes shut tight. From my vantage – good old missionary position – I was looking straight into her eyes as she finally opened them. "Still resisting your own arousal, eh?" I observed.

Her eyes stayed open. "I guess," she whispered, "it's still something to do with guilt." She shrugged, then added, gracing me with a bashful smile, "Just like the smiling business, I'm not really sure I deserve it."

"Well, shit," I complained. "I don't want to lecture again, but, hey," I tried to use a big-brotherly tone – that was more than a little at odds with our position, my penis still turgid, still inserted – "it was just being naïve – a bit gullible, maybe – that got you into this. Well, naïveté is not a fault. So there's nothing to feel guilty about." I was getting on a roll, again. I felt like a revivalist, preaching at the altar. "Listen, girl, your financial debt will eventually be cleared, so don't go hanging onto this unnecessary guilt. Forgive yourself. Let it go. Let yourself go." She said nothing, just nodded and gave me a subtle, thoughtful smile. Imitating a school teacher, I said, "We'll try again, tomorrow," and left it at that. I clambered off her supine form, recovered my abandoned raiment and returned to my desk, whistling softly.

Later that week, at the end of a Friday that didn't let up until late, as I finally cleared my desktop, I looked over at Penelope who was doing the same. "Well, Ms. Lord. What do you say we put the week to rest with a bang?"

"Of course, Mr. Jackson," she replied, sounding for all the world like she was agreeing to lock up when she left. Her apparent dissociation continued to amaze me. Nonetheless, she quickly logged off, walked over to my desk and began to caress me, seductively removing my jacket and unbuttoning my shirt so she could glide her hands across my bare chest. I sat still, feeling myself relax, as she ran her hands softly over my nipples. Then she took my hand and led me silently to the couch.

Flipping her skirt up, she sat, bare bottom on the soft fabric, and pulled me by the belt to face her. Without a word, without a rush, but with a studied smoothness and grace, she carefully removed my cock from the confines of my pants, dipping her head forward so that she could tickle me with her pointed tongue. I resisted the temptation to grab her ears and thrust while she slowly, teasingly licked around the helmeted head before sucking my swelling member into her warm mouth. I let my hands fall to her chest, inside her gaping blouse, and fiddle idly with her nipples. The warm, firm sponginess of her breasts, the stiff insistence of her erect nipples was, in itself, arousing – not to mention the magical motions of her mouth and lips. Quickly, almost too quickly, I felt the heat of crisis rising with my iron-like erection.

Abruptly, I pulled out, pushed her back and shoved my sword into her deeply, stabbing without regard for anything but my own gratification. Despite the thinly veiled savagery of my entrance, Penelope was open, warm and welcoming as her vagina swallowed me whole. Her slick, thick lubrication attested to her arousal, and she heaved up violently against my thrusts. Like beasts in rut, we grunted and roared, smacking together, mashing our pubes together into one seething mass. I could feel the molten mass of release boiling in my loins, the pressure building; but beyond that I could feel Penelope's core temperature rising as well. Her eyes stared ahead with a glazed concentration as she held onto my shoulders, pushing against me, whimpering and sighing. Her quivering and quaking traveled the length of her body, and I could feel her legs tensing across my back as her inner muscles gripped and released my insistence. Her jaw trembled, slightly agape.

Arching onto her shoulders, throwing her head back, she pushed onto me once more, lifting her back and hips completely clear of the couch. "Unnngh!" she cried, in a piteously muted voice. She was so close.

Ramming myself deep into her, I muttered, "Let yourself go," just as I let loose. Volley after volley of semen spurted from my sceptre, scalding her insides. It was just enough to put her over, at last, and she screeched, thrashing her head from side to side, digging her nails into my arms as she held me fast. I froze for a moment, and lodged deep inside, my cock pulsed against her convulsions, spitting and spurting for longer than ever. As she relaxed her grip on my arms, letting her legs fall from my back, I started up thrusting again. My cock remained rock hard and began twitching once more. Penelope's genitals, still highly sensitive, slowly rejoined the onslaught. It was only, probably, a few moments, yet Penelope's response rapidly became convulsive as she tensed against me, eyes rolling back, and screamed pathetically like a wounded beast.

The apex having been met, we slowly crumpled until we lay – me pressing her onto the couch, her enduring limply – mutually exhausted. "Holy shit!" I muttered a few times. I couldn't quite think of anything else to say. Penelope just lay inert under me, but the hint of a satisfied smile crept onto her lips and settled there.