Countinued From,  The Boss And I

You can catch up on The Boss and I..Ep 2, HERE.



We continued in this way for almost three months – I would spend a half hour before any meeting with my arms wrapped around her hips, holding her up off her chair and letting her thrust and buck against my mouth as I slowly licked and tongued her out of her mind. I was in heaven – a gorgeous, sexy, wonderful woman was almost dependent on me for pleasure. I was fairly sure I was her only source of orgasm at this point – from her reactions to my touches, I don’t think she was pleasuring herself at all anymore. If she hadn’t had a meeting in a couple of weeks, she would often cum within only a minute or two.

However, the emotional quandary continued. I wondered whether I had feelings for this woman – and if I did, what I should do about it. If I tried to change our arrangement into a romantic relationship, I risked losing everything. I was fairly sure that the dichotomy between our relationship and our physical intimacy was getting to Cleo as well – whenever I would slip into her office, she would look at me with a mix of anticipation, desire, and an odd sort of confusion, as if she was not sure how she should emotionally react to my presence anymore.

Eventually, the question was answered for me. We reached a tipping point one afternoon. Cleo had a meeting scheduled over dinner with not one, but two clients, and I slipped into her office almost a full hour before Diane had to leave for the restaurant. She seemed surprised to see me that early, but she turned her chair nonetheless and willingly surrendered her pussy to me. I loved the first sigh she gave when my mouth touched her. It was a sigh of pleasure, of relief, and of a satisfied anticipation, as if she really did look forward to these sessions.

This time, though, I had decided, I was going to take my time. I deliberately avoided her clit – no matter how much her hips reached for me or how much she tried to twist herself to get contact there, I kept from touching it, running my tongue over her lips, sucking and nibbling at them, and then swirling my tongue around her opening without entering, tantalizing her. After almost fifteen minutes of this exquisite torture, she actually surrendered to it, letting her body relax and just enjoy the gentle, restrained caresses of my mouth. I used my whole mouth, my lips and tongue and even my teeth, lightly nipping at sensitive flesh, teasing her until she was just breathing deeply and shaking ever so slightly, all of her willpower going into not pleading with me to pleasure her more directly.

I dipped the tip of my tongue into her ever so slightly, and heard her catch her breath. Then I withdrew, swirling around her opening, and dipped in again without warning, again barely entering. Another little gasping breath, her hips quivering. I waited a long moment until I felt her hips lift, and then licked her opening firmly, not entering, and felt her jerk, a tiny whimper escaping her. I looked up at her face – her head was pulled back, her mouth open, her eyes shut, her body totally relaxed other than her somewhat tense hips. I smiled, swirling my tongue around her a few more times to hear her gasp, and then, in one long, slow, firm thrust, buried my tongue inside her, wiggling and squirming it against her inner walls.


I drew my tongue out at that, looking up in surprise and eagerness, and swirled my tongue a few more times, lashing it against her opening, tapping sensitive little crevices here and there, until I heard that tiny little whimper again. Then I plunged my tongue as deeply as I could, swirling it inside her.

“Oh, yess…”

I almost moaned at the exclamation from her, and found the sound so wonderful after all the months of listening to her silence that I pulled my tongue out again, hearing her whimper immediately in protest. I proceeded then to tease her unmercifully for five full minutes, caressing her outer lips with my tongue and lips, stroking the hood of her clit with my upper lip but never her clit itself, my tongue tantalizingly circling her opening time after time. To my delight, though, her body stayed relaxed, letting me keep control. Finally, I fluttered my tongue at her entrance, drew another whimper from her, and then, lifting her hips slightly, sank it deeper than ever into her body, my lips caressing her slit from top to bottom as I filled her with my tongue.

“Oh, sweetie…” She moaned out.

This time, I did moan. Everyone in my life called me Zainab. I hadn’t been sweetheart to anyone since I was a child. To hear a real endearment on her lips…I had to hear it again.

My tongue teased, darted, swirled – and then lashed her clit, lightly but continuously, driving her almost up out of her chair.

“Oh, my god,” she moaned. I slid my tongue down her slit and inside her again. She moaned.

I was like a child with a toy – I did anything that I could think of to make her moan again and again for me, and even though sometimes I sensed her trying to hold them in, she seemed to have surrendered too deeply to stop herself. I started taking her toward her delayed orgasm, fluttering my tongue intermittently on her clit, in between slow, searching thrusts inside her. I made the touches lighter and lighter, almost not touching her at all, feeling her hips rise into the air, and then fastened my mouth to her, sucking deep but gentle on her clit, lashing it with my tongue.

Oh! Oh, god…oh, god, sweet sweet Zainab…” Her exclamation trailed off into a long, shuddering silence, and then an outright squeal as she climaxed deeply, flooding my mouth with her sweetness. She would have bucked right out of my arms if I hadn’t been holding her tightly.

“Oh, Cleo,” I whispered into her pussy as she relaxed – so softly that I don’t think she could hear me. I massaged her trembling hips and thighs as she slumped, splayed open and totally limp in her chair.


We definitely seemed to have passed some sort of barrier after she first moaned my name. We both apparently realized that, whatever the complicated emotional underpinning, what we were doing was extremely pleasurable, and didn’t seem to be harming either of us. When we worked, we were as we always had been – friendly and professional. When I was between her legs…now, she voiced her pleasure, if with restraint, moaning and whimpering, occasionally squealing when I did something she especially liked. Her moans of my name – especially the diminutive form of it that I loved to hear from her lips – were still rare and precious when I earned them.

Much of the time, Cleo would lie back in her chair with her free leg over my shoulder and her other leg up on her desk, and I would take my time pleasuring her while slowly running my hands over her legs and her hips as much as I liked – which was a lot. She loved when I massaged her feet with my hands while I massaged her clit with my tongue. She squealed the first time I cupped her ass and let her thrust herself to orgasm on my tongue entirely on her own.

She definitely was giving in to the entire process in other ways, too. More and more often I would arrive for one of our sessions only to find her panties already gone, or would feel her press her leg against my hand or arch her hips to my touch without my having to guide her. She would signal me with her sounds when she wanted something – if I was teasing her too much, or she wanted contact somewhere else, she would guide me with whimpers or movements of her body.

On one rare occasion when she needed me to work on a Saturday because of a meeting she was having at a local church picnic, of all things, she actually wore a dress to the office – the first time I had seen her in anything but a skirt and blouse. This, of course, provided me an incredible opportunity. With her dress up around her waist, her creamy hips and thighs totally bare to my hands and her body laid back comfortably, I took the opportunity to explore not only her flat stomach – and much enjoyed feeling the quivers and tension in the muscles there – but slid my hands up higher, and for the first time, touched her breasts. They were soft and silky smooth, and their weight felt perfect in my hands.

The first time I touched them, she gasped, arching against my hands, but her hips pulled back with a hint of nervousness. I almost laughed at the idea of a woman who had my tongue buried inside her being nervous about me touching her breasts. I drew my hands back, exploring her torso, and my tongue soon encouraged her to writhe against my hands. I returned to her breasts, gently massaging them, and, already close, she arched, whimpering loudly. When I tugged softly at her nipples, it was enough to push her over the edge, and I luxuriated in the feel of her nearly bare body bucking under my hands.

Now, we had found entirely new territory to explore. Within a few more sessions, even in her usual blouse and skirt, Cleo would be laying with her blouse open, her bra and panties gone, and her body exposed to my ceaseless caresses, giving her body entirely over to me to drive to higher and higher pleasure.

All along this path we were treading, though, I never once suggested or at all hinted that I wished her to return the favour – indeed, we both seemed to shy away from any possibility of that ever happening. I dressed conservatively to work, and she made sure that her body did not brush mine in any way that might be taken as a returned caress. Both of us seemed fearful to cross that boundary, knowing that if she ever returned the pleasure I had given her, we would be lovers in truth.

Even now, I am not sure why I feared that so – perhaps even the threat of losing such a lovely, albeit incomplete, relationship was enough. Perhaps it was something else. I doubt I’ll ever know.


It was inevitable, I suppose, that despite our enjoyment of our “arrangement”, something would interfere and finally give our emotions a real chance to complicate things.

I sat at my desk, typing out a series of memos and emails to different people on my daily contact sheet. Cleo’s last meeting had been a few days ago. We had become a great team – with my help, she had been dominating meetings even more than usual, and the firm had picked up so much business that we were seriously contemplating expanding the firm entirely – though Cleo had seemed hesitant to expand, since she really didn’t need to work the ridiculous hours that most lawyers do.

Firing off another email, I glanced at my inbox and saw that another email had just arrived – one from an address I didn’t recognize. Opening it with a frown, I saw a long series of short messages – apparently, I had been accidentally included on an email string. This happens frequently in any office, of course, so I went indifferently to delete it, but then a single word in one of the replies caught my eye – my name.

Unable to help myself, I scrolled curiously back through the chain of messages.


– I received your quote for the renovations. Can you refer me to a legal employment agency to fill out my staff?

That message was from Cleo. The next was from an address I didn’t recognize, but was signed with a name I did recognize – the owner and operator of the building in which Cleo’s offices were located. Apparently, Cleo had inquired about the costs of expanding our firm, complete with office renovations and new staff.

“Easily – the firm in the offices above yours just completed their renovations, and hired some new staff. They mentioned that they were very happy with their new staff – I’ve used the same staffing agency myself. They can supply all the paralegals you might need, and a truly qualified legal assistant.”

I stopped in surprise, glaring a bit at the message. What did he mean, “truly qualified”? I was fine at my job, and Cleo had certainly never complained. Far from it, I thought with a tiny smirk.

– It would be nice to have some of my own paralegals, for a change – sharing them can get pretty annoying. I’ll definitely need some help finding at least one assistant who actually knows her stuff – the last two I’ve had in here had terrible recommendations, and the most recent one couldn’t type her way out of a paper bag.

I stopped again – this time, in shocked dismay. I couldn’t believe that Cleo would really think that about me. She had always seemed pleased with my work, and had complimented me several times – she even seemed grateful to have an assistant she could work well with.

My almost nerveless hand hit the delete button, and the offending email vanished instantly. I shivered, staring blankly at the screen. How could she think…how could she fake all that? Why?

Some part of me, the logical part, maybe, thought that it might be a misunderstanding. Maybe she meant the girl before me – from what I’d heard, she hadn’t lasted long.

Of course, I couldn’t deny that the law was no specialty of mine. I had picked up bits and pieces, certainly, but I had no formal training or education in legal matters. Law school had never been a financially viable option for me.

I slumped in my chair. Maybe Cleo did need a real legal assistant. After all, if she were going to expand her practice, she’d need a full staff, maybe even a partner or two, and assistants who could offer their own legal insights, not just a glorified secretary like me.

I worked for the rest of the day in something like a dream, going mechanically through the motions of my emails and memos, copying down meeting minutes, barely paying attention to what I was doing. I made sure to leave before Cleo finished for the night so that I wouldn’t have to speak to her, not trusting myself.

Half of me felt as though what was happening was only inevitable – good things usually came to an abrupt end before they should, in my experience. The other half felt angry. I found myself questioning everything that had happened. I wondered whether Cleo had ever even really liked me, or if had just tolerated me. Whether she truly enjoyed what I had been doing to her, or whether she had just used me.

That night, though, as I climbed into bed, I could not stop the fantasies returning to me. As my fingers began to tease along my slit, I could not help but imagine the heaven I had found again and again with her, with the taste of her, the sound of her ecstasy and the feel of her skin on my face and mouth while I savored her. I writhed under my hand, and reached my first climax quickly, gasping and shaking. I lay still, eyes closed, Cleo’s beauty in my eyes and her moans in my ears.

Then I recalled the words I had read, and my anger returned. The memory of her soft, pleasured moans returned – but now the sounds were harsh, cynical, somehow soured. That delicious surrender in her body as she relaxed each time beneath my questing tongue turned into something else – something accompanied by a smug laugh, the sense of getting something that one wants, not a true desirous surrender.

I bit my lip, my anger increasing until I was nearly in tears – and I found my fingers moving again, this time fast and hard, almost grinding into my sensitive skin. The pleasure came in waves, harsh jolts up my spine and through my stomach, tightening it until it nearly burned. I grimaced, digging two fingers into myself. Instead of savoring the memories, I cursed at them now, glowering at the image of my boss that floated before my confused mind.

For a few brief moments, I hated her. Hated this confusion, this sick fear that was choking me.

“Damn you, Cleo!” I gasped, growling as I arched up off my bed with my second orgasm, this one hard and sharp, wrenching my spine and causing my legs to spasm so hard that they immediately began to cramp. I curled up immediately on my bed in a fetal position, the pain mingling with my still-fading pleasure.

Finally, I relaxed, the cramps dying out and my breathing returning to normal.

It was so frustrating – I wanted to be angry. I wanted to be furious, to storm into her office and quit – or even show her what I knew about the law. Maybe trap her in some kind of situation where I could sue her, make her pay for this pain I was feeling.

I wanted so badly just to give over to that fear and anger.

But I couldn’t. I couldn’t hate her. I know now, of course, why I couldn’t hate her – some people can hate someone they’re in love with, but I’m just not built that way. I didn’t realize that at the time, though. The bizarre arrangement, the strange story of our relationship had walled my feelings off deep inside myself and hidden them under layers of fear, self-delusion – and an honest wish not to hurt Cleo, or make her life more complex or difficult than it needed to be.

At almost any other time in my life, I would have probably just quit my job and drained my savings account on holiday trying to figure out how I had botched things so badly. This time, though, I couldn’t just walk away. I’d stick around long enough to find out what Cleo had meant. If she didn’t want me around, then so be it.



Zainab, could you come in here?”

I looked up, and for the first time, I didn’t just get up and go in. “What’s going on?” I called back.

There was a brief pause. “I need to prepare for my three o’clock.”

I glanced at my clock. Barely two. “Now?” I asked.

“Now?” She sounded surprised. “Um, yes, now.”

I bit my lip. I almost said no – I swear, I almost said it. I didn’t, though, of course. I couldn’t help myself. “Coming,” I called back.

In her office, I closed the door, and looked at her, my heart twisting all over again at those beautiful cold brown eyes staring across the desk at me, though they seemed surprised and concerned at the moment.

“Is something wrong, Zainab?” Cleo asked.

I opened my mouth to shout at her – but, again, of course, I didn’t. “No, nothing’s wrong.”

“Good,” she said slowly, still looking concerned.

I knew there was still an hour before the meeting, but I knew that I wouldn’t be able to pleasure her for that long the way I felt now…I’d break in two from sheer emotional trauma. I resolved to make it quick – to just get her off and be done with it. Some part of me tried to be clinical, calm, and indifferent. Do it fast, I told myself flatly. Get her to come and she’ll leave you alone.

I stepped around her desk, and she turned to meet me. I saw the slight widening of her eyes, the little break in her lips, but my flat thoughts dismissed what I saw. Just lust, I thought. She needs it, no question – that doesn’t mean she has any feelings for me. You’re just a walking vibrator at this point, I told myself brutally.

I knelt down, slid up her skirt, pulled her panties down – just a bit roughly, I’ll admit – and slid my mouth back against her again. She sighed, and I quivered, almost breaking just in that instant, my eyes filling with tears as my lips tasted her sweetness, that tanginess that I so loved, while that anger glittered deep in my mind and other feelings, complicated and frightening, bubbled just underneath, threatening to break free. I knew she wanted me to take my time, but now I didn’t want what she wanted. I wanted to hurt her – but I couldn’t hurt her. I wouldn’t give her what she wanted, though. She’d get what she needed – to come – and that was all.

I ran my tongue firmly over her slit, feeling her twitch in response with a soft whimper, and my tongue softened for a split second, caressing her lips like the petals of a flower, easing them open and sliding within – but my pained heart wouldn’t allow me to melt into her again. My tongue hardened, stabbing at her clit almost roughly, and she jerked with a startled gasp, her thighs almost gripping my head as she reacted to my firmness.

I grabbed her legs, my anger heating me, and I took that anger out on her pussy, on the soft, delicious flower that I had worshipped all those times before. I lashed it with my tongue, stabbing and darting my tongue here and there. By now, I knew every weakness in her. I knew where to flutter my tongue to make her jerk, where to stab it to make her gasp, and where to suck her in to drive her over the edge. I made her come brutally fast, with a strangled, startled little squeak, and let her twitch rapidly against my face, my eyes closed and my mouth hard on her soft flesh.


**To Be Continued**


Until We Meet Again Next Week…