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It Gets Complicated

"She not only had feelings for him, but a fantasy, that was going to happen NOW!"

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At not-quite-thirty, I was still the youngest lawyer in Robert’s office, and so when we had the opportunity to take on a four-year contract with a large legal publishing company, those duties got dumped on me. It turns out, I was okay with that. Though it did complicate my lurid daily teasing with Julie, Robert’s newly hired receptionist. Wow, was she ever hot. And she loved to play games with my head, in a sexy way. But that’s yet another juice-covered story I’ll think about telling you later.

The legal publishing firm we had contracted with had its offices well over an hour’s drive east of our office’s location, but luckily, I only had to be physically in the offices of Peaks Legal Publishing on the first Wednesday of each month.

I had already hired a growing flock of editors as part of my responsibilities, who had absolutely zero background in the law, but who had both writing experience and highly varied “life experiences” which meant I had now assembled a team of about 27 newspaper reporters, English professors, magazine writers and editors, and just about anyone who could make my client’s product, legal case summaries, more readable by your average well educated professional who would be an instant new customer, if only they could understand the legal jargon.

Accountants, engineers, construction foremen, or any such professional who had never been to law school needed to be able to understand the summaries produced by Peaks Legal Publishing. The marketing strategy relied upon by Peaks assumed that editing the summaries of legal cases to make them more reader friendly would make them more marketable to entirely new customers. They sought to accomplish this by having me teach a pool of people who were hired precisely because they had no past legal experience, how to understand an opinion written solely for lawyers by a judge. Then, the strategy was to have our editors rewrite the judge’s opinion in everyday terms. No small project.

Although I was young, excessively confident, and as they say in Kentucky, "ten feet tall and bullet-proof,” but even so, four years seemed like a tighter deadline with every passing monthly meeting, although we were all in daily contact by email and video conferencing through the rest of the month.

It was beginning to challenge me that my contractual requirement forced me to hire only people who were from completely diverse and non-legal backgrounds in their previous lives, including one of my very first hires, Cassie. She, however, was uniquely skilled at understanding complex terminology and concepts. She was fun and easy to work with.

Cassie had been an editor for a fashion magazine in New York, but had moved back to her home town near Cincinnati to become a Cheer Leader for The Cincinnati Bengals. I shit you not. She practically begged for the chance to get back into editing, now that she had settled back in her hometown neighborhood in a modest apartment. She didn’t seem to mind taking about a twenty percent pay cut to write for me, as opposed to jiggling her jugs for thousands of adoring fans.

Cassie was well educated and absolutely brilliant. She picked up on the legal terms I had her sorting out daily and defining for the rest of the new editors in my project group. Cassie had in fact become so involved in helping me move the project forward that Peaks Legal Publishing agreed with Cassie that it was money well spent for me to meet with her once a week for lunch on my expense account closer to home so we wouldn’t have to make the painfully long-ass drive to the Peaks office building every week. Besides, I have to admit, there was more than a friendship growing between us.

Still, I hadn’t had that Certificate of Dissolution of Marriage signed off on in my pending divorce, and Cassie sometimes wore what appeared to be an engagement ring. I didn’t know exactly what was going on, and so I made an extra effort to keep everything absolutely professional.

As well, Peaks Legal Publishing was a massive, worldwide, corporation and I didn’t want to complicate my contractual relationship with them. The position I had lucked into with Peaks Publishing did bring in a nice constant stream of revenue. It was more than enough to pay the office rent and to cover Julie’s salary, so I did not want to do anything to risk that set-up. Still, at barely thirty and being around the tantalizing Italian complexion of, sculpted, toned, and just over-the-top sexy Cassie on a regular basis, well, I couldn’t help but begin to look forward to our weekly lunch meetings.

We had definitely become a little too relaxed in each other’s company, and then one day I took us even closer to the edge when we met up in the parking lot of a nicer than usual restaurant for our weekly lunch. I suggested that Cassie and I take turns carpooling together to the monthly department meetings. “Carpooling, to save gas, you know... doing our share to save the environment.” I fumbled with my words as I saw signs of reluctance in her.

Cassie giggled, looking down and away from my face, her long, dark brown Italian hair falling over her face, hiding her deep green eyes and pouty lips from my view. I thought I had really messed up, maybe pushed it too far to have others at the office possibly see us arriving together. There were more than enough rumors floating around about the two of us already. The amount of sexual tension between us was simply impossible to hide, though we both tried very hard.

“Uh, you’re not worried about the rest of the team gossiping when someone eventually sees us riding together?” Cassie raised her eyes to meet mine again as she asked, with some reluctance in her voice.

“Ah, bull!” I fired back without the slightest hesitation. “You know there’s no rule anywhere that says employees can’t date, so who the hell cares what anyone says. Besides, we’re not dating, we’re taking turns driving that long-ass trip to the office once a month. I refuse to live my life being scared by what somebody might gossip about.” I concluded, perhaps a bit too confidently, as if I’d been thinking or fantasizing about it for a long time. Of course I had been, but still, I didn’t want things to appear that way.

“Okay,” Cassie smiled, responding so quickly that I began to wonder whether she might have been waiting for me to respond like that. “So, here’s my home address,” she scribbled on the bottom half of her note pad that was sitting on our lunch table as we waited to put in our drink orders and discussed absolutely nothing about work. “And there’s gates out front that you need to punch in a pass code for, so pull up to the keypad and just punch in one, seven, six, three.”

Cassie said slowly, teasingly, batting her long dark Italian eyelashes at me as she wrote the pass code on the same section of note pad and tore the bottom half of the page off neatly. She folded it, then scooted up beside me on the semi-circular bench upon which we were seated. She pressed her thigh up against mine and gently pushed the scrap of paper into my shirt pocket. “You drive first until I get used to this situation!” She smiled and wagged her manicured finger at me, still pretending to be slightly uncomfortable being seen riding with me to the office.

Then, as if her scooting up beside me in the fairly private and rounded booth hadn’t been odd enough, she placed her hand on my thigh as she continued to sit tightly up against me, looking me in the eyes, and then asked: “Eric, this is sort of embarrassing, but can I ask you something, quietly, sort of in your ear?”

I was surprised at everything that had just happened, but my heart did begin to race when I thought of Cassie whispering in my ear as we sat in the last booth in the back corner of the restaurant, in about as much privacy as could be had in the entire place. “Sure, Cassie,” I almost whispered in response. I rearranged my seating position slightly in order to be facing her dazzling green eyes more directly.

“Good, um...” Cassie hesitated as she leaned still closer to me and also placed her right hand on my chest as she leaned forward. “This is really hard for me to bring up, Eric, oh, I’m not even sure I should, but, do you mind? This is really personal, I mean? Maybe too personal?”

I could smell Cassie’s Chanel perfume, I felt the softness of her dark, almost black hair against the side of my face, and I could feel her hot breath against the skin of my face and neck. I wanted to hold off on responding for as long as possible, just to enjoy the moment, but I had to give her an answer. “Cassie, it’s no problem, really. I think we know each other well enough for you to ask me something personal,” I coaxed her to continue. “Do you want to ask me later, maybe go out to the parking lot?” I asked.

“No, no, I’m just gonna say it, even though I’m afraid, and just get it out there,” Cassie said as she slid her right hand up toward my shoulder, pulling our faces still closer. She then leaned in toward my right ear and began to whisper: “Um, well, I’m not sure exactly how to say this but I’ve just noticed, since the day you first interviewed me, that there’s this sort of, um, like an electric buzz sort of feeling all around me when I’m talking to you, and well, okay, now I’ve said that out loud, uh...” Cassie paused as she now almost nuzzled my ear. I could tell she was extremely self-conscious about whatever this was heading toward.

I leaned in toward her as she did the same to me. Now, feeling her head rest against mine, I could feel both of us breathing with a slight tremolo as the sexual tension built exponentially upon itself between us. The waitress came walking toward our table, but upon noticing our position, politely pretended to have forgotten something and disappeared back around the corner.

Seeing the waitress heading our way made me fumble my response terribly. “Cassie,” I attempted to make her more comfortable, realizing how dangerously exposed her as yet unasked question must have been making her feel. “Cassie, it’s alright. Anything you ask me is completely alright, just relax and get it all out, and then if you want, we can talk about it.” ‘Wow!’ I screamed at myself inside of my head. ‘I could have done that a hell of a lot better,’ but before I had a chance to fix it, Cassie continued, still whispering softly in my ear.

 “Eric, I’ve had these feelings from the very first time we talked, and well, they’re just getting stronger, and now I’m pretty sure you’re feeling them too.” Cassie repositioned her face to gaze directly at me, seemingly into me, with her glistening emerald eyes. She reached around my neck with both hands and clasped her fingers tightly. “Eric,” she shook me surprisingly firmly with her hands in a tight weave behind my neck: “Eric, I have to know if you’re feeling these, this... this whatever it is that I just have to think that you’re feeling just like I am. And no half-ass answers please, if it’s not there, it’s not, but... oh for Christ’s sakes, I’ve even started having this crazy fantasy about us... but don’t freak...”

“Cassie, stop!” I demanded, ending her fumbling and rambling questions. “Cassie, this ‘electrical buzzing’ you’re talking about between us is so damned strong I literally wake up counting the days, or the hours, until I’m going to see you again.” I had, of course, promised this would remain forever my little secret, but what the hell was I supposed to do? I couldn’t bear to see her suffer like this. I realized my feelings for her were perhaps stronger than I had anticipated.

Her face lit up and she broke her clasp from around my neck, sliding her right hand down my chest. “Wow, Damn, Eric,” she let out a long sigh of relief.  “Whooo! I’ve been up sometimes for hours at night worrying about how I’d ask you and what your answer might be, but my God!”

Cassie was now obviously much relieved and far more relaxed as she bounced excitedly in her seat, jiggling her slightly oversized breasts, and laughing as she spoke.

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She teased, “Then you won’t mind if I do this!” as she simultaneously kissed my lips gently but quickly, and slid her right hand down to my crotch, rubbing, cupping my soft cock just hard enough to start things growing in her hand, and she concluded with: “Alright, just making sure you meant what you said.” But she sat, still cupping my cock and balls beneath the table as she purred with a naughty smile at my “growing” discomfort.

But to my surprise, Cassie tried to continue her response. “Okay, so now I might as well tell you about the fantasy part of this too, I mean since I’ve come this far and we’re sort of in the perfect place to get into it,” she continued with both excitement and anticipation more than evident on her striking, tan face with the emerald eyes that seemed to shine as if they had their own light source, even in the subdued lighting of the restaurant.

Our waitress again appeared in the distance and she looked me dead in the eye.  I just shook my head at her emphatically in a panicked “NO!” response to her standard question of “Can I get you two anything to drink?” that should have been coming our way had she actually approached our table. To my great relief, our waitress smiled and again disappeared around the corner, leaving us in relative privacy, seeming almost to be enjoying what she saw obviously playing out.

Our waitress’ appearance had reminded me that, regardless of how much I was adoring this moment of openness I had just experienced with Cassie, not to mention the fact that her hand was still wedged tightly into the crotch of my Dockers, we were in a very public place, and I was becoming very obviously aroused.

“Uh, Cassie, wow, I’m really glad we got that all cleared up, but uh, you’ve gotta let go of... uhhhh, ohhhhhh, Cassie?” I stuttered in a panic as she unbuckled my belt and began to unzip my pants beneath the tablecloth. “Hey now, Cass, uh... uh no... let’s go out to my truck, okay?” I begged as I attempted to reassemble my clothing and spun in every direction I could turn my head in a panic.

No!” Cassie panted with an animal-like lust. “Now comes my fantasy, Eric. This is a perfect just-public-enough place to do it as I’m likely to find, and so this is it, Eric, get ready to cum hard, right here, right in this booth, got it?” her voice trembled with excitement as she simply told me what was going to happen next.

I wasn’t sure I wanted this to happen as it actually was playing out! Sure, I had been feeling that constantly growing buzz of sexual tension for as long as Cassie had. Hell yes, I wanted her to get me off, right there in that restaurant, if I was going to be completely honest with myself, but I also did not want Cassie making all the rules. A guy likes to be at least halfway in charge, and right now I was just taking orders.

“Alright, babe, you want to play dangerously, let’s play dangerously.” I said sternly, then asked: “Can you pull just enough of that tablecloth this way if I slide down in the seat a little bit to cover what’s going on here while the waitress brings me a Scotch, on the rocks?

What!?” Cassie gasped in astonishment. “Oh, Eric, I get it, you think I’ll back down, don’t ya? Well go ahead and order then, and sure, just slide down a weeeee little bit more and I can hide things close enough,” Cassie responded as her hot Italian blood jumped at the challenge. She kept one well-manicured sexy hand on my cock, while reaching up to the center of the table with her other. It began to occur to me that perhaps I should back down, but the gauntlet had been tossed by me, and there was no way I was going to pick it up again.

“Here’s a menu, just in case the tip of your swollen dick starts to peek out over the top of the tablecloth, though.” She giggled as she handed me the menu, then she leaned forward and sucked my cock into her mouth, getting it nice and extra wet so she wouldn’t have to pause in her project should the waitress approach, which, in a moment of panic for both of us, happened just as I was turning the menu right side up in my hands, and Cassie’s head was emerging from beneath the tablecloth.

“Uh--She dropped her purse!” I explained a little too quickly to our patient waitress as she now stood over our table with a huge grin, nodding in response. “Um, I’ll have a double Scotch and soda on the rocks and oh, I’m sorry Cassie, did you say you wanted the house red or white?”

Cassie turned to face the waitress, her left hand still gently toying with the head of my cock. She was now forced to wipe some slobber, which had run down her damp chin, with her free arm and mumbled, “White, please.”

We both laughed so hard as to be more than obvious as the waitress turned to walk away, and Cassie laid a wet kiss on my lips, without ever letting go of my now throbbing erection under the table.

Isn’t it going to smell funny over here at some point when the waitress gets back, Eric?” Cassie asked, crunching up her nose at me as she reveled in the upward-ratcheting danger level. She then decided: “We’d better not put the drinks on your expense account, and I think we also need to leave that waitress one hell of a tip!” She had absolutely made up her mind to see this thing through. All the way.

“Ah, shit, Cassie,” I tried to speak clearly as I caught my breath. “Right now the only ‘tip’ I care about is the tip of my cock that you keep running your fingers over, but there’s something different,” I couldn’t quite figure out what Cassie was doing to the head of my dick, but it felt unbelievable and strangely unlike anything I had previously experienced.

“Oh, you noticed my engagement ring then, huh?” Cassie asked with a raised eyebrow. “I got it big enough to put it over my thumb and that way I can use it to play with your ‘frenulum’ ya know? I think that’s what this part right... heeeeere... is called.” She continued, rubbing the base of her thumb, with the ring around it, ever so gently over the little triangular area at the base of my dick head which made my body begin to shake, just as our waitress arrived with our drinks.

“Thank you, ma’am,” I said as calmly as I could, through glazed eyes as the waitress left our drinks and walked away from the table wearing a mischievous smile. “But Cassie, this isn’t completely fair, you know? I mean, you’re not in too awfully much danger of being exposed yourself! So let me have a peek under that short little skirt.” I sighed, as I picked up my Scotch and drank half of it down in one gulp. “Come on, now, at least let me get a little taste of you and then I can finish you off really good with my tongue once we get to the back seat of my truck, okay?”

Cassie smiled and scooted both of us more toward the center of the semi-circular booth as she reached underneath her wonderfully short skirt, bending and twisting, then flipping her tiny sandals around and dropping a nearly microscopic pair of black panties onto the table. She spread her legs as she continued her expert ministrations to my throbbing dick.

“Ah, a little magic trick for entertainment I see. Impressive!” I said in as calm a voice as I could muster, jumping at the opportunity to regain some of my composure while Cassie lost her rhythm as she performed her little “magical thong removal” trick under the tablecloth.

“There’s someone who’d like to make your acquaintance, Eric.” Cassie whispered in my ear as she pulled her short skirt up high enough to reveal a tiny triangle of short black hair just above her swollen and dark pussy lips. They were darker than I’d imagined, and hung pendulously low, engorged now, dripping Cassie’s juices onto the Naugahyde restaurant booth.

“Here,” she said quietly in my ear as she audibly slid her right middle finger into her dripping pussy, pulled it out, then held it for a moment under my nose before letting me slurp her finger into my mouth in order to suck it clean of every drop of the slippery nectar as I watched her eyes flutter. That little flutter of eyelashes made my body again begin to spasm.

“Oh fuck,” Cassie whispered to me, “Hang on one sec! I want to see you jerk yourself off, right now... oh,” she groaned as she slipped her wet finger back into her oozing pussy, “I want us to cum together, Eric, oh please, please, let me watch you jerk your cock right here while I finger-fuck myself, Eric... please...” Cassie begged, more so pleaded, hardly in even an attempt at a whisper any longer.

I was overcome with lust by that point and didn’t care anymore. I pushed the tablecloth far enough under the table to fully expose my pulsing cock to Cassie, and also making her engorged pussy lips, which were creating a puddle on the seat, easily visible to me. She began to slide her middle finger in and out from the top, brushing her throbbing clit along each stroke.

Immediately, I found I had to push the table just a little further from our bench as Cassie’s long, muscular, outstretched legs began to tremble uncontrollably. Her mouth hanging open in an “O” shape as she stared at my cock. Seeing her face, I involuntarily lifted my ass so far off of my seat as to make my shaft visible from our waitress’ usual place of approach as I came nearer my final release for Cassie, jerking my slimy pre-cum and saliva-covered cock with my left hand for Cassie to watch.

Then, I had an ingenious idea, and I slid my right hand under Cassie’s leg where it joined her perfectly formed tight ass. The wetness Cassie had created made my move seamlessly simple, and as my fingers found her engorged pussy lips, I bent my middle finger upward, slipping just the tip of it into her drooling pussy, which then began to spasm as her tight little cunt tried to suck my finger inside.

The moment she felt my finger enter her pussy while she also finger fucked herself, staring at me jerking myself off in what was now practically plain sight, Cassie let out a massive shudder, biting her lip and wadding the tablecloth up in her tiny fist. Upon seeing that, my balls pulled up tight and exploded, shooting hot white cum onto the tablecloth as Cassie’s left hand reached over while she came like a geyser and grabbed the exploding head of my dick. Oh, my God, my eyes rolled back as did Cassie’s, while we each enjoyed a massive, simultaneous, and messy orgasm.

Our lungs still burned as we launched into uncontrollable laughter. Cassie grabbed for the closest napkin and dunked it in her water glass while I worked at maneuvering the table back into its correct position. She stretched my boxers over my slightly deflated yet still non-concealable cock as she hurriedly used the damp cloth to sop up as much of the damage as she could. We sat, leaning against one another, hand in hand, finishing our drinks in near silence, other than the occasional outbreak of spontaneous laughter from both of us.

As soon as we were both almost presentable to walk out of the restaurant, which now surely must have smelled as if an orgy had taken place there, I left enough cash on the table to cover the drinks with a far more than generous tip.

“Do you think we should come back here next week?” Cassie asked with a smirk as she licked my cheek while we walked across the parking lot.

“Well, hmmm, could go either way,” I pondered. “I left a big enough tip that the waitress might be very happy to see us indeed, but on the other hand, they might just call the cops next time.”

We both laughed until our sides ached as I walked her to her car. Cassie stood with her hand on the door handle and her other hand caressing the side of my face. “Eric,” she asked softly, looking deep into my eyes with her electrical emerald stare. She momentarily just stood there, now holding my face between her hands, “Eric, do you think I could leave my car here tonight? Maybe you could bring me back early tomorrow morning to get it?”

“I’m still technically married, you know?” I said, feigning reluctance.

“Yep, and I’m engaged, so we’ve got a lot to talk about, don’t we?” Cassie laughed, as we held hands while walking to my truck.

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Written by kentucky_esquire
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