As we sat together over beers, I imagined what she would look like with her wrists bound, her mascara running, the skin of her ass red and beginning to bruise. She was pretty, her smile effervescent, quick-witted and conversational. I had been captivated by her from the first moment she walked into the office. For months, we had been flirting with one another over morning coffee and taco truck burritos at lunch. I had finally worked up the nerve to ask her on a proper date. Here we were, sinking pints, her cheeks going rosy and her hand finding mine across the table, and all I could think about was how badly I wanted to bind her, beat her, and fuck her.
Emily had graduated from a UC school with a degree in some field completely unrelated to our own. She'd told me early on after meeting her, though I'd forgotten almost immediately; I was so struck by this girl in chunky black glasses, a cardigan, and scuffed black boots that almost everything she'd told me for the first week had gone in one ear, out the other. Now, time had passed so as to make it awkward and me seem an ass were I to ask her just what the hell she'd spent four years studying, so to be honest? I had no clue. All I knew was Emily was good at our job, and in the time since she'd been hired, she and I had spent a lot of time together banging out projects.
Our group had been flown out to Austin for a tech conference and training seminar about a month before. The first night in town, we had decided to head out together as a group. Henry, one of our leads, had lived and worked at the Austin branch the year before, so he knew some local spots and offered to take us around. We had ended up at a bar called the Yellow Jacket Social Club, a spot with a gravel patio and a bunch of reclaimed wood giving off a modern-day saloon vibe. Emily had been there, and we had spent the night together chatting outside beneath the myrtle trees, doting on some mutt that was loitering around the outdoor tables so as to cut the awkward tension between the two of us.
As the moon had risen higher that evening, and the gin found a hobbit hole in our guts, our chairs had edged closer to one another. Emily's fifth well gin and tonic had found its way into her lap, somehow, sending her leaping out of her chair and then blotting her legs. I had done my damndest not to watch her chest as it bounced while she hopped from foot to foot, but between her cleavage and her impossibly round ass, waving about as she turned to clean her chair and attempted to dry her jeans, I was staring a hole through her clothes.
Emily's ass was, well... you know the scene in Jurassic Park where the scientists are in the jeep and they see the dinosaurs for the first time? Then they stand up, mouths open? Like that. You probably couldn't have tracked the amount of time I'd stared at it with a powerpoint presentation. I would come up with reasons to walk by when I knew she was in the break area. I had learned when she arrived, typically, in the mornings just so I could be nearby when she would walk to and from the coffee makers. Emily's ass was burned into the backs of my eyelids like I'd stared directly into the sun for days. That night, she'd caught me looking right at it. Or so I thought.
To my relief, as she sat, a big smile on her face told me that what I thought had been her seeing me perving her backside had gone unnoticed. I felt a small rush of embarrassment, but that gave way to the distraction of attempting to focus on our conversation while I was flooded with fantasies of my co-worker.
Since pretty much day one, the Emily in my head had been my own pornographic dream girl. My tastes in women tended to be... specialized. In high school and college, I had had my fair share of the standard vanilla hetero experiences. Christy Johnson, one of the color guard in the school marching band, had given me my first blowjob in the back of my old Ford Taurus. She'd taken my virginity in a dingy motel room after our junior prom. I'd had girlfriends here or there after, some in college, but it hadn't been until right before I'd graduated I'd come face to face with the realization that while heavy petting and doggystyle were fun, my tastes tended to be a bit more... aggressive.
I had never had opportunity to truly explore my desires. To start, they had been fairly confusing. My parents were the a-typical atomic unit guardians, high school sweethearts almost forty years married, who had by osmosis instilled in me instruction to find a nice girl, open doors for her and court her proper, and then marry her at a country church for plenty of lights-off missionary sex. The concept of sexual submission, of the exploration of the pleasures brokered of pain, were so completely at odds with the internalized vanilla views inherited from my mom and dad that the first time I'd stumbled on a fetish video on my favorite porn site and my cock had gotten so hard it practically ached, I'd had to take a walk for over an hour and spend the rest of the evening soul searching for assurances that watching three men use a woman as their oral slave didn't make me a serial murderer.
Tentative curiosity had eventually revealed my internal truths. I had come to accept that I was a sadist - I had had to spend hours on the internet researching terms I had never heard used in day-to-day life, and I had only been able to do so skulking on the wifi at a local coffee house like I was some sort of clandestine cyber-criminal. I had also realized that I was extremely attracted to the concepts of sexual obedience, submission, and service. However, even with all my self-probing, I'd never acted on my urges, even with the lovers I'd had in more recent times.
All that idealized instruction from my television sitcom family about nice girls had come crashing headlong into my secret side when I'd met Emily. In my head, in the privacy of my small apartment in the dark hours of late nights, I had spanked her ass for hours with my hand, with a belt, with paddles and crops and whips and straps and I'm pretty sure a boat oar one night I'd drunkenly jerked myself to sleep thinking of her. I would picture her in my lap, eyes wide and a little afraid, as I slowly, so fucking slowly, raised her skirt up and over her perfect legs. I would take my time, caressing her skin, gently cupping her ass, and then I would begin, slowly tapping her with my palms, building up a fury until she would be crying in agony and begging me to stop. I would imagine the look her face might have when I forced her to squat on her heels, forced her to sit on her freshly-spanked ass and then proceeded to guide her, command her, while she obediently sucked, kissed, and licked my cock worshipfully.
Needless to say, some days, casual hangouts with Emily at the office were a bit tense. All those images, and more, shot through my brain like the sounding pistol of an Olympic race the moment I'd seen Emily squirming around with her cocktail all over her pants. Satisfied I'd slipped by her without being seen, we'd gotten back to talking. A few minutes later, she'd said something to the effect of needing to get out of her pants, and I, in my drunken idiocy, had responded, "Oh, yeah, we definitely need to get you out of your jeans." A well-intended comment from me had brought the conversation screeching to a halt and coaxed the color in my face from raspberry red to merlot purple. Just then, Emily had busted out laughing, almost howling. Not long after, we'd parted ways back to our hotel rooms, me kicking myself wondering how I could be so dumb as to say something like that.
However, whatever fears I'd had that she might find me a bit off-putting, or worse... creepy, were quickly soothed when Emily became even more social with me upon our return home. This, of course, delighted me. In the weeks that followed, our conversations were more frequent, and oddly, the flirting had continued. I attributed it to the sort of friendships you make where you cross that barrier of flirtation and then everyone in the social group lets out a breath as if to say, "Finally, now we can all stop pretending to be so square all the time."
One afternoon, Emily had forgotten to write an important piece of documentation that was needed for an presentation our group was scheduled to deliver that afternoon. She had come to me in a panic, and together, we had gotten it finished just in time for our meeting. After we had laid out the information and finished up in the meeting, headed back through the building from the conference room, Emily had turned to me, joking, and said, "Jeez. I'm such a bad girl today. I do believe, sir, I need to be taken over someone's knee for a spanking."
I had been stunned. She had strolled away not long after, but her little quip in passing left me floored. Fantasizing about Emily kicked into overdrive, something I would've thought impossible. For days, in my head, I spanked her, I fucked her while she was tied to beds and radiators and the plumbing in dark basements, I gave her commands to fulfill and punished or rewarded her accordingly. It was bleeding over into my day-to-day work, almost every hour of the day.
One afternoon, after I realized I'd just spent the better part of half an hour staring out the window by my desk as I daydreamed of my dick in Emily's ass while my hands wrapped around her throat, I realized something had to be done. I didn't know what, exactly, but I couldn't tend my brain any longer. Not sure what to do were she to say no, I mustered up the courage to ask her on a date. "Hey... look, I'm not sure how to say this, so I'm just gonna'.... can I take you out for beers Friday?" Thankfully, she'd said yes.
Which lead us to where we were, sitting at the table in the bar, having a pleasant conversation about Game of Thrones and the merits of Uber when drunk while I pictured how she would look with her panties stuffed in her mouth and clothespins hanging from her nipples.
"You know," she said, her voice bringing me back to reality, "I was beginning to wonder if you were ever going to ask me out."
"Well, you know, we work together. I've liked you since pretty much the day we met," fuck it, I thought, I've already got her out on the date, may as well be honest, "But I couldn't tell if you felt the same, and I didn't want to make things weird at work."
"Oh?" she replied, quirking an eyebrow. "And did I do something to tip you off? What made you ask me?"
"I just couldn't take it, anymore."
