I started work at the new job on a Monday, like you do. It only surprised me that the office was entirely full because it was a bank holiday: Presidents' Day, or Columbus Day, or somesuch. Regardless, every cubicle had an occupant on that particular Monday. My newly assigned tiny workspace was situated in a corner, a posh location by large corporate office standards in this city (I had two real walls). I took a few days making the cubicle my own. I hung a few modern art prints. At the end of my first full week, I was fairly well settled, and started assessing my prospects.
As a 30-something single guy, the 21st century provides a plethora of ways to meet women. The Internet, for example: I have profiles on two dating sites. Still, though I'm slim and fairly fit, and not an unattractive guy (except that I'm pretty hairy), I hadn't had much luck. Pub crawling had done me no better, except for a handful of ill-begotten one-night flings (not that I'm complaining). I wasn't looking for a wife, just for someone I could enjoy my time with both outside and inside the bedroom. So, work is as good a place as any to meet new people, and a new gig meant new possibilities.
My new office was, fortuitously, staffed mostly by women. After having been there a week, though, I had already limited the field substantially to five potentials. Of those five, there was really only one that drew my immediate attention: Chelsea.
Chelsea was, I'd say, on the short side of average height at maybe 5'5", though it was hard to tell since she always wore heels. The heels were part of her consummately professional image. While other women in the office sometimes wore skirts or dresses, Chelsea only ever wore suits. At work she was all business, and it showed in how she presented herself. She kept her wavy brown hair at shoulder length, always immaculately groomed. Her nails were always painted or glossed, and she kept them long enough to let you know she was a woman, but not so long that you'd think she was vain about it. Chelsea's face contained large, deep brown eyes and thin lips. She accented her natural beauty in a simple but classy style, wearing very limited jewelry, usually pearls. The suits did little to mask that her petite frame held the essence of woman: gently curving hips, tight round butt, firm legs, and a modest but appropriate bosom. She wasn't cold, per se, but she was somewhat guarded. This was a woman on the move. For her, work was work, and her personal life was none of her co-workers' business.
That said, it hardly surprised me that after another two weeks of trying to crack her shell, I was getting nowhere. She made small conversation, but nothing revealing. Chelsea never let anything slide that she didn't want to. She had warmed up to me somewhat, as compared to how she interacted with the women in the office, but eventually I resigned myself to the fact that Chelsea would probably be a no-go.
That resignation was still fresh in my mind when, returning to my cubicle from lunch one Friday afternoon, I encountered a lovely, round, perfectly heart-shaped ass. Not a bare ass, mind you, but one snugly contained in a black skirt, leading downward to pale stocking-sheathed legs and three-inch heels. I couldn't see her face immediately, as she was bent over retrieving some paper from the cabinet beneath the row of printers just outside my cube. "Oh excuse me," I said, stopping short to prevent myself from falling over this poor unsuspecting woman.
"Oh, I'm sorry!" said the woman. She stood quickly and turned to face me. It was Lynn, the office admin. Admin is an interesting choice of words, I guess, since Lynn was old school enough to prefer being called a secretary. She was certainly not one of the women who'd made my top five prospects list. Lynn had to be in her early sixties, and so had easily escaped my earlier attention. If she had been younger, I could easily have seen myself pursuing her: pale skin, bright blue eyes, and red hair. As it was, her hair was still red but she was graying slightly at the bangs and temples; if it was a dye-job, it was a damned good one. Her crisp blue eyes were framed by large gold wire-rimmed rectangular glasses, and what skin I could see on her face and neck was loose from age. She wore, perhaps, too much makeup, including bright red lipstick, and a purplish blue mascara. Lynn was on the short side, around 5'2", but like Chelsea, always wore heels in the office. As she stood, I caught a waft of her floral perfume.
"Sorry, Zach," she apologized again, flattening the front of her skirt against her thighs as she stood. "I should really be more careful in these narrow spaces."
"It's okay," I told her. "I should pay more attention when I'm turning corners." Lynn smiled gently and returned to what she was doing. I went back to my cubicle and sat, sliding my chair close up to the desk to hide my hard-on underneath. The appearance of that plump, round ass stuck straight up in the air had caught me off guard, especially considering I had only moments before been fantasizing about Chelsea. I took a deep breath, but couldn't stop myself from peeking out of my cubicle at Lynn again. She was bent over again, about eight feet from me, with her ass pointed straight at me as she continued to retrieve reams of paper from the cabinet. She may have caught me looking as I withdrew my gaze, but I wasn't sure.
Throughout the rest of the afternoon, I tried to put Lynn out of my mind. Nevermind that the idea was a little out there, since Lynn was literally twice my age. Beyond that, she was married, and I tried to stay within the lines on that particular issue. Barring extreme circumstances of course. Still, I couldn't escape my own perverse thoughts. I found myself looking at Lynn in a newly sexualized light. For instance, I had never noticed before how closely her outfit clung to her body. That day she was dressed similarly to how she always dressed: a black skirt that hugged her hips and buttocks and flared slightly at the knee and ended mid-shin. Her top was a baby blue cashmere v-neck sweater over a white collared blouse. The sweater was snug and fit her well, and I had simply neglected to notice how large her breasts were. The total outfit showed her shape, accentuating her curves, without demanding attention. It was unassuming yet alluring. Lynn wasn't slim, exactly, but she was very nicely shaped, especially considering her age. I found my imagination drifting, picturing her removing her top, then her bra, letting those large, pale, luscious breasts fall, bouncing slightly as they did....
"Zach?" a voice asked, snapping me from my daydream. I turned in my chair to see none other than Lynn standing in my so-called doorway.
"Oh, sorry Lynn. Must have spaced out there for a minute," I admitted, glad my erection was tucked safely under the desk. "I guess it's been a long week."
Lynn smiled sympathetically, her bright eyes sparkling. "Well good news, then! It's five o'clock. You and I are the last ones here, so I just wanted to let you know I was leaving."
"Oh, wow," I remarked, glancing at my watch. "Me too." I snapped my laptop closed and tossed it into my shoulder bag, pushing impure thoughts from my mind.
We rode down to the lobby together in the elevator, making small talk. Lynn politely asked what I had planned for the weekend. "Oh, you know, just living the swingin' bachelor life," I joked. "Buying groceries, doing the laundry, getting a haircut." As we exited the building, we found ourselves walking the same direction. Lynn and I proceeded down the stairs to the subway station about a block from the office. "Are you heading north or south?" I asked.
"South," Lynn said. "I'm just a few stops down."
"Oh, we share a commute," I observed. The train was busy, typically so being rush hour, exacerbated by the fact that it was Friday evening. We crammed ourselves into the jam-packed train car and I found myself standing very close to my newfound crush. Lynn had switched to flats for the commute, so I was standing over her, and the scent of her perfume was a welcome change from the usual odors of the subway. Again, I felt my cock straining against my boxer briefs. "Down, boy," my brain urged. He didn't listen. Fortunately, Lynn had said she was only riding for a few stops.
At the first stop, though, the train braked fairly hard and Lynn lost her footing, falling forward into my chest. She grabbed my arm to catch herself, but my raging hard-on was now pressed firmly to her tummy. I felt my face flush but said nothing. The unintended incursion into my personal space caused my erection to throb. She had to have noticed it, pressed against her like it was. "Are you okay?" I managed as she gathered herself, still holding my arm.
"Yes, thank you," Lynn replied, looking up into my eyes. "Do you mind if I hold onto you for balance?"
Incredible. Maybe she hadn't noticed. I released the breath I hadn't realized I was holding. "Sure. I mean, no, I don't mind." Lynn smiled, and stepped back slightly. Then, she moved her other arm between us and, still looking me dead in the eye, firmly grasped the bulge in my pants. My eyes went wide and my head began to spin.
"Thank you, Zach," she said without flinching. "That's much better." I gave a quick glance around the train car. Lynn's little move was apparently obscured by our two bags: her large purse, hanging from her shoulder, and the briefcase hanging from mine.
"Oh. Well. Um. You're very welcome," I stuttered. Lynn just continued to smile sweetly.
I said nothing else for the rest of the ride. What the hell could I say, anyway? I looked around furtively, avoiding Lynn's gaze. She didn't make it easy, continuing to look up at me until finally she said, "This is my stop." She released her grip on my cock and I felt a mix of relief and disappointment rush through me. "See you on Monday, Zach." She winked and then she was gone, lost in the sea of people in the subway station. I stood there dumbfounded and slack-jawed, nearly missing my stop a few minutes later.
Somehow, I made it back to my apartment. I don't rightly remember the walk home. My mind was spinning and my stomach was doing backflips. I was shocked, but also excited, and very confused. As I entered my apartment, I dropped my bag inside the door and headed straight for the bathroom. I ran a cold shower and quickly stripped. I climbed in and let the brisk water run over me, my mind racing. Did she want me? Was she just fucking with me? What about the husband? Keith, I think was his name. Lynn was old enough to be my mother, and then some. Was that weird? Did I care? If I didn't care, should I care? What did she want from me? Was she trying to make some sort of point? If so, what was it?
Despite my head feeling a bit like it was the inside of a pinball machine, I kept drifting back to that moment on the train when Lynn had unabashedly grabbed my dick. I couldn't deny that it had excited me: my erection wouldn't let me deny that. Inevitably, my desire caused my imagination to flare. I closed my eyes. I pictured Lynn coming into my cubicle at work, hiking up her skirt to reveal the tops of her stockings, then straddling me in my chair and kissing me deeply while caressing my neck and shoulders with her mottled, veiny hands. In real life, I slowly began to stroke my throbbing cock as the shower rained down on me. I imagined my hands sliding up Lynn's thighs to the bare soft skin above her stockings as the kiss intensified, while she unbuttoned my shirt and rubbed my chest. The speed of my strokes increased as my mind pushed the action forward. In my mind, I was kissing Lynn's neck, and sucking on the loose folds of flesh there while moving my hands up under her blouse, lifting it above her breasts. As the imaginary me put his face into her pillow-soft pale cleavage, the imaginary Lynn began rocking back and forth, grinding on my imaginary crotch. "Ohhhh god," I moaned, and realized it was in real life. I came hard, and had to brace myself with one hand as my load spattered the front shower wall once, twice, three times. I groaned as my balls relaxed and the fantasy began to dissolve in my mind.
