It was a picture perfect late spring day in Manhattan. On Fridays like this, the laptop class of work-from-home professionals always managed to occupy every possible square foot of the island’s green spaces, begging the question of whether anyone was actually working.
I’d gone out for a run first thing in the morning, stopped at a Blank Street Coffee on the walk back from Central Park, and sat on a green bench along the avenue near the American Museum of Natural History. Headphones out, I just listened to the sounds of traffic and the conversations of passersby, allowing the warm sun to wash over me.
I was technically on a deadline weekend. I had the first draft of an essay due on Monday, but three days was more than enough time to parse out what I’d been drafting for the better part of the last month. I liked school enough as a kid that it felt only natural to crave the structure of rigid deadlines, the kind that had enabled red-eye all-nighters well into my late twenties.
After close to an hour of procrastination masquerading as reflection and digital detoxing, I made the brief walk back to my place and retreated instantly to the shower.
Clean body, clean mind. Right?
As I stepped out of the shower and into the open space of my apartment, a devilish thought crossed my mind. I had all weekend, after all.
I dropped the maroon towel to the floor, leaving my soft manhood dangling between my legs, and retrieved my phone. Sure, at my age, sexting was a little crass and potentially opening Pandora’s box, but fuck, did it drive Taylor crazy. She was always so well put together in public; she and her husband looked like a picture-perfect, old-money couple everywhere they went.
But when she was texting me, her dirty little secret, those inhibitions melted away. It was quite a shock to find out that a married billionaire could let her hair down to this degree. Trading nudes was one thing, but the last few times, sending one out had successfully lured her into my physical company.
With nothing to lose but time against my deadline, I grabbed my iPad and opened my private photo album. For the most part, Taylor and I exchanged nudes or body parts with plausible deniability: minimal face, few defining details. I settled on a close-up of her feet from several weeks ago, her toes freshly painted Barbie pink and propped up on a footrest in her walk-in closet. It didn’t take long for blood to rush between my legs, my member stirring to life.
Simple selfies of Taylor were enough to get me going, but knowing I was about to touch the stove and send a picture of the proof only made it more exciting. The sun was still up, and here I was, my cock stiffening in my hand, the camera app open, getting myself ready for showtime.
I sighed heavily, my memory flashing to the last time Taylor had indulged my overtures: the parking garage, the backseat of her car. Clothes entirely on, the erection I was presently stroking had snaked through the fly of my pants, penetrating her soaking-wet pussy up under her dress, the two of us caked in orange neon light.
When I caught a particularly good angle, I pressed the white shutter button and smirked. With a few taps, I opened our forbidden text thread and queued up the evidence of my cock’s stiffness next to her older feet picture. I typed out:
“Thinking of you.”
I plopped down on my living room couch, still bare-assed, lazily stroking. Maybe I’d get off before I sat down to write. A clear head usually meant better prose, and thinking about Taylor’s landing strip certainly wasn’t helping the words flow.
I jerked myself off lazily, hoping Taylor would reply or, better yet, suggest meeting up. One minute turned to five, and nervousness set in. At any moment, this could blow up on either of us. Her husband could be in the room. A coworker could see the picture. I should have sent it with invisible ink.
Just as my heart started anxiously beating out of my chest, mercy arrived. Taylor’s name populated on my lock screen. Even better, it said “image attached.” I bit my lip and muttered a quiet, “Ohhh,” to myself. As I thumbed in my passcode, I never used FaceID out of sheer paranoia, I was met with the hottest picture imaginable.
It was the unmistakable sight of Taylor’s incredible, freshly pedicured feet. Her nails were painted a vibrant red that matched her signature lip color, and she wore a gold-link anklet—the kind I loved to bite on while fucking her with her legs up over my shoulders. The anklet I could taste anytime I closed my eyes and flashed back.
As I started to lose myself in the daydream, a question lingered: Was she going to indulge me, or leave me craving more? In fairness, I could never have enough. Her mere existence, let alone her shape, was intoxicating.
But there was work to be done. If I started writing now and pushed through dinner, I’d be in good shape for the rest of the weekend. Maybe I’d even go out, meet some friends for a drink, and catch the end of the Met game.
With my somewhat responsible work plan laid out, I forced myself up from the couch, walked over to my open dresser, and fished out a plain, cream-colored, double-knit collar t-shirt and a pair of light-wash jeans. With my phone tucked safely into my front right pocket and out of my field of view, I grabbed a Modelo branded pint glass from my bedside table, refreshed my water, and finally settled in to write.
The Ikea desk was littered with legal pads, scribbled-out notes, and Post-its stacked on top of regular paper, all surrounding my worn but still fighting 2022 MacBook Pro. After delaying for the first six hours of the day in a masterclass of professional procrastination, I finally got into a decent rhythm.
The nature of my process made the actual writing the easiest part. By the time I started striking keys, I had done weeks of research and knew exactly what I wanted to say. The words flowed with ease. This project was an exploration of stunted adulthood among a group of late-twenty-something guy friends. My one writer friend had noted that it was a bit too close to Lena Dunham’s Girls, but suggested that with some more drafting, it could develop a unique voice as opposed to sounding merely derivative.
At my desk, my back faced the center of the living room. Behind me was a medium-sized blue sectional couch, just big enough to sleep on if you curled up slightly. Beyond that sat a small wooden coffee table holding my completely dead iPad and a worn mass-market paperback copy of 2001: A Space Odyssey.
As I tapped away, I heard the faint sound of footsteps out in the hallway but thought nothing of it. Across the hall lived a family of four making do in a one-bedroom apartment with a dog.
I was right in the middle of writing the concluding dialogue for a scene where the protagonist’s two best friends debate in a bathroom whether to hit one last bar or call it a night, when my front door unlocked in a blink. The door swung open, and standing in the frame was Taylor. Or, at least, my some of the time Taylor.
She stood there stoically, hands resting at her sides, a small black leather purse in her right hand, her permanent Cartier Love Bracelet resting on her wrist, and a black silk dress defining her silhouette. The dress split into a deep V-neck that exposed tantalizing side boob, maintaining a loose shapelessness that stretched down to her mid-calf. Pulling the look together was a fresh pedicure and strappy heeled sandals that boosted her towering figure by about three inches.
She stood silently, her eyes scanning the room with concentrated effort. Taylor came over infrequently, and because every time could be our last, maybe part of her wanted to memorize the space. Her gaze swept past the entry rug, up the hardwood floor, until it finally landed on me at my desk.
Instead of making a biting comment about my apartment, Taylor strode across the room toward the windows on the far side. With every step, her heeled sandals clicked sharply against the hardwood. She deposited her purse on the counter near the record player and stood looking out, the silk dress clinging tightly to her waist and defining the outline of her shapely bottom.
She sighed softly, refusing to look away from the window. Taylor hadn’t even bothered to close the door behind her. It was ballsy giving her a key to both my building and my apartment, but when we were trying to lay low, removing friction was vital. I didn't have a doorman to act as a buffer, and having her ring the bell and wait outside where anyone could see her was a risk we couldn't take.
I ran my eyes from Taylor’s firm butt to the open door and back several times, taking a deep breath. Collecting myself, I stood up, walked over to close the door, and turned both the knob lock and the deadbolt.
Barefoot, I walked across the apartment, retracing her steps. The gorgeous blonde that could never totally be mine, the space where she could get what she wanted and be seen exactly as she was.
I closed the distance between us. Without hesitating, I wrapped my arms around her waist, pulled her tight against me, and took a deep breath of her perfectly styled hair.
Maintaining an intellectual distance, she said, "I have dinner at the Carlyle at seven," failing to acknowledge my presence beyond her strict timeline.
"Oh, Brian is waiting on you?" I asked. She nodded in response.
I guess we were both on a deadline.
With my left hand firmly on Taylor’s waist, I brought my right up to her neck. Gripping her softly, I tilted her head back to expose more skin. I began to plant hard, needy kisses along her neck, sliding my hand down to accommodate the space my lips needed. The blonde sighed as the kisses intensified, her hips subtly shifting against my groin, where my cock was already stiff again.
With Taylor’s head tilted back and the veins of her neck slightly protruding, I ran my tongue up her warm skin, inhaling sharply. She was immaculately made up on the surface, but a hot New York day remained undefeated, regardless of how hard she tried to beat it. There was an intimacy in knowing a partner by the way a hot day altered their scent, and Taylor was the ultimate testament to that.
Keeping my left hand gently holding her head back, I whispered in a snarky tone, "So, what does a pedicure run a billionaire these days?"
Taylor liked to flaunt her wealth. While there were plenty of perfectly fine pedicures that didn't cost hundreds of dollars, she just snicker giggled and replied, "$250. Plus a $75 tip because Carmen does such a good job. Don’t you agree?" She pointed her right hand down toward her vibrant red toes.
I couldn’t deny it, you get what you pay for, and Taylor’s feet looked every bit the price tag. I brought my right hand from her hip up to her mouth, outstretching my index and middle fingers. Taylor, almost in a trance, parted her lips slightly to receive them. Wanting her fully engaged, I commanded, “Wider,” which made her giggle before she obliged.
Taylor eagerly took my digits past her painted lips and began to work her cheeks, sucking in a slow, steady rhythm. As she pleasured my fingers, my opposite hand held her hips in place. My agonizingly hard erection pressed tightly against the denim of my jeans, and I couldn’t help but grind against her bottom. She picked up on the cue and responded in kind.
Swirling her tongue around my fingers, she let out soft moans against them, performing a pseudo-oral tease. Pressing my lips against the base of her ear, I whispered, “Good girl, that’s it.”
At the praise, she popped my fingers out of her mouth. "Look who thinks he’s in control," she said dismissively, rolling her eyes. Then, intentionally arching her back, she bumped her ass hard against my bulge. "Remember, this is my party." She took a step forward, moving flush against the windowsill.
The leggy blonde turned to face me fully for the first time since she’d walked through the door. Placing her hands on her hips in a classic power position, she said, "Clock is ticking," and tapped the face of her Rolex. She raised a fair point; these romps were an adrenaline rush, but they operated on a strict countdown. Her dinner plans were only fifteen blocks away, but even with a driver likely circling the block, Manhattan traffic would be an issue.
She took another step back and pressed her hands down against the window frame, her forearms and triceps temporarily flexing as she hoisted herself onto the elevated ledge. The windowsill was deep enough to sit on comfortably, making it a popular spot whenever I had company. Seated, Taylor locked eyes with me and spread her legs, her feet angled outward at forty-five degrees to open up access to her thighs. The black silk dress was impossibly long, dangling to her calves, which only put a smirk on my face.
I stepped forward to close the gap, the old wooden floorboards creaking under my bare feet. As I drew closer, Taylor began to yank the delicate fabric upward, slowly exposing her legs as if revealing a trap. Every single time I was with her, it astonished me how smooth her skin was. It was as if she’d been born without body hair, permanently polished.
Naturally, with Taylor seated at waist height, I dropped to my knees. Still fully dressed, and without daring to ask if I could get more comfortable, I craned my neck upward and helped guide the dress further up her body.
From down there, looking up into her eyes, she looked eight feet tall. Her legs were infinite, and I savored every inch of them with my open palms, tenderly petting her exposed skin as it was revealed.
In an instant, my head was wedged between her powerful thighs. Her strength always caught me by surprise, and the effortless control with which she manipulated my head to pleasure her was jarring. The warmth of the day clung to her skin, and as my mouth pressed against her wet folds, I could tell our picture exchange earlier had done its job. This wasn't a slow build; she was already riled up.
Taylor’s right hand clutched the crown of my head, angling me exactly where she wanted me. I stretched out my tongue, taking a long, slow lick up her mound, eliciting a sharp coo from her. The sound morphed into a ragged sigh, and she began to complain about her husband, as she often did. "I’d have to hide solid gold in my pussy for him to do this."
Getting caught in the middle of a dying marriage had never been my intention, and I had no plans of ever meeting her other half, Brian. In this moment, I was solely concerned with forcing those exact sounds out of Taylor’s pouty lips. Now, her dress was hiked completely over her curvy, athletic hips, her bare ass pressed against the wood of the windowsill, and my head firmly anchored between her angelic thighs.
Whenever I went down on Taylor, my hands would naturally drop to my sides at the start, letting my mouth do all the work. I began with just my tongue, lapping up and down like a lollipop, before gradually incorporating my lips, moving my jaw, and getting in tighter. The intensity followed the rhythm of her breathing and physical tells.
As I worked harder, those muscular thighs naturally squeezed tighter around my head, muffling the noise in the room. Performing oral became an exercise in pure touch, dictated by how her body shifted rather than the sounds she made. Still entirely dressed save for my bare feet, I was beginning to work up a sweat. As expensive as my rent was, the building's central AC was notoriously poor, leaking out through the older, drafty windows.
Suddenly, Taylor popped my head out from between her legs, though she didn’t release her clump of my brunette hair. "Stand up, now," she commanded, tapping the face of her watch again to emphasize the time crunch.
Stepping back, Taylor slid off the windowsill, letting gravity help yank her dress back down to its proper length, though it remained wrinkled toward the hem. Standing upright on her own two feet, she pointed at my waist. "Off. And stay right there, don’t move."
Trying to play it cool but eager to have the favor returned, I unclasped the copper button of my jeans and pulled the zipper down. Peeling the denim off my sweaty frame, I was left standing in a pair of black Nike performance briefs.
For a moment, Taylor looked me up and down. My broad shoulders kept the oversized t-shirt hanging loose, but my erection was impossible to hide against the fabric of my underwear. She smirked, her eyes trailing down between my legs. "You certainly know how to make a girl feel special, Nick," she drew out, a sarcastic compliment.
Then, Taylor dropped to her knees, the silk of her dress offering zero protection against the hard floorboards. Impatient and never one for formality, she reached straight into the fly of my briefs and pulled my erection free. With my member fully exposed, she extended her tongue, craning her neck to get underneath it.
Under the sunlight leaking through the window to our left, my member cast a soft shadow over her face as she began a pattern of slow, steady licks from the base near my balls all the way to the tip. With each pass, she lingered at the apex, flicking her tongue to tease me, bobbing her head deeper each time.
Building me up to the absolute edge and stopping right before I climaxed was her favorite game. Her eyes would light up as my body responded, her enjoyment turning to pure mischief the moment I reached the summit, only to be denied.
"You know he doesn’t get this," Taylor murmured, taking a firm grasp of my length and kissing down the right side to the base, her mouth coming to rest on my balls. Down there, she resumed that wide, lapping motion, making my knees buckle and forcing me to widen my stance to keep my balance.
She snickered at my reaction. "Don’t go rushing through this, you haven’t done your part yet." She stroked my cock with a firm grip, her bicep flexing as she pumped her wrist, a sheen of sweat visibly glistening in the sun over her shoulder.
With my member still in her hand, Taylor kissed the tip one last time, taking a slow, dramatic lick of precum before standing up. Heels still on, she stood nearly eye-to-eye with me, her makeup beginning to run from the heat. Her red lipstick was smudged, and her eyeliner bled slightly at the corners of her eyes. Even so, she could kill with a simple glare.
Taylor stepped to my right toward the bookshelves next to the TV. She placed her hooded heel onto the second shelf, rolled her shoulders back, and hiked her dress up until it rested on the small of her back. Her bare ass was fully exposed to the room, while I stood almost entirely naked except for my shirt.
"Would you take that thing off already?" she asked, almost breaking character at the absurdity of me still wearing a t-shirt.
I closed the distance, resting my right hand on her hip to steady her against the shelf while taking my member in my left hand. Given her heels, the shelf height, and the current wobbliness of my knees, this standing position was going to be a wild ride.
Looking back over her shoulder, Taylor watched as I lined up my tip with her entrance. I thrust upward slightly and entered her with ease. Our eyes locked instantly, both of our mouths parting in sync from the rush of stimulation.
"That’s it, give it to me," Taylor urged, groaning in pleasure as I began to probe deeper.
The warmup had left her more than ready, but I didn't want to rush. Even on a time crunch, I wanted to savor fucking another man's wife exactly the way she wanted it. Taylor reached back, her left hand finding the center of my chest and gripping my gold link chain. As her fingers locked around my chain, that opulent monstrosity of an engagement ring reflected the glare of the sun into my face. The emerald was worth more than the apartment I lived in.
I placed both hands firmly on her waist—her athletic, toned build was far too wide for my fingers to connect. I pumped forward, my thumbs pressing into the bare skin of her backside while my other fingers gripped the silk fabric of the dress. With each forward thrust, I yearned to lean further into her, pressing my skin flat against hers as I took her from behind.
The leggy billionaire leaned further forward, arching her spine to invite me deeper, which I was all too eager to oblige. As she tilted, her arm knocked several books off the shelf.
"Fuck, fuck, fuck," she blurted out, her curses rhyming perfectly with the rhythm of my pacing.
My hands naturally slid down, taking in the sheer firmness of her shape. There wasn't a wasted morsel on her body—hovering around 18% body fat with a heavily muscular composition. I knew my place in her world, but I couldn't help but firmly squeeze her bare cheeks with both hands. As I dug in, Taylor whipped her head around to lock eyes.
"Oh, you like that?" she teased, biting her lip before throwing her weight backward into me.
Her arms flew out wildly, knocking a whole new stack of books onto the floor as our intensity peaked. My hips, already tired from the morning run, rode a massive wave of sustaining adrenaline. My thumbs were now pressed deep against her crack, my grip holding on as if I were dangling off the edge of a cliff. My right hand slipped inward for a split second, eliciting a louder, sharper moan from her.
Was that...? Fuck, I couldn't hold it anymore. I was going to finish, and she hadn't explicitly signed off yet. This arrangement was entirely about Taylor getting her fill and maintaining control; she’d be furious if I came before she had enough. I grit my teeth harshly, trying to hang on, but she could already feel my rhythm fracturing.
"What, too much good pussy?" Taylor snarked.
Then her expression softened into something primal. "Go ahead, take it. Fill me up, make me yours," she invited with a devilish grin, throwing her hips back even harder against me.
I was done for. Taylor knew exactly what to say, and more importantly, exactly how to move.
I tried my best to milk every single stroke, but her tight, wet heat was simply too much to fight. I felt the swelling surge up from my balls, traveling the length of my shaft and unloading deep inside her. I shot four hot, thick ropes of cum up into her. I tried my best to keep us both upright, but my knees finally failed my mind. I buckled backward slightly, just barely staying on my feet while keeping her stable. Most importantly, I managed to keep her dress completely clear of the mess.
Taylor remained leaning slightly forward, one hand bracing herself against the bookshelf, her dress still bunched over her backside. She took a long, deep breath to collect herself, and then she giggled—a genuine, satisfied sound. It wasn't often that Taylor's real laugh leaked out; she was usually too controlled, too measured. But this was the laugh I actively hunted for, the rare one.
She looked back at me as I finally succumbed to gravity, dropping onto my bare butt right onto the hardwood floor. The blonde didn't say a word. Keeping her dress bunched up, she turned and walked out of sight toward the bathroom. After a few moments, the toilet flushed, and she set about instantly reconstructing her public persona.
Taylor stood at the entry mirror, propped up against the wall. In a blur, she reapplied her red matte lip, never blinking. When she deemed herself ready, Taylor blew herself a kiss in the mirror and smirked confidently. As a finishing touch, she wiped the runny eye liner away with her left ring finger, flashing the ring subconsciously.
As the blonde finalized the last of her look, she came to the part in her hair. She felt around blindly, and quickly panned the room. Taylor was missing one of her chignons. She quickly reworked her hair under the remaining pin she did have and did a quicjk pan to see if she could spot the glint.
Her gold dangling earrings and necklace were perfectly repositioned. Her dress, though slightly wrinkled at the hem, retook its sleek shape down to her thighs. The heels, which she’d never bothered to take off, remained every bit the high-society status symbol they were before she’d decided to come slum it with me.
Taylor glanced to her right, looking down at where I was still a complete mess on the floor. My breathing was heavy and labored, but I couldn't help but smile up at her anyway. God, she really was perfect. If only she were mine.
Instead of offering a friendly goodbye or acknowledging what we'd just done, Taylor simply said, "You know we can’t keep doing this." She grabbed her purse and disappeared out into the hallway.
I sat on the floor for a long time, trying to piece together the whirlwind of the last hour. Looking up at the digital clock on the desk next to my laptop, it sank in that she was going to be incredibly late for dinner. She’d come up with a brilliant excuse, of course; she always did. And for all her protests about needing to end our arrangement, she’d almost certainly break the ice the next time she got the itch.
I forced myself up to my feet and sighed. Work was still waiting.
Suddenly, my phone screen flashed on the desk. A new notification from Taylor read: “Well that was fun, what should we do next time
?”
Topic: Safe Words: Taylor Swift (Read 2532 times)