It was 8:40 as I approached the veranda table, five minutes before Tommy had told me to arrive and just twenty minutes before closing time. The brightly lit courts stood empty, their usual energy replaced by an eerie stillness. Not a single person was in sight. Gloria and I had been in this exact spot twenty-four hours ago, and it was the same table I had shared with the ladies during this afternoon's practice. My heart pounded as I approached, the tension building with each step. I began to perspire, the stress palpable as it tightened my chest and made every breath shallow. It was the most nervous I had ever felt in my entire life. The white noise of the evening and desolate courts amplified my anticipation, making the air feel thick and heavy as I neared the table.
“You’re here late, Miss Amy,” a familiar voice from behind said, startling me and reminding me I hadn’t been alone. I turned to see George, the kind bar waiter in his early seventies, standing there. I had gotten to know him well over the past year.
“Hey, George, you too,” I said with a laugh.
“Last call; can I get you anything before I head out? Mojito?” he asked, with a smile, already knowing my favorite drink.
“Not tonight. I will take a huge glass of whatever white you’ve got,” I replied, my laugh betraying my anxiety.
“Coming right up, Miss Amy,” George said, turning and heading toward the small bar cart set up expressly for serving the tennis area.
Even though nothing significant had happened, I could feel my chest thumping. I looked out at the empty courts, trying to distract myself by reminiscing about the close match Beth and I had played this afternoon, which unfortunately ended in defeat. Despite my efforts, a part of me still tried to convince myself that it wasn’t too late to turn around and pretend this was all just a dream.
“Here you go, Miss Amy, white zinfandel,” George said, jolting me from my daze as he set the brimming glass on the wooden table before me.
“Thanks, George,” I replied with a smile.
“Need anything else before I head out?” he asked.
“I’m good, thanks. Have a wonderful night, George.” I smiled.
As George disappeared, I was left alone once more on the deserted veranda. I glanced at my watch, now 8:45. My heartbeat quickened as I reached for the overfilled glass of wine, spilling some onto the rich teak table due to my jittery nerves. My lips seemed glued to the glass as I took a hurried sip. The anticipation of the squeaky pro shop door opening at any moment weighed heavily on my mind, making each second feel agonizing.
Each minute seemed to stretch endlessly as 8:50 approached, my nervousness growing with every passing second. The white Zinfandel in my glass rapidly disappeared, my hand shaking uncontrollably as I lifted it to my lips. The passage of time felt almost tangible, each second weighing heavily with anticipation. By 8:54, the glass was nearly empty, and my anxiety was intense. My heart raced, and my hands trembled as I tried to steady myself, the dwindling wine mirroring the fleeting moments before my life as I knew it would change.
As if it were intentionally coordinated, the squeak of the pro shop door opening, now a symbol of Tommy’s presence in my world, perfectly coincided with the last drop of wine slipping down my throat. The timing felt almost deliberate, the sound slicing through the tense silence. I knew that turning around would change the fabric of my being forever. “Run!” the struggling angel on my shoulder screamed in a final, desperate plea to keep me whole.
Setting my empty glass on the table, I took a deep breath and turned around to find Tommy approaching, just as he had the night before, clad in the same pair of absurd tennis shorts straining to contain him. The tan line between the basketball shorts he wore every day and the tennis shorts was prominent and drew a focus to his gigantic bulge, only adding to the absurdity of his presentation. I instinctively looked away as if trying to preserve any remaining dignity. The dynamic was different this evening compared to the night before with Gloria. Perhaps it was the entire glass of wine I had just downed like a drunken college student, or maybe I had crossed a threshold. The image I had replayed in my mind for the past twenty-four hours was now right in front of me, at eye level, as he stood over me in my chair.
“Hey, Amy,” he said, looking down with the same arrogant grin that seemed almost permanent these days.
“Hey, Tommy,” I replied nervously, my eyes still fixated on his crotch, not even bothering to look up. The shame of being caught or judged having suddenly vanished.
“Are you ready?” he asked, jolting me back into reality and making my heart race even faster, subtly reminding me of the transactional nature of the evening. The dampness forming between my legs was amplified by the fresh shave I had just undergone for the first time in six months.
My life flashed before my eyes as I gazed up at Tommy’s smirking face, the realization sinking in that $300 of my husband’s hard-earned money was now sitting in his bank account, pre-payment for the service he was about to provide to his neglected wife. Flashbacks of Alex’s disgusted reaction to my outfit that morning and his general disdain for my physical transformation drove me out of that teak chair. I stood up abruptly, leaving my empty wine glass on the table.
Tommy took the lead back toward the pro shop, and as he walked ahead, my gaze was fixed on his candy cane-tanned, lean legs and the tight shorts that accentuated a firm ass only capable of being possessed by someone of his youth. He eventually opened the squeaky door and held it for me to pass through. Once inside the dimly lit shop, now lacking its usual brightness, the door closed behind us. Despite having spent a considerable amount of time there, checking in, renting a ball machine, or browsing the merchandise, I had yet to learn what lay beyond the walls of the main area.
“This way,” he said, guiding me toward the short hallway to the left of the counter.
Trailing closely behind, I couldn't help but wonder where he was leading me. The idea of an assistant tennis pro having their own office seemed unlikely; was this destination an office, or were we heading toward a broom closet instead? The specifics of the "lessons" and their locations had never been clarified. The ladies had never discussed the overall logistics of where the lessons took place; they were more focused on comparing who had received the most orgasms from Tommy, treating it like some competition. As we passed the professionally name-plated doors of each tennis staff office, I suppressed a chuckle when we stopped at the last door at the end of the hallway on the right. The brief laugh momentarily eased my nervousness, even if just for a moment.
The hand-written yellow post-it on the door read simply, “Tommy.”
I could barely suppress my laughter; it was a stark reminder of Tommy’s overall insignificance at the club, suggesting he had landed the job through connections rather than merit. As he opened the door, my earlier suspicion that we were heading to a broom closet proved accurate. The room wasn’t an actual broom closet per se, but a cramped five by five-foot space with a musty odor, likely from his comings and goings all day in and out of the hot Florida sun. Inside was a tiny standing desk with a laptop, a beige fabric chair with metal arms, and worn carpet that had seen better days. The chair looked incredibly ratty; its beige fabric was stained and threadbare, and it was even too shabby for a college dorm. The walls featured only a clock and what looked to be a tennis certificate, indicating the room had been repurposed from a storage space to give Tommy a semblance of an office.
The stark, confined environment felt almost pitiful. I couldn’t help but feel a wave of sympathy for the man I had just paid $300 to have sex with, realizing how meager his workspace was compared to the expectations I had built up in my mind.
Stepping into what Tommy called his "office," I couldn’t help but notice the stark contrast to the other offices with their standard six-panel doors; this one had a cheap, hollow-core door, signifying the forgettable room it had been before being assigned to him. My fleeting amusement at Tommy’s lowly setup quickly faded as the door slammed shut behind me, and he turned to face me. My eyes instinctively locked onto his crotch, and my heart began to race again. The cramped, shabby space only heightened my discomfort, which was now permeated by the faint, overpowering odor of sex poorly masked by a spritz of Febreze.
Tommy, a man of few words, had so far uttered only seven words to me that evening, including his brief introduction on the veranda. I checked the clock, which read precisely 9:00 PM, as he approached with the precision of someone clocking in for a shift. When he closed the distance between us, his kiss came with a surprising and intense passion that took me aback. This level of intimacy was usually reserved for someone you were in love with, not a tennis pro who barely knew your name and whom you were paying to have sex with. A kiss like this wasn’t supposed to take place in a dingy office that reeked of sex. His kiss was anything but routine; it was a vibrant blend of desire, with his lips pressing firmly against mine and his tongue exploring with practiced skill.
As our kiss deepened, I could feel my vagina, freshly shaven for the first time in six months, starting to moisten through the white thong under my tennis skirt. Understanding the months of neglect I had endured, it was as if Tommy chose to open up with what most would consider off-limits in this situation to assert his dominance while testing my commitment to the evening. The kiss was so consuming that it evoked a flood of memories from passionate college encounters. Despite my internal conflict and the urge to protest how far this had deviated from my expectations, I found myself completely captivated by the most exhilarating kiss I had ever experienced, coming unexpectedly from someone I had thought to be one of the most clueless people I’d ever met.
After a few minutes, Tommy suddenly stopped, and I slowly opened my eyes, a clear sign that I was savoring a moment that should have repulsed me. He stepped back to the limit of the tiny room, allowing me space to glance down at his crotch once more. His infamous sly grin greeted my look. His tiny shorts were just as they had been when I first saw them on the veranda. The outline of his flaccid cock, still a whopping seven inches in length, wrapped around to his hip, with his bulging balls giving the impression of a cantaloupe stuffed inside. It hadn’t moved an inch, underscoring that our passionate kiss had affected me far more than it had him. This was yet another continuous reminder of the purely transactional nature of our "lesson."
Again, approaching me as he had done minutes ago with the kiss, Tommy stopped short, extending his arms and placing them on my shoulders. He applied forceful pressure, dropping me to my knees on the thin-padded stained carpet before him. His cock-filled tennis shorts were inches away from my face, and it was bizarre to be so close to something I had thought about for so long, fully understanding the magnitude of what was underneath the tiny shorts. I looked up at him again and met with another smile. No words were spoken as my attention became directed back to his shorts, seemingly against my will. The sheer size of it was overwhelming, and the proximity made it all the more surreal.
He crossed his arms and lifted the sides of his country club-issued white-collar shirt, revealing a body you’d typically expect from a twenty-one-year-old tennis pro: fit but not overly muscular. His hairless torso, including his shaved armpits, bore a faint residue of deodorant, evident from the white streaks left behind where his arms had been raised. The deep tan of his arms and legs contrasted sharply with the lighter but still tanned area of his torso, marked by where his shirt and basketball shorts had covered. Tossing his shirt onto the tiny desk, he looked at me with a wry smile. Standing in only his tiny tennis shorts and shoes, his shirtless form accentuated the bulge in his shorts, and his commanding presence was undeniable.
I had suddenly come face-to-face with Tommy's crotch; his seven-inch flaccid cock seemed to remain unmoved within his tiny shorts. Knowing its appearance when erect only heightened my nervousness and excitement. The tan line created by his oversized basketball shorts, sitting a foot below the bottom of his tennis shorts, accentuated the effect even more. With his hands on his hips and looking down at me, he clearly sensed and relished my nervousness. His bulge was strikingly prominent, the fabric straining to contain it, and I couldn’t look away. The anticipation and tension were palpable, intensified by his silent, confident dominance.
"Take it out," Tommy instructed, his grin widening as he relished my discomfort. My mind raced through a whirlwind of thoughts: Emily at home on the couch with a friend, watching TV; my husband, at this very moment, secretly writing erotic stories in his office, while his own wife stared down the real-life embodiment of his content. Though he had provided us with a lavish lifestyle, he was far from innocent. Did he truly deserve this? Tommy watched me, giving me a moment to grapple with it all, much as he likely had with Beth and Jill a year ago when they faced this same choice, prioritizing their own desires over their own families and morals.
Thoughts of my family, just a ten-minute golf cart ride away, quickly faded as my sleeveless arms slowly reached the top of Tommy’s shorts. The fabric was stretched out by his freakish manhood, pressing tightly against his lean, tanned stomach, making it nearly impossible for me to slip my fingers between his skin and the top button. Tommy’s angle gave him leverage as he watched my struggle with an amused smirk, clearly enjoying my difficulty. After several failed attempts, he finally took over and unbuttoned the shorts himself.
As the button finally gave way, it was clear the tennis shorts had struggled to contain Tommy’s impressive endowment. The button’s durability was a testament to its manufacturing strength, but even that couldn’t hold up under the pressure. With the button popping open, the shorts loosened, providing relief from the constricting fit they had imposed. Tommy placed his hands back on his hips, signaling that his role was done and leaving the next, anxiety-filled step to me. I moved my hands to the sides of his hips, grasping the fabric. Battling one last push from the angel on my shoulder, constantly reminding me of my family back home and the gravity of what I was doing, I fought to stay focused.
Struggling against the resistance of Tommy’s bulge, I slowly pulled his shorts down, revealing his flaccid seven-inch cock. Its sheer beauty made me pause, captivated by the sight. The pictures I had seen did no justice to what I was now staring at. It was the epitome of perfection, larger than my husband even at his most excited, yet completely soft. Tanned like the rest of his body, it was a uniform color, culminating in a mushroom tip that surpassed anything Alex had described in his demented stories on lushstories.com.
"Holy shit," I muttered under my breath, unable to control my reaction.
Lust suddenly overtook me, overwhelming any remaining rational judgment. As I continued to pull down his shorts, the gigantic, cantaloupe-sized ball sack I had seen so vividly in Gloria's photos came into view. His shorts fell to his feet, still encased in worn tennis shoes that carried a faint odor of clay from the courts and white ankle socks with slight stains of the same clay. Tommy’s balls were enormous; unlike the sagging, stereotypical big balls of an older man, they were hairless like the rest of his body, evenly tanned, and seemed specifically engineered to hold the two jumbo Grade-A testicles they wrapped around. The flaccid seven-inch cock hanging over them painted a picture that only made my already wet panties even more soaked.
With his hands still on his hips, Tommy looked down at me, clearly reveling in my worshipful gaze. He stepped a few inches closer, his flaccid cock nearly brushing my face. As I stared at the real-life embodiment of the men Alex had described in his stories, my life seemed to flash before my eyes. My arms moved up on their own, taking his limp shaft in my hand; the first man other than my husband I had touched in more than two decades. Unlike the passionate kiss we had just shared, my touch made his cock begin to expand from its flaccid state. Eight inches, nine inches; it began to grow uncontrollably, with nowhere to go but toward my face. Soon, I found myself staring down the mushroomed barrel of Tommy’s now horizontal cock, which continued to inch closer as it grew.
I paused, overwhelmed by the realization of how many orifices the perfection I was staring at had been inside; every member of my tennis team over the past three days, and most recently, Gloria just the night before. The thought of its journey through so many others left it dirty, filthy, and possibly unsafe. Yet, in that moment, none of that mattered. The pre-cum seeping from the head of his now fully erect eleven inches seemed to beg to be sucked out, a sight I couldn’t mentally overcome. Weakened, I slowly moved in and wrapped my mouth around Tommy. His sigh of relief seemed more like a verbal acknowledgment of having claimed another neglected housewife rather than a sign of genuine pleasure.
I did my best to service Tommy, but I struggled, feeling as though I was attempting an impossible task. The blowjobs I had performed on Alex when we were intimate weren’t going to cut it tonight; he was simply too big. Unable to get past his gigantic head, I quickly added my hands to his shaft, simulating an experienced blowjob with a milking motion. I tried my hardest to provide the kind of pleasure a man like Tommy deserved. To my surprise, his pre-cum had an unexpectedly good taste, far better than what I remembered from Alex. I passionately slurped it out of the hole of the mushroom that had been eleven inches deep in Gloria barely twenty-four hours ago. Tommy clearly enjoyed the struggle and the sounds of fluid transfer; his sly grin never left his face whenever I looked up at him. I could only assume that the ladies had acclimated to his size over time and that my struggle as his new client was part of the pleasure he derived.
I gave it my all with Tommy, likely enjoying the experience more than he did. My mouth quickly grew tired from the struggle to accommodate his size, feeling my jaw stretching and the corners of my mouth nearly splitting. My pace slowed as I tried to manage him. As I worked, my hands were irresistibly drawn to his balls, which were as heavy as they appeared. Their weight was astonishing, hanging heavily beneath his eleven-inch shaft and demanding both of my hands to encompass them fully. Though I had never been particularly interested in balls, his immense and commanding testicles symbolized that he was simply built differently from other men, igniting an unexpected excitement within me.
He abruptly pulled back, the head of his enormous cock slipping from my mouth with a sharp, wet, pop. The saliva and pre-cum that had accumulated formed an opaque layer around my lips, resembling a mustache and beard. As his hands guided me to my feet, a wave of anxiety surged through me, heightening my nervous anticipation of what was next. When he stepped closer, I instinctively tried to retreat, but my legs pressed against the grimy, metal-handled beige chair behind me, leaving me no space to move further. With no room left to escape, Tommy gently pushed me, causing me to fall into the chair.
As I landed in the chair, my tennis dress still fully intact, I felt a dampness on the back of my legs, the remnants of my sixty-year-old teammate's visit from the previous night not yet completely dried. I looked up at Tommy from the chair, which seemed to have absorbed more orgasms over the past year than a seedy porn studio ever could. The chair's metal handles were grimy, and the worn upholstery was stained and discolored, contributing to the musty, sex-scented atmosphere of the tiny office. Tommy dropped to his knees in front of me, the edge of the chair aligning perfectly with his height and crotch as if it had been custom-designed just for him.
Not a word had been spoken since Tommy instructed me to remove his cock from his shorts, which felt like an eternity ago. A wave of apprehension washed over me as I watched him take a moment to adjust himself. It suddenly dawned on me that we hadn’t discussed any crucial details; there had been no mention of condoms, STD testing, or any rules of engagement. As these unsettling thoughts swirled in my mind, his hands firmly pushed my legs back, forcing them against my chest. Now wedged into the grimy chair between its metal handles, I found myself in a helpless position, exposed. My thick, freckled thighs and the white panties beneath my tennis dress were revealed, highlighting the tan line from where my tennis skirt had covered me.