Playdate Plans Pt. 01

Story Info
Redhead babysitter befriends single dad at the pool.
5.6k words
4.62
36.7k
55

Part 1 of the 2 part series

Updated 06/11/2023
Created 05/14/2022
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"Aunt Sarah! Watch me dive!" I patiently raised my eyes over the edge of the magazine page towards the pool. As I watched, Mason splashed below the surface and swam to the bottom four feet down. The bursting swells of his rising bubbles chopped the reflection of the bright morning sunlight. He emerged a few seconds later brandishing a shiny penny; the same penny I had seen him dive after and retrieve no fewer than fifteen times in the last twenty minutes.

"Yay! You got it! Again... Great job, Mason!" I worried that the excitement was waning in my voice after cheering the repetitive triumph.

Checking my phone, I saw that it was almost eleven and his swim class would begin momentarily. The lesson's structure for ninety minutes of our morning came as a relief to me as a novice at babysitting. Lowering my sunglasses to the tip of my nose to make sure he saw me looking at him, I waved the boy out of the pool and over to my chair. After reapplying his sunscreen and adjusting his goggles, I sent him to join the group of children already gathering around the legs of the instructor. My "childcare" duties complete, I settled back on the chaise and resumed my article.

My friends, Deb and Jesse, had left early that morning for a long anniversary-weekend away. I had volunteered to stay at their house to watch Mason, their five-year-old son. Deb had balked, unsure that I could handle caring for a preschooler for four days. Right now, my babysitting duties were as complex as "sitting in a deckchair at their country club for a couple hours"; yeah, I could handle that.

I glanced again towards the class, spotting Mason splashing and paddling with the other kids. Confirming that he was supervised, I let my eyes roam the pool grounds. The complex consisted of three separate pools. In the far corner was the wading pool, occupied by clusters of bucket-toting infants held upright by chatting mothers clad in a uniform of visors and bandeau one-piece swimsuits. Mason's lesson was taking place in the shallow end of the central family pool, the bottom of which sloped away into a deep well for diving boards and a slide. And as I peered over my right shoulder I spied the designated lap pool, reserved for the use of adult members as well as the club's competitive youth team.

Watching the churning lanes of exercising swimmers, I mused that I probably could benefit from swimming some laps in the hour Mason would be supervised in lessons. However, I countered, that would have required my bringing a one-piece swimsuit. Instead, I rolled my eyes at the absurdity of swimming laps as I stared down the yawning valley of cleavage separating the aqua cups of my bikini. In acknowledgement of my babysitting duties, my top covered a responsible amount of my ample bust. And, though the cheeky cut of my briefs showed a hint of my bum, I hid those beneath a pair of soccer shorts in Mason's presence. That said, I didn't trust the knot behind my neck holding my bikini-top in place to survive the stress of a vigorous swim.

I watched Mason and eighteen other kids splash and frolic in the shallows while the patient lifeguard tried to pass out kickboards to begin the lesson. My eyes returned to my magazine, reassuring myself that it was better not to have brought work with me instead since the pool deck was teeming with distractions. I was surrounded by kids splashing, whistles blaring, mothers shouting, and the universal moving background of a summer morning at the pool. Recording zero billable hours for the day would be a pain to recoup next week but backtracking to correct distracted work would be its own problem. Besides, I thought as I turned the glossy page and felt the sun warm my chest and belly, the occasional weekday dalliance was a nice reward for all those long hours behind a desk.

And I soon discovered that even reading my mindless magazine was not something I could concentrate on amidst the bustle of the pool. The background din of splashing and whistles organized into distinct voices as the swim teams' practice let out. A trio of high school boys slowed their gait as they passed my chair, the volume of their voices rising as they boastfully compared performances from the recent meet. Their eyes lingered tactlessly, greedily drinking in the pale humps that swelled above the coverage of my top. I gazed sternly at them over top my sunglasses, silently advising that their raging adolescent hormones still required discretion.

A pair of moms in long sleeved rash guards paraded by, quickly ushering their children to the wading pool. Each cast an accusing glance back at me, then huddled conspiratorially. "Oh, come on, has no one ever worn a two-piece to this pool before?" I wondered, almost speaking the words aloud in my exasperation. I puffed a touchy breath and combed my red hair with my fingers. The brisk action of my ribs and arms set my melons waggling if anyone was paying attention. With my hair away from my face, I returned to my magazine.

The light was blocked as an impediment arrived between the sun and my mag. I glanced up from the page and came face to face with a dripping-wet male torso and blue, square-legged compression swimsuit. Blinking in shock behind my rose gold tinted lenses, I raised my head to find a handsome black face beaming down at me, still beaded with pool water. My mouth hung silently agape in confusion at the stranger's sudden, sodden arrival.

"Hope I didn't startle you, I'm Mark!" the man held one hand to his soaking chest in introduction. "Did I see you with Mason? I didn't know that Deb and Jesse hired an au pair?" From his elevated vantage point, his eyes were unquestionably filled with all but the dearest bits of my jugs. But, unlike the teen gawkers, Mark at least made an effort to disguise his ogling.

I shook free of my stupor from the interruption -- and from Mark's bulging, spandex-forward greeting -- and sat up in my seat as I held out my hand. "I'm Sarah," his wet hand enclosed mine as we shook. "And believe me when I say I am NOT a childcare professional, just a soft-hearted friend who's maybe in over her head. To be honest, I'm such a bad babysitter, I have no idea what to do with him this weekend." I giggled, explaining about their trip and my four-day adventure in parenting.

"That's so kind of you to volunteer like that; it's always so hard for parents to find time to be alone together..." Mark trailed off and blushed, grinning juvenilely as he realized he had just invoked the image of our mutual friends banging. I also smirked and blushed like a naughty child at the suggestion.

While we were on the subject of ogling, Mark's fit stomach and chest demanded more than a casual glance. However, the real attention-grabber was the captive bulge in the front of his trunks. My libido dumped a shot of lust into my bloodstream, and I choked down an amorous sigh at the warming rush. With a concerted effort, I forced my eyes north back to his face.

He cleared his throat to change the subject. "Uh, anyway, my daughters, Michelle and Theresa, are friends with Mason at school, so it's great that they can see each other here, as well. Those are my twins there, with the boards." He pointed to the pool, where two little girls kicked across the water towards the lane dividers.

I fixed my sunglasses atop my forehead as I watched the ongoing lesson, feeling the fresh rebound behind my bikini cups as I moved. Mason followed the girls' lead, kicking zealously as he tried to catch up to his friends. "Wow! They're really kicking butt out there!" I complimented his daughters' advanced swimming ability.

Mark beamed with pride. "Yeah, it's great to get off an overnight O-R shift in time to bring them out here." The way he casually dropped that he was a surgeon, I debated if he was trying to impress me. A glance at his hand didn't reveal a wedding band, but he could have taken it off for laps, I supposed.

He looked down at his body as if realizing for the first time that he was soaking wet. "And, of course, I can get in a couple laps myself. I didn't get you wet, did I?" Mark laughed, pointing past me to three nearby chairs where his family's towels were draped. I shook my head 'no' as I weighed the entendre in his question. As he smiled at me, his eyes settled back in the tantalizing seat of my cleavage.

"Do you swim every day?" I arched my back subtly and plumped my tits up and out, having a little bit of innocent fun with the good doctor. His mouth fell open for a moment, then he caught himself.

"Not as much as I wish I could." He stammered. "Sometimes it's hard to balance work with home and the kids... since the divorce, even harder." I nodded as he volunteered his marital status. He patted his trim stomach judgingly, "I should probably be better about it though." I smiled, shaking my head, and giving him the obligatory 'oh, please' wave of my hand.

The sound of a whistle from the pool drew my attention, but the instructor was calling the students back to begin the next lesson. In the lap pool, a gaggle of old women slowly paddled in a gossiping cluster, taking advantage of the vacated lanes. With the approaching lunch hour, the deck had largely emptied out, and Mark was the only man remaining not including lifeguards.

He grinned and shrugged, acknowledging the exodus. "Yeah, when I work nights, a lot of the time I end up as the only man here by the time I finish my laps. Can't say I mind having the locker room to myself." He chuckled again as he checked his watch. "In fact, I should hurry up and get changed; there's still like forty minutes left in class, but if I'm still getting dressed when it lets out, all the moms will think I'm default chaperone for all twelve boys in the class!"

Mark held out his hand, and we shook again. "It was a pleasure meeting you, Mark. It must be nice for Deb and Jesse to have such a lovely companion for when Mason hangs out with his friends." I wasn't entirely ready for him to send me back to my suddenly less captivating magazine.

He thought a moment, then took his shot. "Hey, I have an idea... you said that you're having trouble coming up with a plan for tomorrow. Since you're new to taking care of a kid, how about we get them together a playdate for tomorrow at my house? It's supposed to be a really nice day, so Mason and the girls will be content to tire themselves out running around the backyard; they basically take care of themselves like that. Meanwhile, I can make us some margaritas and have our own grownup playdate in the safety of the air conditioned indoors..."

I enthusiastically accepted; my only hesitancy was if I would tell Deb that I'd used her preschooler to pick up dudes at the pool. Bending forward to reach into my bag for my wallet, I let my tits bob and recoil against the hold of my bikini's cups. I smirked as I gave the handsome doctor a final enticing show for him to think about until we met up tomorrow. Straightening, I handed my business card to Mark as he pretended not to have been engrossed in my flirty display. I flicked my eyes downward, wondering if I had seen his shorts becoming tighter. My tummy jolted naughtily, convinced that I was right.

Mark smiled eagerly as he bid an awkward goodbye and hurried toward his belongings. From the pool, his girls waved with excited energy as they spotted him. He waved back, juggling his towel, gym bag, sunglasses, and my card still clasped in his fingers. As he headed toward the locker room, I saw his sunglasses slip unnoticed from his bundle of stuff, landing silently on the seat of a lounge chair as he passed. They remained as he disappeared into the locker room.

I sat for a few minutes, watching the glasses over the glossy top of my magazine page as my wicked mind frolicked through a thousand forbidden scenes. "What kind of 'playdate' might we get up to?" I imagined going to my knees on the kitchen tiles, greeting face-to-face the eager member that had struggled behind his swim trunks, then sucking Mark to a balls-draining orgasm while he kept watch out the window. I closed my eyes, switching between vivid, vulgar scenes: maybe he'd lift my skirt while I was reaching into a cabinet for glasses, or bend me over the counter as I clung to the far edge, or we'd slip away to a guestroom where I'd ride him on the bed, arching my back to fill his hands with my bare tits, or... I squirmed in my seat, squeezing my thighs together and gasping at the hot, wet pearl forming between my legs.

Recalling my surroundings, I opened my eyes and scanned the empty patio. No one was near enough to hear my sighing, and none of the moms in the wading pool appeared to have noticed my wriggling. My heart thumped rapidly behind my ribs. I felt the red flush on my face and chest, whether caused by sun or libido. Mark's sunglasses still lay undisturbed on the chair.

I peeked quickly over at the class in the pool; the kids were still at their lessons and would be for a while. Taking pains to appear casual, I stood up from the chair, leaving my sunglasses and towel with my bag, then turned in the direction of the locker rooms. The elastic trim of my cheeky bottoms pinched into my glutes as the swimsuit back contracted towards the cleft of my cheeks. My bare feet skipped quickly across the hot concrete of the deck, and I felt a giddy hop in my step as I walked. I paused at the chair, dipping to grab his glasses, then with a sneaky glance over my shoulder to confirm no one was looking, slipped into the darkened men's locker room.

I paused once through the entryway, waiting for my eyes to adjust to the gloomy interior of the cinderblock space. The room was silent at first, and for a moment I fretted that Mark might have already left through another exit. But as I listened, from around the corner I heard the soft impact of a bag being placed on a wooden bench and the whir of a zipper. Walking silently on the balls of my feet, I snuck along the wall towards the corner.

Holding my breath as I reached the cinderblock elbow, I peeped into the alcove to confirm Mark was alone. I spun back and flattened myself against the wall of my hiding spot in my delighted astonishment. I'd arrived right on time: Mark was alone and completely nude, facing away from me and towards the row of lockers as he dried off. My heart was beating so hard, I was convinced Mark would hear it and I covered my mouth with my hand while I regained my composure.

Calming my breathing, I gathered my resolve and fought off the last of my nerves. I fixed the cups of my suit, giving my rack a last, alluring boost. Unfolding one earpiece of his glasses, I stepped around the corner and crept silently behind Mark's naked form.

Mark's tensed buttocks flexed as he lifted a foot onto the wooden bench, rubbing his calf and ankle with a towel. His discarded swimsuit lay on the wood beside his bag. The defined muscles of Mark's back and arms tautened as he bent over, drying his legs. My footfalls were silent on the cold concrete as I tiptoed unnoticed within a few feet of him; oblivious to my presence, he even hummed a few distracted bars from a children's song as he dried. I stood admiring his powerful body for a moment, chewing my bottom lip naughtily as moisture beaded eagerly along my slit.

"Ahem." I softly cleared my throat, finally announcing my presence. Mark whirled in alarm, his naked body turning a half-circle to confront the intruder. The momentum of his spin caused his flaccid dick to smack against his thigh with a fleshy impact. "Hi..." I spoke coyly, my eyes widening at the beast dangling between his legs.

"What the f- What are you doing here?! How long have you been there?!" Mark sputtered in shock, hurriedly raising the towel to cover his crotch.

"Just long enough..." Moving my line of sight to his face, I replied with a smirk, then held up his glasses. "You dropped these back there..." I raised the shades to my mouth, nibbling playfully on the plastic earpiece. Holding his eye contact, I took a step forward, now within arm's reach of him.

Mark gulped as I came closer. "Uh, thanks..." His vision filled with the quivering movements of my breasts as they rode the elevated rise and fall of my ribcage. I speculated what sort of development his towel might be concealing.

His surprise receded and awareness of the situation dawned in his mind. He maintained the towel in front of his groin, but he grinned with purpose as he spoke. "Couldn't wait to bring these to me til I came back outside, huh?"

Without replying, I took a final step and closed the distance between us. Plucking the earpiece from my teeth, I unfolded the second temple, then reached to carefully bring the glasses up to his face. As the shades secured behind his ears, I softly dragged my fingers along his jawline, delicately scratching his cheek and chin with my long, pink nails. Extending on my tiptoes, I stretched up to reach my lips to his, while pulling his face down to meet me.

Our mouths met and embraced, opening and warping as they pressed wetly against each other. My hands braced on his shoulders, holding me in my lifted stance on my toes until I succeeded in dragging him into a hunch so I could flatten my feet. Mark looped one hand behind me, clutching my pert bottom and eliciting a squeak of delight from me as his fingers pinched my tender bum. His other hand stubbornly kept the towel over his crotch. I brought one hand to his wrist while the fingers of my other hand gripped the towel.

"I've seen it," I assured him, kissing him between statements, "and I want it." My hands insistently guided his cover aside and pinned his wrist against his hip. With the towel removed, a broad protrusion rose, poking keenly into my belly. "There, that's better." I grinned eagerly against his mouth as I resumed our kiss.

My fingers encircled his girth, tugging the veiny shaft as our tongues and lips danced above. Groaning at my hand on his dick, Mark dropped the towel to the bench. He pulled me harder against him by his grip on my ass, his erection jabbing against my waist as I stroked him and smearing precum over my skin. His free hand seated itself comfortably on my rack, pulsing and kneading the springy flesh through the aqua cup of my bikini.

Seeming to energize from the feel of my tit, Mark's hand followed the fabric sash upward over my chest, to my shoulder, then to the back of my neck where he found the knot. Now it was his turn to smile through our kiss as his fingers nimbly plucked the tie and unknotted the bow behind my neck. The bands wilted off my shoulders and down my chest, towing the cups with them. My tits bloomed from behind the sagging top, ripe and snowy in the dim light of the men's room.

"Oh, fuck yeah!" Mark exclaimed, taking a bouncy sphere in each of his large hands. The white flesh contrasted starkly as it peeked between his splayed, dark fingers. I arched my back, boosting my tits up and forward, overfilling his hands. The bikini dangled from its back strap, the cups uselessly folded below my globes as Mark gleefully fondled and played.

Amid his fascination with my rack, Mark seemed to have nearly forgotten about my hand on his dick. I hadn't, though, and my tiny, pale fist pumped briskly up and down his shaft, driven by the thrilling feel of his hands on my tits. Breaking off our kiss, I held his gaze as I sank towards the floor.

"Hold on a sec!" he said, slowing me by his drag on my bust. I raised my eyebrows in surprised curiosity, hovering in a squat with his dick wagging at chin-level. He reached to the bench and grabbed the towel, folded it two times into a square, then dropped it to the floor before his feet. "There!" he nodded, satisfied.

"Doctor's orders?" I asked, rolling my eyes playfully as my knees landed on the improvised pad. I silently admitted it was much more comfortable than the cold concrete. Mark nodded again, grinning wickedly, holding his prick by the base, and offering it up for my mouth. I licked my plump lips, pausing for a teasing moment while my hot breath washed over his glans. Then, brushing his hand aside as I belted my fingers around his base, I dipped my neck forward and took his cock into my jaws.

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