Timmy the Ticklish Pool Boy (Patreon)

F/M, 18

The hanging sun left ripples of light scattered across the surface of Vivian Calloway’s pool. The day had proven to be a promising one. A clear sky with minimal heat. The flowers that had started blooming in the spring sang praises to the basking comfort of summer. Vivian’s daughters were gone all weekend on a retreat with a few friends. Her house was sizable and flourished enough to provide all the entertainment a woman could need to stave off the boredom of solitude. She was more than content on such a day to relax.

Vivian, a beauty of her mature age, laid back in a lounging pool chair without a care. A wide brim hat, garnished with a silk scarf, cast a shadow over her face. Her eyes were covered by a pair of glittery sunglasses. A tight bikini clung to her body well, highlighting how well she had always treated her figure. A hot tub babbled off to one side. A small radio playing new age pop accompanied the birds singing just outside of her patio.

Vivian rested with a meditated smile across her face. She turned her head to see the only company she had for the day. Over by the pool, a slender boy, wearing nothing but swim trunks, took a net to scoop up stray leaves that had fallen into the pool. He was well tanned, his hair a shaggy, sandy shade. His chest was firm and as flat as his tummy. His body glistened with a fine layer of sweat. His feet were bare, the bottoms of which blushed with a youthful softness. Timmy, Vivian’s pool boy, pushed his hair back out of his face. He gathered up the natural litter from the pool and dumped it in a small trash bin by the bar.

“Timmy,” Vivian said. Timmy turned to see her up by her chair.

“Yes, Ms. V?” Timmy asked. His eyes sparkled like ocean depths. They were large and eager. His own lips curled at the sight of her.

“You’re still playing baseball?” Vivian asked, coming closer.

“Yes, ma’am,” Timmy started.

“Mmm, I can tell,” Vivian said. She reached down to his belly. Vivian skittered her nails across the skin. Timmy squeaked and recoiled. He gave a soft chuckle before taking a step back.

“Aaahheheheee!” Timmy giggled. “Th-that tickled…” The boy blushed through a smile that stayed glowing on his face. He held the spot and ran his fingers through his hair. Vivian giggled at the boy’s reaction.

“Mmm, sorry sweetie, it was just too inviting,” she said. Timmy felt a warmth come to his cheeks. He stood upright and came closer.

“That… that’s okay,” Timmy said. “Re-really, I don’t mind…”

“Being tickled?” Vivian asked. Timmy’s blush grew.

“W-well… no, not really,” Timmy said.

“Well then, I’ll have to keep that in mind,” Vivian said. A lightbulb turned on. A devious smirk came to her lips. She turned toward the house. Silence. It would only be silence for a while with everyone gone. Vivian knew she could fix that. She turned back to Timmy, a warm expression keeping him welcomed. “I’m going to go get some lemonade,” Vivian said. “Would you like some?”

“Oh, no, please Ms. V,” Timmy said. “Let me.” Timmy started putting down the net before Vivian stopped him with a chuckle.

“Oh, I insist,” Vivian said. “I need to stretch my legs a little and you’ve been working so hard.” Timmy started to object, but Vivian left him with a small stroke on the arm.

Vivian retreated to the kitchen, still enchanted with a devious idea. Timmy’s little laugh stayed in her mind, playing like a soft tune that she could listen to on repeat. She came to the refrigerator and pulled out a pitcher of lemonade. She took out two glasses and poured the sweet and sour mixture into both. After putting the pitcher away, she pulled out a box of Sleep Aid from the medicine cabinet she kept in the kitchen. She took two pills and grinded them down into fine powder. She mixed the powder in with one of the glasses before taking both outside.

“Here you go,” Vivian said, handing Timmy the laced glass of lemonade. “For all the hard work you’ve been doing.”

“Thank you, Ms. V,” Timmy said. With a long series of gulps, Timmy downed the entire glass in one chug. Vivian sipped hers and chuckled.

“My, you were thirsty,” Vivian said. Timmy nodded.

“I was, thank you,” Timmy said. He put down the glass and turned back toward the pool.

“Everything looks as clean and clear as it can,” Vivian said. “If you need to rest, you may.” Timmy nodded again and yawned.

“You know, I may take you up on that,” the boy said. He scratched at his eye and yawned once more. “Wow, I don’t know what it is…”

“The heat will do that to you,” Vivian said. She sat down her glass and took his hand in hers. “Here, if you need to lay down, you can use a guest room.”

Vivian led Timmy to one of her guest rooms, keeping him on the first floor of her house. Timmy walked slowly the entire way, his vision twisting and head swimming as he combatted the exhaustion taking him over. He held his head in his hands. Timmy could barely keep his eyes open long enough to walk.

“Th-thank you… Ms…” Timmy started to say. As Vivian brought him into the already made guest room, Timmy was hardly awake while standing. She helped him down into the bed with a gentle touch. Before Timmy’s head could hit the pillow, he had already succumbed to the mercy of slumber. Vivian situated Timmy’s sleeping body across the bed.

“There, there, you just rest now,” Vivian cooed. She smiled and brushed his hair out of his face. His expression was vacant and innocent, completely relaxed in his restless eye movement. She positioned him across the center of the bed. From beneath, Vivian pulled out a collection of straps and cuffs. Her eyes feasted on the boy’s body, still hearing his ticklish giggle in her mind. She sighed. With a smile, Vivian got to work, thankful that she would have the house to herself all weekend long.

Before Timmy’s eyes could flutter open, a soft smile twitched across his lips. He laid on his back, his head fallen to one side. Timmy let out gentle giggles as his senses slowly returned to him. He woke to a faint, teasing sensation sweeping up the length of his foot. His bare sole scrunched and fidgetted. The plush, warm skin blushed beneath the candy licks of a soft feather. His toes wiggled and squirmed, dancing along with the plume that kissed against his creamy arch.

“Wakey wakey,” sang a voice, as soft and smooth as fine velvet. Timmy blinked his eyes open. He looked upon a darkened bedroom, a ceiling fan overhead spinning a wispy breeze down upon his body. His head swam a little as he slowly regained consciousness. Timmy found himself unable to move much. His arms were splayed and cuffed to the top corners of the bed. His legs were pressed and bound together by tightly strapped belts. His feet hung off of the end of the bed where Vivian sat atop a stool, still swishing a light blue feather up and down his sole.

“Eeehheeheeeeheheeeee… Mmmmmhheeheheheee…” Timmy giggled. A brief wave of worry and trepidation came and went, relived by the smile Vivian wore as she watched him squirm.

“Coochie coo, little Timmy,” Vivian said, her voice teasing his ears as softly as the feather teased his soles. She sat staring back at him. She exuded confidence in her position where the boy’s bare feet laid bound together at the end of the bed, perfectly ticklish and framed as being all hers to play with. Timmy giggled and squirmed against the bed. He was still dressed in what he remembered falling asleep, just a pair of dry swim trunks. His shaggy brown hair splayed across the pillow. He tugged slightly at the binds holding down his arms and watched Vivian closely.

“Whhhheeeeehahahahaaa… whahahahaat?” Timmy asked.

“Just having a little fun with my new tickle toy,” Vivian said. She traced the feather slowly up and down his soft, plush soles. Every swipe came with a light flurry of giggles from Timmy’s lips. His feet squirmed and curled, almost dancing along with the feather that delighted in their warmth. “Tickle, tickle, tickle…”

“Heeheeheehhahahahahaaah!” Timmy laughed. The more relaxed he became with the sudden situation, the easier he was able to laugh along with Vivian’s plan. His conscious mind quickly recovered from the grogginess of medicinally induced sleep. Waves of ticklish delight replaced his instinctual trepidation. His head fell side to side. His feet squirmed, but never in a way that could avoid Vivian’s playful feather. “Heeheehehahaha nnahahahah! I’m sooooahahahah ticklish!”

“I can see that, cutie,” Vivian said. “Such a sweet, adorable, ticklish boy I have here. Coochie coochie coo…” As she kept swiping with the feather on one foot, Vivian quickly added her hand to the other. Her long, well manicured nails started skittering like scurrying bugs across Timmy’s other sole. His foot was large and velvety soft to the touch. The immediate change saw Timmy leaning his head back. He belted out heavier laughter, his body squirming more feverishly than before.

“Nnnnaaaaaaahahahahahahahahaaaaa!!” Timmy cried out. “Aaahahahahah so ticklish!!! So ticklishhhhhahahahahahaha!!” Vivian chuckled. The feather lapped at the boy’s foot, up and down his creamy white arch. Vivian’s nails traced all around his other sole. They scratched at his heel up to the base of his toes, making sure to reach every ticklish inch of Timmy’s foot.

“Someone has some adorably ticklish tootsies, I see,” Vivian taunted. Her playful tools tickled all over Timmy’s helpless feet, leaving the boy rich with hysterical giggling. Vivian smiled through it all. “Mmmm, ticklish boy laughter. The best sound in the world.” Vivian’s nails and feather reached Timmy’s toes after having spent all the ticklish nerves in his soles. Timmy’s squeals heightened. He yelped and blushed deeply, laughing and twisting harder and harder.

“Aaaaahhhhahahahahahahahaaaa!!! Nanahahahahahahat my toesss!!!” Timmy shrieked. The boy tossed against the bed. Vivian flossed the feather through his toes slowly while her nails skittered across the delicate, pink pads. She sat silently listening to his nectary tune of his laughter.

After Vivian had satisfied herself down at Timmy’s feet, she drew back and allowed the boy a moment to catch his breath. She stood and watched him recover, heaving in deep breaths and smiling weakly back at her. His slender torso rose and fell rhythmically. A soft blush colored his cheeks. Vivian twirled the feather in her fingers as she stared down at him.

“Now then, where is ticklish Timmy really ticklish?” Vivian asked, her tone gaming and patronizing. Timmy pulled his eyes away from her for a moment.

“I-uh-e-everywhere,” Timmy said softly. Vivian smirked.

“Good, then we can have fun for a good long time,” she said, looking down at Timmy’s belly. She sat down next to the boy and hovered the feather over his stomach. Timmy breathed in deeply and slowly. He stared down at the plume inching closer to his belly. His hands balled. His lips pulled up into an anxious, yet eager grin. His eyes were wide and yearnful. Timmy bit his lip as he prepared for the feather to make contact. Vivian’s lips curled. She studied his expression as she lowered the feather downward. With a gentle flick of her wrist, she swiped the plume across Timmy’s tummy. Timmy let out a small yelp before squeaking out soft giggles.

“Eeeeemmmmehehehee!” Timmy laughed. Vivian gave his stomach a few more sporadic swipes with the feather, each making the boy giggle and twitch.

“Aww, ticklish Timmy got himself a ticklish tummy?” Vivian asked. She chuckled and nibbled on her lip. She began tracing the feather all over his stomach, skating it from one end to the other in delicate circles. Timmy’s giggles quickly grew into increased laughter. He squirmed against the bed, his tummy wiggling and writhing beneath the mischievous feather.

“Naaahahahahahahahahaa!! Staahahahahaha!!” Timmy laughed. Vivian drank it all in. She delighted in the boy’s ticklish laughter and anxious squirming.

“Coochie coochie coo, ticklish Timmy,” Vivian taunted. “I’m still just teasing right now. I can’t wait to really drive you crazy with tickles!” The feather began fluttering around Timmy’s tummy faster. Vivian brushed it with quick strokes all over, painting every supple inch of the boy’s sensitive belly. Vivian continued to tease him with ticklish phrases. An endless stream of ‘tickle, tickle, tickle’ and ‘coochie, coochie, coo’ played over and over again, each seeming to make Timmy more and more receptive to the feathery stimulation.

“Naaaahahahahahahahaaa!!” the boy squealed with laughter. Timmy blush through the emasculation of being so helplessly tickled. Coupled with the childish phrases that made him feel that much more powerless, he endured the ticklish playtime with a flurry of light, melodic laughter. His head tossed side to side, sending his hair outward in a scruffy mess. Vivian explored all over his stomach with the feather, sweeping across every ticklish spot.

“‘Ticklish Timmy’,” Vivian said with a smirk. “I think that’s what I’m going to call you from now on.” She chuckled. With her other hands, she reached down to brush her nails against his stomach. Just a quick little swipe earned her a sharp yelp from the boy. Another got his light, fluttery laughter to rise into deep, ticklish howls.

“Whhhaaaaahahahahahahaha!!! Naahahahahahahahahaaa!!!” Timmy cried out. His belly shifted wildly, yet remained perfectly vulnerable to Vivian’s ticklish treatment. The skin was smooth and delicate, plush yet firm. As before, Vivian added her nails to tickle along with the feather. She casually wafted the feather over his stomach while her long, red nails danced and explored the area. They scribbled with wispy scratches. They circulated all over, reaching down to both sides and inching back toward the middle. Timmy belted out ticklish laughter, his giggles filling the room and pouring out into the hallway.

“Tickle, tickle, ticklish Timmy,” Vivian repeated, her voice getting louder to rise over his. She giggled, sitting comfortably to work over his ticklish stomach and admire all of his adorable reactions. The boy wheezed through his laughter. His hips twisted and bucked. Vivian skittered her nails up and down the center of Timmy’s midsection. They kneaded at his sides and counted his ribs. The feather twirled around the boy’s stomach, spiraling toward his belly button. As Vivian reached Timmy’s shallow navel, she dipped the fibrous end of the feather down into it. Timmy’s back arched. He let out a shriek that melted into a new fit of ticklish laughter.

“NNNAAAAAAHHHAHAHAHHAHAAHHAHHA!!! STAHAHAHAHAHAHHA!!!” Timmy shouted. Vivian let out small coos of satisfaction with his reactions. Encouraged by the boy’s apparent hysteria, she twirled and twisted the feather inside his navel, having the delicate fibers fluff and scrape against all sides within. She gave it a light touch, the lightest touch she could manage, but even the most delicate approach she could take left Timmy squealing with laughter and pulling at his binds.

“You have the cutest little laugh, ticklish Timmy,” Vivian said with a small snicker. “Mmmm, I could listen to it for hours and hours…” The feather kept a devilish pace twirling around inside his navel. She fluffed it in and out, all while her fingers continued to scribble and scratch around the outside. She studied his movements and did all she could to keep up with his squirming body. She pictured all of the ways she could take advantage of Timmy’s overwhelming ticklishness. Her eyes, upon scanning the boy’s body, fell down to his shorts. Through his restrained thrashing, she noticed it. The thrill racing through Timmy’s ticklish body. The excitement and rush he got out of being so helpless and toyed with by tickles. Vivian grinned and noted Timmy’s telling disposition with the way his shorts started to raise.

“EEEEEEEHEEEHEEHAHHAHAHHAHAHAAAA!!!” Timmy continued to shout. His voice was falling from a fluttery, boyish jubilance to groaning and gasping through his laughter. Vivian savored every last note of it before pulling back once more. The feather fell from his navel. Her fingers relinquished the tender tummy. Timmy laid back wheezing. His eyes fluttered and closed. A faint smile still rested across his lips. Vivian rose from her seat next to him on the bed and came up to his face.

“Poor ticklish Timmy,” Vivian said. “All wrapped up with nothing to do but squirm and laugh for me.” She smiled warmly down at him. Vivian cupped the side of Timmy’s head in her hands, stroking his cheek. She brushed his hair to the side. Timmy tiredly rested his cheek against her palm. He slowly steadied his breath.

“I-I’m… I’m… too ticklish…” Timmy said softly.

“I’m sure you are,” said Vivian. She leaned down to his face, bringing her lips up to his ear. She gently whispered. “But you love it, don’t you?” Bumps scattered across Timmy’s skin. His hair stood up. A heat raced through him that left his throat dry. He nervously swallowed, his cheeks glowing pink. He started to speak, to say what he felt like he should. But Timmy fell silent to the sight of Vivian’s smile. She pulled back slightly, meeting his eyes. “It’s okay, ticklish Timmy. No need to hide it from me.”

“M-Miss V, I…” Timmy started. Vivian hushed the boy by pressing a finger to his lips.

“Shhh, save that adorable voice…” Vivian said. From his lips, Vivian walked two fingers down the side of his face like legs. They strolled casually down his neck toward his shoulder. They stopped just outside of Timmy’s armpit, naked and vulnerable. Timmy swallowed again and pulled back instinctively. He watched her fingers and clenched up as they stopped at the stop.

“Mmmm….” Timmy whimpered. Vivian waited. She lingered over the spot while staying close to Tinmy's face.

"Awww, what's the matter, ticklish Timmy?" Vivian asked. "Have I found a good spot?" Timmy's breath shivered in his throat. His eyes were wide, his attentions fully alert. He bit his lip and huffed deep breaths out of his nose. His lips curled tellingly up at the ends. Vivian behan wiggling her fingers just outside of the boy's armpit.

"Mmmmheheehee…" Timmy whimpered some more. Vivian chuckled.

"I'm not even touching you yet," Vivian said. "You want it, don't you? Does ticklish Timmy like being tickled?" Timmy paused. His eyes shifted between hers and her fingers. His body burned, his secrets lifting beneath his short. Timmy swallowed once more.

"I… y-yes," Timmy said, feeling so much smaller than the woman hovering over him. "Please, Ms.V… tickle me."

"My pleasure," said Vivian warmly.

Vivian’s fingers began lightly dancing down into the stretched hollows of Timmy’s armpits. They tapped and strolled inward, each little poke coming with a small burst of tickles that had the boy twitching and squeaking. His giggles were light and nervous, though always eager for more. His pits were slick. They were soft and plush against Vivian’s tickling fingers. She leaned in close to fully experience his boyish giggles. As her nails began to scribble, never leaving the spot, Timmy’s squirming giggles came faster and more flourished than before.

"Aaahhhhheeeheheheheheheheehahahahaa!!!" Timmy started to laugh. His ticklish laughter fueled Vivian’s fingers and encouraged to keep exploring the spot. Her nails teased quickly with feathery scribbles, scratching faster and faster all over the area.

"Tickle, tickle, tickle," Vivian taunted. Her nails scratched all over Timmy's armpit. Timmy squealed with giggles, recoiling and pulling away. No matter how he moved, Timmy had no escape from the scribbling tickles. "Coochie coochie coo, little ticklish Timmy."

"Nnnnaaaahahahahahahahaaaa!!! Nahahahahahahaaaaammmmm!!!" Timmy’s face flushed a deep shade of pink. His arms and legs pulled at their binds. His head fell side to side. Vivian stayed close to him, releasing her scribbling nails all over his ticklish pit and soaking his laughter.

"Aww, such a ticklish little Timmy," Vivian said. "I'm having so much fun playing with my new tickle toy…" Vivian, keeping one hand locked to one of the boy’s ticklish pits, reached over with the other. Timmy saw through teary eyes her other hand slowly move to his other pit, unable to do anything but giggle and squirm. His hips bucked, thrusting wildly the hardened mass of Timmy’s enthusiasm. Vivian’s nails closed in on the other slender dip. Her fingers wiggled tauntingly. Vivian chuckled, watching Timmy’s wide-eyed expression. She left him giggling and anticipating the tickles getting worse. With a sudden burst, Vivian plunged her scribbling nails down against his other pit, tickling both wildly at the same time.

“NAAAAAAAAHHAHHAHAHAHAHHAHAHA!!! MMMEEEEHEHHHEEHEAHHAHAHAHAA!!!!” Timmy cried out. He threw his head back and bucked against the bed. He twisted side to side, pulling against the binds holding him down. His slick, sensitive pits were left fully vulnerable and begging for tickles. Each slight graze of Vivian’s nails sent waves of tickles exploding through his body. Timmy could do nothing but thrash and squeal with wild, boyish laughter.

“Aww, who’s my ticklish little tickle toy?” Vivian asked. Her hands scribbled and scratched away at both of his pits, leaving Timmy howling with ticklish screams. His laughter poured out of the room and into the halls. It filled the house with a symphony of ticklish delight.

“AAAHAHAHAHAHAHHAAHHAA!!! MEEEEEEEEHHEHEHHHAHAHAHAHA!!!!” Timmy laughed. His senses had long surrendered to the authority of Vivian’s ticklish fingers. They relinquished all of him to her, released in waves of hysterics and euphoria. The rise in his shorts rifted and bounced with his constant thrashing and bucking. Vivian watched all of it while her nails worked over Timmy’s most reactive spots.

“My, my, you really like to be tickled, don’t you, my ticklish Timmy,” Vivian said in a slow, condescending tone. Her nails dug into his pits. Faster and faster they scribbled away, scratching against every single sensitive nerve over and over again. His pits ignited with a chained explosion of tickles. Timmy threw his head side to side. He wailed with laughter, still twisting and arching his back against the bed. “Don’t you, Timmy? Don’t you love to be tickled?”

“AAAHAHAHAHHAHAHAHHAHAHAHHAHA!!!! YEEHEHEHEHEEHESSSS!!! I LAAHAHHAHAHAHAHHAAVE IT!!!!” Timmy screamed. Vivian smiled. Her fingers scribbled as fast as they could inside Timmy’s slick pits. She chuckled at his rousing confession. The boy ‘s face glowed a bright red. His hands clung into balls. His toes curled and legs pulled at their binds. Tears came to the corners of his eyes. His laughter was quickly dying down, replaced by quieter gasps of air. The hysterics left his face pulled back in a clenched smile. His chest heaved. His arms pulled as his laughter became more desperate with each passing second.

“That’s a good ticklish Timmy,” Vivian said. “Coochie coochie coo…” Her nails raked and danced within the delicate hollows of Timmy’s armpits. The flurry of tickles that Vivian released through the spots had proven to be more than the boy could bear. His laughter had fallen silent, broken only through small bursting gasps and wailing laughter.

“OKAHHAHHAAHYYY…. AHAHAOKAY….” Timmy cried out. His head swam. His eyes rolled and teared. The delight he found in the engagement had overwhelmed his senses. Vivian continued to push every last gasping laugh out of the boy.

When Timmy’s body started to tire out and his voice faded to deep wheezes, Vivian pulled back. She stood up and watched as Timmy fought for the air his chest so desperately craved. Sweat dripped off of the tips of his hair. The delicate pool boy could only lay and draw in deep, gasping huffs. His arms and legs lay limp against the bed. His eyelids batted sleepily. The rise in his trunks stayed lifted in a tent of his own exposure. Vivian stroked the boy’s sweaty drenched hair out of his face. She caressed his cheek with an almost motherly embrace.

“Good boy,” Vivian said. “That’s a good ticklish Timmy.” Timmy smiled. Through the dense weariness that left his body nearly immovable, Timmy still managed a faint smile. Vivian’s eyes glimmered down at him. “Did you like that?” Her tone was soft and warm, like freshly baked cookies to his ears. Timmy paused before managing a tired nod.

“Y-yes… Ms…. V…” Timmy said. “Th-thank… you…”

“I thought you would,” Vivian said. “You’re a lot of fun, ticklish Timmy. I just know my friends will feel the same.” Timmy swallowed. His cheeks burned. His eyes widened a bit.

“Y-your… friends?” Timmy asked. Vivian chuckled and turned. She walked to the doorway and flipped off the light.

“Goodnight now, sweetie,” Vivian said. “I’m just going to leave you like that for now. We’re going to have a lot of fun this weekend.”