"...SoyeahIwaslikethatwasoooolastyeareventhoughthecatalogueisfromthisyearbutwhafifoneyearnostalgiaisthehotnewthingI'mtotallymissingoutsowhateverIwentaheadandboughtitand…"
At some point Harold couldn't keep up with Lindsay's rambling about fashion trends and Harold ended up just tuning out, her words beginning to blend into one another in a chaotic word salad. He still tried enough to get an idea of what she was saying and giving her nods and "yes" every now and then to give some semblance that he was listening but at that point, trying to understand became a burden.
Truth be told, while he didn't care for Lindsay's obsession with beauty products and fashion trends, Harold thought that trying to pretend to show interest would go a long way in winning her over. He knew well there was some effort he needed to put in, but geez, he definitely had his work cut out for him.
But still, Harold couldn't help but be into the air headed blonde anyways. She was sweet, caring, kind, friendly, and ready to help or stand up for a friend at a moment's notice. She was passionate about her interests even if Harold didn't share them, but he liked seeing how excited she got talking about them. How her baby blue eyes lit up like stars every time she talked about the latest summer catalog or a skin care routine. He had always been enraptured by her childlike wonder and curiosity, finding it adorable every time she saw or experienced something she never had before.
And most importantly she had the biggest milkers of all the girls in the show. Like hoo boy, she definitely won the gene lottery. Her breasts were bigger, fuller, and perkier than most women older than her. A lot of the men would marvel at them when they think she wasn't looking and talk about them when they think she isn't around. Harold's even heard Chris and Chef say something about them and inappropriately talk about what they'd do to her if given the chance.
But Harold couldn't blame them. Lindsay looked as though she was made to be desired and longed for. She was the very picture of an amazing body and boundless beauty, the kind that any hot-blooded man would kill to get a taste of.
And Harold felt like he was the luckiest guy alive. To be walking next to Lindsay. On the way to Wawanakwa's Aquatic Area. Where he'd most likely see her in the most revealing bikini ever. One that would show plenty of skin and most importantly, her major boobage.
Finally they reached the Aquatic Area. Relief passed through Harold and relaxed all the tension out of his body as he finally had the opportunity to soak in some cool water to escape the dreadful heat. And get a nice view while doing so.
"Man, the Aquatic Area's pretty cool, isn't it?" Harold asked.
"I knowww! Probably the only good thing about this nightmare of an island. Reminds me of my sister's place." Lindsay spoke fondly.
"You talkin' Paula?"
"Yes! Wait, have I told you about her before?"
"Uh, yeah?"
"Aww, you actually remembered! You're so sweet, Hank!"
Harold bashfully chuckled. "It's Harold. And thanks."
When Lindsay had her back turned to Harold as they put their stuff down on the lounge chairs, the nerd did a celebratory fist pump, feeling that much closer to Lindsay.
After he stripped down to his swim shorts, he started flexing, curling his arms up and down and hunching over to show off what little muscle he had, hoping to impress Lindsay with what little muscle he actually possessed. Unfortunately for him, she was too occupied with texting away on her phone.
Giving up on trying to get her attention, Harold headed to the showers to wash himself up before jumping in the pool. It didn't take long until he came back to see Lindsay sitting on one of the chairs with a bottle of sunscreen in hand.
"Oh hey! Came in just in time. I was just about to put on some sunscreen! Wanna help?"
Harold's heart skipped and his throat hitched. The offer of getting to run his hands all over Lindsay's hot young body was like winning the lottery. Just the thought of it made him jittery and short of breath.
Harold was on the verge of screaming his answer but he managed to hold himself back. Instead, he calmed down and cleared his throat.
"Uh, yeah. Sure, no prob, Lin." He answered calmly.
"Yay! Thanks, Harley! You're the best!"
Lindsay didn't immediately give the bottle to Harold. Instead, she got up and started removing her t-shirt and her shorts to reveal her swimwear. And Harold's glasses immediately fogged up.
Lindsay wore a very tight and thin Monokini. As the name implied, it was a one piece suit with wide straps that formed an acute angled V across her torso, showing off her smooth, flat belly while going over the middle of each breast pushing them closely together while their pillowy flesh bulged from both sides of each strap. The straps went over Lindsay's shoulders, making another V that went right over her shoulder blades and thinned as it went down her back until they converged into a narrow meeting point nestled between the blonde's ass cheeks like a g-string.
"Ohh gooosssh…" Harold whispered.
Lindsay grabbed her bottle of sunscreen, squeezing a hefty creamy dollop of it on her palm before sliding it slowly across her bare arms, leaving behind a shine like gold under the sun. Harold's eyes followed her hands when she ran them both starting from her slightly thick thighs, rising to the peak of her arched knees, then sliding down to her ankles.
"Uh, Howard? Are you okay? Why you got drool drippin' there? And why's your face all red like a tomato? You got a sunburn?"
Harold snapped out of his stupor. "Huh-wha? Ah! Uhhh, nothing! I'm fine."
"You sure?"
Harold firmly nodded. "Yeah, totally. Man, you look amazing, Lindsay. That swimsuit really uhh… suits you."
Lindsay smiled and flashed a blush of her own. "Aww, thank you so much, Henry! This is one of my favorites!"
As if that wasn't bad enough, Lindsay began rubbing more sunscreen right on her belly, her hands running several laps over her smooth, slightly squishy skin before stopping to fill up on more of the protective cream. After clapping and rubbing her hands together, she rested her hands on the sides of her breasts before sliding over the tall, wide slopes, getting beneath her suit and rubbing over her nipples, delving in between the deep valley of her cleavage. She gave herself a few light squeezes, and Harold caught the way her pillowy mounds collapsed like dough under her fingers.
Harold had become so mesmerized by the sight, he barely registered that his jaw fell open, that drool was dripping from the corner of his mouth. That his face turned into a burning red and. That his cock was stiffened solid beneath his shorts.
"Hanlon… are you staring at my boobies?" Lindsay asked with a pout.
"Huh? Y-I mean uhh, you j- I errr… yes. I'm sorry." Harold admitted with a shameful hang of his head.
"It's okay. Just… don't do it again."
"Right. I'll just uhhh… look over there while you do your thing."
Crossing his arms, Harold turns around. Unbeknownst to him a sly little smile stretched across Lindsay's flawless face as she stared back at him.
"Anyways, I'm already done putting sunscreen everywhere else. You wanna get my back?"
"S-Sure thing!"
Harold couldn't accept the task fast enough. As he sat near the foot of the cushioned lounge chair, Lindsay sat near the other end, her back turned to Harold. She threw a flirty, eyelash fluttering look over her shoulder as she slid the straps of her monokini down her arm, exposing her chest out of his view, much to his arousal and frustration. With her arm over her chest she laid herself on her stomach, her breasts squished between her and the cushions and her head resting on her folded arms.
"Okay, I'm ready, Heinrich!"
With a gulp, Harold brought his knees on top of the cushion, before putting one leg over until both of his legs flanked hers. He shifted up until he was at the most ideal spot, which had him straddling her ass, his crotch just a nudge away. He couldn't help but let his eyes wander all over her naked, flawless back, admiring how well built and taken care of she was. He especially marveled at the way her upper torso gradually tapered into a thin waist before blossoming into a wide set of hips that gave way to a perfectly round and silky smooth ass. She certainly had the makings of a gravure model.
"Gosh…"
"Something wrong?"
Harold shook his head. "Nah, nothing. All good."
Lindsay huffed air from her nose, knowing full well what was wrong.
Taking a deep breath, Harold squeezed a dollop of sunscreen onto his palm, clapping and rubbing them together before bringing a hand to each shoulder. He couldn't help but give each of them a few experimental squeezes, before gradually making his way down, adding pressure as his hands fluidly glided across her skin like an ice skater across a frozen surface, triggering a few moans to slip from the girl.
"Oooh, Heineken… you're so good at that…"
Harold smiled proudly. "Thanks, I learned how to do that in Spa Steve's Masseuse Training Camp."
Harold continued, adding a smaller dollop of sunscreen before covering the rest of Lindsay's back. As soon as he got to her waistline, every horny desire yelled at him to go lower, to her exposed ass cheeks but he managed to fight them back and keep where he was.
Though Harold successfully kept his hands out of that danger zone, he was more than happy to let his eyes linger at least. Despite the lack of any lotion or oil, the curved surface of her ass still shined like it was thoroughly polished, trapping his lustful gaze.
Lindsay had been watching him the whole time. Noticing his eyes lingering on her ass, she launched it up to his crotch, his pitched tent nestled between her cheeks.
Harold couldn't hold back a breathy gasp. The moment her ass touched his dick, electricity exploded from his loins, paralyzing him in place. His hips bucked out of reflex and he barely stopped himself from grabbing her ass with both hands right then and there.
She hummed in amusement as she felt Harold's body get as stiff as his dick, his breath hitching and his hands hanging shakily in the air. The shocked look on his face almost drew a laugh out of her.
Then she pulled her hips and threw her ass back harder, hitting Harold square in the crotch and nearly knocking him back.
The brief little panic he had over falling threw his hands forward and a combination of self preservation and arousal clenched his fingers into her soft ass flesh.
When he finally recovered, Harold gasped as it hit him. What he just did. What he has his hands on at that moment. Despite what transpired up to that point Harold felt like he had broken some unspoken rule between himself and Lindsay, despite neither really establishing any sort of rule.
"Oh gosh, I'm so sorry Lin! I-I-I didn't mean to-I mean I was about to fall and there was nothing to hold onto and- oh gosh I'm so stupid!
"Heehee. It's okay, it's okay! It was my fault anyways, I uhh… moved wrong. You didn't do anything bad at all." Lindsay said with a smile.
"R-Really?" Harold sniffed.
"Of course! But anyways, I think you did goos enough putting sunscreen on." A giggle snuck out of Lindsay's words as she got up and pulled the straps back over her chest, covering herself once more.
"Uhh, s-sure…" Harold sighed, unsure if he was relieved or disappointed.
"By the way, Hayden. Have you put on sunscreen yet?"
"Uhh I did. Everywhere but my back."
"I can get it for ya, y'know." Lindsay proposed.
"Ahh it's okay. I can get on my own. I can get my whole back thanks to Flexible Steve's Contortionist Camp."
"Aww, pleeeaaase?" Lindsay gave Harold the biggest, saddest set of puppy eyes and a big, quivering lower lip.
There was no way Harold could say no to that.
"O-Okay…" He nervously accepted.
Harold sat at the edge of the lounge chair while Lindsay sat behind, her legs flanking either side of him.
The sunscreen felt frigid on his skin despite how hot the sun beat down on them. Harold shuddered as she felt Lindsay's silky hands slide all over his shoulder blades, meeting at the middle of his lower back before climbing up as one up his spine. He shuddered and he felt himself grow stiff under his trunks once again.
"Man, some weather we're having, huh?" Lindsay randomly asked.
Harold gulped, struggling to process what she was saying through her velvety, spine-tingling touches.
"Uhh, y-yeah… it's pretty, uhhh. Yeah."
"Whenever it got this hot back at home, I always did some naked sunbathing."
Harold gulped. "N-Naked sunbathing?"
Lindsay smiled and nodded, her hands ceaseless. "Yup. Believe it or not, I don't like tanning beds, like a lotta girls do. Rather go natural, y'know?"
Harold jumped a little when he felt Lindsay grab onto the side of his shorts and pull down, as if trying to remove them. Between that and thinking about Lindsay being openly nude was getting him riled up like no one's business.
"Sometimes I wonder if anyone actually saw me. I kinda turn my brain off when I do it so I don't really notice what's going on around me."
Harold gasped when Lindsay's hands crept onto his stomach and up on his chest, her palms made slick by the sunscreen. He could feel his cock twitching as she kept touching him. His trunks grew tighter and more uncomfortable by the second.
Then her fingernails, so quickly, so lightly, brushed along the tip of his erection. Most would miss such a furtive touch, but the jolt hit Harold immediately and intensely, throwing his hips upwards.
"I really hope someone did. Love it when a guy sees me like… like they want me."
"L-L-Lin, oh g-gosh…"
"Hal? Are you okay?" Lindsay asked with concern.
"I a-am totally… totally peachy! Never better!" Harold nervously tried to assure.
Lindsay shrugged. "Okay. But yeah, I bet a guy saw me through his window and started…"
Lindsay drew close enough for her boobs to squish against Harold's back. A hand started slithering down his stomach. The ensuing whisper carried a heavy heat caressed his ear and froze him to the core.
"...touching himself…"
"Ohhh gooshh…"
Lindsay had her hand clenched on Harold's bulge, fingers digging into his cock through his shorts. She gave him a few playful squeezes, drawing little moans and twitches out of him. His hips bucked desperately against her hand, trying to squeeze as much sensation from her as he could.
"You like that, Horace?" The hot whisper snaked into his ear, her tongue close enough to brush against him.
"Y-Yes…" His words tumbled through a strained sigh.
"I betcha do. Mmm feels like you got something big trapped in here and he wants to come out and play. Would you like that?"
Harold groaned. "Y-Ye-pleasee…
"Then let's take it to the hot tub."
Lindsay sauntered over to the hot tub, adding an exaggerated sway to her walk that drew Harold's eyes to the flare of her hips and the bounciness of her ass. When she got to the hot tub, she made sure to stretch her legs out as far as she could, and let them hang just long enough for his eyes to do a full sweep from her toes to her thighs, before finally bringing them into the hot, bubbling water.
Harold didn't make a second thought before getting into the hot tub with her. They sat close enough for Lindsay to lean against Harold's arm as he hung it over the edge.
"So uhh… what's the game plan, Lin?"
The mischievous blonde giggled. "Well first off. I know you got a thing for me, Huell."
"Harold."
Lindsay went on. "I see the way you look at me. It's the same way a lotta guys look at me."
"Uhhh…"
"I know I'm not the sharpest bulb in a drawer, but I know what guys want. And I know what I want. The question is… are you gonna give it to me?"
Harold nearly jumped when Lindsay suddenly hefted her bubble butt onto his lap. She rolled her hips, his erection sliding between her thinly-veiled crevasse. With every brush of his tip against her, he felt a shock hitting his nerves, bringing him deeper and deeper into his lust.
Lindsay hummed and giggled when she felt desperate hands clinging onto her hips and a stiff cock meeting her thrusts halfway. Those same hands started sliding up her sides, fingers creeping closer to the undersides of her breasts before her hands snapped shut around his wrists, ceasing their advance.
"Lin, please… I wa-I wanna cum.." Harold begged.
"Oh? You want it that bad huh?"
Harold nodded frantically.
Lindsay giggled. "Well, then drop those shorts, Hector."
Harold didn't even care she still couldn't get his name right. He jumped to his feet, all inhibitions overwritten by the excitement of getting touched by the busty blonde beauty. He undid the knot that kept his trunks around his hips, letting them fall to his knees and into the water.
Lindsay's eyes lit up and a huge smile stretched her face wide open.
"Oh my Goooosh, it's so biiiig! I didn't know you could be like this!" Lindsay held a hand over her excitedly giggling mouth.
The comment swelled Harold's heart with pride. He never really compared sizes with anyone else but hearing such a confirmation from Lindsay, who he, as much as he didn't want to, assumed slept with plenty of guys, gave him a boost of confidence he had never had before.
"I remember seeing it when you were naked at the Dock of Shame that one time. You looked so adorable how small you were at the time. Looks like you were always a grower, not a shower!"
Lindsay's praise kept Harold's cock solid and standing, while a bead of precum perched at the tip. Lindsay leaned forward as she gave the fist sized head a kiss. The touch of her slick, soft lips lit up his nerves, sending his dick into a hard twitch. She giggled and cooed at it like it was a shivering puppy.
"So cute. Hey, you wanna put it in my boobies?"
Harold blinked, his horny teenage mind struggling to process the greatness of her offer.
"Wha-Huh?"
Lindsay said no more and instead pulled the straps of her monokini down her arms, freeing her prodigious, pillowy mounds with a hefty bounce. Her breasts were literal golden globes, bathed thoroughly by the radiance of the sun, giving them a sheen that Harold swore he could see his reflection on. Each perfectly round fun bag was topped with almost pastel-like pink nipples, like cherries on top of a sexy sundae.
"Boooooobies…" Harold moaned like a zombie.
Holding them both from underneath, she bounced them on her palms. Harold instantly became mesmerized by how malleable and wobbly they were. When the offer finally hit him, he could hear the sound of a slot machine when it got a jackpot.
"Right here, Hilbert." Lindsay said with fluttery bedroom eyes.
Harold didn't delay this time. Holding himself by the base, he stuck his thick cock into the narrow valley of Lindsay's bare cleavage. Her flesh gave way to his advance and molded around him as Lindsay kept her boobs tightly shut. The head of his dick popped up from the top of her breast slit.
Harold moaned, unable to bear the overwhelming pleasure brought by the doughy softness of Linday's boobs. He froze in place, his hormonal mind knowing exactly what to do, but his nerves were too paralyzed to signal the rest of his body.
So Lindsay acted for him, stroking her Double Ds back and forth on Harold's member. Enduring such velvety goodness was a Herculean task the boy seldom had the mental and physical strength for, and after about ten seconds, he started bucking his hips against her, chasing the orgasm that was approaching from the horizon at an alarming pace. He held the sides of her breasts, embedding his fingers into her plush flesh like he was holding onto her hips and having proper intercourse with her.
Lindsay noticed Harold's bulbous head popping in and out of the top of her boobs like a game of Whack-a-mole. Licking her lips, she tilted her head and caught his cock in her mouth, her lips tightly puckered on his glans while her tongue ran circles and straight lines all over it.
"Hahh-Hahhh, Lindsayyy… you-your mouth feels sooo good…" Harold moaned.
Every time Lindsay's tongue lashed over Harold's pisshole, his hips jumped involuntarily, pushing a few inches of his huge cock past her lips, which took her off guard but being used to this kind of thing, she let it slide. Over her tongue.
After a while, Harold's body shuddered hard and his thrusts slowed down and grew erratic. "Argh! Gosh! Lin, I-I'm… I'm gon- I'm cumming!"
Before Lindsay could react, he shot forth several bursts of thick, creamy cum right into her tits. He froze in place, hips spasming and dick throbbing with each spurt. His seed dripped from the bottom of her cleavage and when he pulled out, it briefly tethered to his dick. Lindsay parted her breasts and looked curiously at how his discharge stuck them together.
"Whoa you came so much…" Lindsay said with a pout.
"I-I'm sorry… I uhhh, didn't know I could shoot that much…" Harold sheepishly rubbed the back of his head.
"It's okay, it's okay. It happens sometimes."
Lindsay started wiping her boobs with her hand, trying to gather every splattered spot. Once she got it all, she brought her hand to her mouth, and puckered her lips on her palm, loudly sucking and slurping up all of Harold's cum and gulping every single drop until her hand was clean. She gave a loud "ahh" sound like she just had a refreshing drink.
The sight of her eating up all of his cum like that made Harold's cock blast off back into its prior hardness.
"Ooh looks like, big guy's rarin' to go again!" Lindsay licked her lips as she eyed Harold's plump pecker with hunger.
Harold stiffened when she started stroking it. She gripped it tight as she made a slow, yet smooth journey up and down every thick inch. The way it twitched in her hand with every flick of her wrist slowly started to rile her up.
"You could touch me too, y'knooowww." Lindsay suggested in a sing-songy tone.
"O-Oh right…"
Harold didn't think twice before pushing a hand into each ample breast, each palm holding a fistful of jiggly chest meat. The doughy softness and elasticity of her breasts made it addicting to squeeze them and Harold took as much advantage of his permission as he could. He even went so far as to wrap his lips and lash his tongue on one nipple while he pinched and pulled the other. Then he brought them both together and sucked both nipples at the same time. He pulled with both his lips and his teeth, making the blonde bimbos big boobs stretch like balloons.
"H-Hah… I can't make milk yet, silly…" Lindsay giggled as she felt Harold suck her tits like his life depended.
"I'm sorry… your-mmph. Boobs are-mwah! So f-frickin' hot!"
"Heh. If you think that's hot, you haven't seen anything yet. Can we go back to the chair?"
Harold was tempted to keep enjoying Lindsay's tits for a bit longer, but he found the restraint to give her space. She grabbed the bikini that was wrapped around her hip before pulling it all the way down to her leg. When she pulled from beneath the surface of the bubbling water of the hot tub, she tossed it off the edge. Then she grabbed his hand, leading him back to the chair while his eyes remained glued to her finely sculpted ass.
Harold crawled onto the chair with her. He was close to mounting her before he was stopped by a foot on his chest.
"Wait…have you ever… y'know, done this before?" Lindsay asked.
Harold shook his head. "Nope. Same with everything else we did earlier."
"Oooh, so you're a virgin! Wow, none of the ones I've been with have ever been this big. How'd you never get a girl with this thing?"
Harold shrugged. "Never got this far with one I guess."
"Oh, I gotcha. Well usually the virgins I've been with don't last very long in my pussy. Even with condoms."
"Speaking of which, should we like, use some?" Harold asked.
Lindsay shook her head as she smiled. "No need! I always love going all natural and feeling it all without anything in the way. Lotta guys do, too. And besides, I'm on the pill. So you can cum lots inside me all you want."
"Oh gosh…" Harold blushed hard and his cock pulsed.
"Anyways, we're yappin too much. Let's finally get to it, Horus!"
With "come hither" eyes locked onto Harold, Lindsay laid across the length of the cushioned lounge chair, spreading her luscious legs wide enough to reveal her tight, hairless pussy. She spread it wide open, showing off her mushy pink insides, dripping with her sticky juices and aching to snap shut around a cock at a moment's notice.
"C'mere, Handel…" She huskily beckoned with a fluttering of her eyelashes.
Harold could not mount her fast enough. His erection was solid enough to stay on target as he pushed in. It took less than a second to bury all ten inches deep inside her, to which her snatch snapped shut around him. Harold shuddered hard as he felt the hot tightness consume him, her slick vaginal walls rippling up from the base to the tip in some expert contraction technique.
"Sooo how does your first pussy feel?" Lindsay asked with a dopey grin.
"Gooosh, Lindsayyy…"
Harold groaned while he slumped onto her naked body, her titties cushioning his fall. Lindsay giggled, finding his reaction adorable and understandable.
"Man, Lin… you're so tight! You feel really good…"
Lindsay smiled proudly. "I get that a lot!"
"Really?"
"Yeah, like all my ex boyfriends, ex friends with benefits, my friends' dads, my neighbor Mr. Tran, the entire football team, the basketball team, both of their coaches, my Algebra teacher, the Science Teacher whose class I don't even have, the school janitor, the Vice Principal, the Superintendent, my uncles, my dad, my stepdad, every guy contestant on Total Drama, all the interns, Chris, Chef… and now you!"
"O-Oh."
"But enough about my sex life. Let's start yours out with a bang!"
Harold set a decent pace as his cock split and shut Lindsay's flooding folds. He found her even tighter when he tried to pull back, much so that her pussy tugged at his tip, pulling and lifting his hips. Whenever he pushed back in, the vice-like grip came back to him in full force. His loins burned hotter every time he went balls deep in Lindsay's suckling snatch, which at times kept him stuck briefly.
"O-Oh gosh…" Harold's hips began to spasm.
"Ya like how that raw pussy feels, Herrington?" Lindsay asked with huffs of breath between words.
"Yeah! Yes I frickin… it's so gooood…"
Harold grunted, his hips moving faster, his balls slapping against her ass as Lindsay's cunt kept clenching his cock in all the best ways. He felt trapped, not just physically, but mentally, his brain unable to allow him to pull away because the squeezing heat engulfing loins was too addicting not to keep wanting more of. It didn't help that Lindsay had her limbs wrapped around him and moaned in his ear.
"Oooh, you're hitting me sooo deeep!" Lindsay cried out, back arching and mouth wide open as she loudly expressed her pleasure.
Harold noticed that every time he went balls deep in Lindsay he felt something pucker against his glans like a pair of tightened lips. Whatever it was, it shot a sharp stab of pleasure that shot up the length of his dick every time he struck it. It stuck to his tip briefly before he pulled back but he felt it acutely every time. And it was getting him inches away from the edge.
"Arggghh, Lindsay, I think I'm getting close…"
"Ooh, really?" Lindsay beamed with glee, shining her pearly whites.
"Y-Yes! Ohh gosh I don't think I c-can hold it back…"
Harold was already feeling the sharp pangs of pleasure quickly overwhelming him. The practiced way Lindsay massaged his member was bringing forth his orgasm faster than he could hope to react to and stronger than he could defend against.
Lindsay pulled Harold closer, arm wrapped tightly around him as his thrusts became slow and jerky. She could feel him throbbing hard inside her and her vast experience told her what was inevitably cumming. She brought her lips close enough to his ear that he felt her breath making him shiver.
"Shoot a lot inside me, Harold... Fill me up good!"
"Haaahhh, Lin-Lindsay! Lindsaaayyyy…"
Harold cried out as he ejaculated into Lindsay's waiting pussy, filling her tight, slippery insides with his seed. His cock drowned in his thick, plentiful fluids as it all flowed into the blonde's womb, and leaked out of the cracks between their mashed flesh, pooling on the lounge chair. When he pulled back, Lindsay tightened her pussy's grip, trapping him in place.
"Oh gooosh, Lindsay… I don't think I've ever felt that good before..." Harold laid his head on her boobs like they were pillows.
Lindsay sighed with satisfaction. "It felt good to me, too. You came a lot! Mmm so warm…"
"Sorry if I uhh… wasn't as good as all the other guys you've had before…" Harold shyly looked away.
Lindsay waved her hand. "It's okay, it's okay! I don't really like to compare guys I've been with. The important thing is, I felt good and you did, too. I had fun. Did you?"
A small smile crept into Harold's peach fuzzed lips. "Heh. Yeah, I did."
"Yo dudes!" Harold recognized that sporty red jumpsuit walking into the area.
"Hey guys. What's going on?" Following the aspiring athlete was the gentle giant in his usual tight green shirt.
"Tyler? DJ?" Harold asked in confusion.
"What's happenin', Harold?" DJ greeted.
"Hey, hottie. I see you're letting our boy Harold hit it!" Tyler addressed Lindsay.
"Dang, looks like he shot a lot in ya too." DJ pointed at Lindsay's cum filled cunt.
"Mmm, yeahhh... It's his first time, by the way." Lindsay giggled.
DJ raised a brow. "Oh, no kidding?"
Tyler raised a celebratory fist. "Dude, nice! Surprise you haven't gotten to her by now."
Lindsay nodded. "Yeah, I guess we got the right moment today."
"Well, how was it bro?" DJ asked.
"It was... It was awesome." Harold said with a drunk smile.
Tyler gave a single laugh as he nudged DJ with his elbow. "Heh, don't we know it?"
"Oh right, you two have been with her too, huh?" Harold wasn't surprised.
"Yeah man, every dude has. Even Cody and Ezekiel." DJ nodded honestly.
"What the heck, those two got to her before me?" Harold gave Lindsay a shocked questioning look.
Lindsay shrugged. "Eh. I give it up out of pity sometimes."
Tyler nodded. "I remember my first time with her... We banged on top of the sink in the communal bathroom. Bro, my balls were drained good that day!"
DJ laughed. "For me, it was out in the forest and we were just hanging out talking about animals and the next thing I knew, I was raw-dogging her and nutting in her like... I don't even remember how many times, but it was night when we finished."
"Wow... Sounds like you dudes had great times with her." Harold said.
"Mmm, I know I did..." Lindsay smiled salaciously.
"You ain't already finished yet are you?"
"Uhhh, actually I think I can go again." Harold said, noticing he was still hard while lodged in Lindsay's pussy.
"Ya need some pointers, little dude? Y'know, so you two would have a good time." Tyler asked.
Harold shrugged. "Sure, why not?"
"By the way, this is your first time like... Having sex at all?" DJ asked, scratching his face.
Harold nodded nervously, somewhat ashamed of it.
DJ flashed an encouraging smile. "No biggie. We got your back."
Tyler chuckled. "At least you can still get it up, lil dude."
"And how many times ya…'finished', Harold?" DJ asked.
"Like twice already."
DJ nodded. "Oh, nice. Not a lotta guys can pull that off so easily.
"Hayden, maybe you could try banging me again while they give you pointers, alright?" Lindsay suggested.
"Uh, sure."
"Here, let's do it this way."
Lindsay gave Harold a small nudge, prompting him to pull his worn, cum-drowned cock out of her tight, flooded sheathe. His dick, still solid and standing, bobbed out of her with a heavy sway.
"Whoa, nice cock bro!" Tyler said with a thumbs up.
"For sure. He really packin'!" DJ remarked with a smile.
"Mmm, he can beat my baby sack just like you two." Lindsay commented, flashing a flirty look at Harold.
"Aww shucks, guys. Thanks. " Harold blushed as he bashfully rubbed the back of his neck.
Lindsay shifted her body until she stood on all fours on the lounge chair. She wiggled her ass and fluttered her eyelashes to get him up again, which worked like a charm.
"Yeah, that always gets me goin' too." DJ laughed.
"Crap, it's getting me goin' right now." Tyler folded his hands to hide his bulge.
Harold held Lindsay by her ass cheeks. The sight of her flawless pussy froze his mind in place and pulled his raging hardon forward. His hard, lubricated dick split her soaked, silky slit open and felt her soft flesh spreading wide to accommodate him. She squeezed tight, giving the young man some resistance as he delved inch by inch into her.
"Oh gosh, she feels so good, guys..." Harold spoke breathily.
"Breathe dude. Pace yourself. You're still sensitive." Tyler suggested.
"Yeah man, don't go so hard after you just nutted. Gotta take it a bit slow before you can really give it to her." DJ added.
Tyler nodded in agreement. "True. And you can make her feel good in the meantime. Like so. Move back a bit bro."
Harold pulled back, but kept his dick still inside Lindsay. After sticking his mouth in his fingers, Tyler reached between Lindsay's thighs and started rubbing somewhere on her pussy. Harold wasn't really sure what he was doing, but it was drawing a moan out of the blonde. He watched closely at the way he moved his arm and felt Lindsay's cuntal walls pulsed with every movement.
"Whoa, what are you doing to her?" Harold asked.
Tyler pulled his hand away. "Here, give it a try. Reach under her, reach for her pussy, and look for like a... Hard little button."
"Hard little button?"
DJ nodded. "That's called the clitoris. Or clit for short. Girls love it when you touch it."
"They love it even more when you lick it or suck it or sometimes even bite it." Tyler added.
"It's pretty much the 'instant feel good button'." Lindsay chimed in.
"Go ahead bro, try to find it." Tyler insisted.
Harold leaned forward, his arm curving around Lindsay's body to find her clit. He found the top part of her pussy and felt her outer lips split a bit. He had to slip his fingers between some of her slick pink flesh before finding that "hard little button". The moment the tip of his finger tapped it, he felt Lindsay stiffen and her snatch snapping shut on his shaft.
"Whoa… nice." Harold remarked as he watched the way Lindsay reacted to him rubbing her there.
Tyler smiled. "Right? Ya just gotta take it easy. Have a little fun with it."
"Y'know she likes it in the butt, too." DJ pointed out.
The bigger guy did the same as Tyler, sticking two fingers in his mouth for lubrication before pushing them into Lindsay's puckering asshole, which opened up with little resistance to him.
"Oooh, I forgot how thick your fingers are, Deej!" Lindsay moaned, her back arching slightly.
"For most girls, ya gotta use a little more lube for this one cuz her booty doesn't get wet on its own." DJ said, flicking his wrist as his fingers sawd in an out of Lindsay's asshole.
"But for Lin, just a bit of spit and like ten seconds of fingering is enough for this baby." Tyler added as he gave Lindsay's big butt a few taps as if he was a car salesman.
"Dang. I wish I had a notepad on me." Harold quipped.
"No need. Once you learn by watchin' then doin', you'll never forget." Tyler said.
"Here Harold, you give it a shot." DJ said as he pulled his fingers out.
Harold nodded before sticking two fingers in his mouth just like DJ did. He pressed them two her asshole and sure enough her sphincter opened right up and swallowed both of his digits with ease. Though even with his fingers, he could feel just how much tighter it was than her pussy.
"Ohhh gosshhh, Heifer... Don't stop..." Lindsay mewled in pleasure.
"Yeah man, you should keep thrusting while you do that." Tyler advised.
"Lin sometimes likes it in both holes." DJ added.
"Mmm... I love getting double-stuffed... Helter, do you wanna try doing it with my butt?"
"Uhh, can I fit in there?" Harold asked, noticing how tiny her hole was, even if he could easily slide two fingers in and out of her.
"Sure ya can! Me and DJ both did it at the same time once." Tyler said.
"Really tight fit, but dang it felt good!" DJ said with a smile.
"You two... At the same time?" Harold raised an eyebrow.
"Hey, nothing wrong with sharing one hole with your bro." Tyler said.
"As long as the balls don't touch, it ain't gay." DJ said.
Harold got into position as he squatted and stood on his feet behind her. He held his member up a bit higher and as soon as his head pushed past her asshole, the rest of his shaft followed until he was balls deep a few seconds later. Harold was amazed at how easily she took him despite how big he was and how small and tight her anus looked. And felt.
"Ohhhh gosshhhh…" A deep moan rumbled out of Lindsay's gaping mouth that Harold could never imagine she'd be capable of.
Harold grunted as he pushed his cock in and out of Lindsay's ass. He grit his teeth, trying to endure the way she practically strangled his cock, her tightness even greater than that of her pussy and even he struggled to stay strong while he was sawing in and out of that.
"You're doin great, Harold bro!" Tyler gave the geek a thumbs up.
"Just take it easy and enjoy yourself. Lindsay's holes are meant to be savored." DJ said as he patted Harold's back.
"Keep it up, Handel! Don't stop!" Lindsay urged, while moving her hips back to meet Harold halfway.
Harold's movements were clumsy at first, thrusting at his own rhythm, at an erratic tempo, but it felt like clockwork once he got in sync with Lindsay throwing her ass back at him. The sounds of his steel hard dick splitting open Lindsay's clenching ass as well as the claps of his hips against her big bubble butt echoed all throughout the aquatic area.
Arousal surged through Harold, pushing his hips with long, fast strokes as he took Lindsay's tight hole, stretching her in all the ways he had always wanted to since he first laid eyes on her. Hecould see by the way she moved her hips against him that she was drowning in utter bliss, lost in her happy place, where she truly belonged, her asshole impaled on a fat, throbbing cock.
"So uhh… you gotta really, really pace yourself…" Tyler's gaze darted between Harold and Lindsay, but he found himself mesmerized by the way the former's cock smoothly slid in and out of the latter's ass.
DJ nodded in agreement. "Yeah, can't go too hard too fast or you'll blow in no time. Hey Lin, ya mind slowin' down a bit? For Harold's sake?"
"A-a-ah I can't! I-It's-h-he feels sooo good!" Lindsay cried out, throwing her ass into Harold's thrusts even faster.
Harold became too caught up in his own arousal to focus on trying to last longer. His body quaked heavily and his genitals burned as he drifted closer and closer to his own end.
"Ah geez, Lin! I-I'm gonna blow one real soon!" Harold warned.
"Do it! Do it! Fill my tight little hole with your cum!" Lindsay shouted out in feral glee.
In several strong strokes that ended with both his balls deep in her clenching ass, Harold gave exactly what Lindsay wanted. He felt his testicles twitch and his thick tool throbbed as he filled the girl with globs of his cream. He could see his cum overflowing, sticking to her ass and flowing down her thighs.
Once the boy emptied himself into Lindsay, he finally flopped his sloppy cock out of her sucking, which seemed to pull at him given how he had to put a bit of effort to tug his flaccid member out of her as he got up from the chair. Immediately, his seed flowed out of her tight hole, forming a pooling pile on the cushion of the lounge chair.
"Ohhh gosh… shooo gooth…" Lindsay's tongue hung out, her body twitching in post-orgasmic glee.
"Dang, that's a lot huh?" DJ looked at the way Harold's cum poured slowly out of Linday's anus.
Tyler chuckled. "Made a heck of a mess, dude."
Tyler was cut off by Harold rushing to get back behind Lindsay, who had her ass up but her face smushed into the cushions. He quickly lined himself up, and thanks to his cum-covered cock and Lindsay's ever-flowing arousal, he slipped right into her pussy without a hint of friction. Rather than feel Lindsay's velvety flesh squeezing him like before, his dick slid between her flooded folds like a knife through warm butter.
Almost as soon as he stuck it in, Harold showed little to no mercy or quarter. When he pulled back, he felt and saw his and Lindsay's fluids tether to his crotch in thick, sticky strands, stretching between them as he fucked her in earnest.
"Oh-Oh-Ohhhh ga-hah-ha-hah!"
Lindsay's moans were practically deafening as Harold, compelled by the lust consuming his normally rational mind, started pulling her long flowing blonde locks like reins on a horse while also whipping her bubble butt with his hand, making it jiggle and leaving a pinkish spot on her smooth, fair ass flesh.
"Dang… he's goin' in hard." DJ laughed.
Tyler nodded. "True that… geez, even I never got rough with her even during the first ten times we banged.
"Never thought our boy Harold could be like that. I don't like doing that to girls myself." DJ said.
Tyler and DJ cut their conversation short when they heard Harold's familiar grunts and saw him giving a few hard thrusts before his balls hiked up and he froze in place. Without even a warning beforehand, more cum started flowing into and out of Lindsay's pussy, adding onto what was already forming a thick puddle between them.
"Geez, how many times was that already?" Tyler asked.
"I think that was... Number four." DJ surmised.
Harold didn't stop there and took to flipping Lindsay onto her back. He was on his feet yet again, squatting over her while leveling his continuously raging erection into her pussy, which neither DJ nor Tyler could see under all of Harold's dense, frothing cum practically burying it. But somehow the redheaded nerd thrust right into her and once again buried himself to the hilt, and he was off.
Lindsay certainly had no complaints, as she had been letting Harold do as he pleased while she did nothing to resist or even protest. She let herself get trapped in his web of lust, giggling and moaning and shouting in pleasure so the entire island could hear how much she reveled in getting what little of her brains banged out of her by Harold.
"Not gonna lie... Watching this is getting me a little in the mood." DJ said, rubbing his bulge under his shorts.
"Not gonna lie, I'm feelin it, too." DJ shyly admitted.
"Ya think they'd let us jump in at some point?" Tyler asked.
DJ shook his head. "Nah, let 'em enjoy themselves. This is Harold's first time and we shouldn't get in the way."
Tyler looked a bit disappointed but ultimately nodded in agreement.
"Yeah, you're right. There'll be another time. Maybe after he's done with her."
Tyler and DJ had their attention pulled once again by Harold's grunts, which was also accompanied by Lindsay's own shriek of orgasmic glee. They saw Harold's throbbing cock pumping more of his seed into her hungry hold while he rapidly rubbed her clit and made her squirt like a geyser, joining his fluids yet again and dirtying that lounge chair even more.
And much to the two bystanders' shock, Harold's cock didn't go soft in the slightest and he ended up shoving his cock back up Lindsay's previously used asshole. The teen blonde arched her back as she moaned heavily and her partner fucked her hard right from the jump.
"Okay, that may not be for like a while." Tyler said with a laugh in his voice.
DJ laughed back. "Maybe not even today."
"Little Dude's got more stamina than I thought. But I'm sure he's getting to his limit soon." Tyler predicted.
"Not sure about that. He don't look like he's slowing down even a little." DJ observed.
"Yeah, he's a machine. You wanna like, get 'em both some bottled water or something?" Tyler asked.
"Shoot, I think they need several gallons." DJ corrected.
"Either way, he's gotta learn to stay hydrated if he's in it for the long haul."
DJ nodded. "Totally. Let's go."
The two bigger guys decided to step out without saying a word, figuring that Harold and Lindsay were too lost in their lust for any attempts to get their attention. At that moment, all they cared about was how good they felt and chasing the high of one climax after the next, like they were a pair of sex junkies taking hit after hit.
When DJ and Tyler came back with a twelve pack of water bottles, they had to haggle out of Chef, Harold and Lindsay were still going at it. They didn't even bother calling out to them and simply left the plastic pack nearby. Last they left the two, Harold was lifting Lindsay in his arms, her long, thick legs lifted high up and parallel with her body while he had her in a full nelson and his cock still ramming in and out of her semen-stuffed snatch.
Later in the evening, while DJ and Tyler were getting ready for bed, they both swore they could still hear the "plap plap plap" of flesh on flesh echoing in the distance.