Hadley's Other Cherry Ch. 03

"Push, push, push! C'mon, push harder!"

Coach Snyder walked up and down the length of the gym mat, taking stock of her varsity gymnastics team while they finished up the stretching and conditioning portion of their work-out. Even though their season had already finished, and successfully at that, she wasn't pleased with what she saw.

"C'mon, girls! Just because you're state champions doesn't mean you get to rest on your laurels! Reach past those feet!" She perused the front row of girls, all with their legs stretched out in front of them as they folded in half, reaching for their pointed toes. She stopped in front of one gymnast, her wiry arms tense with effort, her head cradled between her knees.

"Excellent, Hadley," Coach Snyder remarked. She always had a soft spot for the little hardworking, redheaded gymnast. She had been her coach for the past six years and she couldn't believe that Hadley Henderson would be graduating in a few short weeks. Time certainly flies, she thought. "You see how Hadley isn't just reaching for her feet, but past them? You could all learn something from watching her."

Hadley's freckled cheeks flushed pink with pride and embarrassment. She was glad no one could see her face now. She concentrated on intensifying her stretch as Coach walked further down the line.

"Good. Better!" Coach Snyder remarked. "Okay, straddle stretch! Partner up."

As Hadley sat up and looked for Ginny, she clocked Serena Ackerman staring at her and whispering to another cheerleader across the mat. She raised one eyebrow at Hadley, and then whispered something else to her friend. They both giggled loudly.

"Serena! Madison! We're exercising our bodies, not our mouths," Coach scolded them. Serena smiled contritely at Coach Snyder and then glared at Hadley.

"Serena Ackerman is such a bitch!" Ginny whispered to Hadley as she settled behind her and helped her ease forward into a straddle split, "I hate that we have to share our fucking practice with those stupid cheerleaders!" It had long been the arrangement that the varsity gymnastics and cheerleading teams at St. Quentin's Prep did joint tumbling and conditioning practice after their regular seasons ended, but it was no secret that both groups of girls did not get along.

"Everyone knows that cheerleaders are just slutty gymnasts with bad grades," Ginny whispered as she pressed on Hadley's back, deepening her stretch. "I mean, they can't even bother to buy proper leotards for practice. All of them just wear skimpy sports bras and those trashy booty shorts." Hadley giggled then shushed her friend.

"Shhhh, Gin, they'll hear us," Hadley whispered, "We'll get in trouble."

"I don't care if they do hear us," Ginny replied, flicking her ponytail off her shoulder indignantly, "They're bitches. Serena Ackerman has been talking shit about you..."

Hadley felt her heart drop to the pit of her stomach. She had managed to fly under the radar throughout all of middle and high school without incurring the wrath of the popular girls, and she had three weeks left until graduation. She wasn't about to let Serena and her band of airhead followers ruin it now.

"Serena has no reason to say anything about me, good or bad," Hadley reasoned, "I haven't done anything."

"Wake up, Hads," Ginny said, "you totally stole her boyfriend."

"What?" Hadley sat up and locked eyes with her friend, "What do you mean 'stole her boyfriend'?? Colin and I are just going to the prom together. We're not dating," Hadley insisted.

"Oh my God, you can be so clueless," Ginny sighed, "Colin and Serena broke up and then two weeks later he asks you to the prom? You might as well be dating, because Serena doesn't see it any differently..."

"Splits, ladies!" Coach Snyder barked, "This isn't social hour, Virginia." Ginny waited until Coach walked past her until she rolled her eyes.

"Hey! Who's side are you on?" Hadley hissed at Ginny, as she slowly sunk into a full split. She tried to concentrate on pointing her toes instead of the sick feeling in the pit of her stomach.

"Yours, stupid! That's why I have to tell you what I heard. Serena was totally talking about you in the locker room before practice. To anyone who would listen!" Ginny raised her arms over her head in emphasis.

Hadley felt a lump rising in her throat as she studied Serena across the mat. The beautiful cheerleader always wore a full face of makeup to practice, but she had to hand it to her, she was incredibly strong and flexible. Hadley watched as she stretched her long smooth legs into a split, pressing her body into the floor, then raised her arms in the air while flicking her long, perfectly highlighted ponytail over her shoulder triumphantly. Serena was wearing a skimpy but expensive pair of pink booty shorts and a matching sports bra that barely covered her round tits. The pink jewel in her pierced belly button sparkled in the middle of her tanned, toned stomach. She smirked at Hadley.

Hadley couldn't tell if it was the intense feeling of the jeweled butt-plug pressing deeper into her asshole as she stretched into a split, or Serena's piercing stare in her direction, but she started to blush red with indignation.

"Fine," she whispered to Ginny, "After practice. Tell me then."

********

"Okay... here we go..." Ginny said, placing Hadley's coffee frappe in front of her carefully, trying not to spill her own. They settled into their usual booth at the back of the coffee shop. Hadley stirred her drink with her straw nervously, while Ginny scoped the room to see if anyone they knew was in earshot. When she was satisfied no one would overhear their conversation, she turned back to Hadley.

"So I was in the locker room bathroom before practice. I got sick of Madison Hayworth flashing her huge tits around, so I went to change in the stall and I overheard Serena talking shit about you... It wasn't nice." Her blue eyes flashed angrily.

"Jesus, Gin, just spill it already," Hadley spat out. She barely touched her drink except to keep swirling it with her straw. Her stomach was in knots.

"Fine. She was telling her band of blond idiots that the only reason Colin asked you to prom was because you begged him. She said that you promised to give him your virginity if he'd take you prom. And then she said some other things I won't repeat."

"What? But that's ludicrous!" Hadley sputtered, the freckles on her cheeks darkening in anger. "I'm not even..." Hadley caught herself just in time. She had managed to keep her 42-year-old lover a secret and she wanted to keep it that way. No one knew that Jack had taken her cherry a month ago. No one, that is, but her and Jack.

"You're not even what?" Ginny asked suspiciously.

"Nothing," Hadley replied quickly, becoming very interested in her drink all of a sudden.

"Okay, I thought you were hiding something, but this is too much," Ginny insisted, "First you go out without me on the weekends, then you want me to cover for you in case your parents call, and you've been totally distracted, checking your cell phone for texts every few minutes, but you seem to care less that the captain of the Football Team is taking you to prom. I've tried to mind my own business but you're clearly not acting like yourself: what the hell is going on with you??"

Hadley averted her gaze and stared at her hands.

"Hadley, I'm your best friend, but I swear to God, if you don't tell me what's going on right this instant, not only am I not covering for you tomorrow night, but I'm calling and telling your parents that you're out and I don't know where you went."

"Fine! Fine!" Hadley conceded. "I'll tell you! But you have to promise, and I mean cross-your-heart-hope-to-die-stick-a-needle-in-your-eye-promise that you will not breathe a word of what I tell you to anyone. Promise me!"

"Fine, okay, I promise!" Ginny agreed, relieved to be finally hearing the truth from her friend. Hadley didn't know where to start.

"I've... I've been seeing someone." Hadley confessed, her gaze on the table.

"I knew it!" Ginny hissed, "Who? A boy from church? ...a public school boy? ... a college boy??"

"No, no one like that."

"Well, where did you meet him?" Ginny probed, "How come I don't know him?"

"He's my Dad's boss."

Ginny sat in a shocked silence for what felt like minutes. "What. The. Fuck. Hads. Your Dad's boss?? He's gotta be old... he's gotta be..."

"He's forty-two," Hadley whispered, "His name is Jack."

"Oh my God, Hadley, that's sick... he could literally be your father. Is he married??"

"No, no... actually, he's divorced." Hadley admitted, blushing.

"Oh Jeez, that's perfect. And what if your parents find out? You're not like... doing it... with this guy, are you??" Ginny's eyes bulged wide. She couldn't believe her quiet, shy, innocent friend was telling her this. Hadley met her gaze and nodded slowly.

"Jesus Christ," Ginny said, clearly in shock, "you lost your virginity to your Dad's boss...?? He must be a total sicko..."

"It's not like that, Ginny," Hadley snapped, "This is why I didn't want to tell you..."

"Fine, fine, I'm sorry..." Ginny retorted apologetically, "So he's... nice?"

"He's really nice. And he's super sweet to me. It's not like you think... he makes me feel grown up. And he's super charming and handsome and experienced. He's taught me so much..." Hadley could feel herself blushing, thinking about all the times he's coaxed a toe-curling orgasm from her tiny body, making her shudder and squeal under his expert touch.

"Wow..." said Ginny, still absorbing all of this, "So does he have a nice... you know...?" Ginny winked and held out her pointer finger to indicate which body part she was referring to. Hadley laughed and slapped her hand away.

"It's very nice," she offered.

"I can't believe you lost your virginity before me," Ginny said mournfully, "I'm a bit jealous. I always thought I'd be first..."

"Me too, Gin," Hadley said quietly, "But you know, it's not a contest..."

"I know," Ginny sighed, "God, you're such a dirty bird! Forty-two? I hope he's hot!" Hadley just smiled to herself. "For God's sake, Hads, what are you going to do? You're still going to go to the prom with Colin, right?"

"I don't know..." Hadley said, furrowing her brow, "I don't actually feel like it. Besides, it seems like it's been causing nothing but trouble anyway. Maybe I should just skip prom."

"You can't do that!" Ginny exclaimed, "It's too late to back out now, prom's next weekend, the limo's rented, you have your dress... and besides, you'll make Colin super angry if you stand him up! You can't miss prom! We've been planning this for years!"

"Fine," Hadley agreed, but she was still not entirely convinced this was a good idea. Oh well, she thought to herself, it seems like it means a whole lot more to Ginny than it does to me. I can't let her down. "So what about you, Ginny? You still thinking about doing it with Ted?"

Ginny nodded as she sipped her drink happily, "Prom night's the night!"

It certainly is, Hadley thought to herself. Inside her panties her stretched rosebud throbbed around the metal plug.

**********

Jack was in an amazing mood that day.

He'd just gotten off the phone with his decorator. He had ordered all new furniture for his brand new apartment and the last of it, a $10,000 white leather headboard he had commissioned for his brand-new bed, had arrived that morning. It was looking like he would finally be checking out of the hotel suite which had been his home for the past 2 months and moving into his new place tonight. He felt like celebrating.

"Have Marie hold all my calls, Scarlett," Jack ducked out of his executive suite and nodded to his young, nubile secretary. "And come in and take a memo."

"Take a memo" had long been his code that he wanted to fuck any and all of her tight holes ASAP, and even in the rare case that he actually wanted her to take a memo, he usually found himself craving her lips around his cock afterwards anyway. Scarlett smiled slyly, nodded and walked over to the receptionist before letting herself into his office.

As soon as she walked through the door, she gasped as Jack gripped her by the back of the neck and bent her over his leather couch. He pushed her tight pencil skirt up past her hips, exposing her juicy heart-shaped ass, her meaty pussy lips barely concealed by a bright green lace g-string. Jack pulled the thong to the side, exposing the brown crinkle of her anus and knelt behind her as began lapping at her backdoor like a hungry dog.

Jack got lost in eating her ass and pussy for a few minutes, contented to feel her fleshy ass closing in around his face. Scarlett groaned and moaned and ground her booty into her boss' face, enjoying every second of his thorough tongue-reaming.

Soon Jack's tongue managed to push past the slackening ring of her rosebud and he started fucking her opening with his tongue. She smelled earthy, like soap and sweat and the musky perfume of her juicy snatch and Jack groaned in pleasure, savoring the taste. His prick hardened and grew as he ate her. After a few minutes he pulled away and pulled himself to his feet: he needed to fuck that dirty asshole.

He straightened up to remove his shirt and tie and turned to lock the door to his executive suite. Scarlett laid back on the couch while Jack walked over to his desk and retrieved the lube. She peeled her panties off and dangled her ass off the edge of the couch, her red-painted toes wiggling in anticipation.

Slowly coating his mammoth cock with lube, Jack stood over Scarlett and examined her exposed pussy and asshole. Ever since Hadley came into his life, he had lost his taste for any other pussy but hers, preferring to take Scarlett's ass when the inclination arose. He didn't even have to ask her anymore, Scarlett just offered her ass to him first.

Sure enough, as soon as Jack squirted some lube on his finger Scarlett grabbed her ankles and held them up and back, exposing her brown eye to Jack's ministrations. She pushed out with her muscles, and Jack easily probed her butthole with his lubed fingers, preparing her for the imminent invasion of her ass.

Jack withdrew his greasy digits and lined up the bloated head of his fat dick with her open asshole. As soon as he pushed against her brown eye, it gave way, opening itself to his thick tool. Jack clenched his teeth, slowly sinking into the liquid heat of her ass, as it squeezed his cock like a warm, wet fist.

He grabbed her ankles as he fucked her, pushing them up and back to give himself an unobstructed view of her tight butthole stretched around his shaft. He humped her faster, gaining a steady rhythm, his heavy balls slapping against her as he fucked in and out of her slick chute. Scarlett reached a manicured finger between her glistening pussy lips and played with her swollen clit contentedly while he boned her ass.

After a few minutes of solid assfucking, Scarlett came hard, liquid gushing from her empty pussy. It dripped down her meaty lips to her straining bootyhole and onto his pistoning cock, lubing the shaft as he fucked in and out. Scarlett was the only woman he had fucked who could squirt just from anal sex, and to think just six months prior she had been an anal virgin...

"Hold that ass open," he instructed her. She reached down and spread her fleshy cheeks wide from below. Jack pulled out to admire his handiwork. Even without his thick member stretching her open, her asshole gaped wide, a dark "o" waiting to be impaled on his dick.

Jack inserted his meaty tool again, this time just the tip. He teased her winking anus with the head of his cock for awhile, her tight ring suckling on the bloated tip like a small mouth. Jack reached down and massaged her sticky pussy while he fucked her in earnest, sliding into her slippery rectum again and again.

Scarlett's fat nipples pressed against the silk of her blouse, straining against the fabric in two hard points as her huge jugs wobbled back and forth. The bitch isn't even wearing a bra but somehow I feel nothing... Jack thought. He could feel his hard-on waning, and he humped her harder, gritting his teeth in determination. My cock cannot fail me now...

As had been his habit of late, he closed his eyes and thought about Hadley: her lithe teenage body, her innocent face with the upturned nose dappled with freckles, the lush cherubic mouth, the almond-shaped green cat eyes, the pale creamy skin of her flat tummy, her smooth graceful legs, the chubby lips of her sweet teenaged pussy, her little round ass, and the light pink rosebud between those round cheeks. In just a week that hole would be his for the taking. He imagined sliding his lubed up prick into Hadley's untouched virgin ass...

The thought was too much to bear. Jack came with a groan, pulling out of his sweaty secretary's butt, and nutting all over her open ass and pussy. Her soaking snatch was bathed in his pearlescent cum as he emptied his balls in a series of short shuddering spasms. Jack squeezed the last drop from the tip of his spent peter and let it drip from his foreskin onto her pink lips and down her ass crack, wetting the already sopping leather below.

He suddenly felt incredibly uneasy. And guilty.

Jack stood up and staggered toward the window to catch his breath. Why was he feeling so guilty?? His whole life, even while he was married, when the opportunity arose to fuck a beautiful woman he took it, and never felt guilty afterwards. What was wrong with him?

"Thanks, Scarlett..." Jack whispered hoarsely as he hurriedly put away his shrinking schlong and zipped up his trousers. He grabbed his shirt from the chair and proceeded to dress himself. He turned away from Scarlett as she reached for a box of tissues to stem the flow of his jism onto the upholstery.

Get yourself together, man, he said to himself. He thought about Hadley's trusting face looking up at him and he felt sick. He needed to get out of there, to clear his head.

"I'm going out for a bit, Scarlett," Jack said distractedly, "Take a long lunch for yourself and I'll be back later." Scarlett nodded, studying her handsome boss as he practically rushed out of the room. She sat by herself in his office for a few minutes and cleaned herself up. While she wiped the remainder of his sperm from her abused pooper with a handful of tissues, she couldn't help but wonder: what's up with him?

*******

After a long swim, a quick run on the treadmill, fifteen minutes sweating in the sauna, and a cold shower, Jack started to feel more human again.

"Bye, Mr. Cummings!" Becky, the blond gym receptionist waved after him, winking slyly at him as he walked past her. "See you again soon!" She leaned forward and her fake, tanned tits strained at the fabric of her black sports bra.

She had been eyeing him since she started working there and Jack finally gave in to her flirtations one day after work a few months ago. Becky had wandered into the men's locker room with some pretense of refilling the towels and caught sight of Jack's huge, flaccid meat in the shower. After she locked the door and joined him under the warm water, she knelt down and fellated him expertly to his full size until he lifted her up and fucked her up against the shower wall. She had cooed and babbled as he rammed into her tight meaty snatch, moaning in his ear how he was the biggest and best dick she'd ever had.

He immediately felt sick again. He managed to mumble his goodbye and rushed out of the gym, practically slamming into two women entering the gym as he left. He uttered a quick apology and stepped out onto the sidewalk into the blinding sun. He didn't know where he was going but he started walking.

He didn't know what was wrong with him. He was going to see Hadley tomorrow night and he wanted to be unemotional and in control when he saw her. She wouldn't understand if he behaved this way: she was eighteen, but so innocent in so many ways... He was her first, yes, but she was young, beautiful: she could have any man she wanted. What did she want with an older guy like him anyway? If he betrayed any weakness, she would drop him as fast as he had dropped any number of the women he had been with... Kick him to the curb and move on to someone else...