Hadley’s Other Cherry Ch. 01


“Jack? So what is your feeling about reassigning the Fulton account?”

Jack Cummings snapped out of his reverie. He had just been thinking about the last time he ate Hadley’s perfect peach of a pussy until she came in a squealing, toe-curling orgasm. He only got to see his 18-year-old princess on the weekends and it was driving him to distraction. He might as well have not been in this upper-level management meeting.

“Um, I’m sorry… what was that Tom?” he asked, trying not to sound too sheepish.

“Your feelings. About the Fulton account. Should we let the New York office handle it? You’ve got a lot on your plate…” Tom Sharp tried not to roll his eyes. Jack’s head had been somewhere else this whole meeting.

“Fine… that’s fine,” Jack said. Tom frowned. It’s not like Jack to just pass up an account.

“Great, so it’s decided. Let’s table the rest of the account strategy until Monday… It’s too beautiful a day to not be out on the golf course, right? Meeting adjourned.”

“You okay, buddy?” Tom approached Jack and asked him as the rest of the execs left the board room.

“Yeah, I’m fine…” Jack said, aware he had a lot of covering up to do. “Just signing all the divorce papers this week. Making me edgy.”

“I’m sorry, Jack,” Tom felt sorry for the guy, his ex-wife was sure taking him to the cleaners. “Hey, maybe we can play some squash later? Take your mind off the divorce?”

“Sure, that sounds great,” Jack smiled, “I’ll have Scarlet reserve us a court later.”

“Great,” Tom smiled as he watched Jack walk back to his office. “See you later.”

Jack passed his twenty-four year old secretary and tapped on her desk. “Office” was all he said as he walked past her and through the door to his executive office. Scarlet hung up the phone, checked her face in the mirror she hid in her desk drawer, grabbed her memo pad (for show) and followed her boss into his office with a shit-eating grin on her face.

“Close the door,” Jack said, and Scarlet closed the door and locked it.

“I need you to put our Monday Executive meeting on the calendar,” he said, opening his belt buckle and sliding his pants and underwear down. His long, meaty cock sprang free, almost at full mast.

“Sure thing, Mr. Cummings,” Scarlet said approaching him.

Jack sat down in his desk chair, stroking his cock and staring at his nubile, young secretary. Her black hair was tied up in a flirty ponytail. She brushed her bangs out of her big blue eyes and licked her lips, always painted in her signature red lipstick. She knelt between his legs and began taking over for him, tugging on his growing erection and sliding the foreskin back and forth as the tip of his cock swelled to it’s full size.

Ever since Jack had started fucking Hadley Henderson, his employee’s nubile daughter, his hunger for Scarlett had waned slightly. Thoughts of fucking the pretty strawberry-blonde gymnast consumed all of his thoughts and fantasies, and their many weekend rendez-vous had left him quite satisfied… except in one way. While he fucked her pretty pussy until she was sore and could barely walk the next day, he never attempted to fuck her asshole. Jack was worried that such a depraved act might scare away his innocent young goddess and he couldn’t risk that. But still, thought’s of Hadley’s perfectly round gymnast’s ass and the tight pucker between her cheeks drove him to distraction. He craved her sweet asshole. So until he could take her ass, he would settle for the next best thing: Scarlett’s back door.

Jack looked down at the nubile 24-year-old servicing his cock, slurping away happily as he fucked her face with his long thick member, red lipstick smearing along the shaft. Jack reached towards her upraised rump and pulled her skirt up towards him, exposing the skin of her bare ass. “Good girl,” he thought with a smile, “coming to work without panties…”

Jack sucked his middle finger into his mouth, wetting it, then slowly snaked it into the tight hole between her rounded cheeks. Scarlett gasped and moaned, sucking his cock harder, as his finger sank deep into the liquid heat of his young secretary’s tight backdoor. He fingerfucked her butthole for a few minutes with one, then two fingers, opening her up while she continued to blow him enthusiastically. Finally, he had had enough. He needed to take her ass.

“Bend over,” he ordered her. Without any further prompting Scarlett got up hastily from the floor and bent over his desk, mashing her round tits into the tabletop and raising her meaty heart-shaped ass in the air. He felt like a depraved monster, but Jack craved her ass so much he didn’t have time to mess with her pussy today. “That’s right, and spread your cheeks,” he growled low, jacking his thick meat and staring at the delectable sight before him.

Scarlet Büyükesat Escort reached her red manicured fingers behind her and pulled the fat cheeks of her round rump apart, exposing the winking pucker of her asshole. Scarlett was no stranger to taking his large cock up her ass and it showed. The brown puckered ring showed a slight slackening and the hole gaped slightly into an appealing “o” before he even slid in. Her bare pussy lips peeked out below her inviting asshole and he began to rub the tip of his cock between her wet, distended labia as he reached into his desk for the lube bottle. He cracked the lid and dripped a generous amount on his shaft before pressing the opening of the bottle up against her brown eye. He squeezed slightly and let a dollop of the cold lube coat the entrance to her anus. Before it could run down he grabbed his greased-up tool and pressed the bell end of his throbbing cock against her wet, gaping hole and pushed.

“Unnnfff…” Scarlett grunted as the slippery head pushed past the rubbery ring with a pop. Jack clenched his teeth, sliding his fat log deeper into her welcoming ass. She didn’t need too much time to get acclimated to the sensation of his huge cock invading her asshole, and he didn’t give it to her. He spread her cushiony ass cheeks wide with his palms as he began sliding in and out of her slackening passage.

Damn, her asshole looked amazing wrapped around his cock, he thought as he continued to bone her from behind. Her hands now free, Scarlett snaked her fingers between her legs, diddling her clit happily as her boss began to pound her back door in earnest. Jack savored the obscene sound of his hard thighs slapping against his helpless secretary’s upturned rump, watched her writhing on his desk beneath him.

After a few solid minutes of fucking her ass, he pulled his still swollen cock out of her butt to admire his handiwork. Her asshole gaped open lewdly, and he moaned at the sight.

“Look at that fucking hole gape,” he said to himself, pushing apart the fat cheeks with his hands. He watched her open asshole wink and flutter until it almost closed up again, and then quickly pushed his dick back inside her contracting anus. He teased her like this for a few minutes, pulling out and tapping the head of his wet cock against her open ass a few times, then pushing back in for a few strokes.

Each time he pushed his way back in he forced more air up her butthole until her asshole squelched and farted lewdly around his pistoning cock as he plowed her hard. She was so wet he could feel his nutsack getting drenched with her liquids, every time his heavy balls slapped against her puffy lips.

Soon he felt that familiar tingle and pulsing building in his nuts. Jack always came in copious amounts, but it had been at least 12 hours since the last time he came, and he knew he was ready to blow a huge load. And he decided to do it right up his eager secretary’s asshole.

“I’m cumming, oh God, I’m cumming…” he panted. He clenched his butt and ground his hips into her, his pulsing cock buried deep in her fleshy ass, as he spurted thick jets of his hot jizz inside her. He felt her hungry asshole milking every last drop from him, as he drained his balls with a sigh. When he pulled his softening cock from her ass, a torrent of thick cum bubbled and dripped out of her gaping hole and onto his leather desk chair.

“Oh yeah, let’s see that load, push it out,” he whispered to her. Scarlet grunted and pushed out with her butt muscles and some more of his cum escaped with a wet fart and splattered on the gooey leather below.

“Now lick up that cum like a good girl…” he said, watching her with pleasure as she kneeled in front of the desk chair and licked up his load like a kitten at a saucer of milk. He watched as one last drop of cum, still clinging to the rim of her abused pooper, slowly dripped from her ass onto the carpeted floor below his desk.

As he watched Scarlett’s slackened hole start to close up again, Jack’s unending appetite turned his thoughts to Hadley’s sweet like pink pucker of an asshole. God, how he longed to take her ass, to see her tight, lithe body take his whole cock up her tiny back hole. But he was worried she was too small, that he would hurt her, or worse scare her off. Jack frowned. But hadn’t Scarlett been a novice to anal when he first hired her? Jack was a man who knew how to get what he wanted. He’d figure out a way, and even now a plan was shaping up in his mind: He’d buy his little princess a present.

Jack reached out and patted Scarlett’s soft round ass. “That’s a good girl…” he sighed. “And if you don’t mind, tell anyone who comes by that I’m out for the afternoon. I have to run an errand.”


Later Elvankent Escort that night, Jack poured himself a whiskey in his hotel room, and drank slowly as he watched the city below his peaceful 24th floor window. He looked forward to when his new apartment would be ready and he could christen his brand new sheets with his sweet little gymnast.

He was snapped out of his reverie by the sound of his phone vibrating with a new text. He reached for his phone and unlocked the home screen.

Done with practice. Yr place in 1 hr? H

Jack smiled as he typed his reply.

Excellent dear. Don’t change your clothes. See you soon.

A few seconds later her reply popped up:

Lol… Ok c u soon!

She had signed her text with little hearts and an emoji of a blond girl blowing a kiss. Jack chuckled to himself. She really showed her age.

He reached for the little white box on the windowsill, fingering the pink ribbon he had wrapped around it as a present. His cock stiffened in anticipation. “Be patient,” he told himself. But still he couldn’t help but smile.

An hour later he heard a familiar gentle rapping on his door. He went to answer it and was pleased to see Hadley waiting outside. Her long strawberry blonde hair was tied up in a bun on top of her head and her cheeks had a flushed, pink glow. Her tight blue leotard flattened her already tiny breasts against her chest, and the short gym shorts she wore over it, did nothing to conceal her lean legs or her tight little ass.

She smiled at Jack and giggled. “You wanted me sweaty, here I am.”

He leaned in and kissed her soft pink lips. They tasted like strawberry lip gloss. She giggled again. “You gonna let me in, silly?”

Jack allowed her entry, and he couldn’t help slapping her round little ass as she passed him. “Ow!” she said, in fake outrage.

“That’s what you get for sassing me, young lady,” Jack replied, licking his lips. He watched Hadley carelessly shuck off her white tennis shoes and sling her heavy gym bag off of her shoulder and onto the floor. He sat down in one of the armchairs.

“Come here, Hadley,” he beckoned to her to come to him with his finger. She smiled as she gracefully slid across the carpet until she was standing in front of his chair.

“What a silly pair of shorts these are, my dear, they barely cover anything. You wear these outside, young lady?” Jack ran his hands over her tantalizing young body. The tiny shorts bunched up against her puffy little pussy mound.

“Yes, of course I do,” Hadley shrugged, watching him as he ran a finger up her inner thigh and lightly up over her little slit. She gasped and shivered.

“Take them off,” Jack said. She slid the tiny shorts down her slim hips and daintily stepped out of them, kicking them towards her gym bag with a quick flick of her foot. He could see that fabric of her tight leotard pressing into her wet slit, riding up and wedging itself between her round cheeks in back. He leaned forward and inhaled her sweet scent through the fabric. Hadley sighed.

“You miss this sweet little peach?” she said naughtily to him. He moaned and licked at her pussy through the fabric.

“Of course I did, my dear, it’s all I think about…” he replied. Well, he thought to himself, almost everything. “Take off your leotard, Hadley,” he said, “and lie down on the bed.”

Hadley peeled the garment off quickly and threw it in the pile with the rest of her stuff in the corner. Jack watched her, delighted, as she scampered across the room to the bed, her lithe naked body exposed to his hungry gaze. She climbed onto the bed, swaying her tight ass back and forth at him, teasing him. “On your back, Hadley.”

Hadley giggled and rolled over. She grabbed her ankles and brought them back towards her head, opening her delectable little crack for him. “Is daddy hungry for his baby’s little peach?” she asked, naughtily.

“Oh, you know I am,” Jack replied, as he approached the bed, loosening his tie. A few months as his lover had made her naughtier, bolder.

When he reached the end of the bed, he gazed down at Hadley’s perfect pink slit, the chubby hairless labia, with just the hint of her swollen clitoris and inner lips peeking through, the sweet tuft of strawberry blond hair on her puffy little mound, and the object of his affection, her tight little pink knot of an asshole lay hidden below, between her round asscheeks. He sighed as he kneeled in front of her wet slit, inhaling deeply as he pressed his face into the wet groove.

“Oh God,” Hadley moaned as his expert tongue lapped at her swollen bud. “That’s so good, daddy.” Jack’s cock was hard as a rock listening to her moan and wiggle beneath him. He continued sucking on her Beşevler Escort sweet teenage pussy. He was in heaven.

“I can’t stay too late tonight, Jack,” Hadley moaned, enjoying the delicious sensations coursing through her body. “It’s a school night, and I think my parents are on to me. And Ginny’s sick of covering for me. She says if I don’t tell her who my boyfriend is, she’s going to tell on me. Oh fuck…”

Hadley had to stop her narrative as Jack grabbed her ankles and pressed them up and back towards her head, exposing her tight butthole to his gaze. He lowered his head and started lapping at her sensitive back door.

“Oh God, Jack,” Hadley moaned, “Yes….” When he tried to wiggle his tongue inside her tight little ass, she instinctively flexed her tiny body, moving away from him, the sensation was too intense. Jack growled and pulled her back to his mouth. He continued to tease his tongue against the tight opening. With his right hand, he began to diddle her clit while he ate her ass, soon she melted into him, opening herself to his wet tongue.

“It feels so wrong…” Hadley moaned, smiling in spite of herself. She felt so lucky to have found this strong, sexy, more experienced man to initiate her into how wonderful sex could feel. If her friends even had half an idea of what she let him do to her, they would be in shock.

Just then, Hadley felt her climax washing over her, and she gasped, her wet pussy and ass spasming around Jack’s hungry lips and tongue. He felt her throbbing then release in satisfaction.

Jack stood, wiping her wetness from his face and reached for the box on the windowsill. Smiling, he placed it next to her sweaty, panting face.

“Hadley, sweetheart, I got this for you.”

“A present? For me?” She squealed and sat up as she opened the box, sitting cross-legged at the end of the bed. Jack watched her with pleasure as she untied the pink ribbon and opened the lid, lifting out the small metal object.

“What is it?” she asked, puzzled. The shiny metal object had a rounded end, the size of a small radish, the other end had a sparkly pink jewel. “Is it jewelry?”

Jack laughed, “It’s a toy, Hadley, a special toy that gives you pleasure. It’s called a butt plug.”

Hadley’s eyes widened. “You mean it goes in your…” She blushed.

“Yes,” Jack said, laughing at her refreshing innocence, “it goes in your butt.”

“And that is supposed to feel… good?” she asked, dubious about her new gift.

“You like it when my tongue is there, don’t you?” he asked, already knowing the answer. “Roll over, I’ll show you how to use it, dear. That’s a good girl.”

Hadley slowly passed Jack the metal plug and rolled over onto her belly as she eyed it with suspicion. Jack pulled a small pink bottle of lube from the gift box and applied a little to his finger and the end of the toy. “Get on your hands and knees, please.”

Hadley climbed onto her hands and knees, her small upturned ass facing the end of the bed. She gasped as she felt Jack’s wet fingers slowly circling her asshole, she clenched her butt in response. “Now we don’t need too much lubricant this time, as you’re already pretty wet, but you just lube up the toy and your asshole and then slowly and gently ease it in.”

Jack applied the tip of the cold metal plug against her wet pink knot and pushed. Hadley gasped. “Try and relax for me,” Jack requested, “Concentrate on opening up your muscles back there.” Hadley took a deep breath in and out. Jack had bought the smallest size they made, but it was still an invasion for her tiny body.

“I don’t know if I’m going to like this, Jack…” Hadley said through gritted teeth.

“It’s okay, sweetie, just give it a try and if you don’t like it, you don’t have to use it.” Jack had seen her response to his touch, saw how his tongue and fingers on her sweet his asshole drove her wild. He knew that she would grow to like it, she just had to give it a fair chance.

“Oh fuck oh fuck oh fuck…” Hadley chanted as the plug slowly entered her tight hole and suctioned itself inside. It was fully lodged up her tight ass. The pink gem sparkled between her ass cheeks.

“That’s a good girl,” Jack cooed, “give it a second for your body to adjust to it.”

As a gymnast, Hadley was used to pushing through uncomfortable sensations, and as she breathed through the wretched discomfort she felt her full ass relax slightly. “Try moving around a bit,” Jack suggested. The odd sensation was still there, like when her mother used to use the rectal thermometer to take her temperature, but something about it felt perversely good. She reached back and felt the plug with her fingers.

“I like the pink jewel part,” she said, wiggling her hips back and forth. She climbed off the bed and sauntered around, experimenting with the different sensations.

“I want you to wear it home,” Jack said, “and I want you to practice putting it in and out every day until I see you again. Your ass is in training.”

Hadley giggled and looked into his dark brown eyes. “In training for what?”

“For my cock,” he replied.


To be continued….

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