Hadley's Other Cherry Ch. 03

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"Now, Mademoiselle," Nathalie said, "For this set you must take off the modesty underpants." Hadley blushed as she slid the tiny g-string down and stepped out of it carefully. Nathalie smiled at her. "You have a beautiful body, my dear, don't be shy. This will really get him going, I guarantee it."

Nathalie handed Hadley a pair of pink satin panties trimmed with black mesh and lace. Hadley thought they seemed pretty normal until she noticed a big hole where the crotch should be. Hadley gasped, "But... but... these have no...they're open..." she blushed bright pink.

"Exactement," Nathalie replied with a wicked smile, "Put them on, trust me."

Hadley gingerly stepped into the panties and pulled them up. She caught sight of herself in the mirror and immediately blushed. The panties seemed fancy and ornate with their lace and satin and bows, but they did nothing to cover her puffy pussy lips, which were left exposed, framed by only a thin strip of black lace.

Nathalie then dressed her in the matching bra, a black mesh underwire bra with a bow in the center. The cup part of the bra was so low-cut it went under her small breasts, lifting them slightly but doing nothing to cover her teacup-sized tits or her pointy pink nipples.

After she had adjusted the straps, Nathalie stepped out from behind the screen and excused herself. "I must go help Sebastien with something in the stock room, if you will excuse me. Should you require anything, please ring the intercom and I will return."

Hadley thought it was odd that Nathalie would be leaving now, but Jack just nodded. He knew Sebastien had trained his employees in the utmost of discretion. She obviously had felt that this outfit might require a private moment for him and his young lover. Jack smiled as Nathalie quietly closed the door behind herself.

"Are you hiding from me, Hadley?" Jack called to her behind the screen, amused, "Come out so I can see you."

Slowly, Hadley peered from around the screen. She didn't know why she felt so shy all of a sudden. Jack had seen her naked many times, but somehow this lingerie made her feel more exposed.

The look on Jack's face when he saw her emboldened her slightly. She lifted her arms over her head and posed for him, showing off her graceful, lithe body for him. The high heels accentuated her petite frame, lifting her tiny tits and round ass. Jack drank in the lush sight of this teenaged goddess exposing her most private parts to his hungry gaze. His cock stiffened immediately in reaction.

He licked his lips as his eyes traveled up and down her young body: her small perky tits topped with mouth-watering little pink nipples, the milky white skin of her flat stomach, her toned smooth thighs, and the chubby bare pussy lips peeking out of the black mesh panties below. "Hadley, I'm... speechless," Jack told her, smiling. He beckoned to her with his finger, "Come closer please..."

Hadley giggled and she shyly teetered over to him in her gold heels. When she was about a foot away from him, Jack reached forward and grabbing the pliant flesh of her round bum, pulled her exposed pussy towards his face, planting his own lips on the fleshy split between her legs.

Hadley moaned as she felt his tongue snaking between her nether lips, seeking out her clitoris. Jack pulled his head back and studied her sweet teenaged pussy, the lips now wet with his spit. "So beautiful..." he moaned, "So fucking beautiful..."

He pulled Hadley to him and she climbed onto his lap, straddling his hips until her pussy was grinding into him. She could feel his thick charger stiffening through the thin fabric of his suit pants. Jack kissed her soft mouth, lifting her slightly so he could free his now hard erection from the confines of his pants.

Holding his fully erect cock upright, he parted her wet lips with the swollen head, using the leaking tip of his rod to tease her little sensitive clit. He kissed and bit at her lips as she wrapped her arms around his shoulders, her long silky hair forming a curtain around them. She helped him remove his clothes as she continued to grind on his fat tool, lubing the head with her juices.

He growled low in his throat as he wrapped his arms under her thighs and stood, lifting her light body as if she were no heavier than a rag doll. His strong hands palmed the round globes of her ass as he slowly impaled her on his thick erection.

Hadley had to bite her lip to keep from crying out, the sensation of his mammoth meat stretching her open and displacing the plug in her asshole was almost too much. She felt light-headed. Jack held Hadley's petite body up against the wall as he bounced her on his cock, his muscular buttocks clenching and unclenching as he thrust into her again and again.

"Such a sweet... tight... little pussy..." Jack grunted in her ear, "So beautiful and so sweet... it feels so amazing wrapped around my cock...You like my big meat stretching your pussy, baby?"

"Yes, yes, yes... l love it... I love it... I love it..." Hadley whispered, practically chanting it over and over again as he held her and fucked her against the wall.

After a few minutes, Jack slowly lowered her to her tiptoes, groaning as his slippery fat dick slid out of her wet little cunt with a plop. He took her by the hand and led her over to the full-length mirror. He turned her around so her round little backside was pressed against his erection. He brushed her sweaty hair away from her neck and whispered in her ear, "Come here, baby. I want you to see how beautiful your sweet pussy looks while I'm fucking you..."

He wrapped her arm over his shoulder and lifting her legs up from underneath her thighs, he hoisted her tiny body into the air again. Hadley looked between her splayed legs at her swollen shiny pussy lips in the mirror, framed by the black lace of her crotchless panties, as Jack lined up his glistening knob with her vaginal opening and slowly impaled her on his shaft again.

Hadley was mesmerized by the sight of his huge dick, shiny with her juices, splitting her chubby pussy lips open. She watched with pleasure as he sawed in and out of her tiny opening, the fat pink lips stretched taut around his thick, slippery shaft. Jack sucked one of her perky pink nipples into his mouth, and reached around to rub her exposed clit as he bounced her on his cock. Soon Hadley forgot that they were in a store, as she began squealing in orgasm, her tight cunt throbbing and spasming around his pistoning tool.

That was all he could take: as soon as he felt his princess begin to let go, Jack unloaded what felt like buckets of cum into her wet twat.

"Oh fuuuuuck, baby," Jack moaned, "I'm cumming... I'm cumming, baby... I'm nutting that tight little pussy... " Hadley could feel the warm viscous liquid flooding her, filling her up. In the mirror she could actually see his balls spasming as they unleashed their thick seed in her cunny.

Slowly, carefully, Jack lowered them both to the couch, Hadley still impaled on his cock. When she leaned forward onto her hands and knees, his spent prick slid from her open twat and a puddle of thick cum oozed from her stretched hole. It pooled in his belly button as it continued to leak from her body. Jack loved the sight of his creamy load dripping from her juicy teenaged cunt, the glazed, swollen lips and plugged asshole framed by the black lace of those naughty undies.

Jack laughed to himself, gently patting her panty-clad ass. "Well, Hadley," he said, "I guess we're buying you these panties..."

*************

The early morning sunlight streamed in through the two-story windows in Jack's penthouse apartment, the light and heat stirring Hadley from her otherwise peaceful sleep. Jack had slung his arm over her as they slept, and now she wiggled her naked body free, careful not to wake her sleeping lover as she crept out of bed and down the glass stairs to the bathroom.

The fancy lingerie set that Jack had bought her last night was strewn all over the floor along with their clothes. Hadley bit her lip and smiled to herself as she tiptoed over the piles of discarded clothes, remembering how much fun they had had the night before, christening about every surface in his new apartment with their wild sexual gymnastics.

Jack had insisted that Hadley wear the satin and lace crotchless panties out of the store and to dinner at a nice restaurant, where Jack had discretely fingered her exposed pussy under the table, her thoroughly-used hole still leaking his sperm, until she left a big wet spot on the leather banquette. He pulled her into his lap during the cab ride home, grinding his throbbing meat against her slick folds, and they barely made it into the elevator in his building before Jack gave into the need to probe her cummy pussy again. He bent her over and fucked her against the mirrored walls in the elevator, their hands leaving sweaty palm prints and her breath fogging up the glass as he pressed into her from behind. His thick ejaculate still coated the inside of her walls, lubing his sudden intrusion into her tight orifice.

As soon as the elevator doors opened into his apartment, Jack lifted her up again and carried her inside, his erection still buried up her slick cunt. They fucked like animals on every surface they could find: against the glass windows, on the steel kitchen countertops, bending over the dining room table. The memory made Hadley blush with pleasure.

Hadley sat on the toilet and relieved her bladder, the steady stream of hot piss stinging her poor, sore pussy. When she was done, she washed her hands and stared at her reflection in the bathroom mirror. She turned around and leaned forward, spreading her asscheeks so she could study the green jeweled plug lodged firmly in her tight asshole, another present from Jack. Last night, after their marathon fuck-fest, Jack presented her with the large green butt plug in a velvet bag. Though it took some coaxing with his fingers and tongue and a lot of spit and lube, Jack finally worked the fat plug up her ass. He was very pleased with her progress, and it took a lot of control for him not to try and fuck her butt then and there. If she practiced with the biggest plug all week, he told her, she would be able to take his big cock in her virgin ass by prom night.

Hadley's poor stretched asshole felt very sore but she was determined to keep the plug in a little longer, at least until she got home. She was starting to enjoy the full feeling in her bottom, and after all, she didn't become a championship gymnast by being afraid of a little pain...

Hadley tiptoed back across the living room floor, this time retrieving her new panties and bra from the white carpet and setting them on the chair before sneaking back upstairs again.

Jack was having the most amazing dream: in it, he and Hadley were making love in a speedboat out on the water, the sun glinting off of their faces as she laughed, delighted, and the ocean sprayed around their naked conjoined bodies. He rolled over slowly and noticed Hadley's place in bed beside him was empty.

He sat up and immediately saw her: her naked body was framed in the window, the sunlight turning her orange hair into a golden halo as she stood looking out the window at the street below. She gracefully lifted a leg, stretching and humming to herself absentmindedly while she admired the view. She was the most beautiful creature he had ever seen.

"Good morning, Angel," Jack said hoarsely, smiling at her. Hadley smiled and let her leg drop to the floor in one fluid motion. She walked over and stood next to the bed.

Hadley always thought Jack was a handsome man, but this was the first time that Hadley had seen him first thing in the morning. The scruff that had grown on his normally clean-shaven face gave him a sleepy, rugged, masculine look. She reached out a hand, brushing it against his rough cheek. Jack gently kissed her small fingers tenderly and smiled. Pulling her down to him in his strong arms, he kissed her sweetly on her soft pink mouth, his probing tongue parting her lips as she sighed and melted into him.

Jack usually woke up with a raging hard-on, and today was no exception. As he held Hadley's soft naked body against his, she could feel his thick charger stiffening against her thigh. She needed to taste him.

Slowly, Hadley lowered her head, planting a trail of gentle kisses down Jack's chest, her long downy hair tickling the skin of his chest and stomach. When she arrived at the object of her desire, she grabbed his thick member in her small fist and sucked the swollen tip into her warm wet mouth. Jack groaned as she suckled on the sensitive head of his dick. He gently brushed her hair to the side so he could watch his shiny tool slide in and out between her soft lips. Slowly, he began to grind his hips upward, fucking her face gently from below.

She cupped his balls with her hand, tugging gently on the heavy sac while she hummed and slurped contentedly on his meaty cock. Jack needed to slow down or he was going to blow his load in no time. Though it pained him to stop her, he gently lifted her head off his swollen prick. A thin string of saliva stretched from the tip of his tool to her wet mouth. She looked up at him, her lips swollen and her green eyes glazed with lust.

"Come here, baby," Jack whispered to her, patting the bed next to him as she crawled up his body, "Come lie here. I'm going to make you feel so good..."

He kissed her flushed cheeks and the freckled bridge of her nose again and again as he ran his hand down her lithe body until his fingers reached the chubby split between her thighs. He gently parted her nether lips and teased her swollen clitoris with the tip of his finger. When he felt her liquids seeping out of her tiny opening, he eased two of his fingers inside. Hadley whimpered and tensed her small body against him.

"Does that hurt you, Hadley? Are you sore?" Hadley winced and nodded slightly. Jack hated to admit it but they might have overdone it last night. But he couldn't help it: he couldn't get enough of her. "Here, baby, I'll be so gentle..."

Jack lowered his head to her swollen pussy and gently lapped at her wet split with his tongue. Hadley ran her hands through his hair as she moaned and shivered in pleasure.

After a few minutes eating her sweet pussy, Jack withdrew his fingers from her drooling twat and ran them down her crack until they found the fat metal plug lodged in her little, pink asshole. He tugged on the plug while he sucked her clit, and Hadley groaned in response, squeezing his head between her small thighs. Slowly he worked the plug in and out of her ass until it slid slowly from her tiny body. Hadley suddenly felt very empty.

"F-f-fuck me, Jack," she moaned, shivering. Jack looked up at her. Her eyes were shining as she nodded her permission. "Please, Jack... I want you inside me."

That was all the encouragement he needed.

"Turn over, baby," Jack said to her, "Get on your hands and knees for me." Hadley rolled over onto her tummy and raised her tiny tush into the air. Jack grabbed her slim hips in his large hands, holding her steady while he knelt behind her. Holding his heavy cock in his hand, he slowly fed his pulsating dick into her snug pussy. Hadley groaned as he filled her full.

Gripping her smooth flanks, Jack pushed in and out of her widening passage, each time he pulled out slightly, the hot walls of her teenaged cunt clung to his pistoning shaft like a warm fist.

Of all of the positions Jack fucked her in, doggystyle was by far her favorite, and Hadley moaned and wailed as he humped her, his huge dick felt like it was fucking her inside out. She reached underneath and feverishly diddled her clit as she took the pounding, until her pussy dripped and juiced, lubricating his passage.

As Jack steadily quickened his pace, he palmed her round booty, enjoying the feeling of the firm flesh in his hands, her tight cunt throbbing and squeezing around him like it was milking his prick. He spread her cheeks apart and studied her asshole as he fucked her. The tight pink balloon knot had stretched open slightly, gaping ever so slightly into an inviting hole about the size of a dime, clear lubricant still glistening around the rim.

Hadley felt Jack's fingertips brush across her sensitive anus and she shivered in response. Still thrusting into her small body, Jack sucked two of his fingers into his mouth and then slid the slick digits into her open backdoor. Jack finger-fucked her bootyhole as he continued to hump her, sawing the thick digits in and out in counterpoint to the thrusts of his cock.

The intense sensation of being fucked in both of her holes proved to be too much for Hadley. She came in a screaming orgasm, her small fists gripping the white bedspread as her tiny body almost came off the bed. Jack rode out her orgasm but soon he was cumming too, pulling out as he sprayed her teenaged cunt with his sperm, and then pushed back inside her for a few shallow thrusts, his churning balls erupting into her juicy pussy.

He came with such force that when he pulled out of her, some of his load squirted out of her still-spasming pussy and onto his deflating prick, the rest making a small puddle of their combined juices on the comforter below them.

"I guess we've officially christened the bed, sweet thing," he murmured in her ear, pulling her petite body against him and wrapping her in her arms. She giggled in response, her eyelids heavy with pleasure and exhaustion. He kissed her face and stroked her hair as they both came down from their intense orgasms.

After they lay there contented for a few minutes, Jack said, "I'm very proud of you, my dear. Not that I'm surprised, but you've been incredibly diligent about your anal training. This bodes well for next weekend..." Hadley sighed deeply and burrowed into his chest. Jack sensed something was worrying her.

"Are you nervous, Hadley?" Jack looked down at her small, worried face as she drummed her slender fingers against his chest.

"No, not nervous. Just frustrated, I guess," Hadley offered. Jack felt his stomach tense: was she frustrated with him?

"Why, whatever is frustrating you? Please tell me and I'll make it better." He stroked her silky strawberry blond hair and studied her furrowed brow intently. After a few minutes she responded.

"I guess I don't know what to do about prom," she replied. Jack's relief was palpable when he realized he wasn't the cause of her angst. He listened quietly as she explained the situation: how she and Ginny had been planning their perfect senior prom since Junior High, about the beautiful dress she had begged her mother to buy for her, how Colin's flattering invite to the prom made her the envy of every girl in school, and the target of Serena Ackerman's jealous wrath. "And now it feels like it would be less trouble if I just didn't go," Hadley concluded, "Besides I'd rather spend my Saturday with you."

While Jack was genuinely touched by Hadley's honest admission, he admitted to himself that he couldn't let her sacrifice her senior prom for his sake. "Hadley, I would love nothing more than to spend next Saturday night with you, and every Saturday night this month for that matter. But it would be unforgivably selfish of me to deprive you of your prom. Prom is a special night, and it's the last time you get to have one, and I don't want you to regret missing it."

"I know but..." Hadley protested.

"I'll tell you what: let's make a deal. You go and enjoy your prom. Have fun, dress up, enjoy your limo ride, go dancing with your friends. And if, for whatever reason, you aren't having a good time you can always call me, no questions asked, and I will come get you. Is it a deal?" He held out his hand to her.

She searched his face silently for a few seconds and then offered her hand to him. She smiled.