Hadley's Other Cherry Ch. 03

The realization hit him like a ton of bricks: he was in love with her.

He wasn't sure how it had happened, things started much in the same way all of his affairs had. Jack was confident, powerful, used to taking what he wanted, but somewhere along the line he had started to genuinely care about Hadley. Not just care about her: love her. He had always told himself he had loved Vivienne, his now ex-wife, but now it dawned on him that he had simply felt the same way towards her as he had felt towards his car, his fancy suits, their house, any of his valuable possessions: pride, satisfaction, attachment, but not actual love. He was never worried about losing her because he knew he could always replace her if need be. Their recent divorce was painful because it wounded his pride and his wallet, but it had been more of an inconvenience than it had been a heartbreak. But Hadley...

He thought about the way her green eyes sparkled with mischief, the way they watched him, taking in every movement, the way they betrayed so much intelligence and sensitivity and trust... He had no idea how she would react if she knew he fucked other women besides her, but that thought seemed moot now. It seemed that all of a sudden he had lost his taste for other women. Little more than a month ago he barely knew she existed and now he couldn't imagine what he would do without her.

He was in big trouble.

This feeling of vulnerability was new to him and he wasn't sure how to handle it. He thought as he walked down the sunny boulevard downtown: when he was pursuing a woman in the past he usually won her over with gifts and attention, at least that's what did it for his ex-wife. What else did he offer besides his big cock, his handsome face and his money? He shook off his sour mood and formulated a plan.

But first, he would stop and buy that sparkly bracelet he spied in the boutique window in front of him. He felt like he owed Scarlett a present to thank her for putting up with him the past few months. She deserved better and after today he was not going to touch her again.

********

Hadley had been in a rotten mood ever since she had gotten home. Even her father had taken note of her sour face, but decided not to say anything. It was unlike his sweet Hadley to scowl her way through dinner but Harvey guessed that teenagers will just be teenagers sometimes and he tiptoed around it while they ate their dinner in silence. His wife didn't get the memo.

"You excited for prom, dear?" Tricia asked eagerly, spooning string beans onto everyone's plate. "That Colin is such a handsome boy..."

"Yeah..." Hadley said absently, pushing food around on her plate with her fork. Colin Flynn was easily the handsomest boy in her class but she had barely talked to him since third grade. The only thing she knew about him was he had been Serena Ackerman's boyfriend for practically all of high school, and they were like teen royalty at St. Quentin's. She was beginning to wonder what he wanted with her. And if it was worth the trouble... Her mother snapped her out of her reverie yet again.

"I've made an appointment with my hair stylist for you and Virginia for Saturday morning. Then I can pick you both up and bring you home. You two still planning on getting ready here?" Tricia asked hopefully. She couldn't believe her only child was about to go to her senior prom, and she wanted to document the entire day. It felt like only yesterday she was pushing her little Hadley in the swings at the playground. She felt herself getting a little misty thinking about the fact that her baby was all grown up and headed off to college in the Fall.

"Yes, I think so," Hadley said, sighing. She wasn't behaving like a giddy senior, Tricia thought. Back when she was a senior and dating Harvey Henderson she couldn't stop smiling the whole month of the prom. Times are different, she thought with a shrug.

"You make sure you finish all that dinner, Hadley Patricia," Tricia scolded her, visibly worried. "I just picked up your dress from the tailor's and he said he's been swamped all week with prom dresses. It's too late to get more alterations done if your gown is swimming on you." It wasn't like Hadley not to eat after practice.

"Can I be excused?" Hadley asked her father. Harvey slowly nodded. Hadley took her full plate to the kitchen and stalked upstairs. When she was out of earshot, Tricia turned to her husband and sighed.

"I just don't know what's gotten into her," she confided.

"Now, Tricia, let her be. She must have a lot on her mind. Please pass me some more of those beans, they're delicious, dear."

Upstairs in her room, Hadley peeled off her uniform and jumped in the shower. She lathered her tiny breasts and armpits. As she sudsed up her pussy, she couldn't help but graze a finger or two over her plugged backdoor.

She grunted, bearing down slightly as she pulled the heavy metal plug from her gripping ass. She rinsed it off and set it on the edge of the tub while she finished cleaning herself. When she ran her fingers over her stretched rosebud it felt strange, slightly looser. She shivered in satisfaction and stepped out of the shower.

She bent over in front of the full-length mirror and pulled her naked butt cheeks apart to inspect the hole between them. It was still small and pink but much to Hadley's satisfaction, it gaped ever so slightly when she pulled her cheeks open.

She straightened up, fishing a jar of Vaseline out of the medicine cabinet and lubing up her butt plug with it, slowly reinserted it into her tiny asshole. She moaned as she felt it slide into place.

Back in her room, she put on a pair of pink booty shorts and a tank top. As was her habit, she settled herself down on the carpet and stretched again while she did her homework. She opened her legs wide into a straddle split, pointing her toes as she leaned forward and typed on her laptop.

She quickly entered the parental control password, and then typed in "tips for having anal sex first time." Message boards and advice columns popped up and she perused them greedily. Most of them advocated going slow, using lots of lube and doing a quick rinse of the orifice before engaging in anal play, so as to avoid any unexpected messiness.

The plug in her ass felt good, as good as her legs felt while she stretched them. Her asshole throbbed thinking about what it would be like to take Jack's big cock up her ass instead. She was no stranger to stretching and training her body to accomplish difficult physical feats, the satisfaction she felt when she accomplished bigger and better tricks was always the reward to her. And in a week all of the training she had spent stretching her asshole would be worth it as she would no longer be an anal virgin...

She looked up at her prom dress where her mom had put it, hanging from the door jam in a clear plastic garment bag. As soon as Hadley had tried on the floor-length strapless gown she knew it was the one. She remembered begging and begging her Mom to buy it for her until she caved. It was easily the most expensive garment she owned, but as soon as she put it on she had felt like a princess, the way the blush-colored chiffon floated around her when she twirled in the mirror.

Hadley smiled to herself. Next Saturday, she would feel like a princess. But not because Colin Flynn was taking her to the prom, and not because she was going to put on that dress. It was because Jack Cummings was going to be taking it off of her.

Just then her phone buzzed with a text message. She went over to retrieve it and smiled at her new message:

Sweet Hadley: tomorrow night we christen my new apartment. Meet me at 5pm, 1501 Market Street, Penthouse Apartment. Yours, J

**********

As Hadley walked through the lush lobby of 1501 Market Street, her breath caught in her throat. As soon as she mentioned the Penthouse, the doorman had waved her past him to a luxurious private elevator. She shivered as the door opened and she stepped inside.

The whole elevator was covered in mirrors and she studied her face and form as the elevator climbed higher and higher to the top floor. She had changed into a flirty short floral sundress after school and brushed her long straight strawberry blonde hair until it gleamed, shining and falling loose to her tiny waist.

Naughtily, she lifted the back hem of her dress and caught a glimpse of her round ass in her thong. She smiled in satisfaction.

Just then the doors dinged and opened and Hadley quickly dropped the back of her dress and stepped inside the most beautiful apartment she had ever seen. The penthouse was an open-plan duplex with floor-to-ceiling windows looking out onto the downtown skyline. The bottom floor had a living room, kitchen and dining area, and a modern glass and steel staircase led upstairs to the lofted bedroom. The entire apartment was decorated in a clean, modern style, looking simultaneously very opulent and very masculine at once.

Jack was waiting for her as she stepped out of the elevator and watched her with delight as her jaw dropped in surprise and awe. He went to her and taking her in his arms, pressed her tiny body against his. He leaned down and kissed her soft lips, which somehow always seemed to taste like strawberries.

"Hello, sweet thing," he whispered into her ear, enjoying the silken feel of her hair under his fingertips. "Welcome to my new home."

"Jack... I don't know what to say... It's beautiful..." Hadley looked up at Jack, her green eyes shining in wonder.

"Thank you, my dear," he replied, pleased with her reaction, "Let me give you the tour..."

He took her by the hand and showed her the downstairs, which she cooed over, delighted: the kitchen with its steel counters and modern state-of-the-art appliances, the luxurious leather couches in the living room, the blue-tiled bathroom with the jacuzzi tub, the glittering panoramic view of the city below.

"...and now for the best part: the bedroom," Jack said, winking as he took her hand and led her up the staircase to the loft above. Hadley gasped when she saw it.

The lofted bedroom was all white, furnished in the most luxurious materials she had ever seen. A soft white fur rug covered the center of the floor, and a modern white chandelier hung from the high ceiling. In the center of the room stood a king-sized bed with a headboard all upholstered in white leather. The luxurious white sheets and soft down comforter gleamed, completing the soft opulence of the room.

Hadley was speechless. She walked over to the bed and ran her fingers over the 1000-thread-count Italian sheets and purred in pleasure. Jack came up behind her, hoisting her lower half onto the bed so she was kneeling on all fours. He lifted her sundress and peeled down her thong to expose the object of his desire.

Hadley lay her cheek against the soft white comforter and let out a soft gasp as Jack proceeded to eat her pussy from behind. He lapped and slurped audibly as he licked up along the delicious split of her wet labia until he reached her tight plugged asshole. He groaned as he circled the tiny orifice with his tongue.

"Hadley..." Jack moaned, his face covered with her sweet teenaged nectar, as he toyed with the plug in her ass, "you're such a good girl..." Hadley shuddered and moaned in response. Jack tongue-fucked her wet, pink pussy like a man-possessed. Soon his ministrations sent her over the edge. Hadley cried out as she came, backing her weeping snatch into his face again and again.

Satisfied, Jack stood up and watched her come down from her orgasm. Her cheeks flushed pink with pleasure and her face glowed. He ran a hand over her soft bottom and patted it gently, then held his hand out to help her up. "Come with me, baby," he whispered, "I have another surprise for you..."

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

After the new mayor had been elected ten years ago, there were only two sex shops left in town: a seedy emporium off the highway that attracted both sketchy types and squealing bachelorettes in equal measure, and an expensive high-end French boutique downtown that specialized in importing both expensive sex toys and fancy lingerie. Sebastien Leclerc owned the latter, and prided himself on the discretion he provided his clientele, most of whom were very wealthy and enjoyed their privacy. As a gay Frenchman in a busy but small American city, Sebastien understood the need for privacy.

Jack Cummings had been one of his best clients over the years, and so when he called earlier in the day, asking if he would close the shop for a private viewing, Sebastien agreed, no questions asked.

If Sebastien was shocked at the age of Jack's young companion he didn't not show it. The well-coiffed and handsome Frenchman didn't betray a reaction as he opened the private entrance for his best client and the very young lady who accompanied him.

"Bienvenue, Monsieur Cummings... Mademoiselle..." Sebastien said warmly, nodding his head in welcome, "Please, come inside."

Hadley had never noticed this store before, and she certainly would never had guessed what the interior looked like from outside. She stared around her in wonder, the red velvet chaise lounges and glass display cases lit by the glow of the exquisite crystal chandelier in the center of the otherwise dark room.

Sebastien nodded to his assistant, Nathalie, and she disappeared behind a curtain to tend to something as Sebastien led Jack and Hadley through a door into a private room. The room was just as opulent as the main shop: the walls were covered in dark, swirling baroque wall paper, flecked with gold accents, the carpet was lush, much like the fur rug in Jack's new bedroom, and in the center of the room was a wine-colored velvet tufted fainting couch. To either side of the couch were ornate wooden end tables and opposite from the couch was what looked like a mirrored changing area with a small velvet stool and fenced in with an ornate carved wooden privacy screen. The whole room was lit with gold and crystal sconces, that let off a dim glow.

"Sil-vous-plait, Mademoiselle, Monsieur, make yourself at home. Nathalie will be right in with refreshments, and I will return shortly." Sebastien turned to go and find his assistant and leave his clients to sit in private for a minute.

As soon as he left, Hadley turned to Jack. "Jack, what kind of store is this? I've never seen anything like this before." Jack smiled at her innocence and obvious inexperience.

"It's a high-end sex shop, sweet girl." He watched her eyes widen. "They sell all sorts of delightful toys and clothing all the way from Paris."

Just then, Nathalie entered carrying a small tray with delicate chocolates and two Champagne flutes. In one, was champagne, in the other, sparkling pink cider. Nathalie was no fool, and knew this girl could be no older than nineteen, and while she knew that it was perfectly legal for a man in his forties to sleep with a young woman of 18, it wasn't legal to serve her alcohol. Nathalie chuckled to herself thinking about it: in France such moral inconsistencies were seen as idiotic.

Sebastien soon joined them, and thanking Nathalie, turned to Jack and asked him in French how he could be of service. Hadley was shocked to hear Jack make his reply in French, but had no idea what he was saying. She smiled as she sipped her drink, feeling slightly self-conscious as Sebastian studied her. Then he nodded to Nathalie.

"We have some brand-new items from Paris that will be quite suitable," he finally replied. He turned to his assistant and instructed her in French, "Nathalie, please bring out the Coquette Collection from the back store room. She looks to be 72 centimeters in the hips, 56 in the waist. A-cup. Thank you." Hadley watched Sebastien wave Nathalie into the other room, and then within minutes she had returned, her arms filled with sheer, lacy lingerie.

"Follow me, Mademoiselle," she said to Hadley, as Jack settled himself on the couch. Hadley followed Nathalie behind the privacy screen, where she watched the woman hang the fancy, expensive lingerie on the wall hooks in a very deliberate, business-like manner. When she finished she turned to Hadley and said, "Please disrobe, Mademoiselle, I will return momentarily. May I ask, what is your shoe size? You seem to be about a six or a six and a half."

Hadley was stunned. "Yes, six and a half... How did you know that?"

Nathalie shrugged and turned to go. "It is my job to notice these things."

Behind the screen, Hadley could see the outline of Jack's form as he sat on the couch. She wondered if he could see hers as she slowly lifted her sundress over her head. She hadn't worn a bra, and she became suddenly self-conscious as she stood there naked except for her thong. When Nathalie returned, she immediately moved to cover her tiny nipples with her arms.

"No need for modesty, my dear," Nathalie said, "Sebastien and I, we have seen it all. Now please take off your panties and put this on please." She held out a tiny flesh-colored g-string, which Hadley bashfully stepped into. If Nathalie noticed the small jeweled butt plug, she didn't say a word. Nathalie immediately pulled the first outfit from the wall and proceeded to help Hadley into it.

The first outfit was a delicate sheer strapless bra and panty set, made of pale green mesh and lace and trimmed with matching bows. The color of the luxurious lingerie offset the green of her eyes. After she dressed her in the lingerie, Nathalie held out a pair of gold heels for Hadley. "It helps to display your natural assets," Nathalie said with a sly smile, "Go show him."

When Hadley had slipped on the shoes, she shyly peeked around the edge of the screen. Her long hair formed a shining barrier, obscuring her young body. She tossed her hair over her shoulder and watched her lover peruse her body. Jack felt his breath catch in the back of his throat.

"Que pensez-vous, Monsieur?" Nathalie inquired from behind the screen, already knowing that if he had eyes in his head this would please him greatly.

"C'est magnifique, Nathalie... Superb," Jack replied, not once taking his eyes from her enticing form. "Do you like it, Hadley?"

Other than her prom dress, Hadley had never worn anything so fine or expensive. "Jack, it's the most beautiful thing I've ever seen," she whispered.

"You're the most beautiful thing I've ever seen," Jack replied, smiling up at her.

"If Monsieur likes this set, then I have something that will knock your socks off," Nathalie said dryly in her French accent. "Come here, Mademoiselle, I have another outfit for you to try."

Hadley disappeared behind the screen with a giggle, and Nathalie quickly disrobed her. Hadley gasped when Nathalie's hands brushed against her sensitive nipples. She felt them stiffening in the cool air and reached up to cover them with her arms.

"It is nothing, Mademoiselle, do not be shy," Nathalie said chuckling wryly, "As I have said, I have seen everything." She turned around to select the next outfit.

Sebastien came back inside to check on his client. He placed a hand on Jack's shoulder. "And how is it going in here, Monsieur?" he asked him. "Everything to your liking?"

"Just beautiful, thank you, Sebastian," Jack replied with a smile. "You always have the best, my friend."

"Nathalie, try the Harlequin set on the young lady," Sebastien called to his assistant behind the screen, "I think Monsieur will be very pleased to see it."

"You read my mind, exactly," Nathalie called back, "I was just about to try it."

"I'll leave you to it, then," Sebastien replied with a smile, "I see you're in good hands. I'm going to go find the special item you ordered last week and wrap it for you. Let me know if you require anything further." Sebastien bowed politely and left the room.