tagFirst TimeHadley's Cherry

Hadley's Cherry


"That fucking bitch!" Jack cursed under his breath as he slammed down the phone. If the second quarter numbers weren't so good, he might have been in a truly terrible mood by now, but luckily Henderson was just updating him on the booming Hong Kong market when the phone rang.

"I'm sorry, Henderson," Jack muttered as he regained some of his composure, "Messy divorce, you understand."

Normally he wouldn't get so worked up in front of one of his employees, but the drama with his soon-to-be-ex-wife seemed to be never ending. First she insisted that she get the house and Jack move to a hotel, and now from this most recent phone call with her bulldog lawyer, it seemed like she was trying to take him to the cleaners as far as alimony was concerned.

"That's quite alright, sir, my brother just went through one of those... nasty business." Harvey Henderson smiled sympathetically. Jack got the feeling that he could have taken a dump on his desk and Henderson would still smile sympathetically: the guy was a grade-A brown-noser.

"Scarlet, can you bring in some ice please?" Jack asked his secretary over the intercom.

"Yes, sir, Mr. Cummings. Right away."

"You feel like a drink before we continue with the Hong Kong numbers, Henderson? After that phone call I sure could use one..." Henderson's face fell slightly, he was eager to continue his presentation, but he wanted his boss' approval more.

"Sure," he said, "I'll have a small one."

Right on cue, Scarlet, Jack's assistant, entered with the full ice bucket. She walked over to where Jack was standing at the bar cart and set the ice down on the tray. Jack could smell her soap and her sweet perfume, and just the scent made him hard, reminding him of all the "private dictation sessions" he had with his nubile young assistant. He thought about that first time he ate her shaved snatch and then turned her over and fucked her little upturned ass right on his desk.

"Anything else I can get you?" Scarlet asked sweetly. She tucked her bangs behind her ear and shifted her weight from one high-heeled foot to the other. It was a pity that his affair with Scarlet (among others) had cost him his marriage, but damn, he thought, as he coveted her tight little body in that hip-hugging skirt, it was probably worth it.

"No thanks, darlin'," Jack smiled at her, "I'll call you if I've forgotten something." He followed her heart-shaped ass as she sauntered to the door and shut it behind her. Jack poured two double whiskeys on the rocks and handed one to his colleague.

"Here, Henderson, this'll put some hair on your chest," Jack said as he handed him his drink. He quickly downed his own and grimaced. "I'm telling you, this living out of a hotel is getting really old."

Henderson was enjoying his boss' sudden casual demeanor. He normally didn't confide in him about any personal matters, and Henderson wanted to take advantage of the situation. If he didn't get that promotion soon, he'd never hear the end of it from his wife.

"Jack, how would you like to come over tonight for a home-cooked meal? My wife, Trisha, is making her signature meatloaf. Might beat room service... what do you say?" Henderson asked hopefully. He could see himself whooping it up with his boss over a wholesome meal, his wife and his daughter smiling and laughing, then Jack offering him the new VP position...

"No, I couldn't trouble you," Jack replied.

"It's no trouble at all. Trisha's been begging me to ask you over for months. You'd be our guest of honor: I insist you come over for dinner."

Jack thought for a minute. It was clear Henderson was trying to win the kiss-up sweepstakes here, that this was some kind of tactical move to ask for a promotion. But, a home-cooked meal sounded amazing, and after the month he's had, it might be just what he needed. He nodded and smiled, "Sure, I'd be honored."

"Wonderful! I'll make sure Scarlet gets the address, and you can come by at 7. Trish will be thrilled." Henderson couldn't believe his luck. After meeting his charming wife and daughter, and eating one of Trisha's delicious meals, the promotion would be as good as his.

The rest of the meeting went well, and by the time Henderson left his office, Jack was in better spirits. He thought he might call a little meeting with Scarlet to celebrate. Now that his wife had left him, Jack was more insatiable than ever.

"Hey, Scarlet? Can you come in here please?" Jack asked over the intercom. Scarlet giggled to herself, and grabbed her notebook, even though she knew she wouldn't need it. Her boss always had a certain tone to his voice when he wanted more than just a memo taken care of. She didn't mind, in fact she loved the attention from her handsome boss, and she knew the ongoing divorce proceedings had to be stressful for him.

"You called, sir?" Scarlet said and closed the door behind her. While she never dressed inappropriately, Scarlet's curvy hourglass body could make even the frumpiest of businesswear seem provocative. The tight black pencil skirts she wore, accented by high heels, always seemed to hug her round bottom, and the ruffly red blouse she was wearing today was cut just low enough to expose a hint of her mouth-watering melons, her fat nipples poking through the silky material.

Jack smiled at his sexy young assistant. He pushed away from his desk and leaned back in his chair. Scarlet smiled, dropped her notebook and kicked off her high heels, sauntering towards her boss with a provocative little wiggle in her step and then knelt between his legs. She reached for his belt buckle with her manicured hands and undid his trousers. She ran her fingernails lightly over the growing bulge in his briefs, and looked up at him, licking her lips. She reached into his underwear and pulled out her boss' massive cock, which was not even fully erect. Jack leaned back in his chair and dreamily closed his eyes as his 24-year-old assistant wrapped her red pouty lips around the head of his cock and sucked him into her warm, wet mouth.

Scarlet had never had such a big cock before she met Jack, but as soon as she had him in all three of her holes, she was totally addicted. She sucked and slurped happily on his monster cock as it grew and stiffened to its full size. She wrapped her fist around the base and still had more cock to spare, which she tried to take as deep down her throat as she could. Jack watched his pretty young assistant service his cock and sighed contentedly. He loved watching his big dick slide in and out of her mouth, her thick lips straining to stretch around the plum-sized head, as she drooled and slobbered on his massive meat.

She pulled his cock from her mouth with an audible pop and a long string of wet saliva stretched from her lipstick-coated lips to the head of his swollen cock, which was leaking precum. She jacked his slippery cock with one hand, totally saturated with her spit, and lowered her head and began slathering his heavy balls with saliva. She sucked each one in her mouth and suckled on it. She moaned as she teabagged his sperm-laden nutsack, and Jack could feel the vibrations through his whole crotch.

After a few minutes of this, he was ready to pop. "Open wide," he said, as he stood and aimed his cock at her pretty mouth, while jerking his cock roughly. She leaned back and looked up at him, opening her red lips wide and sticking out her tongue in anticipation. Jack gave his massive cock a few final tugs and then groaned as the first volley of cum shot out of his churning balls and landed on her waiting tongue.

Not only did Jack have a particularly big dick, but he shot huge loads as well, and today was no exception. Thick ropes of milky cum spurted out of his dick and filled her open mouth. He let a few spurts streak across her cheek and nose for good measure. When he finally milked the last drop of cum from his spent cock into Scarlet's brimming mouth, she swallowed the whole creamy load down, licking the cum from her red lips.

"Thank you, darlin'," he said as he stuffed his lipstick-streaked cock back into his pants and helped her up from her knees, "you were a great help, as always." He winked at her as she grabbed her notebook and heels. "Oh, and Scarlet, honey, could you pick up a nice bottle of red wine and some flowers for Henderson's wife?"


At seven pm sharp, Jack drove through the Henderson's quiet suburban neighborhood and pulled up in front of the charming Tudor House. Jack had played some squash at the gym, showered, shaved and applied fresh cologne before driving over to dinner, and he felt relaxed and in much higher spirits. He grabbed the nice bottle of Cabernet Sauvignon, and the bouquet of purple tulips from the passenger seat, and walked up the well-lit stone pathway and rang the doorbell. After a few moments, a blonde woman in her forties opened the door.

Jack was 44 but he could have passed for 34. He kept himself in good shape, and the few grey hairs starting to appear at his temples made him look handsome and distinguished. Between his lean, muscular six foot frame, his handsome face with deep blue eyes and dark brown hair, and his more than average-sized cock, Jack was incredibly attractive by most standards. And that's exactly what Trish thought when she saw her husband's boss on her front steps.

"Oh hello, you must be Jack! I'm Trish, Harvey's wife. We're so thrilled to have you in our home." She welcomed Jack inside and he entered the comfortable, pleasant foyer. She ushered him into the living room.

"These are for you, of course," Jack said with one of his winning smiles, as he held out the wine and the flowers. Trish cooed over the gifts and batted her eyelashes at Jack. With her frosted blond hair and her tailored capri pants, she reminded him of one of those suburban soccer moms, who dressed up in pink cardigans and pearls just to go to the supermarket. She was pretty attractive for her age, but something about her forced smile repelled him a little.

"These are just the prettiest flowers, Jack! You are so considerate!" she gushed. Henderson entered the living room, thrilled his boss was finally here in his house. "Look, honey!" Trish said, turning to her husband, "Jack brought us a bottle of wine! This is going to go great with dinner. Why don't you boys have a seat and I'll bring you some drinks?"

Jack smiled at his hostess and settled himself on the brown suede sofa. He and Henderson sat in awkward silence for a few moments before Trish re-entered with a tray of cocktails. "I saw the recipe for these on pinterest," she said beaming, "they're like a new twist on an old-fashioned." She handed Jack a drink and watched expectantly as he sipped it.

"It's very nice," Jack said. It was a little sweet for his taste, but the alcohol felt nice after his long workout.

"Our daughter should be joining us, she'll be home from practice any minute," Henderson said.

"Practice?" Jack asked. He forgot that Henderson had a daughter. How old could she be now, fourteen? Fifteen?

"Hadley is a gymnast," Trish said, beaming. "We're very proud of her: she has a gymnastics scholarship to LSU in the fall." She held out a picture of a petite 12-year-old girl in a leotard pointing her toes and leaping on the balance beam. "This is from ages ago."

"She's very beautiful, Trish," Jack said, "I see the apple doesn't fall far from the tree..." Trish giggled like a schoolgirl, and playfully slapped Jack's arm.

Just then the door opened, and in walked the most perfect teenage girl that Jack has ever set his sights on: green cat eyes, long strawberry blond hair pulled into a ponytail, a sweet upturned nose sprinkled with freckles, and delicately curved pink lips like an Italian cherub. Hadley just turned 18, but at 5'2" and a slender 102 pounds, she looks much younger. Jack couldn't believe that boring Henderson and his tacky wife could have created this angel standing before him.

"Hi Mom, Hi Dad, sorry I'm late, practice ran over," Hadley said, hanging up her coat and putting down her backpack. She wore the plaid uniform kilt of the local all-girls' school, and the short pleated skirt showed off her sleek smooth legs, stopping inches below her rounded ass. Jack was instantly hard.

"Hadley, come meet Mr. Cummings, your father's boss," Trish said and ushered the pint-sized goddess into the living room.

"Nice to meet you, Mr. Cummings," Hadley said and shook Jack's hand. Jack smiles warmly.

"Please. Call me Jack," he said. She wrinkled her nose as she smiled at him.

Hadley went to help her mother in the kitchen and Jack studied her as she walked away, her small white tennis shoes, white ankle socks, short plaid kilt, and sky blue polo shirt, the long strawberry blond ponytail hanging down her back that swishes as she walked. Good God, thought Jack, I've never seen anything so perfect.

"She's lovely," Jack said to Henderson, still wondering how this short guy with glasses and a comb-over could have ever produced such a miraculous offspring.

Henderson smiled. "We're very proud of her," he replied.

"Alright, boys, dinner is served! Come find a place at the table!" Trish called from the dining room.

Dinner was fine enough, made even finer by the red wine brought by their guest. They told some work stories and Trish laughed a little too loudly at everything Jack said. A couple of times, Jack looked up from his plate to catch Hadley staring at him with her cat-eyes. The first time he caught her, she blushed and looked away, but after that, he was pleased to find her meeting his gaze, her green eyes twinkling mischievously.

Hadley couldn't help thinking that Jack was the most handsome man she had ever met. At 18, she's never had a boyfriend, but not for lack of offers. She's had several boys from the neighboring all-boys' school ask her out but they just seemed like little boys to her. Some of her girlfriends went out with boys her age, and from their stories, they sounded like total animals. She figured she wasn't missing that much. She always imagined herself with someone older and more experienced, so she resigned herself to waiting until college to start dating. Besides, gymnastics took up too much of her time to bother with boys anyway.

After dinner, Henderson and Trish were clearing off the plates and cleaning up, and Jack and Hadley wandered into the living room.

"So, your mother tells me you're a gymnast?" he asked her, desperate to start any conversation with the bewitching teen.

"Yup," Hadley grinned, "I was all-around elite state champion last year."

"I bet you're great," Jack said, trying to picture her petite body in those skin-tight leotards.

"I'm not bad," she giggled and squirmed her hips from side to side. Jack felt his pants getting tighter. He settled himself on the arm of the sofa.

"Show me some," he said.

"Now??" Hadley laughed bashfully, and covered her face.

"Please?" asked Jack, he smiled a slow warm smile at her.

"Okay, fine," she agreed. She stood in the middle of the living room floor and bent one of her slender legs, sliding her right foot up the inside of her thigh. She extended the leg and grabbed onto the dainty sneaker with her right hand and pulled the leg up to her ear in a full standing split. Jack could almost see under her short skirt, but not quite.

"That's incredible," he said. "Show me another."

"Another, eh?" Hadley thought, and released her leg back to the floor. "Oh I know." The petite blonde planted her palms on the floor and kicked her feet up to a handstand. Her short plaid skirt fell over her head revealing a pair of white cotton panties. Slowly, while balancing on her hands, Hadley opened her smooth creamy legs wide, stretching into a straddle split. Through the white cotton panties, Jack could see the soft bulge of her adolescent pussy, the flimsy material pressed into the cleft of her labia, and delicately wedged into the deep groove of her round asscheeks. Jack was overcome with the urge to press his face into the gymnast's crotch and inhale, lick her pussy through the damp fabric.

"Hadley Patricia Henderson!" Trish yelled, coming into the living room, "I can see your panties! Come down at once."

The pint-sized princess came out of the pose gracefully and stood up again. "It's just my leotard, Mom," Hadley shrugged.

"It's not decent, not in front of our guest. I'm so sorry, Jack." Trish put down a tray of coffees on the table and went back into the kitchen.

"I'm sorry, Mr. Cummings, did I offend you?" Hadley asked innocently. The skin between her eyebrows wrinkled in concern.

"No, not at all, Hadley, don't be ridiculous. I asked you, remember? I thought you were marvelous." Jack winked at Hadley and she felt her stomach flutter a little. Suddenly, she felt a little daring.

"It wasn't really my leotard," she said, a slightly naughty smile curving her cherubic lips.

"I noticed," Jack smiled. Could this teenaged goddess be flirting with me? he thought. Jack took a step closer to her. "I'd like to see your panties again sometime."

Hadley's heart started pounding. Could this handsome man want me like that? she wondered...

"Hadley, it's time to start your homework. Say goodnight to Mr. Cummings and go up to your room. The grown-ups want to talk." Henderson came in carrying a plate of cookies, followed by Trish.

"Yes, Dad. Goodnight, Mr. Cummings," Hadley said and batted her blonde lashes at Jack. Then she turned slowly and picked up her backpack. When she bent over, Jack caught a quick glimpse of her white panties again peeking out from under the short pleated skirt. She looked at Jack while she climbed the steps to her room. Jack watched her until her white sneakers disappeared upstairs.

The rest of the evening is a blur for Jack, he didn't even pretend to pay attention to Trish and Henderson's stories about their trip to Palm Springs. He couldn't stop thinking about the tiny teenage gymnast. Jack felt his cock stir as he tried to picture what she looked like under her panties... Is her bush strawberry blonde too? Or does she shave those sweet little pussy lips bald? Jack couldn't wait to get home and jerk off, get that sweet little squirm out of his system.

Finally, he stood and yawned and politely took his leave. "Thanks for everything," he said, kissing Trish on both cheeks much to her delight, "dinner was delicious and your family is lovely."

"You're welcome anytime," Trish said, dazzled. She was positive the evening was a success.

"See you back in the grind, Henderson," the two men shook hands and Jack walked outside into the night air. As he walked down the walkway to his car, he looked up and saw Hadley looking down at him from her window. She was wearing a short, ruffled, white nightgown. She smiled and waved to him.

She is so delightfully, refreshingly innocent, Jack thought, unlike any of the other women I've been with...

When he was in high school Jack seemed to attract only the really experienced girls, and if he was being honest, he never made time for any virgins. They always seemed like a lot of effort to him, and it never felt worth it. Even his ex-wife had many wild escapades before they met, and he was totally fine with that. But now, something about Hadley's inexperience and simplicity tugged at his heart. He was overwhelmed by his desire for her...

Up in her bedroom, Hadley watched Jack wave, then get into his car and drive away. She has felt wet and tingly between her legs since their interaction in the living room. She lay down on her bed and imagined what it would be like to kiss him and she found herself sliding one of her hands under the elastic waistband of her cotton panties. She parted the wet flesh with her fingers and glided them back and forth over her swollen clitoris. She tried to picture what Jack looks like under all his clothes.

Report Story

byTotalKnockout© 31 comments/ 288805 views/ 390 favorites

Share the love

Report a Bug

3 Pages:123

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: