25 comments/ 171358 views/ 229 favorites Hadley's Cherry By: TotalKnockout "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. Hadley's Cherry Hadley stifled a moan as her cunny throbs and tingles. I have to see him again, she thought. **** Scarlet was in for a workout the next day. Jack had called her into his office the second he came in and wasted no formalities as he laid her on his desk and peeled off her black panties. He pushed her tanned legs up and back and started feasting on her shaved snatch and puckered asshole. Scarlet loved it when he ate her out, and today he licked and sucked at her wet holes like a man possessed . After about ten minutes of licking her out, Jack pulled out his mammoth cock, and slowly fed his pulsating python into her slick cunt. Scarlet moaned as he filled her full, as she tried to adjust to the sheer size of the massive fuckstick stretching her pussy open. He fucked her hard and fast, and with every thrust his big heavy balls clanged against her winking asshole like a brass door-knocker. Jack looked down at his sexy assistant, moaning and writhing beneath him. She was sexy as hell and only five years older than Hadley, but something about her sexiness seemed rehearsed all of a sudden: the red lipstick, the high heels, the black lace panties worn especially for his benefit... He closed his eyes as he fucked away, stretching her tight cunt open with every thrust, trying to imagine Hadley instead: her silky hair and soft pink lips... but his secretary's throaty whimpering and moaning brought him back to reality. Jack grabbed Scarlet's lacy panties off his desk and shoved them in her mouth to muffle her moaning as he felt that familiar tingle building in his balls... The boss had just finished blowing his huge wad inside his squirming secretary when the phone rang. Scarlet was pressing a couple of tissues up against her overflowing cunt to stem the flow of Jack's spunk before she ran to the restroom to clean herself up. When the phone rang, she stood there helplessly, her black panties around her knees. "That's okay, darlin', you clean yourself up," he said to her, "I'll get this." Scarlet smiled gratefully at Jack, pulling up her panties and scuttling quickly to the ladies room before more cum leaked out. Jack reached over and picked up the phone. "Jack Cummings," he said. There was a small pause at the other end of the line and then a small sweet voice said, "...Jack? Hi. It's Hadley Henderson." Even though he had just blown a massive load, Jack's cock stiffened again when he heard the young woman's voice. "Hi, Hadley. How can I help you? Shouldn't you be at school?" he asked, settling into this desk. "Um... I'm sorry. Maybe I shouldn't have called you," the teenager said, "I just... I really wanted to see you again." Jack's heart felt like it was pounding in his throat. "Where do you have to be tonight?" he asked in a low voice. "I have practice until 7 and I was going to sleep over at Mandy's house. I could always lie and tell my parents that's where I am..." she said, a naughty lilt to her voice. "You bad girl," Jack smiled into the phone. "I'm staying at the Regency Marriott downtown," he said, "Do you know how to get there?" "Sure, I think so," Hadley said, now she was smiling, "I've taken the bus downtown before. I can probably be there by eight." "Eight it is, then," Jack said, "Room 1908." "Okay, gotta go," the teenager whispered and hung up the phone. Jack leaned back in his chair and smiled. He couldn't believe his luck. **** At eight o'clock that evening, Jack had just settled into the armchair with a glass of Scotch when there was a small knock on the door. Jack went to answer it. Hadley stood outside his room in her uniform skirt and those white tennis shoes again. It took all of Jack's restraint to not pick her up and throw her on the bed that instant. He knew he had to take his time. "Come in, Hadley," he said warmly. The strawberry-blonde goddess wrinkled her freckled nose as she smiled at him, and Jack felt the all-too-familiar tightening in his trousers. She set her backpack down in the front room and then rushed into his suite, staring at the incredible view of the downtown skyline from his picture window. "Wow what a view," she exclaimed breathlessly, leaning on the ledge and pushing up onto the tiptoes of her white tennis shoes to get a better view. Jack admired her smooth sleek legs and felt his heart quicken as he caught a glimpse of her white cotton panties peeking out underneath her uniform skirt. Hadley looked back over her shoulder and beamed a giant smile at Jack, and he fought the unbearable urge to bend over the tiny teen, pull down her panties and take her right then. "You have an amazing hotel room," she said. She turned around and perched on the window ledge, biting her lower lip and smiling shyly up at her Dad's handsome boss. "I was so nervous about calling you, and coming here tonight..." she confessed, "but I couldn't face not seeing you again." Jack smiled and settled back in the arm chair. He loved how candid and honest she was. "What can I do for you, Hadley?" he asked, a slow smile spreading across his handsome face. "I wanted to spend time with you alone," the young woman replied, blushing beautifully. "I think you're the most handsome man I've ever seen, and you make me feel... tingly all over." Jack felt his cock stirring at her adorable, embarrassed confession. "And you mentioned that you wanted to see my panties again sometime so... here I am." Hadley searched his face for a reaction. She knew she was being very forward and she wasn't sure if she was making a fool out of herself... "I'd like to see much more than that, Hadley," Jack said. All of a sudden he wondered how experienced she actually was... she seems so innocent, but it takes a lot of daring to just show up like this... she is a woman of eighteen and a beautiful one at that. Could she still be a virgin? She was certainly blushing like one. "I've never done this before," Hadley confessed, "Tell me what to do." Jack couldn't believe his luck. Not only did this adorable teen find him to be sexy, but he could potentially be her first! Jack had never had a virgin before and he wanted it to be perfect. "Take off your clothes for me, Hadley," he said, still watching the nervous girl from his armchair. He didn't want to make any sudden moves that would overwhelm her, or scare her away. Slowly, deliberately, Hadley peeled her light blue polo shirt over her head and dropped it on the chair, revealing her slender milky torso and perky breasts only covered by a pink flowered bralette. She knew her breasts were on the small side, and normally she was glad for that fact because smaller boobs were ideal for gymnasts. But now, for the first time, she wished she had bigger breasts, so she would feel more like a woman and less like a girl in front of this handsome older man. She kicked off her white tennis shoes without untying them. Hadley studied Jack's face as she unzipped the short plaid uniform skirt and slid it down her narrow hips, dropping it to the floor. She stepped out of the skirt and stood there before him in just her pink bra, white cotton panties and ankle socks. Hadley pulled the hair elastic out of her hair and shook her long strawberry blonde ponytail free, so that the shining strands fell loosely past her shoulders to the middle of her back. She saw his intake of breath and wondered if Jack liked what he saw. Jack was practically blinded by the beauty of the young woman standing before him, and this without even seeing what was under her bra and panties. "Take off your bra for me, Hadley," Jack whispered, barely able to speak. Hadley reached behind her slender back and unhooked the tiny bra, and the straps fell down off her shoulders. She let the bra fall to the floor, and bashfully cupped her hands over her teacup-sized breasts. "Let me see you, now," Jack said gently, practically holding his breath. Hadley pushed through her nerves and slowly lowered her hands to her sides, exposing her sweet adolescent body to his view. Her cheeks flushed bright pink. I've never seen such perfection, Jack thought to himself, drinking in the sight of the almost-naked goddess before him. He studied her beautiful face with its green cat-like eyes, her delicately-freckled upturned nose, the dimple in her cheek, and pink cherubic lips. Her thick, flowing strawberry blonde mane flowed down past her delicate shoulders to her elbows. He studied her perfect little breasts, the lightly freckled A-cups were flushed with excitement and swelled into two tiny pink points in the cool air. Her petite frame curved slightly in at the waist, and Jack traced the line from her flat tummy down to the elastic waist-band of her cotton panties, which hugged her slender hips and did little to conceal the soft bulge of her cunny lips. "Turn for me, Hadley," he said. The graceful gymnast did a slow spin for him in her underwear, turning on her smooth, slender legs and pointing her small feet in her white ankle socks. Jack studied her mouth-watering bottom, the twin cheeks like a perfect peach. The cotton of her panties were riding up between the cleft of the pert rounded ass, and he noticed two small dimples in the smooth pale skin above the low waistband of her panties. He was overcome by the urge to palm that cute little ass, to smack the soft pliant flesh, to suck and lick her fresh asshole and slide his dick between the cheeks of her adolescent butt. But first, he was going to make love to her. She turned all the way around and looked at him expectantly. "You are so beautiful," Jack smiled his warm smile at her and Hadley melted. He stood and walked towards the naked girl slowly. At 5'2" her head barely came up to his shoulder. He lifted her chin until her eyes met his gaze and then slowly, he leaned in and pressed his mouth against her soft lips. He certainly knows what he's doing, Hadley thought. Jack deepened the kiss, brushing his tongue against hers. Hadley moaned and wrapped her arms around his neck. She had never been kissed like this before. Jack effortlessly lifted the gymnast's small body into his arms and carried her to the king-sized bed. He laid her down at the end of the bed and then lay down beside her, his tongue still swirling in her mouth. Her skin was like silk and her lips tasted like cinnamon lip gloss. Jack's rock hard erection pressed into her hip through his clothing. He held one of her dainty feet in his hand and then pulled off the sock, kissing her sweet toes until she giggled. He gave the other foot the same attention. He looked down into her sweet face and brushed a silky strand of hair off of her forehead. He traced his finger down her wet lips, past her neck, between her budding breasts, down her flat stomach and over the cotton fabric of her panties. The mons of her sex rose in a gentle swell, and his finger traced over it until it reached the split of her pussy lips. "Such a sweet little peach," he said as he ran his finger over her cunny, the cotton fabric pushing into the groove between the soft bulging lips. He tickled at her sex through her panties until he could feel the wetness seeping through the cotton crotch, smell the sweet tangy scent of her arousal. "I want to taste you, Hadley," Jack groaned, "Has any boy ever eaten your pussy?" "No..." Hadley said breathlessly, "Never." Jack reached down and slid his fingers under the waistband of her underpants and he felt Hadley brace herself and stiffen in anticipation. "Relax, honey, I'm going to make you feel so good," he said tenderly, and he slowly peeled the cotton panties down her slim hips, dropping them on the floor. He spread her legs and angled his body between them, giving him the perfect vantage point to feast on her sweet sex. Jack looked down at the most perfect little peach of a pussy he had ever laid eyes on and he felt his mouth water in anticipation. The tender pouting lips of her small cunny were smooth and bald, with only a light patch of golden hair right above the deep split. Jack used his thumbs to open the swollen labia and saw the wet delicate pink folds that ran from the small pink pearl of her clitoris. Clear liquid seeped from the tiny vaginal opening and dripped down, moistening the crack of her ass and the tight pink rosebud between her cheeks. Hadley sighed as Jack lowered his head to her crotch and tenderly kissed her creamy inner thighs and then planted a kiss on each of her hairless lips. He started lapping at her pussy, gently flicking her clitoris with his tongue, savoring the sweet tangy taste of her juices. Hadley began moaning, stars bursting behind her eyes in pleasure. She had never had any man make her feel this way before, and she never wanted him to stop eating her pretty pussy. It would have been a challenge even if he had a normal-sized cock, but Jack knew that Hadley would need a lot of preparation if he was ever going to fit his giant cock inside her virgin pussy. As he continued to suck on her tiny pearl Jack eased his pinkie into the tight entrance of her sex, and Hadley whimpered in response. "Does that hurt you, baby?" Jack asked, watching her face with concern. "No," Hadley responded, "it feels so good..." Jack pulled his littlest finger from her wet hole, licked his index finger and slid it inside. Hadley panted as she adjusted to the intrusion. Jack gently sawed his digit in and out of her tight cunny and suckled on her clitoris sending her into orbit. The tiny teen gasped and bucked against his mouth and finger, as her body shook with the powerful orgasm. Jack slid his finger out slowly and looked into her eyes. He brushed the sweaty strands of hair out of her face as she came down, cheeks flushed and gasping for breath. "Wow..." Hadley sighed. She had never felt anything so wonderful. "I want you to fuck me, Jack: take my virginity, make me a woman," she said to him, looking up at his handsome face. "Are you sure?" Jack asked. His heart was pounding in his chest, his cock longing to bust out from the restraints of his pants. "I've never been so sure of anything in my life," Hadley sighed. "We're gonna have to go slow, honey, I don't want to hurt you," Jack said, pulling his shirt off. Hadley sat up and watched him unbuckle his pants and slide his pants and underwear down in one smooth go. Hadley's eyes widened as Jack's thick long erection sprang free. She looked up at Jack and he could sense the fear in her eyes. "You're so big..." she said, "Will you be able to fit?" "Let's just go one step at a time, okay? I just want to make you feel good, Hadley." Jack leaned down and kissed her sweet cinnamon-flavored lips. As he kissed her, he eased his finger inside her again, and tried to open her up a little in preparation for his thick cock. Her tight opening was slick with her sweet cum making it easier for his thick digit to slide in and out like a small dick. He pulled the finger out and rubbed it over her tender pink nubbin, while he leaned his face down and drooled some spit onto her cunny. Then he lined up both his index and middle fingers at the opening of her vagina. "Take a deep breath, Hadley," he instructed her. He watched her tiny tits rise as she breathed in. "Now breathe out," he said. As Hadley slowly exhaled, Jack slid his fingers into her tight sheath. Hadley winced. "That hurts a bit," she said, wrinkling her nose in discomfort. "It's so intense..." "Breathe through it, baby, it will go away soon," Jack said, holding his fingers inside her and stroking her taut tummy with the other hand. Hadley panted as she adjusted to the intense stretching of her tiny hole. Jack looked down at her tender cunny lips wrapped tightly around his intruding fingers. His cock throbbed longing to be inside her. After a few moments, he spread his fingers apart slightly, stretching her open more. Hadley groaned. "Bring your knees up to your chest, Hadley," Jack told her, and the teen raised her pointed feet, bending her slender legs into her chest. Her labia spread open a little, and he could see the pink knot of her asshole appear between her soft buttcheeks. Keeping his fingers inside her, Jack lowered his mouth to the tiny gymnast's butthole and began lapping at the crinkled pink opening. "Ohhhhhh..." she moaned. He was licking her asshole! It felt so good and yet so dirty... Jack felt Hadley's pussy loosen its vice grip on his fingers allowing him to saw them in and out of the squirming girl's tight hole, while he continued to rim her tasty little ass. Hadley had never been so aroused in her life. Her little clit throbbed as she enjoyed the sensation of her father's handsome boss lapping at her backdoor, his fingers fucking her virgin pussy. "Play with yourself, Hadley," Jack gasped, and the teenager rested her small feet on his shoulders and reached her delicate fingers down to the tiny bud of her sex and began rubbing in tiny circles. "That's right, rub that sweet little cunny for me..." he groaned. Sweet clear nectar dripped out of her pretty peach, saturating his fingers, and Jack could feel her tight butthole flowering open and contracting around his tongue. Hadley felt so alive, she never dreamed this kind of pleasure was possible. "Ah ah ah aaaahhhhhh," Hadley panted and moaned as she came for a second time, her sensitive pussy throbbing and juicing like mad. Jack pulled his drenched fingers from her tight twat and pressed his hand over her whole sex, anchoring her while she sailed through the end of her orgasm. Her flushed pink cheeks and pointed nipples made her even more beautiful, he thought, if that was possible. "That's right, that's a girl..." he cooed, kissing and licking her pink nipples, "You are so pretty when you cum, baby." When she had calmed down, Jack stood and walked over to the nightstand, and pulled a big bottle of lubricant out of the drawer. Hadley studied his hard athletic form as he walked, his defined arms and strong shoulders, his tight muscular butt, his glistening six-pack abs, and below that, his long thick erection swinging between his legs. He was the most attractive man she had ever laid eyes on, and she felt safe with him. He treated her like a sexy woman and an adult, not like a little kid. She couldn't wait for the moment when he would finally make her a woman. As Jack came to the end of the bed, Hadley sat up and looked at his swollen manhood. She had only seen one up close once or twice before, but this one was by far the biggest. She studied the thick long shaft, the plum-shaped head glistening with pre-cum, and the heavy furred balls hanging beneath it. She had only given one blow job before but she did it more out of curiosity than desire. But now the desire to take that giant cock into the warm recesses of her mouth overwhelmed her. She looked up at Jack and wrapped her tiny hand around the thick shaft. "Can I lick it?" she asked, eyes shining. Jack couldn't deny his princess anything. He groaned and brushed Hadley's hair out of the way, as the teenager snaked her pink tongue along the swollen head of his cock. Her fist barely fit around the shaft where she gripped it. She started lapping at the precum leaking from his hole, like a kitten lapping at a bowl of milk. Slowly, she tried to wrap her delicately curved lips around the head and take it into her mouth. It was a tight fit and Hadley opened her mouth wider to accommodate his girth. Holy hell, Jack thought, my cock could be as big as her head! He'd never felt anything so exquisite as Hadley starting noisily sucking him, fellating the head of his cock with her small wet mouth. Finally, when Jack could take no more, he slid his cock out her open mouth, and Hadley pouted adorably. He needed to regain composure. He took the bottle of lubricant and poured a large puddle into his palm and slathered his thick cock with lube. Hadley watched him slowly jack his shiny cock, mesmerized. Hadley's Cherry "Lie back, Hadley," Jack told her, and she lay back on the bed. Jack pulled her bottom to the edge of the bed and then placed her delicate ankles over his shoulders as he crouched down, bringing his thick member level with the opening of her tiny sex. His slippery cock fell onto her tummy with a wet plop and Jack groaned, noticing that even with his balls nestled against her pussy lips, the head of his meaty cock came all the way up past the girl's belly button. It was going to be a tight fit. "Spread your legs a little, baby," he said and Hadley brought her knees a little wider for him. He grabbed his horsecock and starting rubbing the thick slippery head up and down between her labia from her clit down to her tiny hole, teasing her sex, trying to make his impending intrusion easier on her. Then, when she felt slick enough, he pushed the fat tip of his dick further between her lips and right up against her wet opening, then pushed some more. Slowly, he began to ease the plum-sized head inside her, steadily gaining entry until the whole head was wedged inside her vagina. Hadley sucked in a quick breath. Her eyes rolled up into her head as she panted, feeling his giant cock about to split her poor pussy open. "Are you okay, Hadley?" Jack studied her face, wondering if this would be too much for her. Through gritted teeth Hadley whispered, "Pop my cherry, Jack, do it." "You have to breathe, baby," he said. Hadley took in a shaky breath. When she exhaled Jack thrust forward, pushing past the tight resistance with his thick charger and tearing through her hymen in one go. Hot tears stung her cheeks but she had never been so happy. It hurt like hell but it also felt amazing to finally be a woman, to have her virginity taken by this man, she thought. Jack gritted his teeth and tried to keep from moving too quickly. He wanted Hadley to adjust to the feeling of his big dick inside her. Her newly de-virginized pussy felt like a tight throbbing inferno around his cock. Slowly he started moving his hips in a figure eight, and Hadley moaned in response. He pressed his pubic bone against the girl's pink love button and as he continued to grind and rock inside his pint-sized princess, he felt her tight teenage cunt opening up for him. He slid his cock out halfway, his shaft lightly streaked with lube and her blood, and then pressed home again, Hadley grunting from the sheer size of his invading member. "Am I hurting you, honey?" Jack paused his movements and looked down at the naked nymph below him, her freckled cheeks flushed pink and her light green eyes pressed shut. "No, it's wonderful..." Hadley sighed. She opened her eyes and stared up into his handsome face. "It still hurts a little, but I love the feeling of having your big cock inside me, stretching me open... Does it feel good to you?" Jack almost laughed out loud. Are you kidding me?? he thought. "Hadley, my sweet girl, this feels better than anything I have ever felt in my life." Her pretty lips curled into a satisfied smile, and she pulled him down to kiss her. He kissed her sweet lips and ran his large hands over her small breasts. He loved the feel of her sleek lithe gymnast's body and her tiny tits, both milky handfuls topped with a pointy pink nipple. Jack pushed himself up on his hands and looked down the strawberry-blonde angel below him, her eyes glazed over with lust, her knees up by her ears, her tiny feet resting on his muscular shoulders. "Fuck me, Jack," she breathed, "Please fuck me now." Slowly, Jack started sliding his cock in and out of Hadley's tight quim in earnest, her clear lubrication making an easier passage for his pistoning cock. "Ooooh ooooh oooohhhh..." the teenager howled as Jack continued to fuck her tight pussy, his muscular butt flexing rhythmically as he pushed into her rapidly widening hole again and again. Remembering how amazing it felt to rub herself while being filled full at the same time, Hadley snaked her small hand in between her slender thighs and diddled her swollen clit while Jack's monster cock pistoned in and out. For the third time that night, Hadley bucked and shivered in orgasm, her teeth chattering as her cunny throbbed and squeezed Jack's swollen cock. "Aaahhhhhhhhh..." she cried, and gripped his arms with her small fingers. This pushed Jack over the edge: he pulled his wet cock from her spasming pussy and spurted his thick load all over the squirming girl's tummy. "Unnnngghhh," Jack groaned, it felt like his churning balls were turning inside out as he came. White pearly cum pooled in her belly button and dripped onto her tiny blonde bush, as he splattered her body with his huge load. "That was so cool..." Hadley sighed, still light-headed from her powerful orgasm. "Stay right there, honey," Jack told her, and he went into the bathroom, turned on the sink and rinsed the combination of Hadley's blood and his cum from his dick. He wet one of the washcloths with warm water, and brought it out to Hadley who was still spent on the bed, her legs splayed open, her slender mid-section coated in his cum. He bathed her deflowered sex with the wet cloth, cleaning away any residue of their lovemaking from her tender pussy, and then wiped his cum from her trembling tummy. "Did I bleed on you?" Hadley asked, concerned when she saw the evidence of her broken hymen on the washcloth. "It's okay, baby," Jack whispered, "It's perfectly normal to bleed the first time you become a woman. How do you feel? Does it hurt much?" "I feel amazing," Hadley said, "it only hurts a little... can we do it again?" Jack laughed. "Give me a few moments and I'm sure I can arrange that..." he said, smiling. God, where did this perfect little nympho come from? he wondered, thanking his lucky stars. He kissed her freckle-dusted cheek bones and the bridge of her upturned nose. Hadley giggled in response. Jack got an idea. He got up, walked back over to his armchair and sat down. Hadley sat up, watching him curiously. "Come here, Hadley," he said, beckoning her with his finger. The naked gymnast walked over to him gracefully, clasping her arms behind her back nervously. What was he up to? She looked at him expectantly. "I think what I'd really like, while I'm recharging, is a show," he said, smiling wickedly. "A show?" Hadley asked, furrowing her brow in confusion. "Yes, I loved the little show you put on for me in your living room last night. I'd like to see more of your moves." Hadley smiled in recognition. He wants a show? I can definitely do that, she thought. "Okay," she said, gauging how much space she had to manoeuvre, "How's this?" Hadley raised her arms and then planted them on the carpet, kicking her legs up and over her head gracefully in a cartwheel. As her right leg came back down on the other side of her hands, she slid it forward through her planted hands, landing on the floor in a perfect split. "Tada!" Hadley said triumphantly, raising her arms over her head with a flourish. Jack studied her flexible back as it arched, her slender legs open wide, her hips pressing her little blonde bush into the carpet. She was exquisite. "Another," he begged. Hadley smiled, and pivoted her hips, arranging herself into a perfect straddle split. Jack saw her bare pink pussy lips spread open as they pressed into the carpet again, and he felt his cock stirring slightly. She leaned forward on her forearms, pressing her tummy down, arching her back and raising her ass, while pushing her hips through the split so her legs swung around behind her. Then in one graceful movement, Hadley kicked her legs up over her head and balanced on her forearms. Jack savored the view of her her round rump as she straightened one leg behind her, and bent the other, pointing her dainty feet. Jack could feel his breathing tighten a bit as she slowly lowered her pointed feet to the floor in front of her face, one by one. She pushed up onto the palms of her hands, her lithe body arched into a perfect backbend. The creamy skin of her flat tummy was stretched taut as her spine arched up to the ceiling, her delicate ribs showing slightly, her tiny breasts flattened against her chest. Her long hair brushed the carpet. Hadley knew she was giving Jack the perfect view of her exposed pussy as she opened her knees and pressed the balls of her dainty feet into the floor. "Stay just like that," Jack whispered, and he knelt down in front of her spread legs and studied the bare pink pussy lips between them. He ran his fingers over the patch of downy blonde hair on top of her pubis, then leaned forward and began licking the gymnast's flushed pussy as she balanced in this awkward position. Hadley shivered and sighed as Jack sucked and slurped at her tiny sex. Hadley's lithe gymnast's body was such a turn-on to him, and he felt his cock stiffen into what must have been his fourth erection of the day. Jack took each of her calves in his hands and lifted them off the floor, pushing Hadley back into a handstand. "Open your legs for me, like you did last night," he told her, and Hadley obeyed, stretching her straight slender legs into a perfect straddle split in the air. Her whole crotch was now open to his hungry gaze. The smooth labia separated slightly revealing the mouthwatering pink flesh inside and her swollen button peeking out from it's hood. Jack held the tiny girl upside down, supporting her hips with his strong hands while he buried his face her sweet bald pussy like a starving man. Hadley's arms shook as she tried to support herself through the teasing pleasure of Jack's tongue. Just as she thought she was going to pass out, Jack stood and lifted Hadley's light body, bringing her upper body up to meet his and she wrapped her legs around his waist, her wet pussy pressed against his matted pubic hair, his now-erect cock resting between her spread buttcheeks. Jack kissed her lips as he carried her to the chair. He placed her gently on the floor in front of him and then sat back in the chair. "Turn around," he told her, and Hadley looked over her shoulder at him as she turned slowly and gave him her back. Jack inhaled sharply, his face level with the tiny gymnast's gorgeous ass. Hadley felt his big hands run from her lower back down to the round upturned cheeks of her bottom, and she shivered from pleasure. Jack kneaded and squeezed the soft flesh like two small cantaloupes, then he leaned forward and kissed one rounded cheek, biting into the milky skin. Hadley moaned. "God, I love this little ass," Jack groaned, caressing the skin again. He spanked one of her cheeks, lightly. It felt so good, he slapped it again, harder, making a really satisfying smack sound and leaving a red hand print on her tender flesh. "Owwwwie..." Hadley whined and touched where he'd spanked her. She smirked, looking over her shoulder at him. "Why did you do that?" Jack smiled sheepishly. "I'm sorry, baby, I got carried away. Come here..." Jack pulled Hadley onto his lap and cuddled her into his muscular arms. "I couldn't help it, your ass asked me to do it." Hadley giggled and poked him. He reached down and stroked her sore bottom, rubbing away the redness. "Is that better?" "Mmmmmm hmmm..." Hadley nodded and snuggled into his warm chest. "I haven't been spanked since I was eight years old! But then, I probably deserved it." "Were you being bad?" Jack asked. "I'm sure I was being a total brat," Hadley giggles, "I guess I was misbehaving and talking back to my Mom at Church because all I remember is her marching me outside, bending me over her knee, pulling down my pants and spanking me right there in the church parking lot." Hadley shrugged. "It was sooo embarrassing." "Why am I suddenly looking forward to the time when you talk back to me?" Jack grinned wickedly, giving her bottom a few light taps as he pulled her into him and kissed her. "I'm gonna pull you over my lap, and this cute little bottom's gonna be bright pink before I'm done." "Is that a promise?" Hadley flirted, running her fingers through his chest hair. "Don't tempt me, young lady," Jack warned, grabbing her tiny hand, "Not if you want to sit down..." Hadley wiggled away from him. She knew she was playing with fire, and that she probably shouldn't provoke him, but she had to admit, after the initial shock, she kind of liked it when Jack smacked her ass... "I'd like to see you try," Hadley said, sticking her tongue out at him. "That's it," Jack said, standing up, "Get over here." Hadley walked to him gingerly and he grabbed her arm. "Bend over and touch your toes. Now." Jack whispered in her ear. Slowly, the girl bent over and touched her hands to the ground, bracing herself in anticipation. Jack walked around her and gazed lustily at her adorable upturned ass, her pink pussy lips peeking through from behind. He rubbed his hand over her soft cheeks and then he lifted his hand, raising it above her round rump. He lowered his hand to her bare bottom with a resounding smack! and Hadley bit her lip and winced in pain. Jack studied the nice red handprint on her wobbly cheek, then he smacked the other cheek, hard. He yanked her up by her arm and pulled her over his knee. Balancing her on his lap, Jack started raining down loud smacks on her upturned ass. Hadley fought back tears as he spanked her naughty bottom again and again. Finally, after a few minutes, when he was satisfied with the sound spanking he had given her, he rubbed her reddened asscheeks, soothing her sore behind. Stroking her bottom turned into running his hands all up and down her prone form, and soon Hadley was whimpering, moving herself against his hands, greedy for his touch. He grabbed Hadley by the waist and lifted her with ease onto the bed and directed her to kneel on all fours. He pressed his hand into the small of her back, forcing her to arch her back and raise her ass, and he whispered, "Stay just like that." Jack climbed up on the bed behind her, his aching cock now rock hard in arousal. He lowered his face to her ass and starting licking her asshole and pussy from behind. Hadley starting purring, savoring the feeling of his tongue tickling her little pussy lips and tight rosebud. Jack grabbed for the lube bottle and started greasing up his swollen cock as he continued to eat Hadley's squirming ass and pussy. "Oh God, fuck me, Jack..." Hadley begged, "Fuck my pussy..." "Yes, baby," Jack panted, "here it comes..." He aimed his slippery dick at her tight hole and starting rubbing it up and down between her wet lips until the head gained a small entry. Once the head was in, Jack pushed into Hadley's pussy from behind, the petite gymnast grunting from the sheer force of his monster dick splitting her open once again. Jack's thick cock bottomed out inside her, the fat head butting against her cervix with an inch or two left to spare. Jack palmed her ass cheeks and began fucking the little teen doggystyle, enjoying watching his greasy cock slide in and out of Hadley's tight pussy. With every stroke, the girl's swollen nether lips clung to his pistoning shaft. He gripped her hips harder and started pulling her bottom on and off his slippery dick. Hadley could feel the pressure growing inside her clenching pussy and luxuriated in the intense pleasure of being Jack's little fucktoy, no longer a virgin but getting fucked like a whore on her hands and knees. "Uh uh uhhhh," Hadley grunted as he pushed into her again and again. Jack started spanking her little upturned ass as he humped her, making her bubble butt bounce. His heavy balls starting swinging, slapping at her clit and sending little ripples of pleasure through her entire lower body. Jack looked down between her bum cheeks as he rode her, at his cock sliding in and out of her creamy little cunny. He took his large hands and spread her cheeks wider so he could see her tiny asshole winking at him as he fucked into his petite princess. He licked his finger and started teasing her little butthole and this sent her over the edge. "Gaaaaahhhhhh!" Hadley bucked and came, her tight pussy spasming around his swollen cock. Jack held on tight for the ride but as he felt the walls of Hadley's cunt hugging and gripping his cock, he felt his balls boiling over. "Baby, I'm gonna cum," Jack groaned and, not wanting to nut in her teenage pussy, he pulled out of her now gaping hole with a slurp. As soon as his cock hit the open air he shot what felt like a gallon of cum all over the tiny gymnast's upraised ass, bathing her soft cheeks and asshole with his thick goo. "Holy fuck," he moaned appraising his handiwork. Jack grabbed the washcloth and cleaned his spent baby's sticky asscrack, wiping the sperm from her soft bottom. As the wet cloth brushed over her asshole, Hadley shivered. Next time that little asshole is mine, he thought. But for now, he felt like the luckiest man alive. Hadley snuggled into his warm chest and he kissed the top of her head, holding her small body close. He smiled and chuckled to himself, as he drifted off to sleep, the little gymnast wrapped in his arms... "Hadley, my dear," he said, "I think I owe your father that promotion..."