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.

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byTotalKnockout© 30 comments/ 286520 views/ 390 favorites

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