Hadley's Cherry

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"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..."

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43 Comments
AnonymousAnonymous5 days ago

Keep writing these kind of stories. I want to know if Hadley and James kept on fucking.

Campus77Campus773 months ago

This is the first of your stories I've read. Enjoyed it immensely. On to the next one,

AnonymousAnonymous5 months ago

Very Very exciting, I wish I had a a 30 yrs man to had break my cherry when I was 18 years old and may be I would have had a baby by now. Keep writing these kind of stories. More about Hadley and Jake.

AnonymousAnonymous8 months ago

Anal, especially untagged anal, really turned this into a disappointment at the end, as well as made me doubt the 'monster cock' tag, if you put it in a virgin ass that easily. Started out good, then went downhill by page three.

AnonymousAnonymousabout 1 year ago

I really wish there was more!

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