Hadley’s Other Cherry Ch. 02

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This is part two of a three part story. To read part one, go to


To read the first installment of Hadley and Jack’s story, Hadley’s Cherry, go to



Harvey Henderson was padding upstairs with a glass of water when he saw lights shining out from under his daughter Hadley’s door at the top of the darkened landing. He gently rapped on her door so as not to disturb his wife, Trisha, who had already headed off to sleep.

“Lights off in ten, young lady,” Henderson reminded her through the door, “It’s getting late.”

“Okay, Dad,” he heard her say through the door, “Just gotta finish this last chapter for school tomorrow.”

Henderson smiled to himself. So many of his colleagues at work complained about their teenaged daughters, bemoaning their irresponsible and reckless behavior: staying out at all hours, having promiscuous sex, drinking, doing drugs, failing out of school… But not his Hadley. He and Trisha had only been able to have one child, but Hadley was a joy: responsible, respectful, innocent, straight-laced, a straight-A student and a champion gymnast with a full ride to college in the Fall. Henderson sighed contentedly and felt very grateful. He and his wife were either extremely lucky or they had to be doing something right. He walked down the darkened hallway to the master bedroom, and entered quietly so as not to wake his wife.

As soon as Hadley heard the door to her parents’ room shut, she got out of bed and walked over to the full-length mirror on the wall. She studied her reflection. At five foot two, and just under a hundred pounds, Hadley had always been petite for her age, and while she had her small frame to thank, in part, for her success as a gymnast, she couldn’t help but wish she had a more womanly shape.

She lifted her white nightgown over her head and dropped it in a pile on the carpet and stared at her own naked body. She turned sideways, studying her tiny breasts in the mirror. After feeding her Mom some story about regulating her periods, she had finally started taking the pill a few weeks ago, and she wondered, was it just her imagination or were her breasts filling out slightly? She didn’t want huge boobs, as that would interfere with her gymnastics, but even at 18 years of age, she barely filled out her A-cup bra. Her tiny pink nipples stiffened in the cool air-conditioned air.

She lowered her eyes past her flat stomach and down to her pussy. She often covertly studied her teammates’ private areas when they were showering in the locker room, and she was always a little self-conscious about the way her puffy lips made a visible pouch in her leotard. But ever since she started seeing her Dad’s boss, Jack, her opinion about her pussy had changed. It must not look as weird as she imagined, because he loved the way her pussy looked and told her often, calling it her “perfect peach”.

Hadley thought about the amazing tongue-lashing he had treated her to earlier that evening, feasting on her little peach until she came all over his face. She blushed as she remembered the gift he had given her: even now she could feel the metal plug lodged tightly in her virgin ass.

She turned around and studied her round ass in the mirror, looking over her shoulder. Her long strawberry blonde hair hung all the way down her back to her tiny waist. Standing on her tiptoes, she reached behind her and spread her little taut cheeks apart, and gazed fascinated at the sparkly pink jewel peeking out between them. She had kept the butt plug in during the bus ride home, all throughout dinner, homework and her shower, so long that she almost forgot it was there. She loved the little reminder that only a few hours ago, she had her 42 year old lover’s tongue buried in her ass.

She thought about what Jack had said to her, that he was training her ass to take his cock. She shivered just thinking about it. The thought intimidated her slightly, but as an accomplished athlete, she wasn’t afraid of overcoming a physical challenge. She trusted Jack implicitly with her body and her pleasure and if he wanted to fuck her in the ass, she was determined to be the best he’d ever had.

Hadley went over to her desk and perched naked in her desk chair, feeling the plug press deeper in her ass as she opened her laptop. Quietly typing so as not to wake her parents, she entered in the parental control password that her parents thought was a secret. Next time my parents want to keep a password secure they shouldn’t make it “Hadley”, she thought to herself.

She held her breath as she opened the search screen and gingerly typed “anal sex”. She was immediately bombarded with hundreds of images and websites. She typed in “teenager anal sex” and pressed enter. She clicked on the first website. Her eyes widened as it loaded.

The website featured pictures and videos of a brown-haired girl no bigger than Hadley taking a muscular güvenilir canlı bahis siteleri man’s thick hard cock up her ass in a variety of positions. In one picture she was bent over a sofa as the man stood behind her, his massive tool stretching her tiny tailhole impossibly wide, in another he lay on his side spooning her, his tattooed arm lifting her leg high to give his cock better access to her ass.

She saw a link to a video below and covertly turned off the sound on her computer before pressing play. In the video, the same brunette girl was balanced helplessly on the handsome man’s lap, while he held her legs back and fucked into her widening butthole from below. The girl was moaning and biting her lip, and she played with her tiny pussy while he bounced her on his cock. Then the man effortlessly lifted her off of his massive cock like she was no heavier than a rag doll, and she could see her open asshole gaping wide before he lowered her onto his impaling dick again. The girl licked her lips and smiled as she took this thorough ass-reaming.

Hadley felt her pussy start to tingle and get wet as she watched the rest of the video. It seemed perverse and wrong to let a man stick his penis into such a dirty, private hole, but maybe the perverseness of it was what turned her on. A horniness like she never felt before coursed through her body and she felt her stretched asshole throbbing around the metal plug.

The girl in the video’s body looked a lot like hers, with small tits that barely bounced even while she was taking a hard pounding, a flat stomach, and a round bubble butt. The only difference was that Hadley kept the tuft of hair growing on her pussy mound and the girl in the video had shaved hers completely bald. Well, if that girl can take such a mammoth cock, I can probably take Jack’s, she thought. After all, taking his large cock in her pussy was once intimidating and now it was easy.

Hadley snaked her fingers in between her slick pussy lips and rubbed her little clit while she imagined the man in the video was Jack and he was fucking her little asshole. Hadley squeezed her eyes tight and bit her lip as she came in a series of intense spasms.

When she came down from her powerful orgasm, Hadley entered “teen butt plug” in the search engine and studied the images that came up. She found a few pictures that looked like selfies: otherwise normal-looking teen girls posed lewdly in front of mirrors exposing the butt plug hidden between their cheeks to an imagined audience. A few of the pictures even featured bejeweled ones like hers.

Hadley closed her laptop, grabbed her phone and stood with her back to the mirror. She bent over and looked between her legs at her open ass in the mirror. She clicked a few photos, and then stood up to study them. Looking at that jewel lodged between her cheeks and her puffy pussy lips peeking out below made her hot again. She picked out the clearest photo and texted it to Jack with a little winking face.

Sitting up in his hotel bed, Jack reached for his buzzing phone and smiled at what he saw. Slowly, he reached his hand under the sheets and sought out his already stiffening cock…


“…so are you in?”

Hadley snapped out of her reverie and looked up from her gym bag. Her best friend, Ginny, was staring down at her with a slightly annoyed, expectant look on her face.

“I’m sorry… what?” Hadley asked. Ginny rolled her eyes at her. She could barely contain her frustration.

“Jesus Christ, Hads, have you even been listening to one word I’ve said??” Ginny snapped. Hadley shrugged delicately and waited for her friend to repeat her question. Ginny turned her back to Hadley and started vigorously brushing her dark brown hair into a ponytail. Hadley could see in the mirror that her best friend’s freckled face flushed red with indignation.

“Sorry, Gin, I’ve just been a little distracted…” Hadley offered by way of apology. She knew she’d been acting strange since she started to see Jack, and she could sense Ginny was on to something. Ginny Brooks had been her best friend and team-mate since fifth grade and Hadley had never kept a secret this big from her in her life. She just couldn’t risk anyone finding out that she was screwing her Dad’s boss every weekend. She immediately felt guilty.

“No kidding, you’ve been distracted,” Ginny muttered into the mirror. “I was saying that my parents rented a limo for Ted and me, and I wanted to know if you and Colin had decided whether or not you wanted in on it or not. Prom is only two weeks away, you know.”

Hadley did know. In fact, she and Ginny had dreamed about double-dating to the prom since they were in middle school. Hadley had her dream dress picked out before her senior year had even started and she had been the envy of every girl in her class when Colin Flynn, co-captain of the football team, had asked her to the prom. But ever since she had given her virginity to Jack Cummings, Hadley had to admit güvenilir illegal bahis siteleri to herself: she had lost some interest in the prom. As is, she could only see him on the weekends, and frankly, spending a Friday night anywhere but in Jack’s bed felt like a bit of a disappointment to her.

“Oh right, sorry,” Hadley said, pulling her leotard out of her gym bag and heading to the bathroom, “I forgot to ask him. I’ll let you know as soon as I can.”

Ginny sighed as her friend shut the door of the bathroom stall. She peeled her uniform skirt down her hips and tugged her blue polo shirt over her head with irritation. Why was Hadley acting so strange? Wasn’t she excited about prom? Ginny caught a glance of her hot pink push-up bra and matching panties in the mirror and smiled to herself. Her small tits looked a lot bigger in the bra. Maybe I’ll wear this under my prom dress, she thought to herself.

In the stall, Hadley quickly peeled off her panties and stepped into her team leotard. She didn’t dare change in front of her friend today, as she had a little secret: Hadley had been wearing her butt plug to school all day. She decided to pee so she didn’t arouse any more suspicion. She felt her asshole clench around the plug as she squatted over the toilet and pissed quickly into the bowl. She couldn’t help brushing her fingers over the jeweled plug as wiped herself and stood up. She pulled her arms through the tight sleeves of her leotard, making sure the crotch of her leotard held the plug snugly in place. Hadley felt a tingling in her asshole and pussy… she was being so naughty. Jack would be proud.

She flushed the toilet and exited the stall to wash her hands. She caught Ginny’s eyes staring at her in the mirror. “Hey, Hads,” Ginny said smiling, “I think I want to buy some new underwear for prom… you wanna go to the mall after practice?”


“I think prom night’s the night…” Ginny whispered excitedly to Hadley. She bent over, pulling her small tits out of the sparkling push-up bra and then lifted her dark brown hair off her shoulders and pulled it into a twist. She pouted and widened her big blue eyes as she posed provocatively in the full-length mirror. Hadley was perched on the bench in the small changing room, sitting between two huge piles of lingerie while her friend modeled for her.

“…you mean to do it? With Ted?” Hadley whispered. Ginny nodded excitedly. Hadley raised her eyebrows at her friend. “You sure? You’ve only been seeing him for two weeks!”

“Oh, Hads, don’t be such a prude,” Ginny reached out and pinched Hadley, teasing her. “He’s totally hot for me, and unlike you, I don’t want to go to college and still be a virgin.” Ginny considered herself the experienced one of the two, and up until this point, Ginny had always been the first one to try things. Little did she know, thought Hadley.

“Besides, we’ve already done everything else…” Ginny said peeling off the bra. Hadley had been a bit jealous of her friend’s breasts until she realized that without all that padding they were basically no bigger than hers.

“What do you mean everything else?” Hadley asked, suspicious.

“Oh my God, you’re so innocent,” Ginny snorted. “Last night when we were supposed to be doing homework in his room, he totally went down on me. Oh, and I sucked his cock, natch.” Ginny peeled the pair of tiny hot pink panties down her slim hips and then stood up. “By the way, I shaved my pussy. Whaddya think?” She put her hands on her waist and cocked her hip to the side, displaying her naked body to her friend.

“Wow,” said Hadley, not sure what to respond. Ginny’s normally fuzzy pubic mound was totally shaved bald, and Hadley could see her clit and meaty inner labia peeking out from in between her tiny lips.

“Yeah, I heard that guys prefer to eat bald pussies, and I definitely got no complaints from Ted,” Ginny paraded around the changing room stall totally nude and checked out her round ass in the mirror. “Hey, Hads, pass me that blue thong.”

Hadley fished out a teeny electric blue thong from the underwear pile and tossed it to her friend. Ginny stepped into the leg holes and pulled up the tiny panties. Her ass cheeks bulged enticingly around the small strip of fabric, and it barely covered her pussy in front.

“Oh this is totally it,” Ginny said, “Hadley you should get one too. I bet Colin would like it…”

Hadley picked up the light pink version of the same thong and studied it, smiling. She stood up and slid the thong on over her leotard.

“Oh, jeez, Hadley, you’re such a prude,” Ginny teased, slapping Hadley’s ass playfully. Under the thong, and inside Hadley’s leotard, her asshole throbbed around the fat metal plug.

Inside her bag, Hadley’s phone vibrated with a new text message. It read:

See you tomorrow night, my sweet H. Be wearing your plug. Jack


Jack’s jaw nearly hit the ground when he saw the thong.

Hadley güvenilir bahis şirketleri lifted her uniform skirt as she bent over the windowsill, and he saw the thin strip of pink fabric stretched between her taut cheeks, barely covering her bulging pussy lips below. She reached behind and pulled her cheeks open for him and he could see the edges of the butt plug peeking out from behind the thong. His cock stiffened immediately. Boy, was he pleased.

“Where did you learn to do that?” Jack asked her, amused.

“I’ve been studying,” Hadley shrugged. She knew she had pleased him with her display.

“Yes, you have, my naughty girl,” Jack whispered in her ear, pressing his crotch against her sweet backside. “No wonder you get all A’s…”

Jack undressed her expertly, leaving her naked except for the tiny panties. He pulled her face-down over his knees and started rubbing her tantalizing ass, kneading the soft pliant flesh with his big hands. Hadley purred and moaned in response, writhing on his lap.

Jack raised his hand and brought it down, slapping her soft cheek with a loud spank. He gently rubbed away the sting then slapped the other cheek, enjoying the satisfying feeling of her bouncing butt under his hand. He spanked her upturned ass until it had a rosy glow and she was wriggling her body against him, her belly pressed against his swollen cock.

He peeled her panties off with one quick motion and wriggled his fingers inside her cheeks to find the object of his desire. He grasped the little jewel between his fingers and wiggled the plug back and forth. Hadley gasped in pleasure.

Just then Hadley’s phone buzzed, and Hadley wiggled free to silence it. “Sorry, Jack, it’s just my friend Ginny won’t stop harassing me about the limo for prom. One sec.” Hadley impatiently typed her response and then turned her phone to silent.

“Oh?” Jack said, watching her, amused as ever, “when is prom?”

“Next weekend,” Hadley said, “I’m kind of dreading it, actually.”

“Why’s that?” Jack asked.

“Because my friend Ginny is acting like an idiot. She is renting a hotel room to have sex with her stupid boyfriend Ted and she expects me to cover for her. And all I want to do is… spend prom night with you…” Hadley blushed.

She turned to look at Jack. His shirt was open exposing his muscular chest, and his pants were around his ankles. He held his swollen cock in his fist. The bottle of lube was open on the table next to him and his cock was wet and hard. He jerked it slowly as he watched her naked lithe form.

“Come here, baby,” Jack whispered, “come sit in my lap.”

Hadley smiled as she slowly sauntered over the armchair where he was sitting. She turned around and then lowered her heart-shaped ass onto his lap. Jack lifted her legs up and she rested her tiny feet on his thighs. Then Hadley grasped the arms of the chair and raised her bottom up slightly. She patiently squatted over him while Jack disrobed and adjusted below her, until he was naked and holding his slippery cock upright. He pressed the spongy head against the groove of her plump pussy lips until he lined it up with her tight hole, then slowly she lowered her body, impaling herself on his stiff shaft.

Jack groaned at the delicious feeling of her tight pussy squeezing his swollen cock, holding it in its death grip. Her wet soft lips clung to his thick shaft as he humped her tiny body from below, his whole cock enveloped in her warm wetness.

Hadley let the intense sensations wash over her. After a week of wearing the butt plug she had gotten used to it, but now, with her pussy stuffed full of his massive tool, she was more aware than ever of the metal plug filling her ass. She moaned and groaned and Jack quickened his pace, bouncing her light body on his cock. He could feel his heavy balls bounce with every thrust.

She gripped the arms of the chair tightly for balance as he reached one hand around, parted her chubby pussy lips with his thick fingers and started massaging her swollen clit. That sent her over the edge. Hadley came hard in a screaming orgasm, her tight teenage cunt closing around his pistoning cock like vise. Her orgasm triggered his own and Jacked groaned loudly, emptying his throbbing balls into her wet, spasming pussy.

“Such a good little girl,” Jack whispered praise into her ear, his voice ragged while he rode out his orgasm, “that’s my perfect little princess…” She rested against his muscular chest while they both caught their breath. He brushed her sweaty hair away and kissed her freckled shoulders and neck.

After a few minutes, he lifted her petite body off of his shaft, and a copious amount of thick, warm cum dripped out of her stretched hole and onto his spent cock.

Without being asked, Hadley climbed off of his lap and kneeled between his muscled thighs. She lowered her head and started licking their combined juices from his softening tool. She looked up at him, her green cat eyes shining, and licked his cum from her smiling pink lips. Jack groaned in pleasure.

He was starting to feel himself getting hard again. He looked down at her again and held her head between his hands, his fingers tangled in her silky hair, as she bobbed up and down contentedly, her lips suckling on the swollen head of his shaft.

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