Hadley's Other Cherry Ch. 03

"Don't be shy, Hadley," Colin said smoothly, "We're just getting to know each other."

"I'm not shy," Hadley stated coolly, "And since you don't know me very well, I don't think you appreciate just how uncomfortable you're making me feel."

"Okay, okay," Colin gave in, "I'm sorry. I just wanted to tell you how beautiful you looked."

"That's okay..." Hadley whispered.

"We're here!" Ted yelled, interrupting the frosty mood, "Whoooooo! Yeah, prom!" The limo pulled up in front of the country club as Ted passed his flask around. Ginny took a sip of the strong-tasting liquor and cringed. She passed the flask to Hadley and shrugging, she accepted the small bottle. She took a quick sip and the alcohol burned her throat.

"Whoooooo, party!" Colin shouted. She passed the bottle to him. Anything, she thought, to make this evening less awkward.

****************

Prom was a nightmare. The second Hadley walked in with Colin, she could feel everyone staring at them. She wasn't sure if they were staring in malice or admiration, but either way, the extra unwanted attention put her on edge.

As soon as they found their table, Ted and Colin excused themselves to go off to the bathroom to do God knows what. Ginny waved to a girl from her French class and wobbled over to talk to her on her precariously tall heels.

Hadley felt confused and lost at sea. A month ago all of this would have been exciting to her but now it all seemed so far away and stupid. She watched Ginny across the room. She was nodding excitedly in a group of their dolled-up friends, all of the girls admiring each others' dresses. She was just turning to join them when she felt someone tap her on the shoulder.

She whirled around just as Serena Ackerman dumped a full glass of bright red punch down the front of her light pink dress. "Oh, whoops... sorry." Serena smirked, "Looks like your dress isn't a virgin anymore..." She was surrounded by a group of her followers, who all snickered at Serena's daring move. Hadley could feel the tears welling up in her eyes as Serena and her crowd sauntered away.

Determined not to let anyone see her cry, Hadley rushed from the ballroom and locked herself in the handicapped bathroom down the hall. In the harsh florescent light, Hadley surveyed the damage. A large reddish stain dotted the front of her dress, and the punch had soaked her hair and made her skin sticky where it was drying. She dampened a paper towel in the sink and blotted at her dress and skin, trying to wipe away the stain.

When she had done the best that she could, she studied the stain in the mirror. It was still obvious. Her hair was sticky and clumping in places. A lump grew at the back of her throat. "Don't you dare cry," she told herself, "Don't give her the satisfaction." She took a few deep breaths to steady herself and then opened the bathroom door.

She walked down the dimly lit hallway and ducked into the stairwell to give herself a moment to think. As she sat there on the steps in her stained dress she heard familiar voices talking. Colin and Ted were sitting under the stairs, sharing a joint and chatting, oblivious to Hadley sitting on the stairs above them.

"I don't know, man," Colin was saying to his friend, "She doesn't like me..."

"That's not true, Colin," Ted assured him, "All the chicks want you, she's just shy."

"Fucking virgins..." Colin muttered, inhaling the joint, "I don't care how tight her little twat is, I doubt it's worth the trouble."

***********

Jack was sitting at home, enjoying his third glass of Scotch, and trying to read a magazine, but a very bad feeling gnawed at him.. He had felt uneasy all day after he had Hadley's present covertly delivered to her house. He knew he had done the right thing by insisting she go to prom, and even though such a thing would be impossible, he couldn't help but secretly wish that he was the one taking her.

Jack's own prom was about twenty-five years ago, and the whole affair remained an inebriated blur. He had taken Joanne Marshall as his date but the two of them barely made it to the prom itself, preferring to fuck in the bushes outside of the school and again in the bathroom of the teacher's lounge, and finally in the backseat of his beat-up Chevy. She had the most marvelous champagne-glass tits and she squealed like a bitch in heat when he sucked on her sensitive dangling nipples. The memory made him furrow his brow. He knew Hadley was a good girl, much better than him, in fact. But still he worried about what she was doing... and who she was doing it with.

Jack knew Rick Flynn, Colin Flynn's father, and he didn't like him. He owned the Mercedes dealership in town, and Jack and he had played squash together a few times. Jack found him to be a puffed-up conceited man who would brag to anyone who would listen that his son was a star quarterback with a full ride to Notre Dame. Of course, Jack didn't know Colin, so when Hadley told him that he was taking her to prom, he kept his unfavorable opinion of his father to himself. But now that he was on his third Scotch of the evening, he wasn't so sure that was the best idea...

The sound of his phone ringing snapped him out of his reverie. He quickly lunged across the room to retrieve his phone from the hall table. He recognized the number immediately.

"Hadley? Is everything okay?"

She didn't say anything but Jack could hear her sobbing at the other end of the phone.

"Stay right where you are, sweet girl. I'm coming for you."

*******************

Hadley sat on the darkened curb in front of the country club, still crying, clutching her shoes and purse in her hands. Her feet were sore as she was unaccustomed to wearing heels and her dress was already ruined, so she figured a little dirt hardly mattered at this point. She sniffled, drying her eyes on the hem of her dress as her sobs turned to hiccups.

Just then a dark town car pulled up to the curb and a kindly-looking older man rolled down the window. "Are you Hadley?" the man asked. Hadley nodded. He got out of the car and walked around, holding the door open for her. Holding her heels in one hand and her purse in the other she climbed into the leather backseat. When he had made sure that all of her limbs and dress were tucked safely inside the car, he closed the door, and drove her downtown.

Jack had rationalized that between sobering up, getting dressed and calling down to the garage, sending a car for Hadley would be faster and safer than driving himself. But as he waited for her to arrive his worry intensified. He came down to the lobby, and paced as he waited with the doorman for the car to drive up.

As soon as he saw the town car pull up in front of the building, he rushed outside and went to open the door to the back seat. Hadley's tear-stained face looked up at him. "Hi honey," he whispered and he reached down, wrapping her arms around his neck and lifted her out of the car. The driver, Wallace, handed her shoes and bag to the doorman, who held the door open for them. "That's everything, Mr. Jack," he said.

"Thank you, Wallace," Jack replied, and carried Hadley inside the building.

He continued to hold her shivering body against him in the elevator, rocking her gently in his arms while whispering into her hair, "Shhh you're safe now, baby... Jack's here..."

As soon as the elevator doors opened he carried her into his apartment and lowered her to the couch, still holding her in his lap. He stroked her hair and studied her face, brushing away the tears until they stopped. "You don't have to tell me what happened, honey, I just want to know if you're okay," he said, his handsome brow furrowed in concern.

"I'm okay now," Hadley smiled softly up at him, then reached up to kiss him. He held her in his arms and kissed her again and again, brushing his lips tenderly across her eyelids and nose and cheeks, down her neck and back up to her lips again.

"I'm going to draw you a bath, sweet girl," he said, leaving her on the couch as he went to set things up in the bathroom. He turned on the faucet, making sure the water was hot but not scalding. When he looked up, Hadley was standing in the doorway, smiling at him.

Her hair was a wild, tangled mess, her face and eyes were still swollen and tear-stained, her bare feet were sore and filthy, and a big red stain splattered the front her rumpled pink gown. Jack couldn't help it: he began to laugh.

"What's so funny?" Hadley asked, smiling, "Why are you laughing?"

Jack looked at her as he stood up next to the tub, his eyes shining with laughter. "Oh Hadley," he said, chuckling, "You are an absolute mess and somehow you've managed to still remain the most gorgeous creature I've ever seen."

Hadley rushed into his arms and hugged him. Jack rested his chin on her head as he held her close. "I love you, Jack," Hadley whispered. Jack could feel a small lump rising in his throat.

"I love you too," he whispered back.

Carefully, he helped her take off her clothing and jewelry, and then lifted her naked body into the tub. As she settled herself in the warm soapy water, Jack quickly disrobed and climbed into the bathtub to join her, not wanting to be apart from her for a single moment. He tenderly washed her tangled hair, running his fingers through her shining wet strands, and when he finally rinsed the last of the suds from her hair, she turned around and lay back into his body, sighing deeply as she rested on his chest.

They lay in the warm bath together for a while, Jack running his fingers absentmindedly up and down her spine. She shivered against him.

"Jack?" she asked, looking up at him.

"Yes, love," he replied.

"I want you to take my ass." Her serious face studied his intently.

"No, not tonight," Jack said, "You're too tired."

"Yes, tonight," Hadley answered him, "Please. I want to."

"But... you've had such an exhausting day, sweet girl, it will be too much... We can wait until tomorrow."

"I don't want to wait until tomorrow," Hadley stated, "Please, Jack."

Jack brushed her hair out of her eyes and looked into her face. "I'm afraid I'll hurt you... Baby, I couldn't bear it if I did anything to hurt you." The truth of his own confession shook him more than it shook her.

"You won't hurt me, Jack," she replied, smiling, "Please, I've been waiting all week..." She pouted at him and ground her soft little ass into his lap with a laugh. Jack growled low in his throat and pulled her tiny body into his.

"You naughty little devil..." he whispered in her ear.

He continued biting and kissing her earlobe then traveled down the column of her neck, kissing and licking her as she writhed and wiggled against him. He traced his fingers down her spine stopping when he arrived at the green jewel lodged in the cleft of her soft ass.

Still kissing her sweet mouth, he wiggled the plug free and rested it on the edge of the tub. Slowly, he slid his thumb into her backdoor, the warm, tight passage sucked his digit inside without resistance. He groaned at the sensation of her snug bumhole squeezing his thumb, and his tool hardened as he continued to finger and play with her ass. She wrapped her arms around his neck and gave into the intense sensations.

After a few minutes he pulled his thumb from her asshole and still balancing her in his lap, he held his slippery mushroom tip against the entrance of her bum, the head leaking pre-cum. Hadley gasped and tensed immediately when she felt the thick head of his prick poking into her open anus. Jack pulled back and holding the thick shaft in his fist, massaged the small opening with just the tip.They bit and kissed each other's lips for awhile as the head of his cock teased the opening of her warm, wet butthole.

After many minutes of teasing her sensitive rosebud, Jack could feel Hadley hunching against him, trying to work the tip of his swollen tool inside her greedy little butthole. He knew this could only go so far in the bath before they needed to stop, so he lifted her off of his lap, opened the drain and wrapping her naked body in a towel, carried her up the stairs to his bed.

Laying her down on the bed, he unwrapped the towel and climbed on top of her, covering her naked body with his own. She wrapped her lean legs around his waist and continued to grind her wet pussy and open asshole into his erection. Jack groaned in response.

He broke away from the embrace and leaned over to fish the bottle of lube out of the bedside table. Hadley snaked a small finger between her naked nether lips as she watched him.

"Don't think I didn't notice that shaved pussy..." Jack said wryly.

"Do you like it?" Hadley asked.

"Hadley, you could have neon pink pubic hair and I'd still like it," he replied with a wink, "Now scoot your ass towards me, baby... that's a girl."

She scooched forward on her back to the edge of the bed, and without being told, Hadley bent her knees and grabbed her ankles, exposing her pink crinkled opening for him. Jack squirted a liberal amount of lube onto his finger and then applied it to her anus. Working his fingers in and out of her tight chute, he spread the lube around, making sure the inside of her ass was coated with it. When he was thoroughly satisfied that she was greased enough to take his cock, he squeezed some more lube in his palm and began stroking his long shaft with it.

Hadley watched him slowly lubricate his swollen dick until it was shiny and wet, then he lay back on the bed and motioned for Hadley to squat over him. The only way he knew to guarantee he wouldn't hurt her was to put her in control.

Jack held his slippery tool upright as Hadley squatted on her haunches, facing his feet. He guided her bottom backward until the head of his dick was lined up with her wet anus, then held her cheeks apart as she slowly lowered her tiny asshole onto his cock.

"That's my baby... that's a good girl...just work it in like you do with your plug..." he encouraged her. He watched her sleek flanks flex as she began to work the tip of his dick into her tiny tailhole.

After a few minutes of patient exertion, Jack felt the tight ring of her sphincter give way. Hadley grunted as his swollen mushroom tip slowly stretched her wet pooper open and then popped into her slippery butthole. She could feel the ridge of his fat cockhead pushing against the walls of her bowels as it slid in further, disappearing up her tight bum. Perspiration appeared on Hadley's upper lip... she'd never felt anything so intense.

"Good girl..." he purred, "Open that ass, baby... Open that ass for daddy..."

Hadley beared down, pushing out with her muscles as she continued to lower herself on his shaft until about four inches of his huge dick were buried in her rectum. Jack groaned at the sight of her virgin asshole stretched tight around his girth. I could die happy, just like this, Jack thought.

Satisfied that Hadley had worked enough of his shaft inside her without hurting herself, Jack could now take over. Pulling her back against him, he rolled them both over onto their side. Spooning her small body, he lifted her leg to get access to her ass.

His cock had slipped out slightly during the change in positions, and now only the head remained tightly lodged in her backdoor. Lifting her leg high in the air, he pushed into her slippery bottom, sliding in with less effort this time, burying about four inches in her tight butthole.

"Unnnggghhhh..." Hadley grunted, as she felt his huge meat slide into her rectum. She reached back and gripped his arm with her small fingers.

"You okay, baby?" he whispered to her, concerned.

Her eyes were clenched shut and her brow was furrowed in concentration. She nodded. "It's just super intense... oh my God..."

Jack could feel her tight hole struggle to accommodate his girth. Her virgin o-ring was clamping down on his thick shaft like a vice grip. He was amazed at her bravery but hated to see her uncomfortable. "Hold on, baby... daddy's gonna fix it for you..."

Slowly, carefully, Jack pulled out of her warm butthole. If he hadn't had a few drinks earlier the intense friction of her clinging back passage on his prick would have sent him over the edge. Gently lowering her leg, he reached for the lube bottle and popped the cap open with his teeth. Her small stretched tailhole gaped open for a second, exposing the pink slick interior of her rectum, then fluttered closed and open again, trying to regain its former shape.

Hadley pulled her legs up to her chest and lay there in a curled ball. Quickly, before her asshole could close up again, Jack pressed the lube bottle against her winking bumhole, and squeezed a large dollop of the thick clear lubricant into her open ass. He tossed the bottle on the bed next to him, and using the head of his cock to push the lube inside her, he slowly sank back into her greased hole, pleased at how easy it was to enter her back door this time. It felt like his prick was sinking into hot wet quicksand.

The extra lube had eased his passage significantly, and this time when Jack entered her slippery chute, he could fit about six inches of his mammoth shaft inside her slippery ass. Hadley felt a deep pleasurable sensation as he slid past her tight ring. Jack wrapped his arms around her small body and held her while she adjusted to the sensation.

"That's right, baby," Jack encouraged her through gritted teeth, "Just keep breathing..." He watched her breathe in deeply through her nose and exhale sharply, blowing air through her mouth. He brushed the sweaty damp hair away from her face, teasing her earlobe with his teeth, until he saw her face relax slightly into a smile.

"You like that, baby?" he whispered into the side of her neck, smiling as he kissed and licked her neck. "Why don't you play with that little pussy for me?" He lifted her leg again to give her better access to her soft pink pussy mound. She was so flexible that her lean thigh pressed against her torso with almost no resistance.

Hadley reached down and started toying with her swollen clit. The combination of the comforting friction on her pussy and the intense stretching of her asshole felt amazing. She sighed and wiggled her ass against him slightly as she played with herself.

Jack could feel almost the exact moment that her tight ring relaxed and released its vice-grip on his tool. It was still a tight fit, no way that it couldn't be, but suddenly Jack felt he had a little room to manoeuvre in her hot slick back passage. Jack firmly gripped the underside of her leg and pulled out of her lubed ass slightly, before gently sliding back in. Hadley moaned and shivered in response. He rocked her on his cock slowly like this for a few minutes, fucking her butt with only an inch or so at a time.

While still gently humping her ass, he ran his fingers down the underside of her flexed thigh until his fingers met hers. He danced his fingers over hers and tickled her bald pussy lips, now wet with her juices, and then ran his fingers back to where their bodies joined. He could feel his slippery dick as it slid in and out of her slick chute, the tight ring clinging to his shaft on every stroke.

"You feel daddy fucking that little asshole? I opened that virgin hole right up..." Jack loved talking dirty to her while he rocked her on his cock. Hadley smiled and giggled as he whispered in her ear, "So good, princess... keep working that ass... take that big cock deep inside... that's it... that's a girl..."

Soon he found he was sliding in and out of her ass with hardly any resistance. He couldn't push in all the way, but he was long-stroking her with about six inches of dick without a problem. "You're doing so good, baby... " Jack murmured, "You gonna cum for daddy? Come on, I want to see you cum for me, baby... Cum with Daddy's cock in your ass..."