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Cherry's First Time	By : sheisbeautiful-sheisnotme Category: 1 through F > Breakfast Club Views: 5969 -:- Recommendations : 2 -:- Currently Reading : 1
Disclaimer: I do not own Breakfast Club, nor the characters from it. I do not make any money from the writing of this story.

Chapter List
- 1-Cherry's First Time
- 1
April 7^th, 1984, John’s telephone rang, right before he usually set off for his weekly detention. Lately he’d been more interested in keeping his mouth shut and not getting any more academic punishments – they ate into his time with his prom queen. Vernon had a smug look on his face every time Bender didn’t rise to one of his barbs, but John knew who the real winner was. He was the one Claire let do the dirty things he had described in great detail that fateful detention.
“Hello?” he warily asked, not sure why he picked up this early in the morning.
“My parents are going out of town this weekend. Off to visit my brother and his girlfriend.”
John knew exactly what she was saying, and he couldn’t help his heartbeat quickening at the mere prospect of spending the night unsupervised. But he wanted to hear her say it.
“I dunno, Sweets, I’m pretty booked this weekend. Lemme talk to my secretary, see if I can squeeze some time in.” John was sure he could hear her roll her eyes.
“Don’t be an ass, John.”
“I told you, I’m a busy man.”
Claire huffed quietly, then gave in. “John, please come over tonight. And stay.”
Bender had only been over to her house once. That is to say, she only persuaded him once. She had extended the invitation before when she had her almost-mansion to herself, but John had had a hard time looking at everything Claire had, everything he’d never have, and everything he couldn’t give Claire, even if he wanted to.
“Ok, Princess, I think I can fit you in. In fact, I could cancel all my plans and there earlier…”
“Don’t even think about it, John. You don’t have that many detentions left –”
“Easy for you to say. All you had to do was stop going shopping during class to get out of trouble.”
“As I was saying, Allison told me she was going to show up today, help you stave off boredom. Something about having another still life due for art class, I think.” That was a lie. Claire had asked Allison to show up today, as a favor. Claire knew she was asking for a lot of Bender to keep his mouth shut against the man who actually threatened him with bodily harm (oh, she knew about that). The least she could do was find a way to make it less painful for him. Well, short of actually showing up. She was still waiting on college acceptance letters and didn’t want to screw anything up by looking like a defective. She had yet to think of a way to repay Allison, though she knew it would have to be big.
“Have it your way, Cherry,” Bender sighed.
“I’m sure I’ll find some way to make it up to you tonight…”
“Princess,” Bender hissed.
“Now go to detention. I don’t want you blaming me when Vernon asks why you’ve broken your punctuality streak. Besides, haven’t I given you plenty to think about?” John didn’t get a chance to respond before he heard a dial tone. He stalled, unsure if he wanted to fix his hard-on before he went to school or not. He decided against it, not wanting to preemptively celebrate what might happen tonight. He hoped his coat and the brisk walk would solve his dilemma. At the very least, one look at Vernon would make any enticing thoughts flee.
Claire hung up the phone before John could talk her into letting him come over early. As much as the thought pleased her, she knew she could postpone the gratification a little longer. Her parents had taken a long weekend, Friday and Monday included. They wouldn’t be back until Monday night. It took Claire all of Friday to be brave enough to invite John over. The previous time he had come over, her parents had gone out to dinner and had been occupied only a few hours, and she hadn’t been ready to go all the way then.
That wasn’t to say they didn’t spend time together. They’d had a bumpy start, with Claire working up the nerve to call him, only to have him never answer. Half an hour after, he’d called, saying his mother had been “hogging the line all day.” Soon they introduced each other to their friends. Both had acquaintances who made snide remarks, but Bender had glared at his friends and Claire told hers to shove off. John avoided taking her to his house but once begrudgingly spent time in the park near his house, only because it was still light out and Claire didn’t have any of her expensive jewelry showing.
Still, he took her out, treating her to a movie a few times and insisting she eat from the popcorn placed not-so-subtly in his lap. Claire rolled her eyes but laughed to herself. If she wanted to be the prom queen, she’d find someone who treated her like a prom queen. One night he took her to his friends’ heavy metal show at a bar in town. She hadn’t been sure how they’d get in, but when they walked to the front door, the bouncer nodded at them and Bender gave him a “’Sup?” as they entered the establishment.
“You know him?” Claire had asked.
“I work here, Princess. Bussing tables right now, but my boss said he’ll let me start bartending soon. Why?” He had seemed defensive.
Claire had wondered where he got the cash for their outings, but would never ask. Given the graphic snippets John had told them about his family, Claire couldn’t imagine either of his parents sparing pocket change so he could take her out. Now she had her answer.
“It’s just something else I don’t know about you. We just have a lot to learn,” she said, hoping not to start another argument about their different social classes. Claire had fun dancing to the music, watching John head bang and occasionally sing along.
When Claire’s parents told her they were going out of town, her first thought was to tell John. The two of them had been getting more intimate, with John demonstrating what he had outlined in detention – down to her Calvins in a ball on the front seat. They hadn’t yet gone all the way, and Claire couldn’t believe he hadn’t once asked her to sleep with him. He always backed away whenever she gave him a gentle nudge or push, albeit panting, eyes closed, pants tented. She had meant what she said about loving someone when you have sex, especially your first time. And while she didn’t feel that way about John yet, she cared for him a great deal. She had an inkling that with time, she would fall for him completely.
She was also a sexually frustrated teenager. While she was accustomed to occasionally feeling flustered around a boy, John was another story. From the moment she landed on his radar she could feel his intense focus on her and it charged her. She craved it almost from the start. The pull only increased as they shared a brief though zealous moment in the storage closet at school. Since then she was often the one to initiate a kiss, though he was always quick to respond in kind. However, everything she started she stopped, and though she knew she had a right to wait until she was ready, she worried what John was telling his friends. Either he lied and said they went all the way, or she was the tease he once accused her of being.
Claire spent all of Friday debating with herself if she truly was ready to go all the way with him, or if she wanted to because she knew John wanted it. She had voiced these concerns to Allison during their shared lunch period. She was glad Allison had shown up that day, and that the table was otherwise clear. There was no way any of Claire’s other friends would want to listen to her quandary, let alone accept that John hadn’t pressured her. Allison was, to no surprise, a great listener.
“Why don’t you ask him what he’s told his friends?”
“Yeah, that’d go over well. ‘Hey John, you don’t have enough insecurities about our relationship, so why don’t you tell me exactly what you tell your friends about me?’”
“Whether Bender thinks you’re a tease is irrelevant. He knew you were a virgin when you screamed it at us. And since he hasn’t asked you once, like you said, he’s probably not going to start pressuring you, especially since you’ve been giving up the goods bit by bit. You don’t need to take his feelings into account, not for this.
“Ask yourself. Are you ready to have sex with John Bender?”
Claire thought briefly, then said “Yes.”
Allison started to fix one of her infamous sandwiches. “Hungry?” she offered.
“No thanks. I’ve got my lunch. Hey, would you do me a huge favor?”
Once Claire made her decision, she had to figure out when to tell John. Did she want him over right away? No, that was too soon. Plus he had detention, and she’d already asked Allison to give up another Saturday to go. No, she’d call in the morning. She’d be the tease he thought she was.
After the phone was in its cradle, she opened up her closet doors, thinking what she wanted to wear when John took it off her tonight. She decided on a simple shirt and skirt combination: she didn’t want to waste time fumbling over flies or snaps.

When Bender walked into the library, he saw a solitary figure sitting in the back, her body hunched over a sketchbook. He strolled to her table, plopped down across from her and asked, “What is it today, Freaky? A bleak landscape to represent your soul? Or a burnt forest showing your love life?”
Allison didn’t look up as she continued to sketch. Bender took a pocketknife out of his pocket and proceeded to carve as many four letter words as he could into the table.
Minutes later, Allison asked, “Any big plans this weekend, tiger?”
Bender looked up, closing his knife. “She tell you?”
“We had a discussion.”
Bender raised an eyebrow.
“I’ve got condoms in my bag these days,” she continued.
“You and Sporto finally consummate the relationship?”
“As often as we can. Never know when we might need a prophylactic.”
“I’ve got it covered.” John almost always had a box of condoms in his nightstand at home. He might be a high school slacker with nothing going for him, but he wasn’t going to add teenage – or worse, deadbeat – father to that list. And yeah, he might have tucked them into his coat pocket before he left his house. No reason to be unprepared.
John and Allison stayed silent most of the day. John didn’t feel like talking, so he didn’t. He was glad Allison shared that trait, unlike others in their little gang of misfits who couldn’t keep a thought to themselves if they tried.
It wasn’t until they had five minutes left of detention that Allison spoke again. “Have you ever been a girl’s first?”
John thought about it. No girl had ever bled, or seemed unsure of herself, or straight up told him he was her first. Don’t most girls at least tell you if you popped her cherry? “No.”
Once again Allison kept mum as John thought some more. What did he know about girls’ virginity? He knew it could hurt. He knew he’d have to tell her and show her how to do everything, not that she hadn’t been a quick study until now. What if he really hurt her? He could be a little rough in bed, but none of his partners had complained. Would Claire?
Still in his reverie, he almost didn’t hear Vernon dismiss them. He vaguely registered Allison’s leaving and would have missed the car waiting for him had it not honked.
He looked up and saw Claire behind the wheel of her 1980 beige Volvo Coupe.
“Want a ride?” She was wearing sunglasses and a smile, looking his way. “Or would you rather walk?”
John walked to her car, shut the door, leaned over and kissed her, placing his hand on her hip, one of his favorite places to keep it.
“Hello to you, too,” Claire said when they finally broke apart, licking her lips. John was giving her one of his patented smoldering stares already, and they hadn’t seen each other for five minutes. “Do you still want to come over?”
“If I changed my mind I would have told you, Princess. Why? Are you having second thoughts?”
Claire wished they could any kind of progress without them second guessing everything. “If I had second thoughts, I’d have told you,” she repeated, leaning over to kiss him again.
“Then let’s get outta here. Don’t need to be at this shithole any longer than necessary.” Claire shifted into drive and peeled away, leaving Shermer High in their dust.
“Aren’t you worried about getting pulled over for reckless driving?”
“I figure I could stand to be a little more dangerous.”
“You need more danger in your life, Sweets?”
“I’ve played it safe my entire life. I want to have fun. I want to really feel something.”
“I could make you feel something, Princess.”
“That’s what I’m counting on.”
John felt uneasy as Claire pulled up her long driveway. Though he was pretty sure Claire wanted him as much as he wanted her, it was hard to stop the gnawing inadequacy when just one of her family’s possessions cost more than his entire personal belongings put together.
Claire could sense him tense up as she parked in the garage. Yes, she was used to a certain level of luxury, but didn’t John know that she had feelings that couldn’t be bought or filled with expensive junk? She wanted human connection and found it best in John Bender. Who was she to question it?
“I was thinking of ordering pizza, if that’s ok with you,” Claire told him as she led John into her house. “I usually get pepperoni, but if you’d like something else…”
“That’s fine, Cherry. Don’t have to go out of your way on my account.”
“Make yourself at home while I order,” she invited him. Sure, he snorted, make himself at home. Did that include trudging through crushed beer cans and empty liquor bottles? Did that include figuring out the best time to get food from the kitchen in order to avoid his asshole father, only to find the bread went moldy and the peanut butter was gone? Did that include sitting precariously on furniture so it wouldn’t break completely? He was so contemplative that he hadn’t sat down and remained in the doorway when Claire returned.
“This is ridiculous,” she said as she led him through her house again. The first time he was here he hadn’t seen much; Claire had dragged him to her room then out the same way when it was time to scram. Now, she was taking him through the dining room, through the kitchen, finally stopping when they were outside on her back deck. “Do you have a joint on you?”
“You want to get high?”
“I want you to get high. You’re too tense and caught up over shit to enjoy yourself. Light up and mellow out. We’re supposed to have fun.”
John reached into his inside jacket pocket and pulled out a joint he had rolled the night before.
“Got a light?”
Claire walked to the barbecue and came back with a book of matches. John lit the joint, making sure it didn’t canoe before passing it to Claire. She inhaled, held her breath, then exhaled, only coughing a little. Not bad for a girl who had her first drag a few weeks ago. Jeez, how many firsts am I going to be for this girl? John wondered as he felt the tension seep out from his body. Never in a million years did he think he’d be getting high with Claire Standish, possibly as a precursor to having sex. They passed the joint back and forth, both giggling a little bit more with each puff. When the j roached, John licked his fingers and extinguished it, throwing it onto her yard.
John glanced up at Claire and saw she was staring at his lips, licking her own again. He stepped forward and kissed her, pulling her close as he fisted her hair in his strong grip. Claire moaned then honest-to-god rolled against his entire body, renewing his morning erection with a vengeance. Distantly, he heard a noise go off a few times before Claire pulled away, softly swearing.
“Shit, that’s the pizza guy, C’mon.” John wordlessly followed Claire back to the house. She asked him to get plates and glasses out of the cupboard next to the oven. John was normally sure in his hold, but he was suddenly worried he would break something in this fancy kitchen. He didn’t have a single matching plate in his house, and he and Claire were going to eat pizza off freaking china? He cautiously made his way to the dining room, going back for Cokes from her refrigerator. Claire brought the pizza in and it smelled delicious.
“Bon appetite,” she said as she handed John a slice. It tasted as good as it smelled, which was enhanced thanks to their illicit activity on the back deck. He helped himself to three slices. He’d skipped breakfast and lunch again today (like the empty fridge at home gave him a choice) and didn’t each much the day before. Claire ate a slice and a half before declaring herself stuffed. John was sure she wouldn’t have eaten as much if she weren’t so lit up. When she was done, Claire excused herself to wash up. John took advantage to do the same thing. He was still hoping to get lucky and didn’t need pizza grease all on his fingers and mouth as he made a move.
Leaning against the kitchen sink with his arms crossed, John looked up when she walked into the kitchen. She looked in his eyes when she said, “John, I want to have sex with you tonight.”
Without thinking John swept Claire off her feet, wrapping her legs around his waist, stepping forward until he pushed her up against her Frigidaire. He latched onto her neck and thrust into her. Claire let out a surprised gasp. The friction of his jeans against her crotch felt heavenly but she wanted more.
“Jesus Christ, John!”
“Really, Princess, just ‘John’ will do.”
How could he have the brain capacity to make jokes when she could barely remember to breathe? She wanted to level the field a little bit. “My room,” she panted, easing off him to put her legs down. “Let’s go to my room.” John reluctantly agreed, refusing to let go of her waist.
“Lead the way, Baby.”
Claire took his hand and all but raced to her room. John kept up, maintaining some distance up the stairs to get a good look at her ass.
With Claire’s hand on the doorknob, John wondered if he’d be nailing her on some little girl’s bed but was pleased to see a double bed free of anything cuddly, furry, or pink. The room was already dim and with the setting sun he was about to lose all available light.
“Wait,” he said as he turned on the light on her nightstand.
“What are you doing?”
“Believe me, Baby, I want to see what I’m doing, and you want me to, too.”
Claire had seen a few movies where the girl loses her virginity, and each time it happened in the dark. All of her friends mentioned fumbling in the dark their first time, and it didn’t get much better for them any time after.
John kissed her again and wrapped his arms around her, laying her down on the mattress. “Do you trust me?”
“Yes.”
“Then let me show you a good time.”
John stood and shrugged off his jacket, tossing it to land on a chair while toeing off his boots. Finished, he kneeled on the bed again to crawl back to Claire, then ran his hands down her sides, trying to prevent his touch from being ticklish. She was breathing hard and her eyes were closed. Slowly his hand made its way to her back, lifting her t-shirt hem up, exposing more of her tempting skin.
His mouth found her neck once more, lips moving south until he reached the spot where her shoulder became throat and she mewed a delicious whine, a sound that shot straight to his groin and spurred him on. His hand cupped her breast outside the shirt, thumb rolling over her nipple though masked by layers of clothing.
Claire frowned at the lack of direct contact. “Take my clothes off,” she commanded.
“I thought you’d never ask.” With her help he lowered her skirt down her legs, followed soon by her shirt, both articles of clothing landing in a heap on her floor. To maintain fair play, and maximize skin contact, John slipped off his blue flannel and white t-shirt, leaving him bare chested. He lowered himself gently on top of her, placing a hand back on her chest, flicking the nipple hidden by her red lacy cup, then reached around to unclasp her bra. He glanced down and noticed her panties matched her bra. He grinned, appreciating the effort.
He removed her bra, flinging it to its join its brethren on the floor, latching his mouth to her left nipple and cupped the other breast. John licked her nipple, blowing on and enjoying her shudder. Claire wrapped a leg around him, urging him on. Switching his mouth to the other breast, his hand made its way down her body. This was the most amount of skin Claire had ever showed him, and he wanted her to know just what he thought of her amazing physique. His hand cupped her mound outside her underwear, brushing over her clitoris then extending a finger into her as deep as the cloth would allow. Claire moaned louder and wrapped her arm around his shoulders, keeping him close. John’s fingers snaked into panties as he made direct contact with her clit, circling it a few times before dipping his middle finger into her pussy, lubricating his finger, then returning to circle her nerve bundle some more. John’s mouth was by her ear again, nibbling on her lobe while whispering how fucking hot she was, writhing all over his fingers until she threw her head back and cried out, climaxing, legs going taut.
When her body relaxed, she opened her eyes and saw John grin at her in a predatory manner. “I hope you enjoyed round one, Princess.” John lowered her underwear down her exquisite legs, dropping them on the floor with everything else. His jeans joined them but he kept on his boxers.
John lowered his head to Claire’s creamy white thigh, leaving slow, wet kisses up her legs as his hands massaged her firm ass. He spread her legs and pressed his mouth against her clitoris, sucking the bud. Claire’s back arched as she squealed and squirmed while John fingered her again. Taking his time, he kissed her along her lips, adding another finger to her pussy, trying to stretch her a little before he entered her fully. He curved his fingers up, hitting her G-spot while continuing his onslaught on her clit. Claire grabbed his hair as she came again, shouting “oh fuck!” as John pumped his fingers.
John could feel his precum leaking from his dick as he watched Claire orgasm a second time. “Are you ready for this?” he asked, giving her one final chance to decline.
“Ready and willing,” she replied assuredly.
John finally removed his underwear then retrieved a condom he had placed in his jeans earlier.
“Can I try?” John handed Claire the foil square then laid down on his back, arms behind his head.
“Be my guest.” Claire opened the wrapper, tossing it aside, unrolled the condom so that the tip extended, just as she learned in health class, then rolled it down his erection. Making a slight adjustment, John flipped her onto her back, settling himself between her legs again.
“This is gonna hurt, babe,” he warned her.
“I know.”
John guided himself in, trying to be mindful when he just wanted to get this part over with. When he thought he felt a barrier he thrust in, eliciting a short, pained gasp, her nails digging into his biceps. Without pulling out his hand cupped her hip again and squeezed reassuringly, whispering once more in her ear, wanting her to forget the hurt. She rocked her hips, to which he pulled out a little and thrust in. When he didn’t hear any more pained sounds, he pulled out and thrust again. Soon he was able to get a languid rhythm going, with Claire matching his thrusts with her own. She was so fucking tight, tighter than he thought someone could be and she clenched and squeezed without realizing it, egging him on.
John was still attempting to restrain himself until Claire encouraged him, “keep going, John, harder,” and he didn’t need any more instruction. He lifted her hips to aid in his increased tempo, thrusting harder while grinding against her clitoris. Claire wrapped both legs around him, helping him thrust deeper until she shuddered, climaxing and moaning to his staccato rhythm. He lasted until she cried “oh god, John” when he found his own climax, slamming into her a few final times as he called out “oh Claiiiire, yesss baby.”
In a hazy bliss John placed a kiss on her forehead, breathing deeply before pulling out and rolling to her trash, depositing the used condom in the can. He rolled back to Claire, lying on his stomach with one arm casually draped over her stomach, as close to post-coital cuddling as John Bender was going to get.
“Not bad for your first time, Cherry.”
“God, I can already feel how sore I’m gonna tomorrow.”
“Don’t worry, Princess, I know how to make you feel better.”
- 1
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Cherry's First Time