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A Different Kind of First

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“Okay, now grab this end and roll it tightly,” John said as he gently guided Claire’s hand around the joint she was learning to roll. He was having a hard time keeping his fingers at the edge of the paper as they were currently standing on the balcony of his apartment, him shirtless wearing low riding sweatpants and her wearing nothing but his Guns n’ Roses t-shirt. It rode up a little as she bent over to finish rolling the joint and John’s breath hitched a little.

“How’s this,” she asked, picking it up and studying it. She had gotten high with John before but had never rolled one herself. Now, after a good two hours of rolling around in John’s bed, he had decided to teach her how to do it since there’s nothing quite like a post-sex joint.

“That’s good. A little sloppy, but you’ll get the hang of it.” He brought out his lighter and held it up to the roach. He felt himself get a little hard at the sight of her breathing in the smoke and letting it out, sighing in the process.

“Mmm, you want some?” She held the joint out to him but pulled it back just as he was about to grab it. She smiled as she went for another toke, holding the smoke in her lungs as she brought her lips to his, softly exhaling into his mouth and moving her lips against his.

He was a goner.

He chuckled against her lips as he kissed her deeper. She wrapped her arms around his neck, smiling against his mouth. How he had gotten so lucky he would never know.

They stood out for a little while longer, getting higher with each toke and giggling a little harder. After a while she announced that she was cold and they went back inside to his bed.

As they laid in the bed, Claire curled up against John as they laughed together, still feeling the effects of the marijuana, Claire couldn’t help but think about how they had gotten here.

Surprisingly, things on Monday weren’t as difficult as they had thought. Claire had decided that she wasn’t going to let her friends decide who she was and who she could or couldn’t be friends with. Her new friends made her happy, something that she hadn’t been for a while then. All she could think of was her mother and how she probably never had friends like the ones Claire had met in detention and how she probably married her father because he came from money, and they never seemed to be that happy.

So, Claire ditched her old friends (minus one or two who actually accepted her newfound relationships) and hung out with The Breakfast Club for the rest of the year. Of course, she was afraid of what would happen once they graduated a few months later, but Claire had chosen to go to University at Northwestern, so she still got to see her friends whenever she wanted.

This included John, the one person she was most excited to start a new relationship with.

They had been dating for six months now and sleeping together for nearly two. Surprisingly, they fell into their relationship fairly easily. The Monday following their detention they met up in the storage closet they shared their first kiss in, planned a date which turned into a few more dates and a couple weeks later, decided to go steady.

Claire was worried at first that the whole one guy one girl thing would be a real problem in their relationship, but John surprisingly gave up any and all other girls. He had gotten rid of all of his wallet girls, the only pictures in there being of her or of them and their friends.

Still, she had her doubts about things. John had been quite experienced when they started dating, and Claire had very little if any. Sure, she had kissed a few guys, but not many and never for very long. John was her first. Her first kiss with tongues, her first being felt up, and of course her first time having sex. And although John had assured her that she was one of if not the sexiest women he’d ever met, she still wondered how she fared in comparison to the other girls he had been with.

She had never really asked John about his past relationships before, and maybe it was the marijuana in her that gave her the courage to do it now, but she was just too curious and had to know what he thought of her in regard to their sex life.

“How many women have you slept with?” Claire asked, a little more bluntly than she had meant to.

“What?” He stared back at her, incredulous.

“I’m just wondering. Don’t I have some right as your girlfriend to know about your past relationships?”

“I don’t think I would really call them relationships, and no I don’t think you do. You don’t need to know that kind of stuff, Claire.”

“C’mon, I’ve told you about my other boyfriends.” Claire prodded, leaning closer to him and giving him a pout.

“Having a guy on your arm for show doesn’t really count as a boyfriend, Cherry. Why do you want to know anyways?”

“Well, I just figured since you kind of have a reputation, what with all those girls that were in your wallet before and with how much you know about sex, I wanted to know how much experience you’ve really had.” Claire did not add that she was dying to know how many other women she had to compete with in sexual experiences with him.

“I never dated any of those women, Claire, and if you look in my wallet now, you’d see that the only pictures I have in there are of you. So, would you just forget about the other girls?” John pleaded, his hand running up and down her arm.

John had sensed that Claire had always been a little bit insecure when it came to their sex life. Mostly due to her lack of experience. But he was adamant to let her know that she did just fine in bed, more than fine really. Nearly every time he looks at her he’s thinking about how perfect she is and much he wants to throw her into his bed and make her forget about everything for a couple of hours.

“Okay, if you won’t tell me that will you at least tell me when you lost your virginity?”

John looked down at her pleading eyes and her pouting lip and he couldn’t help but acquiesce. “I was fourteen.”

“Hmm, to who?” Claire squeezed his arm, glad to be getting some information out of him. He looked hesitant, but eventually cracked under her soft caresses.

“Stacy Jackson. She was a girl from my neighborhood, about two years older than me.”

“Where did it happen?”

“C’mon, Claire, why does it even matter? Who gives a fuck? It’s in the past.” He got out of the bed then, moving into the kitchen of his studio apartment to get some water. Claire jumped out of bed and followed him, wrapping her arms around his waist and peppering kisses on his neck.

“Please John, I just want to know more about you. We’ve been sleeping together for a while now and I feel like it would really be beneficial if we knew more about each other on an intimate level.”

John grabbed her around her waist then, pulling her in front of him and lifting her up onto the counter.

“Baby, I think we already know everything about each other intimately. I know all your sweet spots, sweets.” He kissed down her neck then, reaching her collarbone and sucking lightly on that spot that always made her melt. She let out a soft squeak as he ran his tongue over it and he grinned wickedly. “See.”

Claire frowned a little as she placed her hands on his shoulders and peered down at him. He smirked as he pecked her lips once before turning to get a glass of water.

“Okay fine, I don’t need to know where it was,” Claire said as she jumped off the counter and went beside him. “Can you at least just answer one question for me?”

John looked back at her apprehensively. He really didn’t want Claire getting the idea that he doesn’t love what they have going for them, because he does. He’d never been as happy as he was with Claire, and as a result was very reluctant to answer any questions that could jeopardize that.

“What’s the question?”

“Is there anything you haven’t done?” Claire winced a little, hoping he wouldn’t be mad. “Sexually, I mean?”

John stared back at Claire, one eye raised. She gave him a look of worry when he didn’t answer, causing him to sigh and put his glass down so he could wrap her in his arms.

“What do you mean by ‘haven’t done’?”

“Well, is there a position you haven’t tried? Have you done it in public? In the shower?” Claire prodded, looking around them before smiling up at him. “On the kitchen counter?”

He laughed a little, his hands squeezing her waist, still a little distracted by her bare legs and the fact that he knew she wasn’t wearing any underwear under his shirt.

“Well, we’ve done it in public. We did it in the bathroom of that one restaurant that you like with the menu where you can’t pronounce anything. And we’ve done it in the shower plenty of times.”

“No, I know that, but I meant before me.”

“I don’t quite see why that matters.”

“Okay fine. Kitchen counter?”

John winced a little, giving Claire her answer.

“Okay you have,” Claire sighed before lighting up a little at her next thought. “Standing up? Not against anything?” John stiffened a little bit before nodding, causing Claire to frown.

“In a pool?” Claire asked, hopeful.

“Yeah,” John nodded. “Hot tub too,” he added, knowing she was going to ask.

“On a balcony?” Claire brightened. John clenched his teeth, wishing for this to end.

“Not this balcony,” he said pointing to where they had previously been smoking. He would gladly take her out there and show her a good time if it would stop her from continuing her line of questioning.

“Oh, c’mon John. Isn’t there anything that you haven’t done?” Claire lowered her head and rested it against his chest. John ran his fingers through her hair and kissed the top of her head.

“Sweets, there’s plenty I haven’t done. I just doubt you’d be into it enough to change that.”

Claire leaned back at his comment with a beam on her face. “You don’t know that! C’mon tell me!”

“Threesome?” John smirked, watching as Claire’s face deflated a little.

“A threesome is totally not fair! There’s a huge double standard. You’d only be into it if it was with another girl. If it was with a guy, you’d be out like that,” Claire whined as she snapped her fingers. John smiled at her antics and pulled her closer to him.

“I dunno, it might not be fair if it was with a girl either. She’d probably be mad at all the attention I’d be giving you.” He brought his smile down to her lips and kissed her then. She melted a little at his words, realizing that he was joking about wanting a threesome. As if she wanted to see another girl with her boyfriend.

“Okay, then what else?”

“More or less variations of that. Orgy. I’m guessing you wouldn’t be into other people watching us fuck and they’re not exactly the easiest thing to find, unless you know any swingers.”

Claire deflated as she rolled her eyes. Was there really nothing he’d never done that she could do with him?

“There is one other thing, but you wouldn’t say yes in a million years.”

Claire raised a brow challengingly at his statement. “Try me.”

“Let’s just say there are some places I’ve never been and never dared to go before, due to a general disliking of the area, usually from the other party.”

Claire furrowed her brows, not understanding what he meant at all. “What?”

He grinned devilishly then, reaching under her t-shirt and running his hand along her bare skin before giving her ass a firm squeeze with both hands.

“Oh!” She squeaked at his abrupt action, confused for a second before a look of realization came across her face. “Oh…”

“I told you you wouldn’t like it. It’s okay though, I don’t have any burning desire to do it. I’m perfectly fine with bending you over the railing on my balcony and letting you know just how fucking sexy you are standing here in only my shirt and questioning me about my experience with sex. Can we forget about talking about it and get back to actually doing it now?”

Claire smiled a little, wrapping her arms around his neck and nodding as his lips fused to hers. He lifted her up, her legs wrapping around his waist as he brought her to his bed, their conversation remaining in her head for the rest of the night.


“Hey,” John smiled as Claire walked into his apartment a couple nights later. Ever since he had gotten his own apartment a few days after he turned eighteen in June, Claire had found the time to come over almost every day. Though she had just started school and so had less time to spend with him, she still tried to be there whenever she had an off day or John didn’t have to work at the auto shop.

“Hi,” she grinned as she greeted him with a kiss. He noticed a small gift bag in her hand then.

“What’s that?” He asked, curious as she began to blush profusely.

“I got you something.” Claire held the bag out to him, bouncing on her toes a little nervously.

“Why? Did I forget an anniversary or something? Are we getting gifts at six months now?” John said, confused because she had never said anything about this before.

“No, no. I was just thinking about our conversation the other day and so I decided to get you this,” she gestured at the gift. John took it apprehensively and removed the tissue paper before pulling a cylindrical bottle out of the bag and reading the label.

“Lube? You got me lube? Geez Claire if it was hurting you before you should have said something so we could stop-“

“Oh no, John. You didn’t hurt me. This is for that other thing we talked about.” Claire looked up at him with a light in her eyes as realization dawned on his face.

“Claire, you really don’t have to do this. I only said that as a joke.”

Claire stopped at this. “So you have done it before?!”

“No, no, that’s not what I meant,” he said anxiously. “I just mean that you don’t have to do this just so that I can try something new. I very much enjoy everything we’ve been doing so far.”
Claire smiled as she wrapped her arms around his neck. “I know that, it’s just that I want to try everything with you. And this is something we can try together. Besides, you said it yourself, you’ve never done it due to a disliking of the area, usually from the other party. Well, I’m agreeing to it, so you have nothing to worry about.”

John sighed as Claire tightened her grip and gave him her “come fuck me” eyes. She pouted a little then, mouthing the word “please” to him, eventually pushing him over the edge.

“Fine,” he caved. “But you have to tell me if it hurts you or if you aren’t enjoying it. No fucking way am I going to live with hurting you when it’s not necessary.”

“Yay!” Claire squealed as she attacked him with kisses. He laughed as she peppered them all over his face in gratitude. “Okay, lets do it!”

“Now?” John asked.

“Why not?! First time, woo!” His girlfriend was a lot more excited about this than he ever expected her to be, but then again she was full of surprises.

“Well, I just thought that we could eat first.” John motioned to the dinner he had recently finished cooking before she got there.

“Oh, right.” Claire ducked down a little sheepishly. “After dinner then.” She gave him one final peck on the lips before moving away to take her coat off.

What had he gotten himself into?


“Okay, I read all about this in Cosmo,” Claire explained as John was busy giving his attention to her exposed breasts. After dinner they had shed their clothes and gone right for the bed. John was hoping to be able to distract Claire for a while before she could go along with this idea.

It wasn’t that John didn’t want to try it. Of course, it seemed like every teenage boys wet dream to be allowed entrance into the so called forbidden zone. If it had been any other girl, he might have jumped at the chance to finally live out this fantasy.

But it wasn’t just any girl. It was Claire, and although she wasn’t shy to try new things and loved exploring in regard to their sex life, he just didn’t think she would enjoy it. It also seemed like the kind of thing that they should have talked about more. He wanted to make sure that she was ready and didn’t want her to regret anything in relation to their sex life. He didn’t want to do this until he was 100% sure that she wanted to do it too, and something told him that the fact that he had never done it was more of the reason she wanted it rather than just wanting to try it in the first place.

Unfortunately, Claire was adamant to try it and kept trying to pry his lips from her so that they could get into position. He hoped that he could distract her enough to make her forget she had ever planned this and let them just have regular sex instead, but it looked like he was going to lose this battle.

“Okay, so I’ll get on my hands and knees and you go behind me. Cosmo said to use a lot of lube, so don’t be afraid to really lather it up.”

“Are you sure you want to try this, Claire? We really don’t have to if you don’t,” John said, holding the bottle of lube in his hand and toying with the lid.

“John! Yes, I want to try it. What’s wrong? I thought you’ve always wanted to do…Y’know.”

“You can’t even say anal, Claire! How am I supposed to believe that you’re ready for it if you can’t even fucking say it?”

“I can say it! It’s just that it sounds so vulgar…”

“And the act of actually having anal sex isn’t? I need to know that you’ve really thought about this, Claire.”

Claire sat up then, fight mode on. “I have thought about it John. I read all about it and I’ve decided that I want to try it. I read that it can be one of the most intimate experiences for a couple to have! I really think it could be a whole new level of pleasure for us.”

John sat back and sighed. “Okay, fine. But you know it’s probably gonna hurt right? It might help if we build up to it a little-“

“I’m fine, John. I know it’ll hurt at first but then it’s gonna feel really good.”

“How do you know that?”

“Well, that’s how it works, right? Otherwise, why would people do it?” Claire looked impatiently at her boyfriend as he raised a brow, scoping out to see if she was truly as confident as she was letting on.

“Fine,” John acquiesced. Claire smiled and pecked his lips again as she got onto her hands and knees and John got behind her.

He started off by snaking his hand around her and stroking her center, hoping to get her a little more excited before they started. She whimpered a little at his action, causing satisfaction in John. He did this for a little while longer before straightening out behind her and squeezing her ass and spreading her cheeks a little. As hesitant as he was to go through with this, he was painfully hard at this point. Mostly because of the beautiful woman in front of him being fully naked and on her hands and knees. It was one of the most erotic sights he had ever seen in his life. He ran his finger over her tightened hole, causing a shiver to move down her spine.

“John? The lube?”

John opened the bottle and squirted some lube onto her hole. He then decided to test the waters with a finger first, inserting his middle one into her and pushing slowly. She gasped at this, and he removed it immediately.

“Are you okay?” John asked, ready to abandon the whole idea right then.

“Yeah, I’m fine. It was just a little bit of stretching. You can do it again.” Claire said, a little nervously.

“Are you sure? We can stop now if you want.”

“No, I really want to continue. Please, John,” Claire begged, determined to see this through.

“Okay, but I’m gonna go slow.”

Claire nodded at this and John reinserted his finger, slowly moving it deeper into her as he felt her clench around it.

“Relax, baby. It’ll only hurt more if you don’t relax.”

She did that then, and to her surprise it began to feel a little more pleasurable. He moved his finger slowly In and out of her before adding a second one. Claire moved back against his fingers a little, which he took as a good sign.

“Okay, I think I’m ready.”

John nodded, adding more lube to her hole and a little into it as it stretched open a little more. He closed the lid and then got into position, lining his length up to her before stopping just before it.

“I’m gonna put it in now. Let me know if it hurts too much, okay?” John asked, holding her hips and giving her a gently squeeze. Claire nodded, pushing back a little against him. John chuckled at this before pushing into her slowly.

John groaned at the feeling of her squeezing him. The feeling of her tightness around his dick was causing him to black out for a moment. Squeezed her hips again as he moved in farther.

“God, baby, you feel so fucking amazing,” he groaned as he thrust a little bit more.
He was feeling euphoric. He never thought being like this with his Cherry would feel like this, but the very idea of him letting her in her like this was a major turn on. He had forgotten all of his apprehension about this idea when he felt her tighten around him. He was so happy.

That is, until he heard Claire squeak a little and voice her pain.

“Ow,” Claire said unintentionally. He could feel her grimace as she tightened around him, realizing that she really was a lot less sure of this than she let on.

“Claire? Are you okay?” John said, having stilled now. He could feel her shaking a little and listened as her breathing quickened a little.

“Mmm,” she winced. “Yes, just- ah. Just keep going,” she urged. Her voice a little shaky and very not reassuring. John pulled out of her then, any feeling of euphoric pleasure abandoned by the sight of his girlfriend in pain.

“Nope, we’re done. You’re obviously not ready for this.”

Claire turned around then, scrambling to grab his arm.

“No, John. I’m fine, really. Let’s just keep going. It’s okay.” She rubbed her hand up and down his arm, tears welling up in her eyes.

“No. We haven’t talked about this enough yet and you obviously haven’t thought about it enough. We can try again when you’ve actually given it more than a Cosmo article reads worth of thought about it.” He moved to get up then, angry that Claire would put not only herself through this, but him as well. He hated seeing her in pain.

“John please! Don’t go.” She grabbed at him again but he moved to put his underwear back on.

Suddenly, Claire burst into tears, causing John to regret everything he’d said.

“Hey, it’s okay, Cherry. Shhh.” John moved to put his arms around her, disheartened by the fact that he had made her cry.

“Oh, I’m such an idiot,” Claire wept, hiding her head in her hands in embarrassment.

“You’re not an idiot,” John said as he gathered her into his arms, his hand moving to smooth out her hair.

“I am though! This is so humiliating. This is every guys fantasy and I managed to ruin it,” Claire sniffled as she wrapped her arms around herself.

“You didn’t ruin it, Claire. I just don’t want you doing something you’re not ready for. Why do you want to do this so bad anyways? Is regular sex not exciting enough or something?” John asked, a little afraid that Claire might have gotten bored with their nightly activities.

“No, it’s not that. Sex with you is very exciting. In fact, I can’t imagine it gets any better.” Claire smiled a little through her tears, but still kept on sniffling.

“Well then what is it? C’mon, you know you can tell me anything.” John lifted Claire’s chin up then, looking into her tear-stained eyes and wiping them away from her cheek with his thumb. She sighed and cradled his hand in hers.

“It’s just that I wonder who it is that taught you everything, and how much better they probably were at all of this stuff,” Claire admitted, lowering her head to avoid eye contact with him.

“Oh,” John said “Well-“

“And you’ve been with all these girls,” Claire interrupted. “And you had all your first times and probably second and third times with them all, and they’re all experienced and probably way sexier than I am because of it, and they probably know exactly how guys like it and I’m over here having to have you teach me everything because I’m such a prude.”

“Hey, you’re not a prude,” John said, forcing her eyes to meet his. “Just because you were a virgin when we met, it doesn’t make you a prude-“

“Well, it doesn’t matter anyways!” Claire went on. “Because I finally found something you had never done, and I thought that if we did it and it was amazing and you loved it, then I’d be the best you’ve ever had because you’d have nothing else to compare it to, but I managed to mess that up and now it’s ruined! Now whenever you think of that fantasy you’ll think of me crying and being a total spaz.”

John waited a little bit as she continued crying, wondering if she was finished with her rant. How could she ever think that she wasn’t the best he’d ever had?

“Claire,” he sighed. “Look at me.” He urged, pulling her chin up once again to look her in the eyes. “How many times do I have to tell you that you’re the best thing that’s ever happened to me? All those other girls I’ve been with pale in comparison to you.”

“But how?” She asked. “How could I be the best? I have no idea what I’m doing!”

“Well, sometimes that’s kind of sexy. I like teaching you these things. I like that you’re learning them with me, and it turns me on like crazy to watch you get the hang of these things and, in my honest opinion, excel at them.”

Claire looked suspiciously at him, as if she didn’t believe him. “But wouldn’t you rather be with someone who was confident and knew exactly what you wanted?”

“You learn these things, Claire. You think I always knew what I was doing? My first couple of times were so unbelievably awkward, I’m almost sure those girls didn’t enjoy it. You on the other hand were remarkable the first time we ever did it and have been ever since.” John shifted them so that they were sitting face to face now. He handed her a shirt so that she wasn’t fully naked in front of him while having such a vulnerable conversation.

He also didn’t want to get distracted while he was trying to make her see that she was everything he ever dreamed of in a woman, and with how he felt about her body, that was bound to happen if she wasn’t at least a little bit covered up.

“I just wanted to be at least one of your firsts,” Claire sighed, her hands in her lap.

“But you are,” John said reassuringly as he grabbed Claire’s hands. “You were the first girl who looked at me and didn’t see some fuck up kid who was going nowhere in his life. You were the first girl who I ever wanted to be better for because you made me believe that I could be. You were the first girl that I ever longed for a future with, because the thought of having one without you made me want to die.” He poured his heart out for her then, grasping her hands in his as he stared into her eyes, his words reaching her soul.

“That’s sweet,” she smiled, running her fingers over his. “You were the first guy who made me want to be better too.”

“Well, that’s why we work so well together,” he laughed as Claire joined him. She moved into his arms then, sitting on his lap as she kissed him.

“I guess I can live without being one of your first sexual experiences. Well apart from this one.”

“Well, hey, if you want sexual firsts, you’re the first redhead I’ve been with,” John raised a brow encouragingly.


“Well, first natural redhead,” he winced. Claire rolled her eyes at this.

“Anything else?”

John thought for a little bit. “I mean, first virgin I’ve ever slept with was you.”

“Yeah,” Claire scoffed. “Because I’m sure that was a lot of fun.”

“First girl taller than 5’ 4”,” he said, scratching his chin.
“Too specific.”

“First girl I’ve slept with more than three times?”

“That hardly sounds like a first,” Claire laughed, getting a little tired of his reaching for something to please her with. He was rambling now.

“First girl I’ve slept with that I’ve been in love with.”

Claire stopped at this one.

“What?” She asked. He apparently hadn’t planned on saying this if the look on his face meant anything.

“Uh yeah. I mean, I’ve been thinking about it for a while now but I didn’t know if it was too soon, and maybe I was scared to admit it to myself anyways but yeah I’m pretty sure I do and if you don’t feel the same way it’s fine but I-“

She cut him off with a kiss, holding his head in her hands as she slid her lips along his and smiled against them.

“I love you too, John.” She grinned at him and he tackled her onto the bed, making her squeal with laughter and happiness that the revelation of how they felt about each other. He kissed her deeply, sliding his shirt up her body. She stopped him and pulled away a bit.

“Are we going for regular sex this time?” She asked, slightly serious but mostly joking.

“I think that would be best,” he chuckled. “I don’t think we should attempt the A word kind of sex until we’ve really talked about it and are ready.”

Claire smiled as she kissed him again. “So… it wasn’t everything you ever dreamed it would be?”

“Well…” John drawled. “It was for about 30 seconds until I saw you were in pain.”

“So you liked it?” Claire questioned.

“I think it was more the fact that the woman I loved was letting me do something so intimate with her rather than the actual act itself.”

“Mmm, so you wouldn’t want to try it again someday?”

“If you wanted to, sure. I’m always down for trying things with you, Cherry.”

“Let’s try the whole making love thing first, okay?” Claire smirked as she reached into John’s boxers, smiling against his lips as he kissed her worries away.