"Don't say it doesn't matter, 'cause it's gonna matter to me, I can't be alone with you..."


“Jamie…”

He pushed back and looked down at her, his focus shifting between her eyes quickly.

Cassidy reached up to play with the ends of his hair, trying to reassure him that everything was alright, “can we go slow tonight; I’m just…”

“Yeah, of course,” he offered up quickly. He lowered his head to her neck, kissing it softly while slowly moving down to her collarbone, then her chest, and then to her breasts.

While he massaged one with his hand, squeezing it softly, his mouth played with the other, first with small kisses before opening his lips around it, grazing her nipple with his teeth. Almost immediately, she felt it go hard in his mouth, and she moaned quietly, tugging on the ends of his hair roughly.

She moved one hand down the side of his body, her fingertips running over the ridges of his ribs. When he lifted his lips, Cassidy’s eyes snapped open to watch him as he brought one hand to his mouth, licked his fingertips and then lowered them to her throbbing entrance.

In all reality, he didn’t have to lick his fingers. She knew she was already wet, and Jamie soon realized it too, seeing as when he touched her, a small grin spread across his lips, obviously satisfied with the fact that he could turn her on that much. His fingertips rimmed her tight entrance, circling it slowly, and beneath his touch, her muscles contracted, feeling his fingers add pressure to her.

“Please,” she mumbled, almost sounding incomprehensible.

Slowly, as if he wanted to spend more time fingering her, he pulled his fingers away and gripped onto his shaft. He bent over Cassidy’s body, looking down at her as she readjusted her legs, spreading her knees further apart for him. When he was all lined up, he thrust his hips forward, pushing the head of his cock against Cassidy’s core. He took a deep breath in, seemingly nervous that he had to be the one to take her virginity. She screamed out as he penetrated her, quickly bringing a hand up to her mouth to quiet herself. Small whimpers escaped her lips as Jamie slowly tried to push himself deeper.

His eyes flashed to hers, stopping his movement as he took her hand in his and held it tightly, lacing their fingers together. He leaned in and kissed her lips, which she gratefully accepted, biting his lower lip as pain took over. Jamie squeezed her hand, trying to calm her down, and her breathing intensified, her chest rising and falling quickly.

When Cassidy was able to control her breathing, Jamie set his forehead against hers, pushing himself further in, feeling her tightness contract around his throbbing shaft.

“Babe, relax…”

Her eyes flicked up to his and she took a slow, deep breath in. With her exhale, Jamie pushed himself in the rest of the way, wincing as she cried out quietly, feeling her muscles pulse around his thick shaft. Once she relaxed again, he began to thrust in and out of her in short intervals, making sure she was all right every once in awhile.

As his slow movements rocked her back and forth, Cassidy felt herself relaxing, and she pressed her fingertips into the back of Jamie’s neck urging him down to her so they could kiss. When the pain subsided, she lifted her hips off of the bed to meet his as his shaft moved in and out of her.

All in all, she felt bad for Jamie. It must’ve been pretty traumatic for him to basically have a girl cry during sex. And mostly, Cassidy was embarrassed that he had to comfort her just to continue. It sounded kind of pathetic to her. Between the motion of his throbbing length inside her, and the consistent pressure it placed on her clit, she reached her first orgasm a few minutes later, smiling while continuous moans spilled from her mouth. With her head tilted back and her body stiff and stretched out, she fell back against the bed, tired after the experience.

Jamie lay still on top of her for a moment, kissing her neck lustfully, until he pushed up from her, and pulled out. He rolled onto his back, pulled the condom off and walked to the bathroom to throw it away. Cassidy was able to catch a glimpse of it before he tossed it into the trashcan.

“Guess it wasn’t that good…” she murmured as he crawled back onto the bed. Instead of cuddling into him, she kept her distance, pulling on the sheets to cover her body in some way.

Jamie looked over at her, confused, furrowing his eyebrows. He shook his head as if he didn’t understand.

“You didn’t…” her sentence trailed off, becoming less audible as she went on until she fell completely silent.

He tilted his head to the side and shrugged once, “it’s alright. You did; that’s all that really mattered tonight.”

“But it wasn’t good for you. Probably the worst you’ve ever had,”

When Jamie stayed quiet, Cassidy groaned and rubbed her eyes, looking around as if she were searching for a way to leave the room.

Jamie grabbed her wrist and pulled her into him until her body molded into his, fitting the curve of each other perfectly. “Listen, it was your first time. And it was great; it was with you. And when we do it again, it’ll get better.”

Cassidy felt nervous again. Although her body was pressed tightly to Jamie’s, she didn’t feel his cock going hard against her hip. Great. Now he found her so unattractive, he couldn’t even get hard. Way to go, Cassidy. Good one.

“You’re beautiful, you know that?” He draped one arm over her waist, “and you’re smart, and the most caring and gentle person I’ve ever met.” He paused, catching her glance and leaned into kiss the corner of her lips as he rested his forehead against hers, “I’m not concerned about the sex. It’ll get better as you get more comfortable.”

“Why me,” she questioned. It came out as a whisper as she placed one hand against Jamie’s chest. “You can have any girl in the world, and you chose the one from Nashville, Tennessee who has never been with a boy in her life.”

Jamie smiled and closed his eyes, taking in the faint smell of her floral perfume, “ultimately I want to be married. Girls who are not marriage material are no longer my focus.” He nuzzled his nose against hers, “and that’s the exact reason Tyler was with Kennedy instead of you. He doesn’t want anything serious right now.”

Cassidy shut her eyes as well, moaning quietly as she kissed his lips quickly. “Jamie Benn, if only my father heard you talking this way,”

He chuckled and tightened his arm around her, “hopefully one day he will,”

Cassidy reached up to kiss Jamie’s lips again, lingering there until their mouths opened simultaneously, getting back into a heated kiss. As she moved, the bed sheet fell away from her body, leaving her exposed once again.

She and Jamie pulled away at the same time, frozen as there was a knock at his bedroom door, followed by it opening just a tad.

“Oh shit, sorry,” Jordie said, backing out of the room.

Jamie turned on his side to face the door, blocking most of Cassidy’s body as she climbed beneath the blankets, pressing up against his body, now completely covered.

“Come on in Jordie,”

The door opened a tiny bit more and when he saw everything was now covered up, he pushed it open wider, stepping in with his car keys in his hand. “Tyler’s at Arrow, and he’s getting into some trouble. I couldn’t get him to leave; he won’t listen to me.”

Jamie groaned and sat up in bed, looking at his phone to check the time, “alright, I’ll be down in a minute.”

Jordie backed out of the room and shut the door. Jamie took another deep breath in and stood up from his bed, moving over to the dresser and pulled out a pair of boxers, shorts, and an old t-shirt. As he slid the boxers on, he looked back at Cassidy, who was sitting up on the bed now, with the white sheet wrapped around her breasts.

He seemed worked up as he pulled on his shorts and shirt, as if this was a normal occurrence. As his frustration level grew, Cassidy felt the need to say something to bring him back to the moment.

“O Captain, My Captain,” she murmured.

Jamie’s head shot up as he slipped his feet into his shoes. Upon hearing her voice, he face grew calmer and he walked up to her, leaning over the side of the bed to kiss her lips gently.

“I’ll go get him, and I’ll be right back,” he pecked her lips once more before standing up and patting his pockets, searching for his phone and wallet.

“Be careful Jamie,”

He smiled and exited his bedroom, shutting the door behind him. Within moments, Cassidy was alone in the house. She didn’t want to walk around; it felt like snooping. And after all, Jamie said he wouldn’t be that long.

But a half hour went by. And then an hour. While she wanted to stay up until he got in, her eyelids began to feel heavy, and without even realizing it, she was fast asleep. Alone, in a big bed, in an unfamiliar house.

---

Cassidy rolled awake the next morning. When she turned to look to her right, she saw Jamie on his back on top of the blankets, still sleeping. She didn’t have a clue of what time he got back in after going to save Tyler. His chest rose and fell evenly, and with the memory of last night still fresh in her mind, Cassidy crawled towards the foot of the bed, sitting on her knees between Jamie’s legs.

She tucked her fingertips into the waistband of his boxers, doing her best to not wake him up. Eventually she was successful and lowered them midway down his thighs. It was another bold move, but it was one she felt was necessary, considering how things had turned out for him last night. Instantly she became nervous as she looked down at his member, slightly intimidated by his length and size given that he wasn’t even hard. Jamie turned in his sleep, turning his head the other way on his pillow. He looked so peaceful, and Cassidy knew that once she began her plan, that look would probably fade.

Gently, she took his shaft in her hands and squeezed her fingers around it. Jamie turned his head to the side again and slowly opened his eyes, rubbing them until he was able to open them completely. When he did and saw Cassidy’s hand stroking him, he shot her a glance.

“What are you doing,” he mumbled, flicking his eyes back down to his waist as her fingers now circled around the head of his cock.

Cassidy bit her lower lip softly as she felt him start to go hard in her hand. “I kind of owe you for last night,” she slid her hand down, and began to lean in, licking her lips quickly.

“Cassidy,” quickly Jamie sat up in bed and set his hand against her shoulder, “you don’t owe me anything.”

She smiled and looked up at him, just barely touching her lips to his. “You’re telling me you don’t want a blowjob,” she squinted her eyes as if she didn’t really believe what she was hearing.

“I’m telling you you’re not obligated to give me one,”

“And what if I want to?” Cassidy tilted her head to the side, smiling softly until she looked away from his eyes, lowering her head down closer to his member as it now began to pulse in her hand.

She kissed the tip gently, slowly opening her mouth around his head, wrapping her lips around him. Jamie fell back on the bed, moving one hand behind his head while keeping the other at his waist. He stared down at her as she flicked her tongue around him, stroking the underside of his shaft with her warm tongue.

As this act continued, Cassidy soon realized she was far too under qualified to be doing this. She didn’t really know what to do next, how far she would go, and most of all, she was pretty nervous about the moment he reached his climax. Maybe she wasn’t ready to have all of him in her mouth. Cassidy flashed her eyes up to Jamie’s seeing that his mouth was hung open as he stared at her, smiling as her lips moved further down his shaft, taking half of him in, while one of her hands gripped onto the base of his cock, squeezing the remainder of his shaft she couldn’t get into her mouth.

He groaned quietly, moving his hand from his waist to the back of Cassidy’s head, gathering her hair in his fist and held it behind her head, giving him an unobstructed view. As her head began to bob up and down on him, taking in as much of him as possible, Jamie rolled his hips up, pushing his length further into Cassidy’s mouth. She gagged at his movement as the head of his cock tapped the back of her throat.

“Cassidy…” he moaned loudly, moving his hand away from the back of her head and grabbed the base of his member.

Cassidy looked up at him and pulled her head off of him, flicking her eyes back down to his hand, which he now used to stroke himself quickly, circling his fingers over the tip.

“Come here,” he managed to say as most of his breath was let out in small grunts.

She did as she was told and crawled closer to him, only to have him kiss her quickly, biting her lower lip roughly. She lay down on the bed, half of her body on his, with one hand pressed against his chest, as the kiss grew more and more heated. Cassidy slid her hand from his chest to his shaft, replacing his hand with hers and began stroking him, stretching to squeeze her small fingers around his throbbing cock.

With her hand and their lips moving in a perfect rhythm, Jamie neared the edge. He gripped at her hair and yanked backwards until her head followed, being pulled backwards, exposing her neck to his lips. The action turned her on, and within a moment, she stopped stroking Jamie as his body went stiff and he bit into the side of her neck. She glanced down at his waist, watching as he reached his climax, shooting a thick load over his lower abdomen. He let out a throaty groan and released Cassidy’s hair, pulling his mouth away from her neck.

They both looked down at his waist, and Cassidy blushed as she buried her head into the base of his neck. She pressed her lips against his collarbone as he sat up.

“Was it okay,” she mumbled against his skin, feeling his arms loop around her body. She then felt herself being lifted up, and when she looked out, Jamie was carrying her towards the bathroom.

Once he pushed the bathroom door open, he set Cassidy on the edge of the sink and went to turn on the shower. “No it sucked,” he walked back to her and stood in between her legs, “that’s why I shot a load all over myself.” He smiled and shook his head, looking down at the white specks over his waist.

He walked back to the shower and pulled the glass door open. Cassidy jumped off of the counter, finally becoming conscious to the fact that she was still naked from the night before. “I’ve got a test to take. And I have to be done with it if I’m going to have a chance of buying tickets to the game tonight.”

Jamie smiled and paused, “you don’t have to pay for tickets. I’ll leave some for you at will call.”

“Good,” Cassidy smiled and crossed her arms over her bare chest, “I was hoping you’d say that. I’m a poor college student.” She turned to leave the bathroom and then looked back at Jamie, “do you mind if I borrow some clothes? Mine got left outside,”

He chuckled and stepped into the shower, letting the warm water run down his body, “go for it. I don’t know how well my shorts will fit you, though.”

He winked and Cassidy rolled her eyes playfully, exiting the bathroom. Back in the bedroom, she rummaged through Jamie’s dresser, pulling out a sweatshirt. She knew it would cover her enough so she could grab her pants from outside. This was obviously a peak in her life; being the girl who had to run around a boy’s house to find her clothes.

She tiptoed downstairs, attempting to be as quiet as possible, mostly because she didn’t know if Jordie was awake, and if Tyler had stayed the night after he’d been rescued. Once downstairs, Cassidy walked through the living room to get outside, stopping short as Jordie was perched on the couch, sipping coffee as he watched TV. Cassidy yanked at the end of Jamie’s sweatshirt, trying to hide more of her body from the elder Benn brother.

Jordie laughed and reached to his side, tossing a shirt and a pair of pants at her. Obviously he had seen her clothes and brought them inside. “I believe this is yours,” he murmured holding up her brightly colored bra.

Cassidy sprung forward and snatched it from her hands, hiding it beneath the clothes she was already holding in her arms.

“And this too,”

She almost died of embarrassment as Jordie held her thong in his hand; the thin fabric hooked over his finger. She took that from him as well, quickly stepping into it and pulled it up her legs. Although Jordie was watching her, at least she had underwear on now; the last thing she wanted to do was flash him.

Notes

This chapter is titled after "Alone With You" by Jake Owen.

Hope y'all like where this is going! I'd love your feedback! :)