Story: First Time, Second Chance

By: Ruby Lis

Pairing: Kurt/Dave, some Kurt/Blaine and Sebastian/Blaine.

Rating: M for sexual situations.

Summary: When Kurt's first time having sex doesn't go quite as well as planned, he discovers that Dave may have the solution to his problem.

Disclaimer: Glee belongs to Ryan Murphy.

A/N: Possible spoilers for "The First Time". Just a quick bit of love for the Pirates. Enjoy! (And, yes, I'm still working on "Paragraph 175").

….

It hurt.

Kurt squeezed his eyes shut, biting his lip against tears of frustration…and pain. He lay on his side, knees drawn up to his chest, arms clutching his waist. He flinched-again-when Blaine's fingers tentatively brushed his shoulder.

"…kurt?…"

"I'm fine, Blaine."

Kurt forced the words out through clenched teeth. He quickly brushed a hand over his face then, very carefully, rolled over, wincing, to face Blaine. His would-be lover pressed his forehead to Kurt's, fingers brushing his cheek and then falling down to curl lightly around his wrist. Kurt nuzzled into Blaine's warmth, heart silently breaking over the perfect, exquisite moment of their first time together being shattered by their inexperience.

…..

Rod Stewart blared through the sound system of Scandals and even then he was mostly drowned out by the dozens of patrons singing along, loudly, to lovers and strangers alike the lyrics to "Do Ya Think I'm Sexy?".

And there, front and center in the chaos, was Dave Karofsky, singing just as raucously as everyone else to his Tina Turner wannabe dancing partner.

He looked like he was having fun.

Kurt hesitated, taking a moment to really watch his former bully and let it sink in that Dave Karofsky was coming to terms with being gay. He glanced around the grungy bar. If coming to terms meant being openly gay in the relatively anonymous safety of Scandals.

Still, he certainly seemed happier than Kurt felt at the moment. The first time Kurt had been here with Blaine and Sebastian, he hadn't had a chance for much more than a quick chat with Dave. Still, the former football jock had told Kurt if he ever need anything to look him up. And, frankly, he didn't know who else he could talk to. Not about this.

"You owe me a dance."

Kurt's voice startled Dave but when he saw the shimmer of tears in those troubled blue eyes, he quickly realized something was very wrong.

"It's a slow dance."

"I don't care!" Kurt's voice cracked. David made polite excuses to "Tina", put an arm around Kurt's shoulders and led him onto the dance floor. Kurt buried his face against Dave's shoulder and wrapped his arms around the jock's waist as if he were drowning and Karofsky was his lifesaver.

"Blaine and I…we…it was supposed to magical." He snuffled into Dave's sweater. "And it was! At first. But then…" His voice trailed off into silence.

"But then what?" Dave prompted gently, trying to follow Kurt's confusing conversation.

"It hurt."

Dave stopped moving. "Blaine hurt you?"

"He didn't mean to!" Kurt looked up, quick to dispel any misunderstanding. "It was...our first time."

"Oh, okay."

"Okay?" Kurt drew back, upset.

David shrugged. "It usually does hurt, at least a little, the first time."

"As if you would know."

A secretive smile played across Dave's lips. "I do know."

"Really?" Kurt asked, face looking hopeful for the first time since he had entered the bar.

Dave wiped his thumb across Kurt's cheek, drying his tears.

"Really. You just need to be more prepared. And learn to relax."

Kurt leaned his head against Dave's broad chest, letting his body sway to the music and being soothed by the reassuring strength of the arms that held him fast.

"What's it like?"

"What, sex?"

"Mm."

"Pretty fucking awesome."

They danced until the song drew to a close. Finally, Kurt spoke up, sounding lost.

"What should I do?"

David swallowed against the tightness in his throat. But Kurt needed a friend now, not a complication. And Dave loved him enough to be whatever Kurt needed.

"I think you and Blaine should try again."

"How?" Those forlorn blue eye looked helplessly into his.

"There's stuff you can get to help…so it won't hurt."

"Like what?"

"Fuck, Hummel, I don't know, just stuff!"

"Why are you yelling at me?"

Karofsky took out a deep breath and let it out slowly. "Wait here."

"But-"

"Wait for me, 'kay?"

Karofsky shouldered his way through the writhing bodies and Kurt drifted over to the bar and ordered a Diet Coke while he waited. Several moments passed. Finally, Dave returned. Wordlessly, he took Kurt by the elbow, guided him towards one of the alcoves on the other side of the club and closed the curtain behind them after they had entered. Dave plopped onto the overstuffed couch and dumped a few items from his pockets onto the red leather.

Kurt hovered by the curtain, eyeing David hesitantly.

"What are you doing?"

David grinned mischievously, "You need to be educated."

He held up a package of brightly colored graduated shapes. Kurt smiled. Those didn't look so scary.

"Butt plug training kit."

Kurt's eyes widened as he dropped the package back on the pile. He looked dubiously at the other items.

"Where did you get all of this?"

"Vending machines in the restroom." He noted Kurt's look of disgust. "Don't worry, they're packaged really well." He held up an unopened bottle. "And I got disinfectant."

"Are you planning on using those now? On me?" Kurt's voice squeaked.

Dave sighed, seeing the fear and distrust. He gathered the items up, shoved them in a plastic bag and handed them over. "Most of them have instructions. Or you can look them up online. If you need anything else, call me."

With that, he hurriedly left before Kurt had a chance to thank him.

…..

It happened again.

This time, Kurt and Blaine hadn't even gotten as far as they had the first night they tried to have sex. They lay side by side on their backs studying the ceiling.

"I don't understand." Kurt was the first to speak. "I read the pamphlets. I followed the instructions on the…toys." He turned his head towards Blaine. "We used lube."

Blaine shook his head, also at a loss.

"Maybe it's me." Kurt whispered.

Blaine threaded his fingers through Kurt's. "Maybe it's both of us.

Kurt panicked. "Are you saying we shouldn't be together?"

"No! God, no. I'm saying we don't know what we're doing. I don't want to hurt you, Kurt."

"You're a little late for that." He couldn't keep the bitter frustration from breaking through but immediately regretted his words when he saw Blaine's face.

"I overheard some of the guys at Scandals talking."

"About-?"

"Mentors."

"I see." Kurt answered coolly, not sure he liked where the conversation was headed.

"Apparently it's not uncommon for a more-experienced-gay guy to, well, mentor a newbie."

"And did you have anyone particular in mind to-mentor-us?"

"Sebastian offered-"

"Oh, I just bet he did." Kurt got out of bed and started angrily pulling his clothes on.

"You went to David for advice. "

"Advice, Blaine, not sex!"

"Maybe you should have considered sex." Blaine said quietly.

Kurt froze. "Excuse me?"

"Look, Kurt…" Blaine sighed. "…can I be honest? Sebastian and David have experience we don't. If we can, I don't know, learn from them so we don't hurt each other…would that be so bad?"

Kurt answered Blaine by slamming the door as he stormed out.

….

Blaine moaned, body pinned to the wall as Sebastian fucked him. And, really, there was no other word for it. He shuddered under those deft, sure strokes claiming him, stirring something in him that he had never felt with Kurt. A flash of guilt. Quickly driven out when Sebastian slid his hand between Blaine's hip and the wall to grasp his dick, the grip lube slick but firm as he pumped him with an expert's touch.

"…so hot…"

Blaine shuddered, groaning as Sebastian nudged his thighs farther apart, spreading his tight ass wide so he could drive deeper into him.

"…ughn…"

"That's it, Gorgeous, come for me."

Blaine cried out, bucking hard against Sebastian as the blonde brought him to climax.

…

Kurt sat in the Lima Bean, coffee growing cold, staring silently at his perfectly buffed nails and thinking that last night's manicure had been a waste of time.

"Penny for your thoughts." Blaine finally spoke, breaking the awkward silence of the past twenty minutes.

Kurt sighed, finally looking up to meet his boyfriend's concerned gaze with a sad, tight smile.

"I was thinking about my first day back at McKinley, when you showed up to serenade me."

"I remember." The dark eye boy nodded, encouraging Kurt to keep talking.

"I told you I would never say goodbye." Kurt laughed, quietly mocking himself. "It never occurred to me that you would."

Blaine quickly took Kurt's hand in his. "This is not good-bye."

Kurt pulled his hand away, bitter. "Well, it sure as hell isn't hello."

"Remember what I said in the auditorium? About wanting to try everything life has to offer? Kurt, I want you to experience this. Even if it means I'm not going to be the one to give it to you."

Blaine paused, reaching for Kurt's hand again and holding it firmly.

"I want this for you because I care about you."

"You're saying you've chosen Sebastian over me."

"I'm saying maybe David can give you what Sebastian's given to me. I'm saying you owe it to yourself to try, Kurt. You deserve so much more than what you've settled for."

Blaine nodded his head towards a far corner where Dave Karofsky sat, alone, watching them curiously as if he were waiting to see how things played out.

"Fine."

Kurt said huffily as he left Blaine and walked over to Dave's table, nervous under the scrutiny of those intense hazel eyes.

"Blaine slept with Sebastian."

Dave sipped his coffee. "I heard."

"He seems to think I should sleep with you."

"No."

Kurt blinked in surprise, taken aback by Karofsky's refusal.

"You don't want me?" He couldn't keep the hurt from his voice.

"Like this? All caught up in feeling sorry for yourself? Fuck, no."

Kurt's grip on his messenger bag tightened. "You think you're so special, David Karofsky?"

"No, I think you are. You matter, Kurt. When the pity party's over, when you're ready to have sex, give me a call."

"Ready to have sex?" Kurt repeated disdainfully, put off by the other boy's straightforwardness.

David shrugged. "I say it like it is, Hummel. Deal with it."

A week later, he called.

….

Kurt let out a soft "oh" of surprise. David's bedroom had been transformed into something…magical…Kurt thought to himself. Gone were the hockey and football posters and now the bare walls were covered in twilight blue light with an overlay of stars playing across them. The bedroom window had been left slightly open, just enough to let in the slight breeze and the soft chirp of crickets, both adding to the feeling of being outside on a cool, fall evening.

"Would m'sieur care to try our finest bubbly?"

"I don't think I should be drink-"

Kurt broke off, giggling as Dave set down a silver tray carrying a Diet Coke and ice filled glass. Continuing his faux French waiter impersonation, he popped the can open, carefully poured a small amount into the glass, then, with mock seriousness waited until Kurt sipped and nodded his approval. Smiling, Dave filled the glass.

While Kurt took another drink, Dave kneeled by his feet, unzipped the fashionista's boots and slipped them off. Kurt giggled again when Dave's fingers accidentally tickled him as he removed his socks. He sat down and drew Kurt's bare feet into his lap, thumbs rubbing delicate circles over his ankles then deepening the pressure, pushing gently into the arches. Kurt sighed, relaxing. Who knew that such a simple thing as having his shoes and socks taken off for him could make him feel so decadently pampered?

Willing to go along with David's playfulness, Kurt stretched out on his stomach on the faux bear skin rug. The fur was surprisingly soft and…Kurt murmured under his breath…arousing.

"Mph."

"You okay?"

"…oh, yes…" Kurt rolled onto his back, enjoying the twinkling walls. "So, now what?"

"We get naked."

Kurt laughed until he realized David was doing exactly that, unbuttoning his flannel shirt, loosening his belt and shrugging out of his jeans.

"Just like that?"

David's eyes-green in this light-sparkled as he folded his clothes and set them aside.

"Pretty much."

Kurt blushed. And yet, it felt strange to keep his clothes on while David was…he glanced with shy admiration at that body…baring all. Nervously, he began unbuttoning his shirt. He glanced up, expecting to see hazel eyes devouring every move and was surprised to see David wasn't even paying attention to him. As if being naked was no big deal. Surprisingly, his attitude made Kurt more comfortable about taking his own clothes off and soon his shirt and pants were neatly folded next to Dave's.

"Want another Coke?"

"I'm good."

David grunted in acknowledgement. Eventually, he came back with another tray. Kurt recognized some of the items, they were similar to what he had been given in Scandals.

"Roll over on your stomach."

"But-"

"What?" Dave waited expectantly for Kurt to finish his thought.

Kurt eyed the tray then rolled onto his stomach, trying to unclench his muscles as he prepared for the next step. Dave worked quickly, lubing a small, thin butt plug and slipping it in before Kurt had time to register what was happening. His ass gripped the silicone between his butt cheeks but there was no pain, only a slight pressure. He waited for more. Nothing happened.

Dave rolled onto his back. After a moment, Kurt experimented and found he was okay to roll on his back, too. Dave reached over and clicked something on the table. The stars in the room began to flicker and rotate. He slid an arm under Kurt's shoulders and scooted closer.

"The Big Dipper."

He pointed out the familiar constellation.

"The North Star." Kurt added, pointing it out.

Dave nodded. "Also called Polaris."

The lay in the dark, watching the stars and Kurt began to relax, cuddling against Dave's chest and listening to the sound of his voice as he explained the myths behind constellations such as Orion The Hunter. When they finished, Dave had him roll on his stomach again. He eased the butt plug out and put a larger one in. Again, Kurt tensed, expecting pain and, while it was tighter, it wasn't anything unbearable.

"Stay there."

"…mm…"

Kurt, growing comfortably drowsy, had no intention of moving and let his eyes drift shut. He heard Dave coming back. And then he felt David's knees on either side of his thighs as the former football jock carefully settled his weight against Kurt's body. It felt good. Something liquid dribbled onto Kurt's back and then broad palms were spreading it to his shoulders.

As David massaged the oil into Kurt's skin, he began to feel it sinking in, penetrating his muscles with a deep, relaxing warmth. David blew softly over the back of Kurt's neck and he shivered at the delicious sensation. He squirmed.

"What's wrong?"

"I don't want you to stop."

Dave chuckled. "Not planning on it."

"But I want to see the stars, too."

"Oh."

Dave sat back, taking a moment to study his room and figure out a solution. Grinning, he got up, carefully lifted the wide mirror from his dresser and set it down on the floor, angling it so Kurt could see the walls and ceiling reflecting the night sky Dave had created in his room.

"Better?"

Kurt sighed contentedly. "This is lovely." He met Dave's gaze, holding it for a long moment as if making up his mind about something. Finally, he nodded. "I think I'm ready."

He heard movement and then the smooth, lyrical voice of Nat King Cole singing in the background.

Dave removed the butt plug and eased himself in until he filled Kurt completely. Kurt whimpered. Dave stretched his body over Kurt's, covering him when he shivered.

"I know, babe." He kissed his shoulder. "Relax. It'll get better in few minutes."

Kurt bit his lip and nodded, wanting to believe this time would be different but fearing in his heart that it wouldn't be. Dave lay still on top of him, like a warm blanket. The fur beneath him seductively rubbed against his bare skin. Kurt could feel himself growing hard. Dave shifted slightly, hitting something deep inside that sent a jolt of pleasure firing through Kurt's nerves and snapping his head back as he cried out.

"You okay?"

Kurt bit back a moan, struggling to hold on to coherent thought long enough to nod.

David pulled out then slowly pushed in again, hitting that sensitive gland that had Kurt gasping and clenching the bearskin rug as he instinctively rolled his ass back to draw David in deeper.

"…oh, god!…"

David drew back out and Kurt whined at the loss of sensation, reaching for him as he pulled away. He laughed as he playfully smacked Kurt's firm ass.

"Turn over."

Pouting, Kurt did as told, blue eyes going wide as David lifted his ankles onto his shoulders. And then he entered Kurt again, their new position letting him penetrate deeper, filling him up and coaxing another low, throaty moan as his dick found the sweet spot and slid over it again and again.

Kurt fisted the bearskin, alternating between quick gasps and long, drawn out moans as waves of pleasure crashed over him. He watched the stars still twinkling in the room as Dave rode his body and none shone as brightly as the love he saw in those hazel eyes as he came.