Chapter 10: Bottoms Up

"Either way, Sebastian, you will bottom for me."

Kurt gently prodded at the tender flesh around Sebastian's hole. He couldn't deny he was excited. And nervous. But mostly excited. He was finally, finally going to lose his virginity properly, and on his terms. And he wasn't a total neophyte, after all. He and Blaine had gone pretty far towards full penetration already.

Blaine... Again Kurt felt a pang of regret that he wasn't able to share this moment with his sweet, loving boyfriend, that they couldn't create a magical first time experience in some charming country bed and breakfast, surrounded by soft, scented candlelight, the sounds of a crackling fire playing gently in the background. But having love just wasn't enough. Making love required skill. So he had to do this, in this room, with this boy, without love being part of the equation. The thought made him bitter, which made him angry, which in turn made him more determined.

Kurt looked down at the prone figure in front of him, that muscular back, those trim long legs, that round firm ass. He felt his cock stiffening, his erection growing in anticipation.

He put his hands on the backs of Sebastian's thighs. "Are you ready?" he asked, his tone still commanding but just on the edge of asking permission.

Sebastian bit his lip. He'd lost his virginity ages ago, but suddenly he realized with a kind of shock that men had two virginities and now he was losing the second kind, something he had never, never imagined would happen. He wanted to say, No, no I'm not ready. I don't want to do this. But how could he? They had a deal. Sebastian's mind whirled furiously but he couldn't think of a way out. He found himself stunned to realize that he was scared. He tried to tell himself it was just fear of being physically hurt because Hummel was totally clueless and if he didn't prep Sebastian properly, some pain would definitely be involved. But deep inside was another fear, fear of being vulnerable, fear of being... of being … found wanting.

Shake it off, he scolded himself. Never show weakness! You show weakness even once and the world will tear you to pieces. Maybe from behind was a good thing, that way Kurt couldn't see his face if there was any pain. And he wouldn't have to see Kurt's face, either, in case he was a disappointment to the McKinley boy. But there was no way he would be – Kurt was a healthy 17-year-old, of course he'd get off. Sebastian glanced back at Kurt and nodded, hoping no insecurity showed in his eyes.

"Let me just..." he said, pushing back and up to rest on his hands and knees. "The angle will be better."

"Okay." Kurt nodded, even though Sebastian couldn't see it. His finger was already slick with lube from applying it to Sebastian's ass, but he added some more. He really didn't want to hurt Sebastian. He didn't want to hurt anyone, that was the whole point of this 'lesson'.

"One finger, I know that's how I should start" Kurt said as he touched Sebastian's hole and -

"Wait," Sebastian said. "First pro tip - I'm going to bear down and make my hole pout. You see how I'm doing that?"

"Yes."

"Okay, now use your middle finger. Put it in just up to the first knuckle. Gently!"

Kurt slowly pushed in, just a bit. Sebastian contracted his anus muscles, bringing Kurt's finger along for the ride. Kurt had successfully breached Sebastian and the Apocalypse had not come. Both boys exhaled.

"Now push further in. Slowly." Sebastian ordered himself to relax, but his body was having none of it. Kurt tried to work his finger further in, but immediately met strong resistance. He pulled his finger out.

"I can't," said Kurt, shaking his head. "It's too tight. I don't want to hurt you." He felt so angry with himself, with Sebastian. Another frigging disaster! Why did I think this stupid plan would work. Maybe life as a celibate won't be so bad.

"Okay... okay," Sebastian's breathing was shallow, as though he were fighting off panic. He swallowed hard. "So ..." He tried to push down the fear and gather his thoughts. You can do this. Don't let Kurt's nerves get to you. "So... you're being too timid." In a perverse way, Sebastian was relieved to have something to criticize so soon. After the amazing blowjob, he didn't think he could have handled Kurt being a natural at this, too. Sebastian's only hope for retaining the upper hand in this power struggle was finding fault with the McKinley boy's performance whenever possible. "It's gonna be tight, that's just anatomy. You simply have to go slow and let your partner get used to it. Try again." There was little choice but to try to sound encouraging. Now that they'd started down this road, it was a matter of pride – Sebastian hated failure. "Push your finger all the way in and then hold it still." He gummed his lips and willed his muscles to stay loose as Kurt did what he was told.

Kurt could feel Sebastian was still plenty tense but he slowly pushed through. When he reached the base of his finger he stopped and waited obediently.

"You alright?" Kurt asked softly, half hopeful, half afraid. It was a strange sensation for Kurt, feeling his finger encased by tender, hot, hidden flesh. Seeing part of his hand stuck in another man's ass was an even stranger visual. Not much fun so far, but Kurt didn't expect any at this stage.

Sebastian was torn – he'd never been breached, and it felt so different from the other way around. He felt so helpless and exposed, emotions he was definitely not used to experiencing. At the same time, he had a strong innate sexual curiosity, and as his anus relaxed around Kurt's finger, his body grew sort of excited and tingly. Sebastian nodded again, more to convince himself than to reassure Kurt.

"I'm okay," he said, trying to keep his tone steady and confident, "Let's rinse and repeat. Do that a couple more times, but don't pull out all the way between thrusts."

As Kurt followed instructions, somewhat to his own surprise, Sebastian began to enjoy the dull pressure, and Kurt noticed the channel around his finger ease.

Sebastian muttered, "Here we go," under his breath and screwed his courage to the sticking place. Time for the real prep. "Now pull out slowly all the way and then push back in again, this time adding your index finger."

Kurt did so, hoping that if he went slowly enough it wouldn't hurt for Sebastian. He'd never gotten so far with Blaine and the whole situation made him both eager and anxious. Kurt felt the tight channel stretch reluctantly to accommodate the larger intrusion. As much as he disliked looking at the preppy boy's smug face under normal circumstances, he really wanted to see it now. Viewing the back of Sebastian's head gave him no clue as to how Sebastian was handling this and that didn't help Kurt's confidence in the slightest.

As a matter of fact, it did not feel very good for Sebastian. His hole was uncomfortably extended and sore. The taller boy began to panic again but fought desperately not to show it. Ow! Shit! Why did I agree to bottom? "G-go a little faster." Sebastian was trying to remember what he normally did to his partners when he topped. Two fingers felt very unpleasant right now, and he hoped moving faster, like he usually did, would help.

It did help. The discomfort eased a bit, though it didn't completely disappear. After several minutes, he knew it was time for the next step. "Now, keeping them together, sort of swirl your fingers around, like you were stirring something."

This is new, thought Kurt, as he worked his fingers inside Sebastian. "Like that?" he asked softly.

"Yeah," Sebastian grunted, still trying to breathe evenly and keep his backside relaxed. The sharp pain was replaced by a dull ache that felt strangely pleasant. He suddenly remembered something else he usually did. What an idiot not to have thought of it before! "Touch me," he commanded. Kurt ran his hand lightly down Sebastian's back. "My cock, you idiot, stroke my cock!" Sebastian snapped. He would have done it himself it he hadn't needed both hands on the bed to keep his balance.

Kurt reached around with his free hand to touch the other boy's limp dick. "It's not – "

"Christ, Hummel, how slow can you be?" Sebastian snapped. He was almost desperate to feel something besides the constant ache. "Just give me a goddamn handjob, okay?"

Kurt began stroking, feeling Sebastian's cock grow harder and longer with each firm pull.

"Yeah. Like that," Sebastian breathed. "That feels better."

Okay, Kurt said to himself. So I've got to distract my partner from what's going on in the back by keeping him aroused in the front. Got it.

"Don't stop... mmh... don't stop stroking me." Sebastian began to squirm and thrust into Kurt's hand. "And don't stop swirling. You're doing - UNGH!"

Suddenly Sebastian felt a jolt, a sort of blissful wave crash through his entire body. It was like no sensation he'd ever experienced.

From above him, Kurt whispered hopefully, "Did I hit your prostate?" Without waiting for an answer, he angled his finger again as he thrust and was rewarded with a deep, primal groan being torn almost involuntarily from the Warber's lips.

Sebastian couldn't speak but he nodded.

Kurt smiled in triumph. During all their aborted attempts and fumblings, he had not managed yet to find Blaine's prostate, a failing that had caused him no small amount of guilt. But, somehow, he seemed to be doing everything right with Sebastian, just going on instinct. Suddenly he remembered what Blaine had blurted out in his frustration during their last attempt. "Something's just wrong with me!" Could that really be true?

Kurt was pulled from his thoughts when Sebastian thrust back hard, moaning as he fucked himself on Kurt's fingers. The Dalton boy was not unfamiliar with the effect brushing the prostate had on his partners when he took them, but he had no idea it felt so intense. His fear and reluctance about bottoming, his strategic goal of destroying Kurt Hummel – all his higher brain functions, in fact – were disintegrating. Nothing mattered except feeling that feeling again, sustaining it, intensifying it, expanding it.

Encouraged by Sebastian's eagerness, Kurt pressed confidently into the other boy's backward thrusts. The channel was now definitely offering less resistance than before, but there was still enough tightness that Kurt knew it would feel fantastic gripping his cock.

"Enough, Kurt," Sebastian gasped (uncharacteristically calling his prey by name) as he pushed back and back, harder and harder, over Kurt's long fingers. He couldn't take the teasing anymore. "I want you to fuck me."

Author's Note: I hope this chapter was okay. Sebastian's certainly changed his tune about bottoming, eh? Reviews would so totally make me squee!