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First Time For Everything

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Dean winced and Cas looked up, concern written across his features.

“It’s fine, I’m fine, you don’t have to stop,” Dean groaned. His eyes were closed tight, his forehead furrowed deep.

Cas leaned up, his bare chest brushing against Dean’s when he found the human’s lips.

“This isn’t something to be endured, Dean,” he murmured. The hunter’s eyes opened then, candy apple green in the light of their shared bedroom. Silently, he nodded, but his jaw was still set.

Cas kissed him again, his fingers temporarily stilled inside his lover’s body. They remained still as Cas’s mouth travelled over Dean’s body, working slowly downward. His tongue flicked over the head of Dean’s half-hard cock, and Dean moaned. It gave Cas the reaction he was looking for, Dean’s body instinctively relaxing around his fingers.

Cas moved experimentally, fingers scissoring Dean’s plaint hole while his mouth worked at the hunter’s cock. Dean groaned, the muscles of his belly flexing and twisting.

“Good?” Cas asked, looking up. Dean had one arm thrown over his face, only his mouth left visible.

“Yes,” he answered, and Cas smiled. Two years he’d been making love to Dean, before they made it to this point. There were hang-ups here, Cas knew. The result of social conditioning and preconceptions whose origins he couldn’t begin to guess.

He didn’t mind. He was perfectly willing to continue using his mouth and hands (and receiving the same in return) but Dean seemed to harbor a second set of preconceptions, one that refused to acknowledge any of this as ‘real’ until they’d ‘really done it.’

Castiel was willing to do whatever made him happy, and that’s how they’d ended up here.

Cas hooked his fingers up again, feeling for the root of Dean’s cock, stroking it from the inside.

Oh, ” Dean answered, his arm tightening over his eyes. Cautiously, Cas added another finger. It slid easily into Dean’s lubed hole, and Dean let out a quiet whine.

Cas listened, his tongue pressed flat against the underside of Dean’s cock, but Dean didn’t make another noise. His body tensed minutely, but then relaxed again.

“I’m okay,” Dean said weakly. “I’m okay, keep going.”

Cas let his grace sweep across the surface of Dean’s mind- not reading thoughts exactly, just judging the man’s condition. Dean whimpered, feeling it happen, accepting the need for it.

There was a nervous anticipation there, Cas felt. Not fear. Not pain.

He moved again, pressing deeper, and though Dean moaned again, his mind did not change.

Cas continued to suck him off, his mouth a counterpoint to the fingers moving inside Dean’s body. Within a very short time, Dean had become acclimated to them, his hips grinding down onto Cas’s hand.

“Are you ready?” Cas murmured, and he saw a flash of embarrassment across Dean’s features, but the hunter nodded.

Cas tore the condom open with his teeth, knowing full well the reaction that Dean would have to the sight. Sure enough, the hunter groaned, letting his head fall back against the pillow while Cas rolled the condom on.

He leaned down, pressing a kiss to Dean’s inner thigh, before using his hands to guide them wider. Dean was blushing all the way down to his nipples, avoiding Cas’s eyes. Cas wanted to tell him that he was beautiful, his body spread and receptive to his mate, but he knew that Dean tended to balk at such endearments. Instead he leaned down, kissing Dean softly, letting the head of his cock brush against Dean’s stretched hole.

He didn’t ask for permission, just waited while Dean kissed him, slow and easy. Eventually the hunter pulled back, looking up at him with a mixture of love and nerves. It was same way he’d looked when he’d broached the subject, suggesting in a mixture of pop references and innuendo that he’d like Cas to anally penetrate him.

“Yeah,” Dean said, answering a question that Cas hadn’t asked. Cas nodded and leaned forward, letting the head of his cock slide into the tight heat of Dean’s body.

Instantly, the hunter hissed and tensed, his body slamming shut against the intrusion.

Dean threw his arm over his face again, a chorus of “sorry” escaping his lips. Cas leaned in, kissing his bared lips, making no effort to push deeper.

“You have nothing to be sorry for. Did I hurt you?”

“No. No, it’s just strange.”

Again, Cas skimmed across Dean’s mind, verifying the truth of the claim. There were words he felt would have been more descriptive than ‘strange,’ but he didn’t comment. Instead he reached down, stroking Dean’s side, gentling him until his body began to relax.

“Would you like me to continue?”

Dean nodded, wordless, unable to ask for what he wanted. Cas smiled at him, unseen, loving the contradictions of his human lover. He pushed deeper, relishing the feel of the hunter surrounding him. His primary concern was not to hurt the other man, but he’d be lying if he said he wasn’t enjoying himself.

He pulled back an inch, groaning as Dean tightened around him again, his body seeking to keep hold of the angel. Unwilling to deny him, Cas pushed in further, working himself deep to the sound of Dean’s whimpers and moans.

He leaned down over Dean, taking the hunter’s hand and guiding it to his softening cock.

“I want you to touch yourself,” Cas murmured, loving the shiver he got in response. “I want you hard while I’m inside you.”

Fuck, ” Dean groaned, but he did as he was told, tugging at his flagging erection until Cas was satisfied. Only then did Castiel begin to move again, withdrawing only an inch before burying himself inside Dean again.

Even with the copious lubrication he’d insisted on using, the friction was glorious. Dean tightened and spasmed around him as the hunter sought his own release, and Cas had to close his eyes before the sight of him became too much. Even then, he couldn’t block out the sound of Dean’s stuttering breaths, the soft whines when Cas pressed fully into him.

“You’re beautiful,” Cas told him, opening his eyes again. “You are the most perfect thing I have ever seen.”

But he said it in enochian, because Dean tended to balk at such sentiments.

The hunter caught his drift, in any case, because his face flushed red and his knees locked around Cas’s hips, pulling him closer.

“Love it when you talk dirty to me,” Dean groaned, fisting his hand in Cas’s hair and pulling him down for a kiss before Cas could correct him.

The action trapped Dean’s cock between their bodies, twin pressures stroking and pressing in, and before too long, he was coming into the space between them. Cas could feel it, wetting his belly in erratic bursts, and like always, Dean’s pleasure brought him to his own climax.

He ground out Dean’s name, his fists tightening in the sheets as he spent into the human’s body. It seemed to go on forever, wave after wave crashing over him, until all he could do was clutch at Dean’s shoulders.

“God, Cas,” Dean groaned. His fingers ran up the nape of Cas’s neck, scratching at the short hairs there. “God, that was good.”

“Mmm,” Cas answered, nuzzling down into the touch. He wasn’t ready to pull out yet. His cock felt hypersensitive, and Dean was already tight around him.




The angel looked up at the sudden concern in his lover’s voice. Dean was staring down to the place where they were still joined.

“Cas, wha- ah!

Cas pulled back, trying to extricate himself, worried that Dean had been torn by his carelessness. He kicked himself for losing focus, for losing himself in the feeling of being inside-

He couldn’t pull out.

He tried once more, gingerly, only to be stopped by Dean’s cry of pain. The hunter’s pink, puffy hole was stretched around him, and when he attempted to pull back, it was obvious that something large was pulling at the rim from the inside.

“Cas- stop it!”

Cas’s mind raced, trying to find an explanation besides the obvious. Dean’s hold was tightening around him with each passing second, and with horror, Cas realized that it wasn’t Dean that was changing.

Lighting fast, he leaned in, catching Dean’s arms and rolling the two of them until the hunter was on top, straddling him. The angle was better, but not by much. Dean stared down at him, eyes wide, his hands planted on either side of Cas’s face.

“I’m so sorry,” Cas whispered, and Dean’s eyes got wider.

“Cas? What the hell is that?”

“A knot,” Cas answered. His voice was thick. “It’s going to last about twenty minutes. I didn’t know. I’m sorry.”

Dean whimpered, trying to straighten and then freezing as the thick knot tugged at his hole.

“Cas, please. It hurts.”

“I know. But I can’t make it stop.” He reached up to cup Dean’s face. “I’m so sorry.”

He tilted his hips up, giving Dean the leverage the human needed to lie flat. Dean took the opportunity, burying his face in the hollow of Cas’s throat. He continued to grow tighter and hotter around Cas’s swelling cock. Each tiny movement was heaven on the oversensitive organ, and only Dean’s whimpers of pain kept Cas from becoming aroused again.

Instead, he wrapped his arms around Dean’s shoulders, trying in vain to comfort him. The hunter was breathing in deep gasps, and Cas could do little but press kisses to his temple.

“Feels like it’s gonna tear,” Dean groaned, and Cas closed his eyes, praying that wasn’t true. “The fuck is this even for ?”

“Generally, it’s meant to keep the sperm inside the vagina long enough to ensure conception.”

Dean snorted, being very careful to hold his lower body still as he did.

“Good luck with that. ” He paused. “You... coulda warned me.”

Cas held him tighter, his fingers stroking through Dean’s short hair.

“I didn’t know,” he admitted. “It’s never done this.”

“Yeah.” Dean’s voice was rough. “Yeah, I think I woulda noticed.”

Cas continued stroking, dropping his hand to rub Dean’s back when his breath grew ragged. The human’s body was uncomfortably tight around Cas’s girth, though it mercifully seemed to have levelled off. Cas began to worry whether Dean actually would tear. The hunter’s breath hitched and Cas realized that the pain had brought him to the brink of tears.

“I’m so sorry, beloved,” he whispered, leaving the last word untranslated. “I would never have done this to you, if I knew.”

“Nnh,” Dean answered. His fingers were tight on Cas’s shoulders, a parody of the action taken in ecstasy only a few minutes before.

Cas pressed his lips to Dean’s temple, fighting back his own tears as he felt the hunter trembling. Gathering his grace, he tried to force it into his errant cock, but there was no reaction. He tried again, trying to push it into Dean this time, trying to relieve some of his pain, but again it was fruitless.

“Thanks,” Dean whispered. Cas nuzzled against his throat.

“It didn’t work.”

“Yeah, but…” Dean winced. “You tried.”

“Of course, beloved.”

Cas hesitated, drawing his hands up to stroke through Dean’s hair again.

“I may be able to dim your consciousness. Reduce your perception until it’s over.”

Dean cringed.

“Never been one to pass out right after.” He turned his head a little, green eyes meeting blue. “Promise not to hold it against me?”

“Never,” Cas answered. He leaned forward, pressing his mouth to Dean’s. The hunter gave a small nod and Cas let his grace flow between them. Dean went limp against him almost instantly. Cas caught him and held him still, whispering words that Dean wouldn’t remember when he awoke.