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Jesse let his hand slide down over Jamie’s front and around his waist, only to work his way up on the skin of his back.

Jamie shuddered once more under the touch, but seemed to like it, closing his eyes with another smile.

Taking the cue, Jesse let himself apply a bit more pressure as he moved up and down a few times before he reached the waistband of Jamie’s trousers—and moving his hand on top of the fabric, his fingers came to rest upon a place he’d longed to touch for what felt like an eternity.

He gave the butt cheek a firm squeeze. Guiding Jamie to raise his leg, it came to rest over Jesse’s hip.

Jesse deepened his kiss and slipped his tongue into Jamie's mouth again, pulling him closer and savoring in Jamie’s moans.

Pulling up his own leg and placing it between Jamie’s, he slid his other arm around him, digging his fingernails into the skin on Jamie’s back.

But wait. He couldn’t go too fast. He had to check in again.

“F-fuck…” he breathed through gritted teeth. “J-Jamie… I… I don’t know if I can h-hold back any longer…”

“Y-You don’t—” Jamie panted heavily. “You don’t have to h-hold back…”

Alright. Jesse reached the waistband of Jamie’s trousers again.

This time, he didn’t hesitate before slipping his hand in, grabbing the naked skin of Jamie’s butt and squeezing it even harder.

He sank into another deep kiss against Jamie’s neck, and pressing himself against Jamie, he felt the pressure of Jamie’s crotch.

Oh god.

Jamie let out another groan, arching his back as if overwhelmed by the pleasure, which gave Jesse the chance to kiss his neck more intense than before.

“Jamie,” he breathed. “I’m going to unbutton your pants, okay? I’m going to touch you… where I’ve never touched you before.”

“O-okay…” Jamie whispered, trembling in Jesse’s hold.

Jesse didn’t even have to look as he deftly slipped the silver button through the hole in the denim and then pulled down the zipper.

He let his fingers move to Jamie’s back again, carefully pulling the jeans down a bit, and then reached into Jamie’s underwear, further than he’d gone before.

Slowly, carefully, he moved downwards until he came to a particularly sensitive spot—gently massaging it for a while, and giving Jamie time to get used to the feeling.

Then he pushed in with the tip of his index finger .

Jamie let out a startled groan, his fingernails digging into the skin of Jesse’s neck.

Jesse pushed his finger in a little further.

Jamie latched onto Jesse, arching his back in response and pulling him into another feverish kiss, and as Jesse tried to press deeper, he realized only now that he would need some kind of lube for this.

Damn it…

If he’d known how the day was going to end, he would’ve been better prepared. Instead, he was left trying to hurriedly think of some kind of alternative.

Sliding his hand back up, Jesse shifted his position until he was half on top of Jamie again, looking down at his flushed face in admiration.

“I… I need to get us something,” he got out, his tone thick and his breath bated. “I’ll be right back, okay?”

At first, Jamie didn’t seem to hear him, apparently too caught in the pleasure to be paying attention. But then the words seemed to register, and he nodded stiffly as he released Jesse’s neck. “H-hurry.”

Jesse didn’t need to be told twice.

He staggered back up to his feet, rushing out into the kitchen and looking for something useful—but since he never needed a substitute before, he didn’t know what to get.

Fuck, this was the worst. With a deep sense of urgency he didn’t like, he spotted his cell phone on the counter and grabbed it, doing a quick bit of research.

…Olive oil?

Really?

He just had to hope the internet was telling him the truth; and hurrying over to his cupboards, he rummaged around for a moment before he found a bottle of olive oil.

‘Extra Virgin’ olive oil, to be exact, which he probably shouldn’t find so funny now that he was out of middle school.

But hell, now that Jesse had felt how tight Jamie was, it was just fair to assume that he truly was a virgin.

Jesse checked the expiration date, a smirk crossing his lips, and then returned to the bedroom .

Jamie was sitting up, leaning against the headboard with his knees pulled up to his chest, and the blanket pulled up over them to cover himself.

Jesse knitted his brows. Had Jamie changed his mind? Was he getting freaked out about everything? Was he just cold? Or did he want to stop after all?

But then his eyes caught the sight of Jamie’s pants, lying discarded on the floor.

Together with his underwear.

“Oh, I see…” Jesse said, biting back another smirk.

Jamie grinned back at him, pulling the blanket up further to hide his blushing cheeks.

And god, how was Jesse supposed to resist that?

Striding forward, he set the bottle and his phone aside on the bedside table, before he opened the drawer and pulled out a sealed condom.

More than relieved he still had some left (it had been a long time since he’d needed one, after all) he put it next to the olive oil. Then he turned to the bed.

He propped the pillows up against the headboard, taking advantage of the break to get the bed good and ready, and then stripped himself down the rest of the way, keenly aware of Jamie’s wide and eager gaze.

Now ready, Jesse crawled back onto the mattress.

He knelt in front of Jamie, ignoring the red in Jamie’s cheeks and the burning heat in his own as he took Jamie’s hands in his.

“Come here,” Jesse whispered. Carefully, he shifted himself against the headboard with the pillows at his back.

Jamie moved to sit down where he’d been directed, taking the blanket with him as he let Jesse guide him onto his lap. The feeling of Jamie’s bare skin against his was heaven. Reaching out, he slowly pushed the blanket open.

The fabric fell softly from Jamie’s shoulders.

Jamie made no protest, so Jesse moved on. He placed his hands on either side of Jamie’s waist, gently pulling him forward. And placing his hands onto Jesse’s chest, Jamie let out a deeply contented sigh as he dropped his head onto Jesse’s shoulder .

Once again, Jesse took his time. He let his fingers wander up and down over the skin of Jamie’s back, slowly massaging him until there was no tension left in Jamie’s body. With every pass, he went farther and farther, until he finally got back to where he had been.

This time, Jamie’s response was even more exquisite; the pressure that pushed against Jesse was hot and thrilling and impossible to ignore.

The impatience in Jesse’s body was overpowering.

“Jamie,” he muttered into Jamie’s ear. “I can’t hold back any longer, but I don’t want to – to hurt you.

The bottle on the table…” Jamie lifted his head, his wavy dark brown hair tickling Jesse’s face as he looked around for the bottle.

And fuck it, the whiff of his hair and the sweat on his back made it even harder. Literally.

“P-please take it,” he managed to instruct, as he pulled one hand free of Jamie’s body and held it out. “And… put some oil into my hand.”

Jamie reached out to get the bottle, looking it over curiously before opening it and carefully pouring a few drops of oil into Jesse’s outstretched hand. “Like – like this?”

“A bit more…” Jesse replied. Jamie poured some more into his hand, the thick but fresh scent of olive oil merging with the steamy musk of the two men as it filled Jesse’s palm. “There.”

Jamie set the bottle back onto the table, looking at Jesse with wide, curious eyes.

“Alright, here we go,” Jesse whispered as he began to rub the oil onto both hands. “Remember: If I do anything that makes you feel uncomfortable, please stop me.”

Jamie answered with a nod.

Slowly, Jesse leaned back against the pillows, guiding Jamie to lay down with him once again.

Jesse started to open him up extremely carefully.

Applying the oil onto the sensitive skin first, he drew small circles as he felt the tightness around his fingertip, before he slowly pushed one finger in.

It was a test, really—a way to make sure Jamie had the chance to take stock of what he was experiencing, and put a stop to it if he needed to, before Jesse went all the way.

He watched Jamie carefully as he massaged the oil in until the muscle began to loosen up, always waiting a few moments to give Jamie the chance to adjust.

After a while, he added a second finger—earning another moan from Jamie.

Jesse eased him even closer with one hand, pushing his fingers further in with the other.

“Je-Jesse,” Jamie muttered breathlessly, lifting his head up.

Jesse paused, but then Jamie’s mouth pulled into a dazed, blissful smile. “That f-feels amazing!”

The words sent a rush of euphoria through Jesse, and he pulled Jamie into one more deep kiss.

Jamie melted into it, and for a short while, they just stayed like that; skin against skin, intimate but unspoiled.

Then, Jesse continued, carefully working Jamie up until he sensed that he had prepared him as much as he could.

Pressing his forehead against Jamie’s, they were both panting for breath.

“Jamie,” he whispered. “What comes now is… the most difficult part. It will probably hurt, but once I’m in, it will ease, and feel better.

I promise.” He took in a few more deep breaths, swallowing as he anticipated the tight heat about to come.

Reaching over to his bedside table, he grabbed the condom.

“Just… relax,” he instructed, “and then when I say to, I want you to try to lower yourself down onto me.”

Jamie slowly shifted himself up, giving him a trusting look as he put a hand to Jesse’s chest. “Okay.”