Cover of The Upper East Side's Last Virginity

The Upper East Side's Last Virginity

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Dan and Serena from Gossip Girl Season 1 Both are 18 years old. Dan has never had sex before and after they have sex the first time, Serena feels guilty it wasnt her first time. So she offers him what no man has ever had, her ass.

Chapter 1: The Brooklyn Loft Aftermath

The bedsprings groaned, a sharp, metallic sound that seemed too loud in the quiet dark. Dan could hear his own heart thumping against his ribs, a frantic counter-rhythm to Serena’s shallow breathing beside him. The single lamp on his desk painted the room in long, dramatic shadows, catching the dust motes drifting over stacks of poetry books and his half-dead laptop. It smelled like his laundry detergent, the vanilla shampoo she used, and something new, something sharp and human.Her skin was cool where it pressed against his side. He stared at the water stain on his ceiling, the one that looked like a lopsided turtle, and tried to figure out what to do with his hands.Should he keep one draped over her stomach?Was that possessive? Clingy? He settled for lacing his fingers together over his own chest, feeling the slick sweat drying there.“Hey,” she whispered.Her voice was rough.

“Hey.”

He turned his head.She was already looking at him. Her blonde hair was a mess, stuck to her damp temples and fanned out across his pillow. In the lamplight, her pupils were wide and dark, swallowing the blue. She was so beautiful it sometimes physically hurt to look at her, like staring at the sun.Now, it was a different kind of ache, tender and bruising.

“You okay?” he asked.She nodded, a small movement.Then her face crumpled a little. “Was it…?”

“It was perfect,” he said, too quickly. It hadn’t been, not really. It had been fast and fumbling and he was pretty sure he’d elbowed her in the ribs at one point.But it was her, and that made it a miracle.

She propped herself up on an elbow. The sheet slid down, and he made himself keep his eyes on her face.“I want to give you something,” she said. Her tone had changed, gone serious and low.“You already did.”

“No.Something else.” She swallowed. “Something no one else has had.”

Dan’s brain stuttered. He couldn’t imagine what that could be.She was Serena van der Woodsen. She had given him her first time, which felt like enough stolen treasure to last a lifetime. “What do you mean?”

She shifted, rolling onto her stomach beside him. She buried her face in the pillow for a second, then turned her head to look at him.Her cheek was smushed against the cotton. “I want you to… I want to give you my ass.”

The words hung in the air, blunt and unbelievable. Dan felt a hot flush spread from his neck to his hairline. He’d read about it, of course, in the dog-eared paperbacks he hid under his mattress, but those were stories. This was Serena.“What?No. Serena, you don’t have to—”

“I want to.” She pushed herself up, kneeling on the mattress. The shadows hollowed her collarbones, traced the line of her spine.“It’s for you.Only you. No one else.”

The no one else hit him like a punch. It was a offering, a sacrifice.A piece of her she was carving out and handing to him, clean and untouched. He saw the guilt then, lurking behind the determination in her eyes. Guilt over a past she wouldn’t talk about, over other boys in other beds. This was her penance, and her gift.His mouth was dry. “Are you sure?”

“Yes.” She reached for the bottle of lube on the nightstand, the one they’d used before. It was still slick, cool when she pressed it into his palm.“Go slow. Tell me what to do.”

His fingers trembled as he fumbled with the cap. The silence was heavy, broken only by the distant wail of a siren on the Brooklyn streets below. He poured too much into his hand, the liquid shockingly cold.“Okay,” he breathed, more to himself than to her. “Okay, turn over.”

She moved with a grace that made his throat tight, shifting onto her hands and knees.He looked at the elegant curve of her back, the pale landscape of her skin. He felt a rush of tenderness so violent it choked him. He placed a shaking hand on the small of her back.“I love you,” he said, the words feeling insufficient.

“I love you too,” she said into the sheets.It was slow, and it was difficult. A negotiation of bodies, a series of hushed instructions and sharp intakes of breath. He was terrified of hurting her, his every movement hesitant, asking is this okay? until she finally whispered, “Just do it, Dan.”

He did.

Her whole body went rigid for a second, a sharp gasp punched out of her.He froze.“Stop?”

“No.Keep going. Just… keep going.”

It was nothing like before. It was tighter, hotter, a searing clench around him. It felt less like sex and more like a violation, a beautiful, sacred violation they were committing together.He watched his hands, pale against her skin, as he moved. Her fingers were white-knuckled, gripping the sheets. He leaned over, pressing his chest to her sweat-slick back, wrapping an arm around her waist to hold her still, to anchor them both.

“Serena,” he mumbled into her shoulder blade.He was crying, he realized. Stupid, silent tears tracking down his nose.It was too much. The intimacy of it, the brutal trust.She was giving him a secret self, a hidden place, and he was being let inside.

It was over quickly.A rush, a shudder, a collapse. He pulled her down with him as he fell to the side, both of them a tangled, sticky heap on the ruined sheets. They lay there for a long time, just breathing.Finally, she turned her head. Her eyes were glassy, distant.She touched his wet cheek. “Why are you crying?”

He shook his head, unable to explain the storm inside him—the awe, the possessiveness, the slight, unsettling edge of horror.He had taken something.She had given it. The power of it was dizzying.“I just love you,” he managed.

She smiled, but it didn’t reach her eyes.It was a satisfied smile, a transaction completed. The guilt he’d seen earlier had receded, replaced by a weary kind of peace. She nestled into the crook of his arm, a perfect fit.Dan held her, staring back up at the water-stain turtle. The room felt different now.The shadows were deeper, the silence more profound. He had crossed a line he hadn’t known was there, and there was no walking it back. She was his in a way she hadn’t been an hour ago. And he was hers in a way that scared him, a way that felt dangerously, irrevocably real.

Her breathing evened out into sleep. He stayed awake, listening to the city, feeling the weight of her gift, and wondering what, exactly, he was supposed to do with it now.

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