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It was 1: 43 am, and Jeff Winger was still awake. It wasn’t the temperature in his apartment—he had already checked his thermostat to confirm that, yes, it was still set to a cool 68 degrees Fahrenheit. It wasn’t his sheets, they were freshly laundered, and the Egyptian cotton felt particularly good against his skin.
Jeff would close his eyes, feeling himself drifting off to sleep, but then it would happen—an image of her soft, pale thighs—another of a sweater stretched tightly over her chest—and his hand would drift south, reaching for his…
There was no mistaking the effect she was having on him. His comfortable boxers (a soft soy/cotton blend) were becoming irritatingly, downright uncomfortably tight. It had been like this the past eight nights. As he got ready for bed, his thoughts would dwell on Greendale, on (shudder) lesson plans for the next day, and of course on his friends—it was only natural he would think of her. But as he settled in for sleep, his class would drift away, as would the Dean, Abed, Britta, Shirley, and so on. But just when he felt his mind becoming clear, Annie Fucking Edison would force her way back into his thoughts.
Jeff, tired of fighting, invited her in. He pictured her stepping into his room, her body barely visible in the darkness. He pulled down his boxers, his left hand closing around the base of his cock. Closing his eyes, he could almost feel Annie sliding into bed next to him, her skin impossibly soft and warm. He could almost hear her whisper his name, “Jeff…” drawing it out just a little longer in the way only she could. “Jeff, I need you…”
Jeff was definitely not getting back to sleep now. Though he had never actually heard her utter the words, it was more than enough to get him thoroughly aroused. He reached his right hand under the sheets to join his left, his erection reaching full size so rapidly; he could feel his pulse pounding as he surged thicker and longer. He imagined that Annie was trailing butterfly kisses down his neck toward his chest, her soft breasts pressing against his torso. Jeff’s hands were now working in tandem along his length. The left keeping steady pressure as his right moved from the middle up toward the head of his cock.
As he did so, Jeff pictured Annie quietly moving her legs over his, pushing herself upright. Her eyes were dark with obvious intent, and Jeff imagined Annie, sweet, lush, Annie, lowering herself slowly, ever so slowly, inch by inch by inch down his hard, huge cock. Jeff whimpered softly as her moans grew louder.
“I always forget how big you are Jeff.”
He bit his lip and nodded furiously, in his mind she was tight and wet around him. Jeff stroked his throbbing cock harder. This woman—this impossibly infuriating, maddeningly bright, ridiculously sexy woman—had him completely undone with nothing more than a shadow of a dream. Sweat beaded at his brow as he closed his eyes. Instead of picturing her in the room with him, he pictured her as she was two days ago, innocently enjoying an ice cream cone as she talked to him between classes. He pictured her full lips and tongue, swirling and licking…
He thought back to their adventures infiltrating Greendale Night School, her crawling around on the floor and earlier writhing around…
And of course, he thought of the night he found her outside the Transfer Dance. He thought of how her lips felt against his, how she looked at him, waiting to…
He pulled her into a kiss, falling, falling into the moment, into her. Just like the past eight nights, Jeff found himself back in this moment again, hurriedly throwing back his sheets as he came, erupting onto his chest and stomach, whispering a plea with her name.
“Annie, I need you…”
*****
She pictured Jeff, his come hot and thick on his skin. His voice husky in a way she noticed in only of a few of their most private moments. She pushed a third finger into her soft folds, her thumb rubbing in quickening circles, her other hand pressing firmly against her stomach—it was only a few seconds away, she knew. She felt the tension building, and she just held it, letting it grow stronger and stronger, wishing it was Jeff.
For the ninth night in a row, she came thinking of him, and for the ninth night, it was almost impossibly intense. She felt her orgasm move in waves through her body, shooting from her the base of her spine to her fingers and toes. She felt every knot in her body undone. As she regained her breath, she was relaxed at last—finally ready for sleep to take her. There was just something about this fantasy—Jeff (already sexy enough) out of his mind for her, unable to sleep because of her. Perhaps it was a bit conceited, but nine nights in a row was difficult to argue against.
She was just about to nod off when she noticed the light from her phone indicating a new message:
“Annie. Can’t sleep. Any chance you’re awake?”
Annie smiled. Maybe she wasn’t so conceited after all.