Jillian’s Nice New Boyfriend

Mason Lakeford
6 min readDec 6, 2018

“So which do you think is softer: This pillow, or my boobs? Hm?”

Jillian stood there, all 5’9” of her, with her wavy sandy-blonde hair (couldn’t decide if it was curly or straight, couldn’t decide if it was blonde or brunette — this was her life, her persona, writ in golden strands) and blue eyes, one hand holding up one of his pillows as her other hand groped at her own chest, gently squeezing here and there. She even wore the strappy little tanktop that was slightly too small on her. Sure, she brought a jacket too; but still, it was fucking cold outside. What was his problem?

Jin, for his part, didn’t even look up from his sketchbook yet had the audacity to wipe some of his black hair away from his face anyway. He was drawing something, as always, as his wrist flexed this way and that as he gripped some expensive-looking artist’s pencil. He was Laidback College Guy personified, in some ways: Wearing the same hoodie and jeans as he had on yesterday, posture like a lazy puddle as he reclined in his dorm-room bed.

Jill frowned. Well, scowled, more like. Heat rose to her cheeks. Her brow furrowed. She threw the pillow at her supposed new boyfriend. It kinda glanced off his shoulder. Her hands balled into fists at her sides, but at least he looked up from his sketching.

“What is wrong with you? I know you’re not stupid. Are you really this dense?” Her voice took on a bit of a squeak when she was frustrated. He tried not to smirk at this. “It’s great that you’re a nice guy and a perfect gentleman, but we’ve been going out for a few weeks now. You’ve bought me dinner. Twice. I’ve been draped all over you when we hang out with my friends. We get one night when your roommate’s out of town and you won’t even look at me? Clearly I want to do more than just hold hands, Jin. You’d think a guy would take advanta — ”

“Have I shown you this one yet?”

He had a thinner, but well-cut, build. Like a Bruce Lee sort of figure. She didn’t like how her belly pouched over the front of her pants.

He was holding up the sketchbook, the one he was working in so intently. It had a glossy black cover.

“No,” she huffed, and crossed her arms. “What’s in that one? More mountains ’n’ shit?”

He let himself grin, at that one. He closed the book, and flicked it through the air. It landed in the mass of blanket somewhere at his feet.

“This one’s… different,” he said. He had such dark, deep eyes. He could be so quiet. But he was the one who approached her, who started talking, who got her number. He was odd, but clever. Funny. Kind. After trying to straddle a line between infatuation and fascination, she fell. She fell hard and fast. He was even a little shorter than her but she didn’t mind at all.

The air in the room was thick, tense, cliché. The two bore new holes through each other’s skulls with their respective gazes in this moment of mutual staring. Neither blinked. She relented, however, the language of her body softening enough to climb onto the other side of the bed from him.

She wanted to punch him. She even raised her fist, and looked at one of his legs, but decided against it. He was watching her. She hated how cute he was.

Her legs curled beneath her and she picked up the book, setting it in her lap. As she turned the page, she felt her insides begin to quiver with the wings of nervous butterflies. Her eyes may or may not have widened slightly, but she was definitely blushing.

There, on the very first page, was her. Topless.

She was standing in front of a dressing-room mirror, in the image; holding up a different bra in each hand, an exasperated look on her face atop hunched shoulders. And in the corner of the room was Jin, sitting there, dejected and flustered in his own way. The whole scene was detailed yet laidback in its style, somewhere between a portrait and a cartoon. Like a caricature without the exaggerated features.

Jillian cleared her throat and calmly, casually turned to the next page. She smiled, but kept herself from laughing at least, at the sight: The next scene was her and Jin again, yes, but sitting on the side of a hill — pointing into the sky, at clouds shaped distinctly like different animals. Smiling. Cuddly. Jin and Jill, that is, not the cloud-animals.

She blushed anew at the next page, featuring their bodies pressed to each other in a bed, caught in the act of both kissing and undressing.

The young woman could feel her new boyfriend’s gaze on her. She did not return the eye contact, but felt unsure whether she was supposed to take her time browsing in depth or quickly peruse at a glance. Either way, she had to admit, there was an odd undercurrent of… fun, in the whole thing.

A page of her, in the nude, while he painted her naked form. Then a bold scene in which her mouth was quite occupied. And then, at the next page, she squinted.

“What is…?”

She held the page up, and pointed, and tried to hold the sketchbook somewhat closer to him. Jin leaned toward it, and placed his finger on the shape she indicated, and swept upward.

“That’s my forearm.”

Her mouth opened, silent for a second before she responded.

“Oh, right. Wrapped against my, to, okay. Right. I see.”

She nodded, and calmly returned the book to her lap, trying not to grin as she enjoyed these revelations from his mind. A vision of her wrists being tied behind her back with a ribbon. A more innocent shot of the pair at a diner. And then the picture that finally made her laugh in earnest.

“I’m not this flexible, Jin…” she said, smirking as she held up an image that was, shall we say, creatively pornographic.

He shrugged, and kept his expressionless demeanor. He was always so calm. She really did hate it, sometimes. Other times, it was… beautiful, in its way.

“So.” She looked up, from the pages, for this moment. More eye-searching between the two of them. “What is this? Your book of perverted fantasies?”

Ah. There it was. A tug, at the corner of his lip. A tell. Like when he told one of his stupid jokes.

“Just some things I… want to experience, with you,” he explained, with an odd sort of halt in his cadence.

“Oh really?” she said, rolling her lower lip through her upper teeth half-commitedly. “You really think I’m into stuff like this?”

She held up the open book to one particular sketch. In it, she was bent over the arm of a sofa. He was… taking her, from behind. His forearm had snaked up the middle of her chest, her torso twisted somewhat, his hand clutching her neck, his other hand raised and hovering over her backside with an open palm.

Jin stared right back at her, in his dorm room, on his bed as they sat.

“I do,” he said. He spoke the words with an icy detachment that chilled her to her core yet lit it on fire at the same time.

“Hmmm,” she said, trying to muster a mock confidence. She swallowed. “Well, I don’t know who you got to draw all these pictures for you, but he seems interesting. Maybe you could give me his number? Seems a lot different from the mild-mannered mister-nice-guy I’ve been seeing latel — ”

“Turn to the last one,” he said. “The one I was working on.”

She hesitated only slightly, before turning the pages, trying not to seem too eager before she found the last one.

She almost rolled her eyes. She hated how clever he was sometimes.

It was a dashed-together rendition, but recognizable, of his dorm room. The sketchbook itself was in the image, tossed to the floor. He was on the bed, in the image, in the same position he had taken in reality. Only, his shirt was off. And she was lying on her belly, between his legs, her mouth at his torso, his hand gently in her hair.

She looked up from the book, and he was already tossing his hoodie to some close-flung corner of the room. She almost gasped, seeing his chiseled body for the first time. She was not prepared for how… fit, he was.

He held up a finger, and crooked it toward himself.

Beckoning her.

This had been such a whirlwind, already. She had a thought, that she didn’t know how the fuck he was doing this to her, but…

But, there she was. Lowering herself toward the bed, toward his body. The back of her head only needing the slightest of encouraging nudges before she pressed her pert lips to his taut skin.

She swept a leg across the covers and kicked the sketchbook to the floor.

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Mason Lakeford

It's a pen name. Writer. Flirt. NSFW account. Dom. Occasionally rude, lewd. Sapiocurious. Sometimes I post smutty stories.