Oops, Oh My

Author: BethanyInc

Type: Gilmore Girls

Theme: Smut

Pairing: The usual

Rating: M

Summary: He strictly wanted to get her Vickies down to her ankles. Tristan & Rory smut. Oneshot.

Disclaimer: I do not own Gilmore Girls or the lyrics to "Oops, Oh My" by Tweet, ft. Fabulous and Missy Elliott.

Author Note: Now, this type of music really isn't the main thing I listen to; but I just think this song is perfect for a Trory smutfic.

Oops, Oh My

Shorty, I strictly wanna spank you
The most I gotta do is spell my name to get your
Vickies to your ankles
I'm serious mommy,
You're fuckin' wit the kid
You know I'm the type
that be crushin' and merkin'
Havin' ladies touchin' the herk
And blushin' and smirkin'

Oops, Oh My

Perhaps she shouldn't have gone for that third shot of fiery Tequila. She was sure, even as steady as she thought she was, that everyone in her apartment building knew she'd had one too many drinks. No, she had seven too many drinks, if she remembered correctly.

Leaning further onto her companion, she let out a soft snort. Of all the people she would have run into on the night of her worst break-up to date, it would be Tristan DuGrey. What a bad boy, he was, too! Insisting she had more to drink that her usual solo Vodka Martini. Well, he just needed to be spanked for being a naughty little boy.

"My place is just up there," she told him, her lip pouting at the obvious slurring of her words. "I pinky promise."

"Oh, I believe you, Mare," he said hotly into her ear, as he grazed the hand that held her to him over the curve of her hips. "Why don't you get your keys ready?"

"'Kay," she consented, pulling her tote bag open and reaching her hand down into the dark abyss. "I wish I had a purse light," she furrowed her brows together and squinted, trying to catch a glimpse of the shiny object. After a moment or so, she let out a cry of triumph and grinned up at her company. "Found them!" She told him happily, pulling the key out of her purse, it's abundance of charms and chains fished out after it.

"Good girl," he pressed a kiss to her temple and eyed the wealth of cleavage he was viewing from his position over her, "No wonder you graduated from an Ivy League school." His speech, though not as good as it would have been sober, was only slightly slurred. He'd had half the amount of liquor, and he was most likely twice the person.

Proud of herself for accomplishing the mundane task of retrieving her keys, she grinned. "It's 28B."

He quirked an eyebrow and glanced towards the number on the door they were just passing, "Mary?"


"We need to backtrack, we passed it."

"Oh," she frowned. Scratching her forehead, she glanced over her shoulder, "Oh! Right, right." She nodded, and took a step backwards, tugging Tristan along with her.

"What are you doing?"

"Backtracking." she answered smartly.

"Smartass," he deadpanned.

"Well it did graduate from Yale," she quipped, stopping in front of her apartment door and slipping the golden key home in its slot. Twisting the key with mild concentration, she pushed open her door, pulling the key out as she walked inside. Tossing said object into the bowl on the table beside the door; she turned around and glanced at Tristan out from under her eyelashes. "Welcome to my place."

"Never thought I'd see Mary's living room so soon," he smirked, closing and locking the door behind him.

"Oh, you'll be seeing a whole lot more than the living room," she promised, as she unbuttoned the buttons of her pea-coat jacket.

She slid her arms out from the sleeves and let the outer article of clothing drop to the floor.

Suppressing a groan, Tristan stepped forward. "Ah, ah," she reprimanded, waving her finger in front of her, signaling for him to step back. "Not yet, silly boy. Don't be anxious."

Running her hands from her shoulders down her supple curves in an attempt to be overtly sexual during her inebriated state, she sent a slow, lustful wink in his direction. Caressing the hemline of her polo, she pulled it up slowly, revealing an expanse of flat, white skin. Languidly her shirt followed her hands back up over her body, slowly pulled off of her, her curled brunette locks falling back over her shoulders and back.

Dropping the garment to the floor, Rory pressed an innocent, French-manicured fingernail to her lower lip, "Oops, there goes my shirt." Doe-eyes, formerly dusty-desert blue, stared at him through a thick layer of black eyelashes.

Her bedroom eyes. God fucking damnit.

Tristan felt his member grow excited quickly. He was going to be ready for anything she dished out to him, and believe you me; she was going to dish out.

Again he went to move towards her, but was once again stopped in her efforts by her fingers. Groaning, Tristan placed his hand over the seam of his jeans and rubbed it roughly, trying to get himself to steady his hormones.

Eyeing him touch himself, before allowing her gaze to travel down his legs, over the wooden floors of her New York City apartment to the polo shirt that lay innocently rumpled on the floor, her fingers went towards the button on her jean skirt.

Tristan watched as her experienced fingers deftly pulled the button through the fabric slot, and slowly traced the zipper down the teeth. The noise of the metal and their erratic breathing was deafening.

Allowing her skirt to glide over the miles of legs she possessed, she quirked a perfectly piqued eyebrow, and yet again gave him her bedroom eyes. "Oops…" she started.

"There goes your skirt." He finished for her.

If he hadn't been rock hard prior to the obvious shedding of clothing, he would have been hard now. Rory Mary Gilmore stood before him; black pumps and scantily clad in only a tiny, red patch of fabric and string and a deep, petal pink push up bra. Signature Victoria's Secret lingerie.

The only thing that even crossed his mind while he advanced on her for the third (and final time) was that he strictly wanted to get her Vickies down to her ankles. Glancing at the clock that blinked at them from the kitchen, he noticed the time; 2:44 AM. Oh, he would be rushing to get to work later that morning for sure.

Before he even reached her, she had slid her slender hand down her stomach, over the red silk, and was caressing the inside of her thigh. "Mmm," she let out at her own stroke.

Tristan almost creamed his pants at that type of sound coming from her mouth. Grasping the lithe, exposed ass of one Rory Gilmore was almost the best feeling he'd experience that night. Using his firm grip, he pushed her groin into his and let out a fierce groan of longing before he smashed his lips again rubies.

He barely gave her anytime to adjust to his body and warmth before he slammed her into the wall to the side of her. Letting out a gasp of sadistic pleasure at the pain in her back, she gyrated her hips into his, locking his covered cock against her center as she wrapped her legs around his waist.

Biting her lip, she pressed her face against his neck as he started thrusting against her. A moan escaped her lips, and her fingernails deftly pulled buttons out of holes as quickly as they could.

"You like that, baby?" he ground out against her collarbone, "you like it when I do this—?" sliding his hand down his pants and adjusting his penis to be almost erect, he once again slammed it against her, making Rory scream out in anticipation. "C'mon, baby… tell me."

Shoving his oxford off of his body, she grasped his chin in her hand and pulled his face close to hers, "Almost as much as you like it." Letting go of his chin roughly, she raked her nails down his pecks, allowing her nail tips to finger and twist his nipples.

A suffering groan escaped one of their lips as they once again rubbed their unexposed privates against the others.

Rory's hands soon found the buckle of his belt and pulled it apart, allowing it to just stay nestled in the belt loops of his jeans. Distracted by the sudden intrusion of her body by his finger, Rory buried her head deep into the nook of his neck and let out a hiss.

Feeling her engorged clit, Tristan thumbed it while pushing her further against the wall to hold her up while his free hand snaked up the spine of her back to the bra hook that imprisoned heaving breasts. Satisfied that the padded constrictor was loose, he slipped it from her tiny frame and tossed it over his shoulder.

Before one could say 'orgasm', Tristan delved his face into the valley of her breasts and bit, licked and sucked every inch his mouth could reach.

Unwrapping her legs from his waist, she removed his hand from her body, and ripped the zipper of his pants down, followed by the button. Moving away from her cell between him and the wall, she hooked her finger into the elastic of his boxers and started walking backwards towards her bedroom, the click of her heels echoing through the muggy apartment.

Tristan managed to slip his shoes and his jeans off as he diligently followed her, his member at rapt attention.

Seeing her in her brazen glory, Tristan reached forward and grasped a breast in his hand, squeezing and memorizing. She tossed her head back in a gasp of shock and bliss, her finger slipping away from the position at the waistband of his undergarments.

Perhaps the liquor still wasn't starting to wear off, or her comfort in her nearly nude body was at its peak, but she kicked her heels off and grasped a hold of his shoulders and pulled him to her, capturing his lips in a smoldering kiss. Enraptured by the rubies rubbing against his mouth, Tristan groaned and jumped a little when he felt his back hit the wall.

Who knew his Mary was such a sex kitten? Not he, that's for sure.

Running his hands down her back, he let his hands settle on her ass, and pulled her to him. He could feel her wetness seeping through the fabric of his boxers and dampening his cock. God damnit this girl was good.

Pulling her lips away from his, she bit her lower lip softly, and slid her hand inside his boxers, allowing it to grasp his penis.

"Fuck, fuck, fuck," Tristan hissed, the crown of his head connecting with the white painted wall.

Long, languid strokes of her hand had him squirming and anticipating more from her. "Baby," he moaned, thrusting into her hand at the same rhythm as her strokes, "I'm going to…"

Pressing a finger to his lips, she smirked as he nipped at it. Pulling her hand away from his inflated body part, she slipped the fabric covering him down his legs, dropping down to pull it all the way to his ankles. Kneeling in the most unladylike of fashions, Tristan nearly bust as he got a clear shot of her ready and willing pussy. Fuckkkkk.

Groping his balls, Rory brought her face closer to his crotch, further testing his readiness by letting her tongue graze over his head.

"God," was the only word besides 'fuck' that his mouth managed to form.

Slipping the wet concave that was her own mouth over his penis, she batted her eyelashes up at the twisted face of her newest lover. Oh, he was going to, that's for sure.

One circle around him. Twice. Thrice times a lick. Switching it up, she cradled him in her mouth between her tongue and the roof of her mouth and sucked.

"I'm gonna… Ror… I'm gonna bust---" and he bust did.

White, hot sticky fluid drowned her mouth and she had no choice but to swallow. She felt him go soft in her mouth and she pulled away from him, allowing her finger to wipe excess fluids off the corners of her mouth.

Smirking, she fisted him, and kissed right below his navel. "C'mon baby," she mimicked in a low, raspy whisper, "get hard for me."

It only took a minute or so of her hand-job to get him ready again. Proud with her success, she stood and slipped her underwear down her thighs and calves and grasped a hold of his hand.

"Lets finish this," she said, pulling him inside her bedroom and snapping the door closed behind them.

Pushing him onto the full sized bed, situated near the door, she smirked. A naked Tristan DuGrey on her bed, seven years after she declared to hate him. Who would have ever of thought that Rory Gilmore was about to have her wicked way with him?

Crawling over him, she situated herself in his lap, her hand holding him up. "Are you ready?" she asked, her brazenness proved by the stroke of her thumb up and down his shaft.

"I've been ready to fuck you senseless for years," he confirmed, placing his hand on top of hers and guiding himself into her slot.

Her warm, wet walls hugged his cock tighter than her mouth had. His eyes rolling into the back of his head, he firmly held onto her hips, and brought her fully down onto him. "Damn," he groaned, as she slowly twisted her hips in a circle, spreading her legs wider in order to tighten the suction on him.

Up and down she started, moving her hand in-between their bodies, resting just on the jut of his hip, prepared to touch herself while she rode him like a good cowgirl would ride a horse.

Tristan held back his pleasure as he watched her perky breasts bounce up and down from his position under her. They were round, mounds of flesh that had his name, and bites marked all over them. "Fuck yesssss." He hollered as he thrust his hips upwards, meeting her halfway as she came down on him particularly hard and fast that time.

Her jaw dropped at how deep he had just penetrated her; her eyes rolling into the back of her head as he loud, raspy moan shattered any silence that could have been left in her bedroom. She was close, and they'd barely been at it for more than two minutes.

"Uh, ugh…" undistinguishable sounds broke free from her mouth as he started shattering her insides with his fierceness. "I'm ssssoooo cccclloosse!" she moaned, furrowing her eyebrows together. She grasped her breasts in her hands and squeezed them together as her head lolled backwards as she rode out a wave of an orgasm.

She hadn't even come this fast when Logan had his way with her.

Moving Rory's hand from between them, he replaced it with his own as he cupped his balls as he continued to thrust into her slot. For a girl who had just crossed the edge, she sure gave a lot of her dwindling energy into making sure he got off.

Her hands on her breasts, and the way the mounds oozed between her spread fingers got him off minutes later.

His little soldiers oozed into the battlefield inside her, mixing with her own juices creating the messiest war of the night.

Biting her lip, her eyes squeezed shut; Rory slowly let go of her breasts when Tristan ran his hands up and down the curves of her torso.

"Mmm," he mumbled, as Rory raised herself off of him, and rolled to his side, her front pressed against his side.

Noticing the black pumps that still adorned her tiny feet, she laughed a little, the effect of the alcohol finally seeping back into her senses, "Oops…" she mumbled.

"Oh my," Tristan said, pressing a lofty kiss to her temple.

Oops, Oh my

Oops, there goes my shirt up over my head
Oh my
Oops, there goes my skirt droppin' to my feet
Oh my
Ooh, some kind of touch caressing my legs
Oh my