Up Late

Story Info
Tony stays up late to get lucky.
4.9k words
4.31
15.3k
4
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
dolenz
dolenz
4 Followers

Tony heard the faint, familiar jangle of keys, the opening and closing of the apartment door. Samantha was home, and it was very late. 3am? He was afraid to look at the clock.

Sam had been out with friends at a bar or a restaurant, which she did every now and again. Despite it being Friday, Tony hadn't had any plans of his own that evening. He'd spent the night laying around the apartment, fixing a serviceable meal, watching a ballgame on television, feeling lonely.

He was lying in bed now, clad in his usual sleepware of white tank top and boxer briefs, reading a book and sipping a glass of red wine. Or rather, trying to read a book - he'd spent the last hour or so debating whether to brush his teeth, turn off the light and call it a night, or stay up to see Sam, whenever it was she got home. He was eager to see her after another long work week.

Now she was home and he was glad he'd waited. Samantha came into the bedroom, her purse in one hand, a removed pair of high heels dangling in the other.

"You're still up!"

"I wanted to see you," Tony explained, as Sam set her things down on the floor, rather randomly.

"Ohhhh, you're such a sweetie." Sam came over to the bed to plant a wet kiss on him before walking over to her closet, unbuttoning her blouse.

She's a little tipsy, Tony mused to himself. He thought he could taste the alcohol on her lips, or at least the bitterness of cigarettes, and Samantha never smoked unless she'd really been drinking. It was the way she dropped her things so sporadically, the fullness of her kiss, wetter than usual, and her subtle little sashay towards the closet, pulling her blouse over her head and tossing it to the floor.

"Had a few to drink?" Tony kidded her.

"Meee?" she replied playfully. With a coy look over her shoulder, she stuck her butt out and pulled her bright red jeans - and her panties with them - down slowly, half-way, giving him a teasing view of her ass crack and the rounded tops of her cheeks. Her playful, uninhibited mannerisms stirred a sudden warmth in his groin, but he watched after her disappointed as she laughed quietly to herself and turned her attention away from him to continue undressing in utilitarian fashion.

Tony didn't stop looking. He kept sneaking glances at her half-naked body as she undressed, pretending to read his book. He admired the smooth caramel-colored expanse of her back, turned to him, as she unsnapped and dropped her bra, then followed the flesh of each leg as Sam pulled them out of her jeans. Three years they'd been together, half of that spent living together, and it was an intimate, familiar view he never grew tired of. She was fit and healthy, a bit of a gym rat - an interest they shared in common, since he worked as a personal trainer. But whereas he was nearing 30 and was a wiry Chinese American, for Sam, as a 35 year old with a white mother and black father, age and genes were catching up to her. As toned and slim as she kept her upper body, everything at the waist stayed plump, round and curvy.

Tony knew she was self-conscious about it, but he absolutely loved it. He coveted the soft thickness of her thighs and legs, tapering at her calves, and the round contours of her big butt, outlined behind the fabric of her black panties. It really was a thing of beauty - too big to be contained by the bikini-cuts, billowing out of the bottoms and creasing against her thighs when she stood again. After pulling on a pair of plaid pajama pants and tossing on an over-sized gray tee shirt, she walked to the bathroom, seemingly unaware of Tony's licentious attention. He watched after her, biting his lip at the evident bounce of her ass through the thin pajamas.

It was very late, but he hoped she wasn't too tired - or too drunk - for sex. He set his book on the side table and slid a hand under the sheets, stroking himself and feeling his hardness grow. Aroused, he knocked back the remaining wine in one gulp, climbed out of bed, and headed to the bathroom.

...

When he came through the door, Samantha was hunched over her sink, rubbing the mascara out of her eyes. She had been all dolled up for her night out. He didn't care if she wore make-up, but Tony generally preferred her face in the same way he preferred her body - naked and natural. Sam had big round eyes that scarcely needed eyeliner to accentuate, and her large full lips only made lipstick gratuitous.

Proceeding to the second sink, Tony prepared his toothbrush and started brushing, never taking his eyes off Sam's reflection in the mirror. He was trying to read her mood. He was horny as hell, sure, but it *was* 3am. He would understand if she was only interested in shut-eye.

Her makeup finally removed, Sam dried her face off with a towel. Tony watched closely, almost staring, eager to see whether the look on her face would betray her inclinations. She finally removed the towel, revealing a wide smile - a good sign. Even better, Tony noticed her take a sidelong glance at where his half-erection tented his boxer briefs.

"What have you been doing tonight?" she asked with some suggestion.

"Ate some dinner," he half mumbled, mouth full of toothpaste. "Watched some baseball on TV." He spit into the sink. "But mostly just been missing you." He rinsed his brush and swished his mouthwash, trying his best to grin and look back at her intently in the mirror at the same time. He spit into the sink again.

"Sorry I kept you up so late. I suppose you want to go to bed now." She said it with a hint of entendre. She was teasing him - and giving him an opportunity. He didn't hesitate in taking it.

"I'm not sure I'm ready to sleep yet." He stepped over to Samantha, sliding up behind her, never breaking eye contact in the mirror. Wrapping his hands around her waist, he leaned into her ear. "Are you?"

"Mmmmmm," Sam hummed at his embrace. She replied by straining her head up and around, smashing her mouth against his, her tongue snaking into his mouth greedily.

Again, the taste of cigarettes was unmistakable. Tony realized Sam hadn't brushed her teeth yet. He also realized he didn't care - in fact, the bitterness was strangely alluring, naughty even. Tony liked how fancy free she was at the moment, probably from the alcohol. It turned him on, but it also concerned him. He broke the kiss and reestablished eye contact in the mirror. "Are you sure you are in any condition to make this decision? I shouldn't take advantage of you." He said it with a playful tone, but he meant it.

"What if I want you to?" Sam replied, a playful scowl balanced with a smile. As she said it, Tony felt her plush derriere push back against his hardness, which by now was unmistakably firm. He growled involuntarily at her movement and pressed his hips forward, grasping her fleshy hips and grinding into her rear in return.

"Anything for you..." He dipped to the side of her neck as he said it, suckling the spot where neck and collarbone met. He flicked it with his tongue and she quivered, back bowing. Eager for skin, the fingers of his right hand hovered above the waistband of her pajamas, inching underneath her t-shirt to trail along her hip bone and the soft edge of her stomach. His left hand was less delicate, grasping Sam's small breast, fingers feeling for the poke of her nipple through the t-shirt.

Tony planned to work her up slowly: suckling her neck, massaging her breast, tickling the inner slope of her hip. Evidently Sam had other plans and grabbed his right hand away from its dalliance on her stomach to press it firmly between her thighs, over her crotch. Tony inhaled sharply, pleasantly taken aback, then exhaled slowly, the blood surging through his body now, his dick growing harder still.

Rubbing her sex through her pajama pants, feeling its contours, her heat radiated through the cotton. Sam's body bowed even further, subtly rocking forward and back onto his hand. After a few squeezes of her crotch in sync with her movements, Tony pulled his hand away from underneath Sam's, causing her eyes to shoot open, catching Tony's in the mirror. Their eyes locked there as he slipped his hand down the front of her pajamas, into her panties, her soft stomach flinching at the contact.

At odds with the urgency of her hand-grabbing, Tony's hand froze at the edge of Samantha's pubic hair. Her breath stopped as his fingers crept downward, tickling the wiry fluff, and she grabbed the counter for balance. His finger finally found the top of her slit and slowly outlined the lips of her vagina, running lightly from top to bottom, then back again. She gasped with breath again and made a tiny thrusting motion with her hips, urging him on. Finally, Tony pressed in his middle finger, ever so slightly.

"Faster," Sam insisted. Focusing on his teasing, Tony had closed his eyes. He opened them now and looked back in the mirror, noticing how she was flushed, clearly aroused, but - frustrated, with a subtle grimace. She was in an unusual hurry this evening. And as horny as he was, he was more than happy to oblige.

He decided to forgo the fingering altogether and try something else. Pulling his hand out of her pants, he hooked a finger into the elastic band on either side of her waist. They locked eyes in the mirror again.

"May I?"

Samantha smiled. "Mmmhmmm."

Tony proceeded to tug her pants - and panties - down, watching and enjoying the full reveal of her bulbous ass as he did so. She had given him that teasing little preview moments ago in the bedroom, but now he could enjoy it all, naked before him in all its glory. Pulling her pants mid-thigh, he let go, and they fell to her ankles. Kneeling behind her, Tony kissed Sam's right ass cheek and ran his hands up the insides of her thighs, urging them apart as she stepped one leg out of the garments pooled on the floor.

Driven by the smell her arousal, Tony dropped further to the floor, almost sitting, and swiveled around square between her spread legs. Intuiting what he was up to (or down to, as it were), Sam leaned flat on the counter, resting on her arms and stretching her lower half out, spreading her legs further to accommodate him. From this vantage he admired her cleft, rimmed with coily brown hairs that thickly clouded her crack.

Craning his neck into her center, he stuck out his tongue and tentatively licked her wetness-delicious. He had to have more. Sam gave a long soft moan and lowered into his face. He held her still, both hands grabbing at the pliant flesh of her butt, and began to kiss her sex, gradually working in his tongue around the hood of her clit, then down between her lips and up again, alternating. She whimpered softly whenever his tongue slid into the slippery cavity of her body, and her breath hitched with each swipe along her clitoris.

"You taste so good," he said, voice muffled.

Tony really couldn't get enough. He began moaning his appreciation back at her, his hips instinctively thrusting forward even while kneeling there on the floor. He became more focused on her stiff clit-relaxing his tongue over it, folding and molding and filling the dips and dimples of her pussy. He could tell she was getting worked up, wiggling and shivering, leaning evermore on the counter for support. Every lick began to elicit an understated exclamation, short punctuations followed by a longer hum: "Aw. Aw. Ahhhhh..."

Towards the end of one long "ahhh," Tony felt Sam's hips buck. She retooled her feet and pushed herself back up on the counter, onto her hands again. At first he thought she was cumming - or just about to - but when she muttered "Up here," he realized she had other things in mind.

As he stood, Samantha turned her head to look back at him. She blinked at him, biting her lower lip, a feigned modesty that was countered by how she used those long thick legs to push her naked ass out in his direction. Tony's stomach fluttered when he realized what she was suggesting. He closed his mouth and swallowed, trying hard to find his composure.

He hurried to pull his pajama pants and boxer briefs down, but had to make an extra effort to get them over his rigid cock, leaving them at his thighs in haste. Holding his dick in his hand, he bent at the knee and pressed it up between her legs, making pleasing contact with her vulva. She shuddered and hummed low in her throat. He quickly found himself at her entrance and fondled the opening with his head, tracing the rim. She was so wet, he could feel it coat the tip of his cock, and he began to poke in to her with very little resistance. His hands no longer needed, he moved them to the upper bulge of her ass and worked himself into her in a circular stroke with his hips and short little thrusts.

"Are. . .you ok?" He had to know for sure.

"God, yes. Fuck me Tony..."

He chuckled at her insistence - and the uncharacteristic profanity - but the sound turned into a grunt as he leisurely pulled back and slid into her completely. Ooh, fuck, this is good, he thought. "Fuuuuck," he repeated aloud. He was completely stunned by the feeling as he started to move in her slowly, his body flooding with sensation as it became one with hers. He was immediately grateful for the incredible view the position granted him. Her big ass concealed the sight of his cock thrusting in and out, but that was more than compensated for by the way its flesh jiggled each time he sank in, his torso pillowing against it.

Meanwhile, Sam was humming low in her throat - "mmmm" - the sound like music to his ears. Not wanting to to disregard her, Tony made a conscious point of looking to Sam's face in the mirror. Their eyes locked and they grinned at one another.

"You like this, baby?" His question was rhetorical - obviously she did.

"Yeah," she whined, her voice a pitch higher than usual. Her eyes fell shut and her lips pursed in an oval, clearly enjoying herself.

Tony grinned devilishly at himself before turning his attention back to Samantha's ass. Massaging it with his hands, he tugged her cheeks apart, allowing him to admire the the arousing sight of his cock pistoning into her vagina. He swooned inside at the thought of tickling her asshole with his finger, or better yet, pulling out and running his cock up her crack, cradling it in her soft cheeks - but he didn't want to push her generosity.

Releasing her ass, he picked up the pace a bit with his hips while running his hands over the smoothness of her lower back, just underneath her shirt. She began pushing back up to meet him as he slapped into her with regularity, their collective breathing growing heavier. Her thrusts backward were not exactly rhythmic - random, almost clumsy - but he didn't notice, his attention consumed by the abiding concern of not cumming right away. He always made sure Sam came first, but this position, not to mention the show they were putting on for themselves in the mirror, was severely accelerating the hot pressure in his balls. He hadn't stayed up this late to only last so long.

Sam's erratic movements solved the problem for him. One errant thrust backward, awkwardly timed, and his cock slipped out of her, sliding across the inside of her thigh. Tony seized the moment to collect himself and draped over Sam's back, holding her close. Their panting joined in chorus as they both took a moment to catch their breath.

"Want to take this to the bed?" Tony managed to whisper between breaths.

"Sure," Sam stammered.

Tony stepped back and took the opportunity to pull his pants off completely. Sam took off ahead of him, though the door, and he enjoyed the chance to watch her naked ass bounce as she went into the bedroom. There, she threw herself onto the bed, onto her back, her legs spread wide, and sat up on her elbows awaiting Tony with a devilish grin. Walking into the room slowly, Tony took a moment to admire her - how her chest heaved against her t-shirt, how her pussy, covered in brown muff, pursed between her spread thighs - before climbing onto the bed himself.

Crawling above Samantha in haste, Tony dropped his head to kiss her, a kiss that hurriedly turned sloppy, open-mouthed and tongue-filled. Sam embraced Tony and turned them both over with playful force until she was astride him. Wasting no time, she broke the kiss and pushed up on her hands, maneuvering her center until it spread over and down upon Tony's erection. Sitting back on it, she settled into a tentative rhythm upon him, rising and falling with her inebriated grace, a little more controlled then her errant thrusting in the bathroom.

Greedily seeking a supplement to the movement on his dick, Tony began running his hands over her body. He began with her full thighs, feeling their softness with his hands, then continued up her body, feeling its outline through the thin cotton tee before cupping her breasts. Their modest size filled his palms, and Tony did his best to work his thumbs across the hard nubs of her nipples. Sam must have liked it, as her movements quickly moved from tentative to rough and demanding, almost bouncing.

Tony's hands went from her breasts, back to her fleshy hips, as if he was guiding her movements up and down on his dick - but really, he wasn't controlling anything. Sam was in full control. As if to prove it, she reduced the bounce to an almost imperceptible grind, and bent down to him.

"I have an idea," she whispered in his ear, as if telling a secret.

"Oh yeah?"

Samantha gracelessly raised off him and spun around, the foot of her pivoting leg nearly knocking him in the head. Tony didn't notice or care, so excited was he at her sudden maneuver.

Fully facing away now, her legs spread over his chest, Sam bent over on all fours seeking to lick his dick. Tony hurriedly pushed up the drape of her t-shirt to get yet another intoxicating look at her naked butt - wide, brown, and supple, cheeks spreading at the bottom now just enough to give hints of her pussy lips. It was a beautiful view, but was nowhere near the proximity he needed to eat her out. Tony grabbed her waist, coaxing her back, and Sam responded, momentarily pausing her ministrations on his member to scoot her knees along either side of him.

Tony felt his mouth water as she straddled his face, the vivacious curves of her behind fully consuming his view. He had dined on her earlier in the bathroom, and now it was time for seconds. Without hesitation, the moment she was in reach, he bent his chin up between her thighs, where his tongue found her wet slit. He slipped it into her with a wiggle, savoring the sour sweetness of her sex. He pulled it back to maneuver his mouth up further, the damp space of her crotch pressing into his face, until he could feel out the nub of her clit with an effective combination of lip, tongue and jaw. He heard Samantha gasp.

It was Tony's turn to gasp at the sudden sensation of Sam's mouth sliding over his erection. It was an unusual angle, the suction of her lips tugging backwards, stimulating the nerves along the underside of his cock.

"Can you taste yourself on me?" Tony asked, in between laps at her center. The thought turned him on to no end.

"Mmmmhmm" Sam mumbled back, mouth full.

Catching his breath, Tony continued to eat away at her. Meanwhile, his hands grasped her ass, squeezing and feeling, playing with its girth. Making love to Samantha with his face while she returned the favor, slurping, licking and sucking his erection, all while playing with the pliant flesh of her generous rear end: Tony realized he caught himself thinking this a lot with Sam, but it was no less true: it all added up to the best fuck he could remember. This was worth staying up late for.

Suddenly, without warning, Tony felt his dick slip from Sam's mouth. She proceeded to crawl away, back down his body. Tony sat-up, pressing his face between her legs for every last possible second. He remained propped on his elbows, watching and wondering what Samantha was up to now. She stopped and sat up straight, hovering over his hardness, and pulled her tee shirt off over her head, tossing it off the bed. Completely naked now, she looked back at him over her shoulder with a wink, then turned back further to grab Tony's cock. Positioning the head between her legs, at the crux of her brown ass cheeks, she pressed it just inside of her pussy.

dolenz
dolenz
4 Followers
12