a life full of regrets

art often forgot the privileges of being a retired tennis player but his latest rebound date, you, seemed quick to remind him. 

heels up on his dashboard, you’re applying lipstick in the mirror when he pulls into the driveway. 

‘that’s your house?’ you gasp, jaw dropping. 

‘yep.’ art replies, looking almost sheepish at your astonishment. 

turning to stare at him in surprise, you murmur, ‘all of it?’ 

he nods as he steps out of the car, opening the passenger door and taking your hand. art leads you up to the front door like you’re a princess.

it’s almost obscene how much wealth is on display, and you’re just in the hallway. whilst art was a man of quiet luxury, everything from the wool of the rug to the paintings on the wall was premium. 

‘my uh-’ art cleared his throat, ‘bedroom is on the third floor.’ 

you missed his meaning completely, turning to gawp at him. ‘there’s three floors?!’ 

art nods again, cheeks flushing red with embarrassment. before he can try his flirting again, you’ve tossed your heels off and padding through the spacious house at an alarming rate. 

he finds you in the kitchen, running your manicured nail along the marble counter. 

‘you ever bent anyone over these?’ you purr, leaning over the counter teasingly. 

art nearly chokes, startled. ‘uh… no.’ he admits awkwardly, hardly able to look at you. 

emboldened by his confession, you strut towards him, already sliding down your skirt so it pools at your ankles. ‘would you like to?’

he’s moving without thinking, his growing erection pressing against your ass as you bend over the sleek countertop. he’s pulling down your thong, flinging it across the kitchen. with one hand on your cheeks, you can hear him fisting himself to get hard. 

‘i’m really more of a bedroom guy…’ art pauses, staring at your glistening folds with his cock in his hand. 

‘please?’ you whimper, voice wanton and pleading in such a way that’s impossible to ignore.

he gathers some of the slick from your pussy and spreads it across his tip, then his own spit before he’s pushing into your waiting hole. with a gasping groan, your head drops down as you feel him enter you. 

‘holy fuck…’ he whispers as his hands grip your hips before he bottoms out in you, feeling every inch of his cock rubbing against your tight walls. 

‘right?’ you pant with a smile, inching your legs apart further. 

‘never… felt… like… this…’ he moans between thrusts. 

in art’s younger years, his most adventurous sex act was eating someone out on their couch. in his marriage to tashi, however, their most adventurous sex act was shower sex after a win, which became less and less frequent as time passed. 

your boobs were smushed against the counter, sliding across the marble as the tip of his dick repeatedly slammed into your g-spot repeatedly. art was relishing in it, the way your mouth was locked open, choking out moans with hazy eyes. 

‘oh- oh- oh-’ you whimper, legs shaking with effort. 

prematurely, and without warning, you felt art’s hot cum filling your hole. with jagged thrusts, he’s spurting salty liquid deep inside you alongside broken moans. you pray that your birth control works as he pulls out, dick floppy. 

‘shit… sorry.’ he mutters awkwardly, ‘are you okay?’ 

you nod, standing up on trembling legs. ‘yep.’

‘did you cum?’ his question is earnest if not a little blunt. 

‘nope.’ you shake your head, half expecting him to send you home. 

instead, art looks mortified. ‘sorry.’ he repeats. 

‘it’s fine, it happens.’ you shrug dismissively. 

‘just-’ he gestures to the counter stiffly, ‘never done that before.’ 

there’s a horrible moment of tense silence before he speaks again. 

with bright eyes, he leans down to whisper in your ear flirtatiously. ‘what do you say we take this to the bedroom next?’ 

your heart swells with a odd feeling of relief. ‘yeah… let’s.’ comes your smiling reply.