“You have something for me, sweetheart?” You asked teasingly, watching Jonathan drop down onto the couch beside you, looking utterly fucked out. His tie was loose around his neck and his hair was a mess— you didn’t even know where his glasses were. 

He handed over his bag and you opened it up, gauging how much cash was inside. Then you gave him a pleased smile and reached out to run your hand through his hair, smoothing it back a little. 

“Mm… good boy.” You murmured, making him blush. “Did anyone give you any trouble?” He shook his head a little in response, not moving it from the couch because he was so tired. “How many?”

“Four.” At your immediate, but subtle disapproval that he didn’t reach your unofficial quota, he quickly added, “But one took a long time— she just kept giving more money to extend it.” 

You hummed in acknowledgment and just stared at him for a moment, watching him try not to squirm under your gaze. “Better luck next time maybe, hm?”

“Yes… m’sorry.” He said quietly, averting his gaze. Your lips curled up a tiny bit, then you dropped your hand back into your lap and looked in the bag again. 

“Any guys?” You asked curiously. He cleared his throat and shifted uncomfortably beside you. 

“Just one this time.” 

“You know, you’d get a lot more customers if you focused on them. Women aren’t really the ones picking up whores off the street.” Your comment was casual, unemotional— just stating a fact. It still made him frown a little though. 

“I know…” He said quietly. You thought about continuing, but you’ve had this conversation with him more than once before, so you didn’t bother. As long as he was getting customers, you didn’t care who he fucked. 

“Are you too tired for one more?” You suddenly asked, your voice lowering into something more sensual. Despite his obvious exhaustion, he perked up a little almost immediately, like he’d been waiting for a reward from you all night. 

“No— I mean... I-I’m kind of sore, but…” he trailed off, unable to find the words. You set his bag on the floor, then reached out and grabbed his tie, pulling him a little closer as you looked between his eyes and his lips. 

“My poor baby is sore, hm?” You said with mock sympathy, making his blush get even darker. “Is it your cock that’s hurting, angel?” He gave you a tentative nod, not sure if you were actually wanting an answer or not. 

You leaned in the rest of the way and placed your other hand on his crotch, making him inhale sharply. He shivered when your lips brushed the shell of his ear and you bit back a smirk at how easily he crumbled with just a few light touches. 

“Well… It’s a good thing this cock belongs to me, isn’t it?” You whispered. Jonathan let out a choked sound and you could feel him twitch weakly under your palm. “It’s mine to use however I want.”

“Yours.” His voice was a pathetic whimper and it was almost like the acquiescence slipped out unbidden. 

“That’s right, angel… So fuck me.” You breathed, gently nipping at the lobe of his ear, feeling his cock twitch again. “I’ve been waiting for you all night…” You cooed, finally releasing him and leaning back until you settled against the arm of the couch. 

He swallowed audibly when you opened your legs, showing your lack of panties. Then he fumbled with his belt and the button of his pants, opening them and giving him room to pull out his cock. It was barely hard, but you knew he could get there soon. 

When he started stroking himself slowly, he hissed quietly and his brows scrunched together in the cutest display of painful pleasure. But he didn’t stop. He just clenched his jaw and kept pumping his cock while you watched with a small smirk. 

“You poor thing…” You cooed mockingly. Jonathan let out a low whine and closed his eyes, breathing through the overstimulation, trying to be good for you. When he was hard enough, he got up on his knees and moved between your legs. 

“Are you sure you don’t just want me to eat you out?” He asked, almost timidly. You raised your brows, giving him an unimpressed look. 

“If I wanted you to eat me out, I’d already be sitting on your face.” You said dryly. He blushed again, but nodded, knowing not to continue “talking back.”

He finally pushed in slowly and you let your head fall back with a low moan as he stretched you open, hearing his pathetic whimpers. The stretch burned in a way that only added to your pleasure, but you couldn’t even imagine how tight you must have felt on his poor cock… 

“So fucking good, sweetheart.” You moaned, finally lifting your head back up to look at him. His face was scrunched up in pain and his bottom lip was clamped tightly between his teeth as he fought to hold back his sounds. He bottomed out with a quiet whimper, then paused, letting “both” of you adjust— it was really just for him though.

“How many times did you come tonight?” You suddenly asked. It was almost comical how relaxed you seemed compared to him as he struggled to cope with the painful overstimulation.  

“Two times.” He choked out, moving his hand to grip the back of the couch hard enough that his knuckles blanched.  

“Think you can give me one more, baby?” He whined at the thought, his breathing still labored. Still, he nodded obediently. “Then fuck me already.” You said impatiently. 

He let out a shaky breath, then started thrusting slowly, gritting his teeth. You moaned softly again, enjoying feeling every last inch of his cock filling you up perfectly, hitting all the right places inside you. 

“Faster.” You ordered, getting bored of this. He obeyed, snapping his hips into you over and over, wincing every time your walls fluttered around his cock. 

He looked so pathetic like this— barely able to handle your pussy, whimpering and whining like a brand new whore, rather than the seasoned slut you’d turned him into. 

“Atta boy… C’mon, baby, you know how I like it.” You cooed, playing with the end of his tie that was dangling over you. He nodded as he puffed out heavy breaths, but finally started fucking you the way you expected— rough, hard, primal… borderline hateful. 

You mewled as your eyes rolled back in your head. Jonathan was finally starting to moan with you as the overstimulation briefly faded, replaced by his building pleasure. Then his fingers were landing on your clit, rubbing firm circles over it, making your back arch off the couch. 

“Fuck… good boy.” You said through a breathy moan. He let out a choked sound when you suddenly yanked on his tie, pulling him down as you lifted up to close the distance, capturing his lips in a kiss. It was mostly teeth and tongue— a sloppy, animalistic display of passion from him reserved exclusively for you that sent you barrelling toward your orgasm. 

His fingers never faltered on your clit and he fucked you harder, faster… finally getting back into his rhythm— reminding you why he made such a good whore. 

When you fell over the edge, he swallowed your sounds in the kiss. You brought your hands up to his hair and tugged on it roughly, forcing a guttural moan out of him. His hips were snapping forward almost brutally, his balls smacking your ass with each thrust, only adding to the lewd sounds of fucking that echoed through the room. 

“Fill me up, angel…” You moaned against his lips. His thrusts stuttered and he finally broke the kiss to bury his face in your neck as he slammed into you one last time, fully sheathing his cock inside you as his orgasm crashed over him. He whined loudly against your neck, his body twitching and jerking from the overstimulation that was quickly replacing the pleasure once again… You smirked a little and carded your fingers through his hair, petting it gently, letting him ride out the painful pleasure. 

He finally sagged on top of you, boneless and completely worn out. He was panting heavily and barely able to keep his eyes open as he laid on top of you, his cock slowly softening in your leaking hole. 

“Mm… that’s my good boy.” You murmured, still petting his hair. When you placed a kiss on top of his head, he let out a soft sound and relaxed into you even more, the exhaustion finally taking over.