Daddy, Sir (Dirty Daddies 2024 Anthology #6)

Chapter 5

Chapter Five

Naomi

The tip of the plug pushed against her stretched hole, making Naomi whimper again. Drew’s fingers had loosened the muscles, but the plug was completely different. It was harder, and as it pushed in, it quickly became thicker. The tapered shape made it both easier and more difficult to accommodate—easier at first and rapidly more difficult as he pushed it inside her.

He moved it back, withdrawing slightly, to give her a moment to breathe before he started slowly pushing it back in. Something shifted in the sensation, and Naomi gasped as he twirled the toy, like he was literally screwing it into her.

“Daddy!” It was getting easier to say, and she could feel his cock jerk against her when she did, which made it more fun to say. With everything that he was doing to her, the control that he was making her lose, she liked knowing she was getting to him, too.

She leaned against him, rubbing herself on the rigid underside of his cock, as he pushed the plug in deep. There was a stinging ache as her bottom was forced to its widest point yet by the thick bulb, then she relaxed as it pushed inside her, and the tight ring of her anus closed around the narrower stem between the bulb and the base.

“Good girl,” Drew said, tugging on the plug slightly, then pushing it in, mimicking what he’d done with his fingers, though it felt very different as her opening had to stretch for the bulb when he was pulling on it. His fingers had been close to the same thickness the whole way from tip to knuckle; not so with the plug. It added an entirely new dimension to the sensations. “You did such a good job taking this plug in your pretty little ass.”

Okay, she could really get used to the constant praise and dirty talk that he seemed to like.

Yes, Daddy, thank you, Daddy, keep it going, Daddy.

Definitely not a bad trade-off.

Letting go of the plug, his hand caressed the upturned curves of her cheeks, and she lifted her butt, offering it to him. He gave her a little slap, hard enough to make a smacking sound but not hard enough to truly hurt. Naomi squeaked, then shook her butt at him some more.

“Why are you getting this spanking, sweet girl?” he asked her, giving her another little smack.

“Am I getting a spanking?” she asked. “Feels more like someone is just tapping my— Ow!”

Ow, ow, ow, ow, ow!

For all that he liked her sassiness, he wasn’t going to tolerate full-on brat, either. He’d gone from light little slaps to some serious swats that demonstrated he meant business—and he had a really freaking hard hand. He didn’t give her a chance to catch her breath. His hand rained down the hard swats, peppering them across her buttocks, hard and fast enough that she felt like all the air had been forced from her lungs.

It wasn’t till he stopped that she was able to get in a truly deep breath and express her reaction.

“ OW !” She rocked forward, as if she’d be able to escape the burning of her bottom that way, even though there was nowhere for her to go, and she had a feeling the throbbing sting was going to linger for a bit. It hurt enough that her nipples didn’t feel so bad anymore. They might have just gone numb, but she was pretty sure it had more to do with the fact her butt hurt too much for her brain to also register what her nipples were going through.

“Want to try again, naughty girl?” Drew asked, sounding amused as he ran his hand over the now-warmed cheeks of her ass.

The sensitive skin tingled under his callused palms, making her shiver and her pussy clench in reaction. The initial slaps had hurt, but now they’d almost immediately subsided to aroused heat… and she wanted more, but not so much more that it turned into a real punishment. Which meant being a little more judicious with her answers.

“I’m getting a spanking because you want to spank the sass out of me, Daddy.” She wiggled her bottom at him. “I think there’s still some left, though.”

His laughter filled the air as he cracked up. His fingers squeezed the sensitive cheek he had rested his hand against hard enough to make her squeal, even as she grinned with pride for making him laugh like that.

“There seems to be quite a bit left,” he responded, still chuckling, when he managed to get himself under control. “Let’s see what I can do about that.”

The spanking started again, not as hard as the previous swats, but still hard enough to make her gasp and writhe, especially because he didn’t give her much in the way of breaks. Firm and relentless was apparently more his style. The burn grew slowly and steadily until she was bucking, trying to squirm away from his hand as it came down again and again and again.

“Daddy! Please!”

“Ten more, sweet girl.” His hand came down again. “That way, I can be sure I spanked all the sass out.”

Naomi let out a little cry as his hand came down on the opposite side, right on her sensitive sit spot. It was starting to really freaking hurt, and the urge to be sassy was definitely gone.

She didn’t want to sass him anymore; she just wanted him to fuck her.

Her butt was burning, her crushed nipples throbbing in time with the spanking being laid down, and her pussy was aching emptily. With each swat, her need for a different kind of stimulation grew, the pain stoking the fires of her pleasure.

His hand came down against her other sit spot, and she cried out, jerking forward, the chain on the nipple clamps swinging from her motion and tugging on the little buds. They pulsed in counterpoint to her bottom, adding to the need growing between her thighs.

Drew

Fuck, he was hard as a rock from watching Naomi’s ass jiggle with every swat that came down on it. The growing heat under his palm was testament to how much she was feeling the spanking, as were her little wiggles and squeals. He loved hearing the way that squeak changed when his hand landed on her sit spot, right underneath the curve of her ass.

Not that he was actually trying to spank the sass out of her. He really liked her sassy mouth. But he also wanted her riding him with a nice hot bottom that he could squeeze and torment while she was using him for her pleasure. He also wanted her to feel the spanking tomorrow, something to remember him by.

Right now, his goal was to make her sore and satiated inside and out, and he felt like he was doing a pretty damn good job.

He counted in his head as he laid down the last swats of her spanking, carefully aiming for spots he had noted were the most sensitive, that made her squeal and wiggle the most. When he was done, and she lay over his lap panting for breath, he smoothed his hand over that nice hot bottom, giving one cheek a hard squeeze that made her jerk again.

“Very good girl,” he said approvingly when she didn’t try to reach up and cover herself, despite the provocation. She knew how to be a good submissive, even if she was an extra sassy one. “How are you feeling? Are you ready to ride Daddy’s cock?”

As he asked the question, his fingers delved between the cheeks of her bottom, finding the base of the plug and giving it a little tug and twist. Her muscles immediately clenched, buttocks moving together in a vain attempt to still the toy’s movements.

“Yes, Daddy, please let me ride your cock!” There was no mistaking the enthusiasm in her voice.

Grinning widely because he wasn’t sure she realized how determined he was to follow through on every single promise he’d made her, he released the plug. She was going to be riding him while it was still inside her, giving her that extra little bit of stimulation.

Lifting her off his lap, he had her stand beside him as he quickly shucked his pants and settled back into his seat. He reached out to hook his finger around the chain hanging between her nipples, using it to pull her forward. She cried out, her hands going up to her breasts, then dropping back down as she remembered not to try to stop it.

Pulling her into position straddling his lap, he let the chain drop again and picked up a condom, handing it to her.

“Put this on Daddy’s cock, sweet girl, then you’re going to ride me until you can’t anymore.”

“Okay, Daddy,” she replied, but there was a gleam in her dark eyes that made him grin. It didn’t take a genius to note the mischief dancing in her gaze nor the challenge. He would be willing to bet money that she was planning on getting him off before she tired out.

He looked forward to her attempt.

In a battle of wills and orgasms, he would bet on himself. As revved up as he was, it was nothing compared to how she would be. And he still had the clamps and the plug on his side. His hands curved around her hot bottom, giving her cheeks a little squeeze as she settled onto his lap.

Ripping the packet open, she tossed the trash to the side, her gaze intently focused on him. Holding the condom in one hand, she gripped the base of his cock with the other, leaning forward to press her lips against his. They kissed hungrily, his hands kneading the soft, hot flesh of her ass, digging his fingers in as their tongues twined, and he felt the wetness of the lubed condom against the tip of his dick.

She slid her hand up and down on the base of his cock, rocking against him so the tips of her clamped nipples brushed his chest, unrolling the condom over him with the other. It hugged his cock all the way down the shaft until it met her hand at the base, which she moved out of the way to complete the job.

Only then did she end the kiss, putting her hands on his shoulders so she could move forward. His cock was sticking straight up, achingly hard, as she positioned the tip at the opening of her body. Looking down at him, she held eye contact as she started to sink onto his dick, her mouth dropping open so she could take a deep breath as she impaled herself.

Drew moaned, squeezing her buttocks hard, trying to thrust up from his sitting position as her pussy slid over his dick, the warm wet heat sending pulses of pleasure through him as she clenched and quivered. His fingers shifted, brushing against the base of the plug, making her rock forward on him as she settled on his lap, rubbing her clit against his body.

“Oh… fuck… Daddy…” Her head dropped back, thrusting her breasts forward to rub against his chest again, the clamps hard points against the softness of the rest of her.

“That’s right, sweet girl, fuck Daddy,” he encouraged.

At another time, she probably would have giggled, but right now, she was too wrapped up in the sensations coursing through her, and he was encouraging it. Leaning forward, he pressed his lips to her neck, one hand sliding up her back to keep her from being able to pull away as her breasts were squashed against his chest, her tormented nipples now caught between them. She cried out, squirming on his cock as he moved his lips over her throat up to the side of her jawline.

Shifting, she turned her head to catch his lips with hers, then started moving as they kissed, pushing herself up so she could sink back down on him. Drew groaned against her lips as she started riding him, her nipples brushing against his chest as she moved up and down, her pussy clenching around him as she shuddered with pleasure.

His fingers tapped against the base of the plug every time she sank down, teasing her senses with the toy that was inside her, giving her an extra little jolt of pleasure in her growing ecstasy. The breathy sighs and moans as she moved atop him were starting to get to him. He was going to need to do something to make her come for him a little faster.