Dirty Daddies: 2020 Anniversary Anthology

by Maren Smith

  Saul smiled, sitting down in the chair next to hers so they could talk. Her gaze flicked back over to the toys and the bear before returning to his. The anticipation in her expression was clear, but so was her nervousness.

  “I want you to try something for me,” he said. While he’d been out, he’d thought long and hard about how he wanted to present this to her. If she said no, then that would be that. The toys would still be used, they’d still keep on going as they had, and she’d get to keep the teddy bear, but he wouldn’t bring it up again. “For the rest of today and tomorrow, I don’t want to be your Dom, I want to be your Daddy.”

  Vicky

  Her stomach flipped in a not entirely unpleasant way.

  Not her Dom, her Daddy. Why did that sound so appealing when it shouldn’t?

  “What does that mean?” she asked slowly. She didn’t want to give him an outright no, the way she had when he’d first told her that he was a Daddy Dom, but she wasn’t sure she could say yes either.

  “It means that for the next day and a half, you call me Daddy instead of Saul or Sir and I’m going to… take charge of you more than I normally do. I’ll make the rules and you’ll follow them, but other than that, you’ll be pretty much free to do whatever you want.”

  “What are the rules?”

  Saul’s lips lifted in a half smile. “No swearing. You won’t have much of a problem with that anyway, you hardly ever curse unless you’re really upset. No putting yourself down. That one I expect a little more struggle with. When I tell you it’s time to do something, you do it, unless you feel unsafe. You’ll still have your safeword. If you’re a bad girl, I’ll punish you immediately. Probably with a spanking but maybe with something else. Like lines.”

  When he said ‘bad girl,’ her thighs clenched together under the table. Writing lines hadn’t been sexy at all, but being called a ‘bad girl’ always got her body’s attention. So did being called a ‘good girl’ for that matter. She was a multifaceted mess of contradictions.

  “What if I don’t like it?” That was her biggest worry. Rachel’s comment about Saul’s needs not being met had really burrowed under her skin. Clearly, he wanted to try this, which meant there was probably some truth to it.

  Reaching out, Saul took her by the hand and pulled her over onto his lap. Immediately, she cuddled into him, seeking the physical reassurance he was offering.

  “If you don’t like it, you don’t like it,” he said, shrugging as his fingers rubbed her thigh and side, soothing her. “We’ll keep doing what we’ve been doing. I’m happy with it, but I’m starting to wonder if Rachel was right and if I’ve missed giving you something you need.”

  Vicky giggled at the very idea. “I was thinking the same thing about not giving you what you need.”

  “As long as I have you, I have everything I need,” he said seriously, shifting her about on his lap so she was facing him. Her legs straddled his thighs, hanging down on either side and he cupped her face in his hands, pulling her in for a sweet, lingering kiss. “But you did a lot better at work after… Well, after I kind of Daddy Dom-ed you a couple weeks ago without calling it that. Maybe it was the spanking, maybe it was something more, but I would like to try. If you hate it, maybe we’ll try maintenance spankings.”

  Okay well, that sounded awful.

  “I’m willing to try the Daddy Dom thing,” she said quickly. After all, it was just a day and a half, right? That couldn’t be too bad. If she didn’t like it, then nothing would change.

  But what if I do like it? the insidious little voice in the back of her mind asked. How do I deal with that?

  But she didn’t get more than a moment to think about it, because Saul was suddenly flipping her around. She landed with an ‘oof’ across his lap, in perfect spanking position.

  “Hey!”

  “And now we’re going to talk about your behavior earlier today, baby girl.”

  Crap.

  Saul

  From her reaction, Saul could tell he’d taken Vicky by surprise, which amused him. Had she really thought they wouldn’t be returning to this morning’s events?

  “But I already did lines,” she whined, wriggling on his lap. He pressed his hand down on the small of her back to pin her in place.

  “Do you really think that’s enough for the way you treated Rachel? Do you think that’s enough for the things you said about yourself?” His other hand rested over the curve of her butt, rubbing it gently as he got ready to spank her. She slumped, head hanging, and he knew he had his answer, but he wanted the verbal confirmation. “Do you, baby girl?”

  “No.” Her voice was soft, resigned.

  “No, what, sweetheart? What are you calling me today and tomorrow?”

  There was a quiet groan before she answered, but she did answer. “No, Daddy.”

  She wriggled again, like her body was reacting to call him that. Good? Bad? It was hard to tell without being able to see her expression, but she’d said it.

  “Good girl,” he praised. “I like hearing you call me that.” Another little wriggle. Saul was beginning to suspect the wiggling was a good thing. His cock definitely liked both the wiggling and hearing her call him Daddy. He was already hard as a rock.

  But he was going to have to control himself, for a little longer at least.

  Hooking his fingers into the back of her pants and underwear, he yanked them down over her butt. As he pulled, the backs of his fingers brushed against her pussy, gliding over slickness, and he grinned. That she was turned on right now was a good sign.

  Vicky

  Calling Saul ‘Daddy’ for the first time did not affect her the way she thought it would.

  She’d thought she’d feel silly or maybe a little scornful. That it would be weird. Possibly gross. That it wouldn’t feel right.

  But… it was kind of hot.

  Kind of really hot.

  Which was a disturbing revelation. She didn’t have Daddy issues. Her parents were great. So why was she so turned on from calling her boyfriend ‘Daddy’?

  Smack! Smack! Smack!

  The need for answers flew out of her mind as Saul’s hand came down hard on her ass, redirecting her attention back to the matter immediately at hand.

  “You are going to stop putting yourself down.”

  Smack! Smack!

  “You are going to stop worrying about Rachel.”

  Smack! Smack!

  “And you are going to start believing in yourself if I have to spank you every day to make it happen.”

  SMACK! SMACK!

  Vicky squealed, legs kicking, tears sliding down her cheeks. Saul was not holding back, and his hard hand stung like crazy every time it impacted against her tender flesh. At the same time, it felt like a huge release as her emotions came tumbling out. She wasn’t just crying because it hurt, although that was part of it, she was crying because she was so mad at herself… disappointed in herself… and frustrated with herself.

  Not just for losing. For all of it. Because she had been so very wrong about Rachel. Because she was so hard on herself when it came to the competition. Because she had disappointed Saul, again. And because she just didn’t know why she couldn’t stop doing these things.

  Smack! Smack!

  His hand fell twice more and then stopped, rubbing her sore flesh. Vicky sucked in a deep breath, a little surprised that he’d stopped so quickly. Maybe the lines did count for something.

  But she’d forgotten about the paddle.

  “Good girl,” he said, rubbing his hand over her tender skin before moving it away. “Now, five more with the paddle and then you’re done.”

  “What?” She screeched the word, bucking on his lap, but the hand on her back prevented her from going anywhere. “Nooooo, Saul, ple-”

  But she didn’t even get to finish asking before his hand pulled back and smacked her hard, right on her throbbing pussy.

  Slap!

  She howled, legs kicking, as the sensitive area burned.
/>   “What are you supposed to call me, baby girl?”

  Shit, crap, right.

  “Daddy, please, not the paddle,” she begged. Was her voice higher? It seemed higher than usual. For some reason she felt a little more vulnerable too, although that might be because her pussy was still stinging.

  “It seems just my hand wasn’t enough to make the lesson stick last time, so yes, the paddle, baby girl.”

  “Daddy, noo-OOOO!” Her plea turned into a high-pitched shriek as the paddle came down across her bottom, the hard wood biting into her already chastened cheeks. It hurt so much more than his hand did and she wailed.

  Her body writhed against his hard thighs, her toes skimming across the floor as she kicked, and tears were sliding down her cheeks. Now she was crying in earnest, her swollen bottom throbbing from the painful discipline. Every blow from the paddle sent a new pang of agony through her.

  Thankfully, it was over quickly, and she hung there, crying and waiting for him to pull her up and cuddle her. Instead, she heard him pick something up from the table and she stiffened, sniffling.

  “What are you doing? Um, Daddy?”

  “Adding another little reminder for you to think about,” Saul said.

  Something slick, cool, and very hard touched her anus and Vicky automatically clenched. It didn’t matter though. There was enough lube on the plug that her tightened muscles couldn’t keep it out and they were forced to stretch as he began to push it in.

  “Relax, baby girl. This will hurt a lot less if you relax.”

  Easy for him to say, he wasn’t the one having a plug shoved up his butt. Vicky panted for breath as it pushed deeper, trying to make her muscles loosen, but it was so hard with the odd sensation of the plastic being pushed inside of her. The toy got bigger with every millimeter that slid inside of her, much wider than his finger, and Vicky whined as the burn increased.

  “Ow, ow, it hurts, Daddy!”

  “It’s almost all the way in, sweetheart.” His fingers moved in soothing circles on her lower back, but that barely distracted her from the sharp pinch as the thickest part of the plug forced its way past her sphincter. Vicky squealed and then sighed as it settled inside of her, the tight ring of her muscle snapping shut around the thin neck.

  Well, thin compared to the rest of the toy.

  It was still uncomfortable but at least it didn’t really hurt anymore. Not in comparison to the rest of her bottom, which felt hot, swollen, and throbbing.

  Saul

  After the first smack with the paddle, the words Naughty Girl had been clearly visible on Vicky’s skin, but each successive smack had marred the legibility even though Saul had attempted to land the blows in the same place. He traced his fingers over the raised areas of the blurred lettering.

  Maybe next time he used the paddle, he’d just give her one hard smack with it across her cheeks so he could enjoy the lettering when it was nice and crisp.

  “Daddy?” The tone she was using was softer than usual. Hesitant. “Is it over?”

  “Yes, baby girl,” he said, giving her bottom a final pat, his fingers tapping against the base of the plug. He heard the quick intake of breath when he did so and grinned. A quick sweep of his fingers a little lower found that her pussy was soaking wet, clit swollen, and she bucked slightly when he touched her.

  He withdrew his fingers immediately, pulling her up onto his lap. An adorable pout was already on her face. She winced as she settled on his lap, whether from the soreness of her butt cheeks, the plug, or both was debatable.

  “Good girl,” he said, stroking her hair and giving her a kiss on the head. “Now I want you to go and put on some comfy clothes. Pajamas, yoga pants, whatever you want as long as it’s comfortable.”

  She straightened, real dismay crossing her expression and replacing the pout. “But… aren’t you going to… we aren’t going to…”

  Now Saul did smile, bopping her on the nose with one finger. “No orgasms for naughty girls. If you’re good for the rest of the day, you can earn one before bedtime.”

  “You’re going to wait that long?” she asked as she got to her feet, pulling her pants back over her butt with a wince and giving his crotch a pointed look. Yeah, his dick was hard as a rock, but he was willing to wait.

  “I want to give your ass plenty of time to get used to the plug before I fuck it,” he said deliberately, enjoying the way she blushed, paled, and then reddened again as the realization came home. Sitting right in front of her while she was standing, he didn’t miss the way her thighs immediately pressed together either.

  “Is… is that part of my punishment?” she asked tentatively.

  Saul laughed. “Oh no, baby girl. That’s just because I want to. Now go get dressed.”

  Spinning her around, he gave her another slap on her ass to get her moving.

  Chapter Six

  Vicky

  It was hard to concentrate on the movie, even though Hercules was one of her favorites.

  Her butt cheeks were still throbbing from the spanking, while her butt kept clenching around the plug inside of it, her pussy was tingling and needy from the lack of orgasm, and she couldn’t stop thinking about what Saul had said.

  Anal sex. Tonight. She squeezed the teddy bear she was holding a little bit tighter.

  Finally, a little corner of her mind whispered. The traitorous little corner that also liked calling Saul ‘Daddy.’

  It didn’t help that his hand kept drifting down over the curve of her ass, fingers seeking out the base of the plug to tap, which was all too easy for him to do through the thin fabric of her yoga pants. And every time he did, she’d clenched around it, making it feel even bigger inside of her, and her pussy would get a little bit wetter.

  By the time the movie was over, she was a hot mess of need, and she could tell Saul was aroused too, but he just sat her down at the table to do some coloring with some crayons and a coloring book he’d bought while he made dinner. To her surprise, the coloring was a lot more fun than she’d thought it would be. She couldn’t even remember the last time she’d used a coloring book. Definitely something to do more often.

  With that to focus on, she almost even forgot about how horny she was and the plug in her butt.

  Almost.

  Saul

  Watching Vicky get totally lost in the coloring while he cooked both amused and delighted Saul. He hadn’t been sure how she would take the idea but thought she might like it. Especially because he hadn’t challenged her sensibilities too much and had deliberately picked up an adult coloring book of mandalas. Maybe in the future they could get some others. She did like kids’ movies and there were plenty themed around those.

  His anticipation for the evening ahead grew with every passing minute, although he made himself focus on cooking and then eating. He wasn’t the only one either—Vicky squirmed her way through dinner, continuously peeking at him when she thought he wasn’t looking.

  Once they finished eating and cleaning up the kitchen—which she helped with rather than return to her coloring—Saul announced that it was time to get ready for bed.

  “It is? I mean… right… okay, Daddy,” she said almost shyly, glancing at the clock and then seeming to remember that there were a few things to do before bed. The hopeful look she gave him made him smile.

  “You were a good girl,” he reassured her. “Don’t worry, sweetheart, you’re getting your orgasm.”

  She brightened up immediately and was so adorable that Saul laughed and pulled her in for a kiss. It was meant to be a cute, gentle kiss, but she latched on to him hungrily and it changed in a flash from sweet to something more intense. His own arousal had been growing all afternoon and evening, and now his cock sprang to life, eager for what came next.

  His hands drifted down to her ass, squeezing the soft flesh and making her gasp. Even though the heat had dissipated from the surface of her skin, he knew she’d be sore, and his groping would add a little dollop of pain to her arousal, which w
ould inflame her further.

  Whimpering, she squirmed against him, rubbing herself all over his front and his cock and Saul groaned.

  With a quick bend of his knees and lift of his hands, he flipped her up over his shoulder ass in the air while she giggled madly as he carted her off to the bedroom.

  Vicky

  Head down, ass up was how she’d expected to end up.

  Instead, Saul had her on her back, her legs propped against his shoulders, practically folding her in half, while he stared down at her, one hand on his cock as it pressed against the entrance to her ass. The position she usually loved so much because of its intimacy was now dauntingly intimate, allowing them both to see each other’s expressions as she lost her anal virginity.

  Her tongue flicked out, licking her lips nervously as his cock began to push against her sphincter. Vicky whimpered a little, even though it didn’t hurt—yet. The stretching the plug had done helped with that.

  But a few seconds made a big difference and she whimpered again as the entrance to her ass began to stretch just as wide as it had for the plug—and without the relief of the thin neck. Unlike the plug, Saul’s cock was just as thick the whole length down and so she was just going to have to stretch to accommodate him; a thought that scared her almost as much as it excited her.

  “Oh!” She arched beneath him as his hips flexed and his cock slid deeper inside of her.

  The burning sensation was even worse than it had been with the plug, but she didn’t want him to stop either.

  In this position, she could see the look of ecstasy on his face as his cock pushed into her, which was hot as hell even as her discomfort grew with every inch that filled her. When he pulled back, retreating a little, it was almost even more uncomfortable than when he pushed in. It felt incredibly odd, as if her sensitive tissues were even more sensitive when he reversed directions.

  Then he thrust, going deeper and Vicky squirmed and panted beneath him, trying to adjust to the invasion. It hurt, it did, but in a way that made her empty pussy spasm.