On a Sunday morning, Cindy would typically lie about, taking the ‘day of rest’ seriously by binge-watching some serial she’d been following or reading a book. After breakfast she might go out to do some window shopping, but rarely stopping to buy. In warmer weather, an afternoon by the pool might be called for, followed by a warm bath. The bath often figured into her Sunday fun, luxuriating in the hot water, sometimes with bubbles but nearly always with her hand between her legs, fingering herself to several orgasms driven by her fantasies of a stinging red bottom.
She would certainly have a bath today, and those orgasms would be sweeter still with the added reality of last night with Simon, which not only fulfilled one of her spanking dreams but also created a meaningful connection with the man she’d longed for for quite some time.
She still found it hard to believe that not only had they finally come together, but it was their shared interest in spanking that made it possible. Her first-ever experience last night had more than met her expectations, no doubt due in part to it being Simon who spanked her, and he’d be coming over tonight to be taken over her knee, realizing her desire to give a spanking. Still, she wasn’t without some nagging doubts about how she’d compare to the stunningly gorgeous Monica.
With that in mind, Cindy’s Sunday was not so lazy as she dashed around her apartment, straightening up her typically messy living quarters. Dishes were washed along with a general tidying up that she did only when it got too much for even her low standards, but it was vacuuming carpets, dusting, and even changing the sheets on her bed that went well beyond her typical domestics.
She turned the bedsheets down invitingly as her last tidying task and rewarded herself with her usual Sunday bath with scented bubbles forming a small mountain and her favorite dildo close at hand. She sank within the insulating foam that kept the water hot, sighing as her body relaxed from her exhausting morning. Surprised when the heat of the water revived the sting in her bottom, her mind immediately recalled her dream come true, and she added caressing, squeezing, and even pinching her bottom to her usual palette of masturbation practices.
Her arousal grew quickly with the added stimulus of real-life activities, past and future. Her middle finger filled her slit traversing the deep valley between her meaty lips as her mind provided the dialog. ‘Please spank me, Simon! Spank my hiney!’ played over and over in her head as her finger on her clit sparked the first energetic climax. Though she didn’t usually have a script for these activities, her fingers would typically find their way inside, pounding her pussy at an ever-increasing pace, but today she saved that for last when the dildo built anticipation for Simon taking its place later.
Simon’s Sunday was spent in nervous anticipation for his evening with Cindy. Trying to understand why, he determined that he wasn’t concerned about her overdoing it like with Monica the last couple of times but, oddly, wondered if it might not be extreme enough. He’d be lying if he said he wouldn’t miss at least some of Monica’s dominance, but he knew she expected to escalate well beyond his present limits, which wasn’t where he wanted to go. Still, he wouldn’t mind if Cindy ordered him to lay on the bed so she could pound his face into the mattress with her pussy or to tie him to a chair, bent over, and ready for a good, hard spanking.
Remembering concerns he’d had with Monica, Cindy was likely that ‘someone closer to his age’ he’d thought about when wondering whether Monica might ditch him for the same reason. At the time, he considered it inevitable that he’d be replaced by Monica’s ‘someone,’ but had hoped it wouldn’t be anytime soon and planned to ride it out as long as possible. What he hadn’t expected was that he’d find that someone first and still worried about how Monica would handle it.
As the day wore on, his anxiety ebbed. Aside from her age, Cindy had many other attributes that, although decidedly different from Monica’s, were very appealing to him. She was beautiful in her way, her cute face fitting perfectly with her naughty, little girl persona, and he looked forward to being her ‘Daddy’ and spanking her equally cute hiney. But tonight, it would be his turn, and though he didn’t know what sort of scene or character she’d employ, he knew he didn’t have to worry about it getting too intense. The balance of the afternoon found him excited about the evening to come.
Not waking till almost noon, Monica was thankful for the absence of a hangover but wasn’t entirely free from the effects of last night’s surprising activities with Derek. First, she didn’t feel fully rested and walked around in something of a daze for the first hour or so. Mentally, however, she felt better than she had since things started going south with Simon. Derek showed virtually no resistance to her authority and proved his devotion at every step. She hoped he’d call to set up another evening with her soon.
The night’s success had her wondering whether her doubts about how dominating she wanted to be were driven by Simon’s reluctance and/or experience, not her desires. She’d been inwardly defiant of those who might think of her as less of a Domme for denouncing some of the BDSM precepts. Those feelings were gone now, as she suspected Derek was both more experienced and willing to accept a submissive role. As these thoughts played out in her mind, she also cautioned herself against expecting too much and knowing communication was still crucial to understanding their needs.
She was on the internet getting some ideas when her phone rang. Lacking a caller ID, she was usually hesitant to answer such calls, but knowing she didn’t have Derek in her contacts, she answered.
“How’s my beautiful Miss this morning?” he asked.
Derek was up early, as always, and had been waiting to call her until he was sure she would be up as a polite gesture but also as an acceptance of her dominion over him. He couldn’t be happier about the prior night’s activities. Not only had he had sex with the most beautiful woman he’d ever been with, but she seemed to know just how to put him in his place, his place beneath her. He couldn’t wait to be looking up at her again, whether that was staring into her pussy, descending onto his face, or from his position near the floor as he was bent over her knees for another punishing spanking.
“I’m just fine, Big!” she lied, still not quite herself. “I trust a sore bottom reminds you to be on your best behavior?” she added, caught off guard and not quite ready for the usual banter.
“Yes, Miss. I’d love to show you again how well-behaved I can be!” he said, fishing for an invitation.
“Again? I don’t recall you being all that well-behaved the first time!” she countered, getting into the swing of the repartee.
“I’m sorry, Miss! I guess I need more training. Perhaps we can fit it in before I go out of town Tuesday morning!?” he offered, making a request for Monday night without sounding like he was suggesting it.
“I’ll text you my address. Be here Monday at eight! You don’t want to be late!”
“Thank you, Miss! I’ll be there!”
With another date set for Monday, Monica and Derek could relax, knowing the other wanted to continue. They hadn’t discussed the next time before she left, leaving them both in limbo. Derek got to work planning for his trip, knowing he wouldn’t be able to stay focused with the impending time with her on his mind tomorrow. Monica spent a lazy late afternoon in the hot tub, enjoying the contrast of the cool air and hot water while her fingers played between her legs in anticipation of having Big in there again.
Simon was at Cindy’s door fashionably late, confident there would be no repercussions as a result, not that he would mind if there were, but he didn’t think that was Cindy’s style. He was happy it wasn’t when she appeared in the open doorway.
“Oh wow, Cindy! You look so sexy!” he said as he held her waist at arm’s length, taking in her visage, though she looked embarrassed by the compliment. A tight white crop top with a scooped neck showed her perfect tits and tummy to best advantage, while her ultra-short denim shorts drew attention to her slender legs. The outfit didn’t scream sex the way Monica’s had, but it was equally arousing in its promise of what lay within.
“Thank you! Why don’t you … Oh!” she cried as she was pulled in for a romantic hug and kiss. “Mmm! Thank you again! Do you want to come in, or …” she started but was interrupted again when Simon moved them into the room for another more passionate kiss. “Wow! Hello to you too!” she said as she flung the door closed while remaining in his arms, short kisses and piercing eyes saying hello in their own way.
“Come!” she said, taking his hand and leading him to the open kitchen.
“Something smells good! Italian?”
“Yeah. Lasagna, but it’s got about fifteen minutes more to bake. Would you like some Chianti in the meantime?”
He accepted the wine, sharing light conversation while the lasagna finished baking. Cindy wanted to ask him more about Monica and how she dominated Simon, as she figured he must have liked it to some degree to continue for the weeks they were together. She wondered whether she should adopt some measure of it but put that discussion aside to avoid it negatively impacting their time tonight, though she did have a plan for getting started.
“That was delicious, Cindy! You obviously like to cook!?” he said when they’d finished eating.
“Not really. I make a few things pretty well, but I’m barely average with most dishes. More wine?” she asked as he stood and started clearing the dishes, giving her a good segue to her plan. Standing behind him as he placed the dishes on the counter, she put her arms around him, her hands going to the closures of his pants, and opened only the belt. “While I go and get some things ready, I want you to clear away the dishes and then take all your clothes off except your underpants. Understand?”
“Yes, Cindy!” he replied excitedly and flinched when she grabbed his crotch, stroking his hardening dick a few times before leaving him to his tasks.
She didn’t really have anything to get ready, apart from taking her shorts and blouse off and donning the lacy black bra that matched her cheeky panties. She watched him through a slit in the door as he first started putting dishes in the dishwasher and then paused in thought. He seemed to have decided that removing his clothes was the more important task and switched to opening his pants' belt, button, and zipper. Using his toe on the heel, he removed his shoes and let the pants fall around his ankles. Reaching down, he removed the socks and pants and put them on one of the chairs. He had just started on the buttons of his shirt when she returned.
“You look … delicious!” he said when he saw her padding barefoot into the room in her black underwear.
“Thank you, but you haven’t finished your job, have you?” she said with a firm but pleasant tone.
“It’s only been a couple of min …”
“I gave you two simple tasks, and you haven’t completed either of them,” she accused.
“I’m sorry, Cindy. I was just …”
“You know ‘sorry’ isn’t enough when you’ve been so naughty. Now I’ll have to complete your tasks. Do you know what I do to naughty boys?”
“No, ma’am,” he said, calling her ‘ma’am’ as a less extreme title in recognition of her authority, as opposed to the ‘Miss’ he’d used with Monica.
“You’ll find out soon enough. Come with me!” she instructed, taking his hand to lead him to her bedroom. “Stand here,” she said, stopping before an armless chair and pointing to the floor. Opening his shirt, she pulled it off by the sleeves and tossed it aside.
“Am I gonna get a spanking, ma’am?” he asked in a pouty tone.
“Yes. Over my knee and on your bare bottom, but don’t call me ma’am. I’m not your mother or some old lady. Now stand here at my side.”
“Yes, Cindy,” he said, hoping using her name was what she preferred. He liked that she was telling him what to do in a firm but friendly voice, unlike Monica’s disparaging tone. He’d do whatever she asked of him simply because he wanted to, not out of fear of reprisals.
“Now, I’m going to take you over my knee, pull your sexy little underpants down,” she smiled as her hand caressed his covered cheeks, “and give your bare bottom a good spanking. That’s what you need, isn’t it?” she asked.
Cindy had found the dialog around spanking surprisingly arousing. Every time she heard the word ‘spank’ in any of its forms, she got a little more excited. The threats, descriptions, and demands using that word all added to her appreciation of the act.
“Yes, Cindy. Please?”
“Please, what?” she asked, wanting to hear him use the word too.
“Please spank me. I’ve been a naughty boy and deserve to have my bottom spanked,” he replied, enjoying the repartee as much as she.
“Good boy. Over my knee,” she said in that same gently firm voice while pulling him down by his wrist. In position now, her hands caressed and squeezed his cheeks, intending to arouse them both as she toyed with the cute butt she’d admired for so long.
“Mmm, that feels good, Cindy.”
“Yeah? You like it when I squeeeeeze your cheeks? Well, that’s not what you’re HERE for, is it?” she replied with one good smack for emphasis.
“No, Cindy!”
“You’re here because you need to be SPANKed! And we both know it’s not a real spanking unless it’s on your bare bottom!” she said as her fingers slipped under the elastic of his tight briefs. He rose up to let her pull them down, and once past his cheeks, she pushed them down to his knees, where they stayed loosely while her hands returned to fondling his ass.
“You know, I’ve always enjoyed looking at your cute butt, Simon, and what better way to enjoy it than over my knee, naked and waiting for a GOOD … SPANKING!” she said, delivering the first of many spanks to come.
“Oh God, Cindy!” he cried as all the dialog and foreplay came brightly into focus with the stinging spanks she seemed to know precisely how to give. As hard as any Monica had started with, they felt different … better somehow, perhaps because she intended to please, not to inflict pain. If he had any doubts before about whose lap he’d prefer to be on, they were gone now.
“Oh, Simon! I hope you’re enjoying this as much as I am! I really love spanking your cute, little hiney!”
“Yes! Oh, God, yes! Spank my hiney, Cindy!” he cried, adopting her word as she seemed to like it.
The spanking continued with only occasional pauses as she relished the sight, sound, and feel of his bottom yielding to her hand.
“I’m so happy, Simon!” she said, sounding on the verge of tears as she stopped to soothe the dark pink stain spreading across his cheeks. Bending down to kiss each cheek, she pressed her face into the pliant flesh while he moaned in appreciation. “Happy that you like getting spanked! Happy that you like spanking me! And happy that we found each other,” she said with tears running down her face.
Simon could hear it in her voice and rose from his position over her lap to sit instead and hold her to his chest.
“It’s just that I was beginning to believe I’d never find someone to do this with, and I wasn’t getting anywhere trying to get your attention, and now … now, this is so perfect and …” she stopped there, afraid she’d confessed too much. She looked up from his shoulder, and, with his hand on her cheek, he kissed her with as much tenderness as he could.
“I feel the same way, Cindy,” he said when their lips separated, admitting to himself that he’d never felt this strongly about any woman before and kissed her again trying to impart that feeling to her.
“Oh, Simon!” she started with a smile, and her tears wiped away by his hand. “You’re such a naughty boy, and you need a good spanking!” she declared, trying to get the evening back on track.
“You don’t have to. That’s enough for …”
“No-no-no! Get back over my knee, young man! You’re gonna get your hiney spanked!”
Happily back in position, the spanking resumed with the intensity and pace slowly ramping up, and a hundred or so spanks later, he declared this the best he’d ever gotten. He thought he might have to direct or coach her, but she was a natural, seeming to know exactly what he wanted.
“Mmm, your hiney’s getting pretty red! Have you had enough?”
“I’ve only had enough when you’ve had enough!” he said, offering her complete control.
“Ooo! My panties just got even wetter, but I suppose I could do another fifty … or more!” she said with a devilish laugh as she spanked each cheek several times at a quicker pace before switching to the other side.
“Ow! Ow-ow-ow-ow!” he yelped in response, adding, “No! No, don’t stop!” when he felt her lighten up. “Oh, wow! That was the best!” he declared when she did finally stop well beyond the promised fifty.
She’d taken her cues from him the night before, added some flavor of her own, and couldn’t be happier with his compliment. Caressing his red cheeks lightly, she hadn’t expected the color and warmth of his bottom to add to her arousal. She’d looked at her red bottom in the mirror several times the night before, but this was proof positive of their mutual joy now realized.
“May I offer my gratitude?” he asked as he rose from her lap at her suggestion.
“On the bed?” she phrased as a request rather than a demand.
They both stood inches from each other, smiling broadly. She leaned in for a kiss, but he put a finger on her lips to put the kiss ‘on hold’ and reached around to unclasp her bra. She shrugged it off her shoulders, and he bent to kiss and lick each nipple in turn before kneeling to remove her panties. They fell into each other’s arms like magnets drawn together, and pressing their naked bodies together for as much flesh contact as possible, their hands fell naturally to spanked cheeks. Pushing, pulling, and grinding their loins together, aural and physical responses made what they both wanted obvious.
“Oh God! I want you inside me so bad!” she whispered close to his ear.
They moved to the bed with Cindy kneeling first on its surface and, still holding his hand, pulled him down on top of her as she lay. He knew she wanted penetration, but he couldn’t resist the sight of her swollen and inviting pussy with its closely trimmed patch of hair on its mound.
Laying between her legs, he gave her beautiful tits all the attention they deserved as she pushed each fleshy orb into his face. Looking up and smiling at her closed eyes and ecstatic facial expressions, he licked his way down between her slippery, wet lips. Fingers, lips, and tongue tasted and teased her sweet pussy until she was writhing on the bed. Pushing it into his face, she came with jerking hips and trembling thighs as he continued licking, prolonging her rapture.
Her body only quivering now, she pulled him back on top of her, whispering, “Fuck me!” in his ear. Kissing first her neck and then her lips, he felt her reach down to take hold of his cock, not to be denied again. “C’mon, fuck me, Simon!” she said more insistently. “I want your cock in my cunt!” she added, surprising him with her vulgarity.
Lifting to support himself on his knees and locked arms, he let her guide him into her oh-so-tight tunnel. She let go once he was on the way in and put her hands on his warm ass pulling their hips together and gasping, “Oh God!” loudly once he was deep inside.
“Oh, that feels so good!” she said in his ear as he lay atop her again.
Only now did he realize she’d never commented on or even seemed to notice his larger-than-average size, and rather than be offended, he saw it as another welcome contrast to the ‘big is better’ Monica.
He moved in slow, short strokes, watching her face for the bliss he hoped he was providing. Her eyes showed so much pleasure when they opened, and her smile only added to his joy. Thinking only of her arousal had the added benefit of diminishing his as he feared he’d cum too quickly this first time tonight.
“Oh yeah! Oh God! Ungh!” she moaned almost continuously as she lifted her hips to meet his coming down and lengthening his stroke as she quickened the pace. “Uh! Uh! Uh!” she grunted with each stabbing thrust. “I’m cumming!” she cried a minute later. “I’m cumming! Cum with me, Simon!” she pled, and it didn’t take much to make that happen for her as he was so close and straining to hold back.
They cried out together when it hit them, and he fell atop her, kissing her face and neck as they both struggled to breathe normally. He rolled to his side, taking her with him, staring at her pretty face as their eyes carried on a conversation.
They lay in bed together, luxuriating in each other’s presence, occasionally going to the kitchen or bathroom but returning quickly to their embrace. They felt so close already, and neither had felt this way about someone before. Their mutual interest in spanking had much to do with it as they’d found someone they could trust their secret with, but there was more to it.
They’d only spent a bit over an hour pleasing each other and another hour just lying together, but neither felt the pull to resume. They were more than satisfied sexually and enjoyed just being together, saddened when it came time for Simon to leave.
“I wish you could stay tonight,” she said with his arms wrapped tightly around her chest as he lay behind her.
“Me too. Maybe Friday night?”
“Ohh, does my hiney really have to wait till then to get spanked again?” she pouted as she turned to face him. “Ooo!” she yipped when he reached over to smack both cheeks at once and laughed.
“No, I suspect you’ll be naughty enough to earn another good spanking well before then!” he said, and she nodded enthusiastically. “I would rather stay in bed with you in the morning as long as we want rather than having to get up and go to work!”
“I agree! Mmm, I can’t wait!” she replied as they enjoyed one last naked hug before he had to leave.
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Could Cindy and Simon be any better matched? They seem to have a great future together, but there's still Monica to deal with! What will she have to say about Simon abandoning her for Cindy? I really appreciate 'Likes', 'Favorites' and comments if you enjoyed my story and ... THANKS FOR READING!!!
