Cindy had managed to get Monica’s address from the HR system. Being in IT had its benefits. She didn’t know when he’d be going to her home but guessed it would be after dark, whether to avoid being seen or just to add to the atmosphere.
She arrived on Monica’s street a little before nine o’clock, noting the nearly dark house and one dimly lit room upstairs. Simon’s Honda was parked in the driveway next to her BMW, so she seemed to have judged the timing correctly.
She considered going to the front door to see if she could hear anything but chided herself for being too nosy. ‘I’m not a stalker!’ she defended herself, though she felt like one. It was just that she’d been trying to get Simon’s attention for over a year now, and while he didn’t show anything more than friendly interest, she now knew they had something so exciting in common; she couldn’t let this opportunity pass and felt like more knowledge was key.
She decided it was worth the risk, so she got out of her car, walked past Monica’s neighbor’s home, and made her way to the front door. In the ultra-quiet neighborhood, she could just barely hear muffled voices from within, but not loud enough to make out what they were saying. Perhaps from the lit window above? She tried the doorknob, and it turned! She knew it was wrong, but she couldn’t help herself.
She stepped quietly inside the foyer and saw his clothes strewn on the floor by a chair with the hairbrush still on its seat. As she pictured him over the woman’s knee getting his bottom spanked, her arousal rose rapidly. She sat in the chair and imagined Simon over her knee waiting for her to spank him, and her hand slipped under her skirt to paw at the damp gusset of her panties.
She knew she shouldn’t chance staying too long as any minute one of them could come down the stairs, from which she’d be visible, but when she heard Monica’s voice from the upstairs room, she froze, wanting desperately to hear what would come next.
“We’ll start with twenty-five on each cheek,” she heard Monica say.
“Oh my God!” she whispered to herself as she rubbed her pussy furiously, listening to Simon getting his fifty swats.
When it was over she put Simon’s clothes on the chair, remembering incorrectly that she’d pushed them off to sit down and left before she might be caught. Curious as to how long Simon would be with her, she waited in her car, entertaining herself with her fingers in her pussy as she imagined herself making such a statement with Simon over her knee.
It was nearly an hour before he left, and she tried to imagine his state of mind as he walked down the steps to his car. He walked slowly and even stopped twice to look back at the door and upstairs room as though reconsidering something.
He drove home wondering about where this was going with Monica. He enjoyed what she did for him when it was his turn as a recipient of her favors, but he still didn’t like the belittling comments she gave him. He started to believe that he wasn’t really cut out to be submissive, which disappointed him. All the times he fantasized about his two favorite activities, pleasuring a woman with his tongue and fingers and bare bottom spankings, it was with the element of submission to her will. Giving endlessly with his only reward a bright red, stinging bottom.
He couldn’t see how those things he liked would fit into any other sort of relationship. Would he spend so much time in a woman’s crotch if she wasn’t demanding it or forcing it on him? Similarly, how would he end up over her knee getting the long, hard spankings he craved if it weren’t by the hand of a domineering woman punishing him because of some perceived mistake or improper behavior?
He slept fitfully as he tried to decide whether he should, or even could, continue with Monica. He hadn’t come to a conclusion by the time he actually fell asleep in time to get in only a few hours before work tomorrow.
Surprisingly, he and Monica were having similar thoughts again, though their viewpoints were decidedly different. She’d compromised several times to meet Simon’s expectations, but now her own were no longer being met. She’d gotten a real thrill out of lashing him with that strap, even though she was so apologetic once she realized it had really hurt him. That time with him was as close as they’d gotten to an authentic Dom/sub relationship, and it gave her a taste for it that wouldn’t be denied, regardless of how Simon felt about it.
Questioning whether she could wait to slowly bring him along as her sub or if he’d ever get there at all, she wished there was a way to find someone already trained who might help her learn the lifestyle. She realized it left her in the same position she was in before Simon, except that now he had whet her appetite for it and knew it was something she didn’t want to do without. But that didn’t help in any way to find such a person.
Throwing on some jeans and a loose-fitting T-shirt, she went out to her favorite local bar for a drink. The bartender, Jason, was always there to listen, especially to the gorgeous Monica. With the bar pretty empty at ten-thirty, she had his attention as they discussed life’s philosophies, each speaking of personal experiences without giving any details.
After a couple of Johnny Walkers neat, she left to return home, avoiding the playroom that was only a reminder of her predicament. She lay in bed realizing she and Simon hadn’t even discussed a next time, and she decided that was probably for the best. Maybe she’d feel differently in a week or two, and with the help of the scotch and a partial conclusion, she finally slept.
Cindy arrived at work a little earlier again, hoping to catch Simon before work started, but then thought better of it. She didn’t know what state of mind he was in, but he hadn’t looked happy when he left Monica’s last night, so she’d give him some time and maybe approach him at lunchtime.
She was happy with that decision when she saw Simon wandering into their work area as though in a daze. She didn’t know that insufficient sleep added to his confused state of mind. He smiled when he saw Cindy and gave her a friendly ‘Good morning!’ before sitting in his cubicle and logging into the Help Desk system with the memory of Cindy’s clandestine discoveries at the back of his mind.
Cindy walked by his desk to go out on a call, and he noticed she was dressed more attractively again. ‘If only she was available and into some of the things I like,’ he thought fleetingly, but she had a boyfriend. And she was so cute and wholesome; she’d surely laugh in his face if he attempted to discuss spanking with her. Maybe he’d have to give up on ever finding someone to share his fetish with and try to get someone like Cindy to just have some fun with.
The morning dragged, with his predicament always at the forefront of his thoughts. A new worry made things even worse besides his lack of proper sleep. What would Monica say or do if he wasn’t available to her anymore? He’d cross that bridge when he came to it; if he ever came to it.
He was heading out of the office for lunch when Cindy started walking with him, making idle chit-chat. When they got outside, she pulled him aside, saying she had something to ask him. He wasn’t used to her being quite so flirty with him, so he gave her a listen.
“I was wondering if you’d like to go out for a drink or something after work today?” she asked with her trademark cute smile and dimples.
“Oh. Cindy, I don’t …” he started, but thinking he might be passing up a chance with her, he had second thoughts about declining. ‘Why of all days is she doing this today?’ he asked himself.
“I have something I’d like to talk to you about … that I think you’d be interested in,” she offered.
“Okay. Sure. Where?”
They agreed on a local English pub offering drinks and food, with Cindy hoping to extend the date into dinner. They both walked away a little happier than before, though Simon was just a bit worried that her ‘something to talk to him about’ would involve seeing him in Monica’s office on Monday. He struggled to devise a believable reason but was unsuccessful when it was time to meet her at the pub.
“See you at O’Malley’s!” she said as she walked past his desk.
“Yeah! I’m just finishing up this ticket. I’ll be about five minutes behind you,” he said, making an excuse to give him more time to dream up an answer, again without luck.
“Simon! Over here!” she called to him from a booth with high walls separating it from its neighbors. “I’m having Merlot,” she offered when the server showed up about the same time as he did.
“I’ll have the same,” he said, noting one small thing they had in common: a love of red wine.
“I’m so glad you could come!” she said, putting her hand on his, a friendly gesture he appreciated.
“Cindy, what about your boyfriend? Tom, was it?” he asked.
“It was Tim, and we broke up ages ago. We never really had anything in common anyway,” she replied with a smile.
They talked shop for a while and moved on to more personal topics about family, likes, and dislikes. A more intimate tone to their conversation gave Cindy a segue into what she wanted to discuss. She put her hands in the middle of the table, a gesture Simon took as an opening to explain they were here. Her hands were warm but shaking slightly.
“So, there was something you wanted to talk to me about?” he asked, opening the door for her.
“Yes,” she replied, grasping his hands more firmly. “Simon, this will probably sound strange to you. Will you promise to hear me out and not bolt out of here?” she asked with pleading eyes.
“Yes, I suppose so,” he replied dismissively, but inwardly still curious whether this had anything to do with Monica.
“No ‘I suppose so,’ Simon. Promise me! Please? I promise you’ll like what I have to say in the end.”
“Okay, I promise.”
“Thank you. First, I’d like to explain my teasing comment about seeing you going into Monica’s office on Monday,” she said, with warning bells sounding in Simon’s head. “Don’t be mad at me, but … but I was listening to your conversation from the office next door. No! Don’t leave! You promised!” she begged managing to keep one of his hands in hers. “I know what you’ve been doing. Or rather what she’s been doing to you.”
Simon’s face turned beet red, and he looked away, not wanting to see her eyes, which were probably laughing at him. He almost left again, but he glanced at her face, and she wasn’t laughing or accusing him of anything. If anything, she had a sympathetic face, so he decided to stay and listen.
“How do you know what we’ve been doing?” he asked, challenging her conclusion.
“I heard what you said. ‘I love it when you take me over your knee and spank me with your hand’ and ‘I’d really like another OTK spanking!’” she said with a pained look, knowing how he must be feeling.
Simon looked away again, getting even redder if that was possible. ‘How do I reply to this?’ and ‘How do I continue working with her?’ his mind questioned, berating himself for the foolish idea that he had any chance with Cindy.
“There’s nothing to be embarrassed about, Simon! Lots of people do it!”
“How do you know what we were really doing? That was just talk!” he replied defensively, trying to find a way out of this situation.
“There’s more,” she said with a grimace. “‘We’ll start with twenty-five on each cheek,’” she said, revealing her intrusion last night. “I heard them, Simon. I’m sorry!”
“So. You know everything? How is this not something to be embarrassed about? I really like you, Cindy, but how can I face you now when you …”
“Because I like it too!” she interrupted quickly, “I like spanking!" Letting him digest that for a moment, she added, “I’ve had an interest in spanking for as long as I can remember,” she replied, crying real tears now for fear she might lose him still.
“What!?” he asked in shock. “Wait! What’re you saying?” he added, not believing he heard what she said correctly.
“I’m saying that I’m into spanking, too. And I’d really … really like to give you a spanking if you’d let me!”
“I’m sorry, Cindy. I’m finding this very hard to believe! You would have had to come into Monica’s …” he said, and then it hit him. “You were in the foyer! You put my clothes on the chair!” She nodded her confession. “So you heard other stuff, too? How do I know you won’t get all domineering, too?”
“No, I didn’t hear anything else. I left after I heard her spank you. With very wet panties, I might add!” she said with a small smile that grew when he took her hands again. “And I don’t want to dominate you. I just want to do something together that we both like!”
“Monica got more demanding each time! How do I know you won’t want to once we’ve started?”
“Be … because I’d … I’d like you to spank me, too!” she admitted and let that sink in before continuing. “In fact, you could spank me right now if you wanted for eavesdropping and invading your privacy! You know this isn’t something you can bring up in idle conversation, but when I heard that you … that we like the same thing, I was so happy that I finally had something that would interest you. I’m really sorry, Simon, but I’ve wanted to be with you even before I knew!”
Simon slid in beside her, took her face in his hands, and kissed her gently. Separating, their eyes connected, and suddenly, they were wrapped in each other’s arms, kissing passionately. With all the uncertainty and accusations out of the way, they each felt like they’d found a long-lost friend. Somehow, they’d managed to get through a strange and challenging discussion and finished gaining a new best friend who shared their secret and, most likely, a lover as well.
“I’ve thought about asking you out many times, but I didn’t think I’d have a chance with you! And then there was Tom!” Simon said, offering his own confession.
“Really? Me?! I’m nothing special,” she replied, but she could see the answer in his eyes and kissed him again.
“Yes, you are! You’re always so happy and friendly, and you’ve got such a cute face,” he said, wiping a tear from her cheek. “And a cute little butt, too, I might add!” he said with a smile.
“Not too cute to spank, is it?” she asked, returning to their favorite subject.
“No way! I can’t wait to see it in my lap!” he smirked, “But … I’ve never spanked anyone before.”
“Neither have I, and I’ve never been spanked either, but I can’t wait to be taken over your knee for my very first!” she said, hoping that would be now, or at least tonight.
“Tonight?” he asked, sensing her urgency, and she nodded. “How about Saturday night? I only had a couple of hours of sleep last night, and I’m still a bit sore, so I’m not really at my best.” He could see her disappointment. “Don’t you want your first to be special? Not rushed into? Besides, you won’t believe how excited you’ll be till then, knowing what’s coming!”
“Okay. I’m so happy, Simon!”
“Me too! We’ll go out for dinner and then to my place to make our first time an event to remember!”
They spent another hour together, comparing notes about their shared fetish; when the interest started, what they thought they liked and disliked, and some favorite words, positions, and implements. Simon shared a little about his concerns with Monica and what had turned him off, but he held back about what else had turned him on.
They left as their discussion wound down, and his lack of sleep was catching up with him. Cindy was over the moon about how it had gone with Simon, deciding it couldn’t have worked out better, and anticipation for Saturday was already building.
Simon was also thrilled, thinking he’d found the right person to relearn this lifestyle with, but he still worried about what Monica would do. If things went as he expected, there was no way he’d want to be with her again, and, at the moment, he couldn’t see how to end it with her without her getting angry and possibly jeopardizing his job and maybe even Cindy’s if Monica knew it was she who stole him away.
At work the next day, Simon kept his cool, but Cindy couldn’t help acting alternately flirty and childish. She couldn’t wait to be taken over her ‘Daddy’s’ knee, and her actions were intended to goad him on. He didn’t take the bait until late afternoon when he warned her.
“Cindy! If you keep this up, you’re gonna get a spanking!”
“Ooo!” she squeaked at first, having waited forever for someone to say those exact words to her. “I’m sorry, Daddy! I’ll be good,” she added, timing this interplay when no one was in their area to overhear.
Simon took her to his favorite steakhouse, and with a carafe of Cabernet, he offered a toast. “To bare bottoms!” He couldn’t wait to see hers, but her excitement was palpable, so they avoided further conversation about what was coming to let the anticipation build. What would typically be a leisurely dinner eventually became rushed, and they skipped any after-dinner treats.
“I think our dessert is waiting at my condo,” he said with a final clink of their glasses.
“Yes, please! Let’s go!” she replied, practically shaking with excitement; the wine had done little to temper it. The fifteen-minute drive was spent in silence, with hands held tightly.
They arrived at his home on the corner of the top floor of a five-story building. Simon explained that the location was very private to set her mind at ease on that score, but the truth was that she’d let him spank her on a park bench right now; such was her excitement.
When they entered, he flipped the lights on, and she was very impressed with his well-decorated home. He gave her the ten-cent tour, skipping his bedroom for the moment, and they ended up in the kitchen. She accepted another glass of wine that helped a little to quell her jitters but fell into his arms for an ardent embrace and tongue-tangling kiss.
“You’ve been a naughty little girl, haven’t you, Cindy?” he said in character getting the festivities started.
“Yes, Daddy! Are you gonna spank me?” she said with a perfectly pouty face and childish voice.
“Yes, you’re going to get a good spanking on your bare bottom!” he replied as he took her wrist and led her back to the dining area, where he moved a chair into the middle of the room and sat down. He had thought he might start on the sofa, but her scenario and character called for a more traditional approach. He looked at her expectantly and caught a small smile she couldn’t hide.
“Don’t you have something to say?” he said, ad-libbing.
“I’m sorry, Daddy!” she offered, unsure what her line should be.
“Cindy, you know you’re supposed to ask for your spanking! It shows you accept your punishment!” he said, loving her cute attempt to hold back a smile with a bitten lip.
“I forgot, Daddy! I’ve been a bad girl, and I need to get spanked on my hiney!” she said, hoping he wouldn’t drag it out any further, and she wasn’t disappointed.
“Over my knee!” he instructed, pulling her down on his lap and helping her get into position.
‘Oh my, God! This is so amazing!’ she thought as the one thing she’d wanted for so long was about to be given to her.
She’d dressed carefully for the occasion with a cream-colored camisole blouse, sheer enough to reveal a half-cup bra beneath. She wanted to wear slacks so that when they and her panties were pulled down, only her bottom would be exposed, so she chose a tight pair with a side zipper to show off what Simon called her perfect bottom, yet make them easy to open and pull down.
She loved the feeling of his hands softly caressing and gently squeezing her cheeks, which made her already damp panties even wetter. She lifted her hips, pressing them harder into his strong hands.
“I’m sorry, Daddy! Please don’t spank me too hard!?” she said when her impatience got the better of her.
“I will spank you as hard as I feel necessary to give you what you need!” he replied with a clever double meaning, as what she needed was a sexy first spanking, not punishment.
“Ooo!” she yipped at the first startling smack, then, “Oh, wow!” with the second. It was everything she hoped for as a steady barrage of spanks landed on alternate cheeks. She loved the helpless position, the sound of his hand, and mostly the feel. Lifting her hips, she signaled a desire for harder smacks, crying, “Oh yeah! Oh yeah!” when they came.
“Is my naughty little girl enjoying her spanking?” he asked, not sure whether he needed to stay in character or not.
“Thank you for not pulling my pants down, Daddy!” she said, telling him that was exactly what she wanted him to do.
Simon was more than happy to oblige, and moments later, he was tugging on the waistband while she rose from his lap to let them pass. He would have preferred to take them off, but she’d been clear about what she wanted. He smiled at the full-coverage white cotton panties she wore in keeping with her juvenile persona.
Moaning loudly, she loved the feeling of increased exposure, with parts of her back and upper thighs feeling the room's cool air, though her raised cheeks were already warm. Simon’s exploring fingers touched bare skin teasingly while she squirmed in delight.
He hadn’t expected to enjoy this so much, initially feeling like he was just doing it for her, like all his efforts to please, but there was something about her willingness to lay in his lap and have her sexy little butt spanked while she pretended to be ‘daddy’s little girl.’ And now her tight white panties hugged every curve, exceeding his prediction of a perfect bottom.
“This is going to hurt a bit more, but it’s necessary for you to learn to behave,” he said, still caressing the half spheres of her ass, or rather her ‘hiney,’ as she preferred it be called.
“I’m sorry, Daddy! I know I need to be spanked! Oh! Ohh! Oh my God!” she cried at the increased intensity and intimacy of his hand on her bottom.
Squirming in his lap from the sheer ecstasy of finally getting the spanking she’d wanted for so long, and given by someone she already had a great deal of affection for, had her almost delirious. The sharper, stinging smacks on her panties were like electric shocks that diffused through her body but concentrated in her pussy. She spread her legs slightly to let him know he could touch her, and oh, how she wanted him to touch her!
Simon was still taking it easy, knowing that the first time didn’t need to be painful for it to be enjoyable. He had a good idea of what she was going through; his first experience not long ago left the memory fresh. He smiled when he saw her legs part within the limits of her pants around her thighs and decided it was time for a break.
“Ooo! Oh yeah! Mmm!” she cooed as his finger ran the length of her slit, the sticky wetness amplified. Again, with her hips raised, she pushed herself against his hand, wishing her panties were down so he could finger her properly. She kept herself up when she felt his left hand tugging the elastic. “Oh God!” she cried when his other hand left her crotch to assist with the lowering of her panties.
Simon was beside himself, loving the sight of her both cute and sexy bottom. There was not a female bottom more perfect than hers, and his hands were instantly back kneading her warm pink flesh as soon as he’d pushed them down to join her pants around her thighs.
“My God, Cindy! You have the most beautiful and enticing bottom I have ever had the pleasure to see or touch!” he enthused as his hands played with the silky smooth mounds of soft, yielding flesh.
“Mmm, that feels so good! Oh, Simon, this is so much more than anything I’d imagined, and now I want my first bare-bottom spanking so bad! Please spank me?” she pled and lowered herself back onto his lap, crying, “Oh God!” with the first smack.
The feel of his hand raining stinging spanks down on her naked flesh raised her arousal to the point that she thought she might cum right there and then. Squirming and continually crying out as he spanked gradually harder, the word ‘Ow’ finally entered her vocabulary. Still, it wasn’t a complaint as she relished the perfect spanks that had just the right combination of pain and pleasure.
Simon couldn’t believe his good fortune as Cindy was seemingly the perfect partner for him. He loved watching her gyrating body absorbing the stinging smacks and wanting more. Her firm bubble butt jiggled with each strike in a most exquisite way, and even the sting in his hands added to the ultimate pleasure of his splendidly naughty girl.
Realizing she wasn’t going to cum just from the spanking but needing that release so badly, she again pulled her legs as far apart as possible. “Ohmigod! Ohmigod!” she shrieked as Simon switched hands, his right going right to her slippery wet pussy, while his left continued spanking at a slower pace.
“Oh! Ohh! Hoh! Hoh! Don’t … don’t … don’t stop!” she howled as his finger found her nub and rubbed it mercilessly. “Ungh! Ungh! Oh-oh-oh-oh-oh! Ahhhmmm!”
Simon’s hand was covered with her juice as she experienced the most incredible orgasm ever, leaving her panting and shaking on his lap. When she moved to get up, he helped her, sat her in his lap, and took her in his arms for a bear hug that she gratefully accepted, her head on his shoulder as her breathing slowly recovered.
She lifted her head and smiled before kissing him with all the passion she could muster.
“It’s pretty amazing, isn’t it?” he asked when their lips parted.
“Amazing doesn’t begin to describe it! Thank you so much for making my first time so … so perfect, so unforgettable!”
“I very much enjoyed it, too, and I hope to have the chance to do it with you many more times!”
“I already can’t wait till my next one, but isn’t it time for the ‘thanking for the spanking?’” having learned the phrase from some of the same spanking porn as Simon.
“It is! Come with me!” he said, taking her hand after she pulled her pants up enough to walk and led her to his bedroom, where, in addition to the bed being drawn down, another chair sat conspicuously in the middle of the room.
“Ooo, maybe I won’t have to wait very long for another?” she asked expectantly. She quickly pushed her pants and panties back down, shaking them off over her feet before turning to open his shirt. While she opened his buttons, he pulled her blouse up over her head, and she stopped for a moment to see his reaction to her smallish tits in the half-cup bra, happy that he was smiling appreciatively. With his shirt pushed off his shoulders to drop to the floor behind him, she reached back to unclasp her bra and slowly let it drop, noting his eyes glued to the tits she worried wouldn’t compare favorably to Monica’s.
“You’re so pretty, Cindy,” he said softly, genuinely, and reached to pull her into a hug, both moaning as their bare chests pressed together.
The hug became a long, loving kiss, after which Cindy declared him overdressed and knelt to open his pants, pulling them down with his underwear. After helping him step out of them, she rose to take his cock in hand and mouth. Guiding him backward toward the bench, he sat with her face in his lap, licking and sucking him fervently.
Only briefly did he compare her technique to Monica’s and though she wasn’t as proficient, there was something about Cindy that more than made up for the difference. She didn’t deep throat him, and when he came, it was on the floor, not in her mouth, but he appreciated her lack of experience that had a wholesome quality to it when compared to Monica’s extreme persona in both her looks and actions. He already saw Cindy as someone with whom together they could grow and have a relationship based on more than sex.
They spent a joyful evening together, giving with hands and mouths. Cindy continued to surprise Simon with her enthusiasm while holding some skills back, intending to always have something more in reserve. What wasn’t surprising was that she’d ask for another spanking, which, though playful, was all the more exciting for their nakedness. Simon pulled out a few tricks of his own when he devoured her dripping pussy with his face firmly planted between her rosy cheeks as she bent over the bed.
It was an enchanting night, but without a word between them, they knew they should wait to share a complete joining for another day.
--===<<<O>>>===--
Well, that worked out nicely, didn't it? But what will Monica think when she inevitably finds out? Come back for more, and please remember to 'Like' and/or 'Favorite' my story if you enjoyed it and ... THANKS FOR READING!!
