While Cindy was across Simon’s knee for the second time on Saturday night, Monica was back at a stool with Jason serving her favorite scotch, a new tumbler replacing the empty as Jason ‘kept ‘em coming’ as instructed. She was trying to sort out her feelings, unsure if Johnny Walker was helping, but at least it dimmed her disappointment.
Having spent the last several Saturday nights with Simon, her first feeling was one of loneliness as she’d looked forward to each weekend with him regardless of their relationship's up-and-down nature. She wasn’t even sure if she should call it a relationship, but she missed the red-bottomed, pussy-munching ‘boy’ who captured her fantasies more than any man before him. She could feel the arousal between her legs when she thought about his ability to make her cum explosively with his tongue entrenched in the valley of her steamy, wet lips. More than once tonight, a slight shiver passed through her body at the memory, quelled with another sip of the golden liquor.
On the other hand, it was the very up-and-down aspect of their play that had her accepting a lonely Saturday night despite several quickly subdued thoughts of calling him at the last minute. These thoughts were decidedly confused as she’d loved the squeals and gasps when she pushed Simon past his limits but felt badly when he challenged her on them. Was that because she genuinely didn’t want to hurt him or didn’t want him protesting her authority?
After the first time, they’d both expressed chagrin at the belittling way she’d treated him, and she had wondered if she was cut out to be a real Domme. She was ready to take on anyone who would argue that point with her as she would decide just how domineering she would be, not someone else going by some archaic rules governing a Dom/sub arrangement.
But then Simon would accept being led a little further down the path of submission, giving her the hope that they would learn where that path led together, only to denounce her actions as too extreme. She hated him for that, feeling like he was testing her, going along with her dominating play only to be stopped when it was just getting interesting, leaving her with unsatisfied needs.
She concluded (for the moment) that though he’d nurtured this desire within her, she wouldn’t be satisfied with his on-again/off-again approach to giving her what she needed. She’d like to find someone fully committed to the lifestyle, whether another trainee or someone well-versed in submission looking for a new Domme. The latter would be more desirable if she could keep him interested enough to learn her role thoroughly, though either choice left her back where she was before Simon: a woman whose needs weren’t fulfilled by the latest male to fall prey to her stunning physical appearance.
As if on cue, a handsome young man sat on the stool beside her.
“Can I buy you a drink?” he asked with an unassuming, pleasant smile.
“Not if you’re gonna sit there and talk to me while I drink it!” she replied caustically, cutting him off at the knees.
“Hey, okay. Sorry for disturbing you,” he answered sincerely and ordered ‘another’ from Jason when he turned up.
Derek had been at the bar for a couple of drinks, admiring the attractive blonde trying to drink away her problems and attempting to conceal her beauty with baggy pants and a rock’n’roll T-shirt. He wondered if she would recognize him from the brief meeting a few months ago if he waited long enough.
He sat there, minding his own business, just to maintain a presence that he hoped would eventually attract her attention in a good way this time. He smiled slightly when he noticed her looking at him occasionally with a neutral glance that lifted his hopes.
Apparently, he was also a ‘regular’ at this bar, and during brief breaks in the Saturday night action, Jason would engage him in conversation by asking about his ex-girlfriend; was she really gone? … his travels and even the networking devices he peddled. The whole discussion engineered between them to lure Monica in.
Monica was listening; her curiosity piqued at the mention of the products he sold. She’d thought something looked familiar about him but attributed it to the drink and maybe some wishful thinking. Least of all she didn’t want to open a business dialog in this setting and her currently muddled state of mind, but there was something intriguing about this stranger who maybe wasn’t a stranger after all. Eventually, inquisitiveness got the better of her.
“You look vaguely familiar. Do I know you?” she asked trying to place the face now turned toward her.
“I wouldn’t say you know me, but we’ve met before,” he said, giving back a little of what she gave and leaving the sentence hanging in the hope she’d remember. She didn’t. “I’m with WebCom Devices. We met once a few months ago in your office on a sales call.”
“I remember now. I told you I didn’t get involved in equipment choices of that kind and referred you to my head of network administration. You weren’t in my office long. I also remember chiding my admin about taking the appointment in the first place.”
“Honestly, I think she succumbed to the charms you seem to be able to resist,” he boasted, which drew a laugh from her.
“Monica Moore,” she said, offering her hand, surprised when he took it to his lips for a gentlemanly kiss, which she took as a little too showy and pulled it away.
“Derek Johnson. Nice to meet you again, Monica,” he said, discouraged by her rejection of the gesture he intended to be humble.
“So, did we buy anything from you?” she asked, turning to face him.
“No, you didn’t, but I figured you put the kibosh on it.”
“Don’t flatter yourself. I said nothing to my staff about you. I guess you just weren’t on your game,” she said more as a tease than a put-down.
“Ouch! Do you treat all men this way?” he asked, more intrigued than insulted.
“That depends on whether they can … take it!” she said, pausing for effect and wondering if this kind of banter might flush out the sort of man she sought.
“And how do you know if they can?” he asked, sliding partially off his stool to move closer to her.
Derek had been very taken with her at that first meeting, impressed with the way she dispensed with him and his products so authoritatively. He’d heard the first bit of the scolding her admin got before he exited the lobby and hoped he’d encounter her again in more friendly surroundings, though it wasn’t her friendliness he was after. He liked a strong, demanding woman, but he’d had more than enough of them try out for the part and fail to convince him. He suspected Monica would be different.
“I have my ways. Are you applying for the job?” she countered, getting very interested to see how this turned out.
“Is there a position available? I wouldn’t want to take someone else’s,” he teased.
“Yes. As it happens, I’m looking for someone who knows how to follow orders.”
“Well, I know how to do what I’m told, Monica. Or should I call you …?”
“You can call me Miss!” she said moving close enough to smell the liquor on his breath and imagined he could smell hers as well. A bit nervous, she was on shaky ground, making it sound like she was more experienced than she really was, but she’d give it a shot if he went for it.
“Okay, Miss. My friends call me ‘Big,’ he said, smiling to see if she’d pick up on the joke.
“Big?” she queried. “As in Big Johnson?” she said with a laugh.
“It’s a long story.”
“Is the … story really that long? Or is it just for a laugh?”
“Most find it an appropriate nickname,” he boasted.
“Touche … Big!” she said, offering her glass as a toast and impressed with his moxie, if not his claim. “So. You like being told what to do. Are you naturally obedient, or do you need consequences for when you’re not?” she asked, her innuendos acting like an interview for the position beneath her.
“A little of both, but I know when I’m wrong and accept the ramifications,” he replied
Getting both interesting and arousing, the conversation was almost too good to be true, and ever the skeptic, she worried it was all bluster, though the quivers between her legs said differently.
“The ramifications, as you call them, can be rather painful. Are you ready for that?”
“They wouldn’t be much of a consequence if they weren’t, would they?” he replied, their eyes burning holes into each other. “I can bend over and take it,” he added.
“Are you ready to bend over and take it just because I want to give it to you?” she challenged him.
“Even better,” he said, hoping the last qualification had now been met.
Monica was sold and wished she could snap her fingers and transport them both to her playroom. Still, despite her panties being already decidedly damp, her warring instincts warned her that she’d had too much to drink to make an accurate assessment of the situation. This was a naturally confrontational situation, and her distrustful side told her she was jumping in too quickly, but her pussy disagreed, and she decided to go ahead with one concession; she wouldn’t take him to her home. He didn’t need to know where she lived … yet.
“Well, we might need to test that. Do you live nearby?”
“Ten minutes away,” he replied, taking the hand she offered.
“I’ll follow you there,” she said with another bit of caution, wanting to be able to leave on her own if necessary.
Fifteen minutes later, they were standing in his fourth-floor condo, having only spoken in clipped phrases in the elevator and past the other doors to his corner unit. Decorated in distinctly masculine tones and furnishings, she appreciated the atmosphere. She heard a fountain when he opened the sliding glass doors and went to look. He excused himself for a minute, leaving her staring at the colorful water shooting ten feet or more into the air before returning to the lake from which it came. She found the sight and sound oddly tranquilizing and walked away, realizing tranquil was not the way she needed to feel at the moment.
Derek had slipped into his bedroom to take the wooden paddle he occasionally used on himself and laid it expectantly on the bed. He’d made it to the kitchen and was pouring some wine when she turned away from the balcony, clearly looking for him as her eyes cast around the room.
“Would you like some wine? Miss?” he added the honorific after a pause for emphasis.
“No, thank you. I’ve had enough for tonight, but you go ahead if you like.”
“Are you sure? It’s a rather good Zinfandel!” he persisted.
“Derek, the first thing you need to know about me is that I don’t like being challenged. My saying something once should be enough!” she scolded, assuming her role and somehow feeling more comfortable in it with a more mature candidate.
“Yes, Miss. I understand,” he said in a manly tone, unlike Simon’s comparatively immature voice. “Is there something else I can do for you?”
“Yes. You can take all your clothes off!” she demanded.
“Wouldn’t you rather we were in the bedro …”
“Derek! What did I just say to you!”
“Yes, Miss. Sorry, Miss!” he said and hastily began undressing, leaving the proof of his ‘Big’ nickname for last. He kicked off his boxers and stood straight up with his arms folded behind him and ‘Big’ waving in front.
“Such a shame,” she said as she took it in her hand and pulled him behind her toward his bedroom. “You might have had a chance … a small one, but a chance … to show me how Big performs, but you gave me a reason to test your ability to accept ‘ramifications’ instead.
They’d reached a short hallway with several doors, but only one was open. She looked to him for verification that this was the bedroom, and he nodded. They entered the room, which was similarly decorated, but the bed, in dark earth tones, was turned down. The paddle on the bed caught her attention, and she smiled devilishly. ‘No namby-pamby, over my knee, naughty little boy spanking for this one,’ she thought, drawing another comparison to Simon.
“Do I have to tell you what to do, Derek? And make it even harder on you?”
“No, Miss!” he replied and obediently bent over the bed with his legs apart.
Thrilled to succumb to her demands, he thought fleetingly about how long it had been since he was last in this position. His girlfriend at the time, who’d gone along with his fetish for his sake, had had enough and left him in this same exact position without delivering a swat. Staring at the mattress and waiting for the first, his excitement ramped up when he saw the paddle disappear.
Monica was surprised by its weight, swinging it through the air to get used to its heft, and was even more impressed with what he was ready to take, though this wasn’t the type of paddle you spent several minutes with.
“Twenty swats!” she declared, “Are you and Big ready?”
“Yes, Miss! Thank you for being so lenient!” he replied, signaling his ability to take and want more.
“Careful! It won’t take much for me to add to or even double that number!” she cautioned, tapping the paddle against his cheeks.
“Yeow!” he yelped with the always-startling first swat, followed by grunts and ‘Ows’ as each swat landed with several seconds between. With more intensity than he was used to at the beginning, he decided not to provoke any additional swats; still, he got the stinging pain he’d not had for quite a while and had high hopes for Monica.
“There! That’s the twenty, and I see you managed to avoid any extras!’ she said, worried she’d gone too heavy with him in her excitement with someone who expected more. She reminded herself to listen and watch for clues as to how to proceed, lest she lose another prospect by missing signals and moving too quickly. “Get up!” she commanded, standing with him once he rose. Making a bit of show of it, she pulled the scrunchy from her hair and shook it out like a model in a shampoo commercial.
He stood a foot or so away, watching her shake her hair loose, and was caught by her locks whipping across his face. This was the gorgeous face framed by her white blonde hair he remembered from his all-too-brief meeting with her.
“Take my clothes off!” she ordered.
He lifted her T-shirt up slowly till her amazing tits were revealed in an ordinary white bra and then up over her head. He reached for and pulled the drawstring open to the pants that gave nothing away insofar as her figure was concerned, but rather than let them fall to her feet; he drew them down as a drawn-out unveiling; her tight, white bikini panties were the first to show, and then her luscious thighs that he couldn’t wait to stroke. He removed her sandals along with the pants and put his hands on her calves, about to slide them up her silky smooth legs.
“Uh-uh! No touching … yet!” she said, getting a smile from him.
Standing again, he reached around her, deftly unclasping her bra, and slowly like before, he pulled the straps forward till his hands supported the perfect tits he’d only imagined, and then, lowering his hands, the fleshy mounds fell gently against her chest. He had to fight a strong urge to take one of them in his mouth.
Kneeling as if to pray at her altar, he looked closely at the tumescent mound between her legs. Her panties were slightly disheveled but still tight over her perfectly puffy lips, the shadow of their separation barely visible, enhanced by the increasing dew that formed a gray line between confirming his belief and hopes that she was clean-shaven. His tongue involuntarily licked his lips in anticipation of touching and tasting her.
Monica could see the thoughts going through his head, enjoying the worship and desire evident in his face, which she wanted to be planted firmly between the lips he practically drooled over.
“Take them off,” she said softly, knowing he didn’t need a command.
With his hands flat on her hips, a finger on each side slipped under the elastic, and with his palms lightly grazing her silky smooth legs, he pulled them down and off as she lifted each foot in turn, moaning softly in appreciation.
“Sit cross-legged and put your hands on my ass,” she said, wanting to feel his touch again, and inched forward when his hands slid up from just below her cheeks to caress and squeeze them as one would a large pair of tits. She could see his nostrils flaring, taking in her scent.
“Mmm, what a heavenly fragrance! Please may I have a taste, Miss!?” he pled.
“Tilt your head back,” she instructed and took another step forward till her pussy hovered a fraction of an inch over his waiting lips. “No tongue yet!” she warned as her lips splayed over his nose and mouth, with her hips rocking slightly, scratching the ‘itch’ in her slit. “Now. Make me cum on your face!”
Though he felt like devouring her till his face was painted with her precious juice, he needed to impress her to ensure another night like this and cautioned himself to take it slowly, let her control the pace and fervor.
His tongue snaked through her teeming slit, wiggling side to side before reaching the top, where he coaxed her clit out of hiding, then left it wanting with another trip down to dart into her tunnel. Moving up again, this time with the flat of his tongue pressed hard against her swollen lips, he reverted back to his tongue’s tip to flick her clit. His hands kneaded her firm buns, holding them like a large juicy watermelon pulling her pussy to his mouth to drip its juicy nectar on his face.
She could tell the difference between Derek’s and Simon’s technique as Derek’s years of experience showed a maturity and building purpose. Simon’s eagerness, while exciting, was clearly gained from all those impatient girls he’d so impressed in college. She’d like a bit of both, she finally concluded and became a bit impatient herself.
Grasping his head firmly with both hands, she pulled his face into her sticky, wet crotch, moving her hips to direct the attention of his nose, mouth, and tongue where she wanted it. Alternating between pummeling her pussy with his face and using her lips like a paintbrush to cover his face with her milky syrup, her gyrations became increasingly spastic in the minute or two before she came.
An explosion with the flavor of both her lovers erupted inside her, and she was grateful for his steadying hands on her ass as her body shook, the ecstasy prolonged by his tongue. When she finally calmed down, she stepped back and motioned for him to stand.
“Very well done, Big!” she complimented, using the now-proven nickname. “You’ll be rewarded for that, but not till later,” she said, stroking his stiff shaft a few times and testing his patience, getting a smile in return. “I feel like smacking that cute butt of yours again!” she declared. Seeing a leather chair in the corner, she led him to it and pulled it away from the wall, instructing him to kneel on its seat.
Standing before him and leaning into the corner, she teased him by touching her body provocatively. He groaned when her hands caressed, squeezed, and pinched her tits, a pleasure he hadn’t had yet. As if sensing it, she leaned forward, placed them on either side of his face, and pushed them against his cheeks. When he tried to turn his head to lick them, she pulled them away. She tried it again with the same result, but this time, she walked behind and spanked his pink ass at least thirty times, hard and fast, and she smiled when his hips rose, begging for more.
“You need to learn that you must ask before touching!” she scolded, giving him another ten.
She disappeared momentarily but returned to face him, holding the paddle and her free hand up, offering him a choice. His eyes selected the paddle.
“Do you have a safeword, Big? You might need it!” she threatened.
“Bicycle’, Miss!” he replied, watching her walk past, taking practice swings through the air. Positioned at his side, he could see her back, his eyes staring at her gorgeous ass. “Yeow!” he yelped with the first swat that was startling only in its intensity as he saw the wind-up and delivery, enjoying watching the movement of her ass as she stepped into the swing.
“How many? Another twenty?” she asked.
“Fifty, if it pleases you, Miss,” he replied, not assuming that more was better from her point of view but wanting to try to take more than he ever had at one time.
“Very good. We’ll start now in groups of ten!” she said as she drew her arm back for the first volley.
“Oww! Oh, fuck!” he cried as the first ten landed a bit faster than before, providing a building burn and sting as both cheeks took every hit. The second ten had him questioning the wisdom of his request for fifty. ‘At least she’s not increasing the intensity,’ he said to himself, adding, ‘Yet?’
Monica was going to wait to let him cum until later in the night but changed her mind when considering what she wanted from ‘Big’ when the time came. Laying the paddle down on his back, she went to her handbag for a butt plug and the necessary lube she carried ‘just in case’ and returned to his proffered end.
He felt the lube dribbling between his cheeks and hoped it meant what he thought; another unfulfilled fancy, confirmed by the pressure of her pushing the plug into his clenching hole. It took several tries before she managed to get the wide part of the smallest plug in her arsenal past the muscles guarding his hole, but once in, she twisted and tugged on it to accentuate the full feeling it provided.
“Ready for thirty more, Big?” she asked as one hand teased his ass, the other his cock.
“Oh God! Yes, Miss!” he sighed as she stroked him dangling between his legs and wondered how long he’d last as he’d been hard since they left the bar. When he felt the paddle lifted off his back, he steeled himself for the remaining swats, only to find she’d changed the pattern when the eleventh landed. Groaning and pulling away from his tormentor, he was afraid she was going for the entire thirty, gasping with each impact of the severe paddle. He almost used his safeword but breathed a heavy sigh of relief when she stopped at fifteen and resumed occasional strokes of his cock.
“The last fifteen with the paddle,” she declared.
With the way she said it, he wondered whether there was more coming without the paddle, but his attention was quickly focused on the intense swats and burning pain they created. Just barely enduring the final fifteen, he reached back to rub his flaming red ass only to have his hand slapped away.
“No! No rubbing yet! You stay right where you are!” she commanded as she took his cock in hand yet again to return it to its full size after the paddling had diminished its hardness somewhat.
“Oh, thank you, Miss!” he said between panting breaths as she stroked him more consistently this time.
Switching to her left hand on his cock, her right wandered between his sac, the plug, and his crimson-red cheeks. Having coaxed him back to full size, she spanked him with her hand, and he responded instantly. She could feel him straining to hold it in as the pace increased and the light spanking became continuous.
“Oh fuck! I’m gonna cum, Miss!”
“Go ahead, Big! Shoot that load onto the chair,” she said just before he did, several long stringy ropes of semen landing on the seat of the chair between his knees.
She rubbed his back and cheeks gently to soothe his frayed nerves as he went from gulping gasps to deep, sonorous breaths.
As the only break she allowed, he was soon on the bed, being directed into various positions and practices, all intended to make her cum over and over again. She sat on his face or lay on her back with his head between her legs as he licked, poked, and stroked her to countless orgasms that were beginning to take their toll on her as well.
Summoning all her remaining strength, she again sat on his face, but this time facing away so she could suck his cock, ensuring he was ready for the finale.
He could see her energy waning as they progressed, and it was even more apparent with this last position as she just held her pussy in position for him to lick while she half-heartedly sucked him. She turned around as if to ride him but struggled to hold herself up while guiding him in, her breathing more labored than at any time that night.
“Do you need some help, Miss?” he asked.
“Yes. Fuck me, Derek!” she pled, losing some of her dominant demeanor. “Fuck me hard!” she said just firmly enough to sound like a demand.
Moving to lay beside him, she lifted her knees and spread her legs, inviting him to show her just how big he was. Supported on one hand as he guided himself into her sloppy, wet hole, penetrating slowly but steadily, he put his other hand down beside her and let his hips do the work. Halfway in, she was grunting between gasps.
“Oh fuck!” she cried, “Give me all of him, Big!” While he was no longer than Simon, his girth made all the difference. He hadn’t felt all that much thicker in her hand or mouth, but her pussy sure felt the difference, as she felt fuller still while he gradually increased his pace.
Wanting to use his hands, he grabbed her hips and pulled her up so he could kneel while pulling her onto his shaft and pounding her pussy relentlessly. She came once after just a couple of thrusts in this new position with only her shoulders supported by the bed, feeling like she was just hanging off his lunging cock, and her body trembling in his hands.
Like a ragdoll in his grasp, her body shook involuntarily with the orgasmic waves that continued unending, one climax bleeding into the next until finally, with a few short pounding jerks, he came. The throbbing pulses were felt inside with her pussy stretched to the max as he held her in place until he, too, collapsed on the bed beside her, the two of them struggling to breathe normally.
“Okay, Big, I’ll admit. It’s a very appropriate nickname!” she said, laughing and gasping simultaneously.
Not feeling so dominant now, she dropped the pretense and let him snuggle up behind her, his hands caressing everything he could reach to soothe and calm her overblown nerves. Lying together without a word for quite a while, she eventually decided it was time to go and sat up. She gave him a long, grateful kiss before getting off the bed to retrieve her clothes.
He smiled when she stuffed her bra and panties into her handbag rather than donning them, but when he moved to get up, she suggested he stay, and she’d let herself out. Leaving her business card on the kitchen counter, she knew he’d call soon.
As she drove home, brief flashbacks of the evening came to mind, and while she smiled intermittently with individual memories, they couldn’t hold her attention. Between the alcohol and unexpected extreme exercise, all she wanted to think about was sleep and concentrate on driving to ensure she’d reach her bed safely.
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Is Big going to replace Simon, or might she find room in her life for both men? Read on and see! I hope you'll 'Like' and/or 'Favorite' my story if you enjoyed it and ... THANKS FOR READING!!
