“Good morning, Cindy!” Simon greeted his colleague the following morning as he always did. Only when she replied did he look up briefly, then did a double take as she looked different somehow. Older, possibly?
She smiled when he looked again, her more austere appearance, created with her reddish-brown hair left down, some make-up, and a more business-like attire having gotten his attention. She walked by his cubicle repeatedly, testing whether he stopped to look each time. He did.
Simon had always liked Cindy; her friendly demeanor and girlish looks had him considering asking her out several times when their small talk seemed to provide an opening for him to ask. He didn’t. Despite her youthful appearance, she was a few years older than him, had a boyfriend, and was a more senior member of the Held Desk staff, so he assumed she’d turn him down and spared himself the embarrassment.
“So? Did you get your work done last night?” she asked, emphasizing the word ‘work. “When I saw you go into Monica’s office, I thought you might be up to something, but then she came, didn’t she?” she asked when she stopped at his cubicle with a knowing smile.
“Huh!? I don’t know what you …”
“I guess Monica really needed something taken care of? That only you could … handle?” she teased with a devilish voice, giggling as she walked away. ‘That oughta get him thinking!’ she said to herself.
Simon wasn’t sure what to do. Evidently, she’d followed him last night as she knew he‘d been in Monica’s office but must have concealed herself somewhere as she also knew Monica had arrived later. His mind raced as he ran through all they’d done and … said!! ‘Oh God, I hope she didn’t hear our later conversation!’ he thought. If Cindy knew what he’d done for Monica, that might get a little sticky, but if she heard their discussion and his open admission of what he liked, that would be extraordinarily embarrassing.
He tried calming himself with scenarios that might explain what she saw. Maybe she just saw Monica arrive while passing by, but then she wouldn’t have seen him as he was waiting under her desk by then. She’d also said she had seen him go into Monica’s office, which meant she’d been watching for at least fifteen minutes. And then there was the odd phrasing of, ‘but then she came.’ It was an unusual way to say she’d also arrived, but it could also be taken in a sexual context.
He remained nervous all morning, but Cindy returned to her usual friendly disposition in the afternoon. He tried to chalk the whole thing up to his imagination running wild, but it remained in the back of his mind for several days.
Wednesday evening arrived, and he was again waiting in Monica’s driveway till eight o’clock. Over the last two days, he’d considered telling Monica about Cindy’s innuendo but decided not to, fearing she might retaliate against Cindy somehow.
So he was once more excited about another evening with Miss. His bottom showed only a bit of color still, but there was no pain, and he was very much looking forward to a spanking despite the fear of Cindy knowing. He decided he’d be a little late, hoping that would provoke an early trip over her knee. He’d even dressed in elastic waist slacks to facilitate their quick removal.
At about five minutes past, he was walking up to her door, half expecting to see another ‘Come on in!’ note, but there wasn’t one. He rang the doorbell and heard a stern voice say, “Come in!” Just the sound of her voice in that tone had him excited. He opened the door and gasped at the sight before him.
Dressed in nothing but a pair of black satin bikini panties and spiked heels, she sat in a straight-backed chair in the center of the foyer. She’d never revealed so much so soon, and even her position, sitting in a chair with her legs together, suggested he was in trouble; good trouble!
“Close the door, but stay right where you are!” she instructed without moving a muscle. She loved the sight of her young lover standing in the high-ceilinged foyer like a penitent schoolboy about to see the headmistress.
“I saw you waiting a long time in the driveway, Simon. Would you care to explain that?”
“I was just waiting for eight o’clock, Miss! So I wouldn’t be early.”
“And yet, here it is, seven minutes past when you finally came to my door! Why is that?”
“I … I lost track of time,” he stammered.
“I don’t think so,” she interrupted. “I think it was quite intentional, but whether it was or not, you’re late, and the result is the same.” She paused as she watched the bulge in his loose-fitting pants grow. She hadn’t planned this, but given the opportunity, she saw it as sort of an ironic peace offering. “Come here!” she commanded, pointing to the floor on her right. “Pull your pants down and get over my knee!” She watched him tug the pants down quickly, and his fully erect cock popped up as though on a spring. “No underwear, Simon? Even a better reason to begin with a good spanking tonight! Over my knee!”
She tugged on his arm, and he practically fell across her lap, her hand smacking his bare bottom before he’d even settled in. Her thighs closed with his cock between, and she’d already delivered a half dozen firm spanks to alternate cheeks before she noticed the purplish tinge remaining from his stint on the spanking bench. She didn’t want to spoil the mood by asking if he was okay, especially since she was sure he’d orchestrated this ‘punishment’ by being late.
She stopped for an early rest, and with her hand on his near cheek, she squeezed it while watching his face. A moan and his raised hips gave her the answer she expected, so she resumed spanking his upraised bottom to his usual appreciative gasps and groans.
She continued for several minutes with short breaks to ensure she could continue, his lifted squirming hips giving her the ‘thumbs-up’ she was looking for. She had another idea that would show her intentions were strangely conciliatory.
“Get up!” she said, knowing he’d be expecting it to stop and his smiling eyes told her that would be okay. “Take all your clothes off and bend over the chair!”
Without delay, he removed his shoes so his pants could follow. His jacket and T-shirt were next, which he pulled up and off without touching the buttons. He became a bit nervous when she got up and he saw the hairbrush in her hand. Still, she wouldn’t be using it long if he was right about her intentions. Bending over as instructed, he placed his hands on the back of the chair but moved them to the seat at her command.
Monica enjoyed continually surprising him, even if it was all relatively tame compared to their last meeting, and standing to his left with her back to him, she began. He’d told her that the hairbrush could be a most painful implement if used brutishly but also the most exciting, with an air of maternal discipline adding to the sharp sting.
With a little less force than her hand, she covered his cheeks with a deep, rosy glow, the growing but manageable pain from which was precisely what he wanted from a ‘good’ spanking. That he could see her gorgeous ass shimmy with each stroke was an added bonus.
Ready to bring his intro to their night together to an end, she paused and, with the stiff bristle side of the brush, lit up every nerve ending in both cheeks.
“You like getting spanked, don’t you, Simon?” she asked as she laid another six hard smacks on the same spot of his lower cheek.
“Yes, Miss! Oh! Oh my God!” he cried as the bristles were used to light him up again.
“Tell me!” she said, giving the other cheek the same treatment.
“I love it when you spank me! Ohh!” he reacted to the prickly bristles being dragged with a bit more pressure across the freshly stinging cheek.
After another round with ten spanks on each side, he was squirming uncontrollably with the intense sensations that were almost too much, yet he couldn’t get enough. This was precisely the kind of spanking he spoke of when he said he could take it all night.
“We’re almost done, Simon. Then you can show me how thankful you are!”
With her free hand on his back, she resumed the hairbrush paddling, letting up just a bit and switching sides frequently. When he started squirming to evade her hand, she knew he was ready for her next surprise, and he gasped aloud when her hand slid from his back, around his side, and underneath to grab his bobbing cock.
After a couple of long, slow strokes, she stepped up the pace in sync with her other hand, still paddling his bottom. As the pace quickened, she could feel his cock throbbing as he strained to hold back the coming explosion. Concentrating on the last couple of inches, her fingers deftly teased the tip while stroking and spanking faster and faster until …
“Ahhhhh!” he cried when he came, shooting his load onto the chair and floor beyond it.
“C’mon, Simon!” she said, still holding his dick, giving him no time to recover, and pulling him behind her like a child’s pull-toy. She let go when they came to the stairs but took hold again at the top. Leading him into the playroom, she sat on the vanity bench and pulled his face down between her legs, forcing him to kneel while she mashed his face into her steamy crotch.
She hoped she’d placated him by pleasuring him first and now felt entitled to some of her own. She let him tongue the gusset of her panties for a minute or so before pulling it aside to offer him her naked pussy.
“Lick my cunt, Simon! I wanna cum in your face!” she declared and started pulling her panties off, leaving it to Simon to complete.
‘So far, so good,’ Simon thought, still a little apprehensive about how far she might push him again, having the effect of him holding back a bit and not fully immersed in their play. It didn’t help that before his face was embedded in her crotch, he saw the spanking bench set up again, though in a different position, with the head end up against the end of the bed, even with its surface. With a mixture of arousal and concern, he wasn’t sure he wanted to be strapped in and put her in complete control again. Her tasty pussy was slowly drawing him in, though, and he couldn’t help giving it his all.
“Oh yeah! Just like that!” she gasped as he slathered her wet lips up and down, and side to side, his tongue moving at an ever quicker pace. After a few minutes, she could see it coming, and though she tried to contain it to build further, it overwhelmed her, and she came with vicious jerks of her hips into his face.
Not to be deterred, Simon continued, as usual, and she came again, though not as potently as the first. She’d had enough and called for a pause in the action by closing her legs and standing as soon as she could, taking him in her arms to compliment and thank him for what he’d done.
“You’ve noticed the spanking bench,” she observed when his eyes were repeatedly drawn to it. “I know that such a bench featured in your fantasies, so we’re going to try it again. We’ll forgo the straps this time,” she phrased as a command but offered it as a compromise. She waited for Simon’s thoughtful look to pass and give her an answer.
“You’re right, Miss, it did, and I enjoyed it up to a point last time, but then …” he paused, leaving the rest unsaid. “What if you only strap my legs in? Would that give us both some of that same feeling without me worrying about …” he almost finished with ‘what you’ll do next,’ but that seemed unfairly harsh.
Wanting to return to a feeling of control and not negotiating about what she could or couldn’t do, she took his arm and led him to the bench, ordering him to mount it with clipped phrases, and Simon willingly obeyed.
“I’m leaving your arms free, young man, but if you try to interfere, I’ll switch to the hairbrush or even the strap with the slightest provocation! Do you understand?”
“Yes, Miss! I only want to please you, and I’ll try to be good!” he replied in a fashion that accepted her revived dominance.
“Good! We’ll start with twenty-five on each cheek! Ready?” she said but didn’t wait for a reply before beginning.
Only now did he realize she meant twenty-five in a row on each cheek, and with them all concentrated on the lower part stretched tight due to his position, the sting built quickly, and though he was still apprehensive, he found he enjoyed it. Knowing what to expect on the other side made it feel even better. He wanted to cry out to act as though she was truly punishing him, but he walked a fine line there, not wanting her to stop for fear she was truly hurting him.
“Good boy!” she said and walked into her ensuite bathroom.
Simon heard the familiar sound of metal buckles and hoped she’d do what she’d done last time with the strap-on. Being penetrated, spanked, and jerked off all at the same time had created sensations unlike any he’d experienced before. He closed his eyes to concentrate on feelings alone since he couldn’t see anything anyway.
“Are you ready to get fucked, Simon? Hm? I’m gonna stuff this nice, big cock in your ass!?”
“Yes, Miss!” he replied as the first drops of lube ran down the valley between his cheeks to her waiting finger, which, after a quick twist in the pooled liquid, was quickly inserted, pulled out for more lube, and then thrust in again even harder. “Oh, Miss!” he cried as she finger fucked his tight hole.
While her finger repeatedly plunged into his ass, the other hand was liberally coating the rubber cock with more lube. When her finger came out, he immediately felt the pressure of the phallus pushing its way in like a battering ram and grunted with each lunge until his sphincter finally gave up the fight and allowed its entry.
Monica was thrilled with her new aggressive attitude, showing Simon that she controls his ass in more ways than one. She only went in halfway the first time, pulled out for a reload of lube, and then thrust all the way in with one smooth stroke.
Continuing with her vigorous attack, she grabbed his hips and pulled him onto her ‘cock’ to increase the intensity further still. Sprinkling in a liberal number of hard spanks, she had him grunting and begging her not to stop, which she had no intention of doing, instead planning to ram his ass harder and much longer than last time.
When she finally took hold of his cock, jerking it in time with her thrusts, it took no time at all for him to cum, leaving him a quaking and gyrating mess on the bench while she stayed inside him, pulling back and punching back in with just an inch or two. She considered trying to make him cum again, confident that she could do it, but cognizant of the amount of time confined on the bench, she decided to move on to the next and last use of the bench tonight.
Gasping at the sudden withdrawal of the rubber dick, he turned to look at her as she moved to his side and made a show out of removing the straps, then running her finger through her slit.
“My turn!” she declared and got on the bed facing him with her legs spread. “Mmm, nice and wet,” she said with her finger sliding between shiny lips. “Oh, I bet you’d like a taste of this, wouldn’t you, Simon?”
“Oh yes, Miss! I love licking your pussy!”
“Hmm, we’ll see!” she teased as she shifted forward, laying it on the line between the bed and bench, just out of reach, while stroking and poking. “Ooo, can you smell it, Simon? My pungent pussy?”
“Yes, Miss! Please give it to me?” he pled.
“You might not be so eager when you see the workout I’m going to give your tongue once I free you from the bench! Do you promise not to use your hands? Or do I have to strap them in again?”
“I promise, Miss!” he said, still reluctant to give up that much control.
Inching forward, her ass slid onto the end of the bench, eventually beneath his head when she grasped it and pushed it into her crotch, wiping her pussy with his face. Her juice smeared from his forehead to his chin; she pressed his mouth between her puffy lips and let go.
Simon almost wished his arms were strapped down as he had to fight the urge to bring them into play, thinking that it might also enhance her pleasure, but he still wasn’t ready to chance displeasing her.
While it still wasn’t what she’d hoped for with this unique bench, the position was much better. Her body was supported by the bed and her ass by the bench, with her legs dangling over the edge while Simon gave her one of his best performances. She noted how he obediently kept his arms on the rests while his head moved every which way, giving every bit of her pussy his rapt attention.
She came twice in rapid succession and would have gone for more but was now excited to move on to the next activity she had planned. She released the straps from his legs, and he got up, similarly stiff like last time; though the pain was decidedly less, there was considerable residual sting from his previous spanking.
When he reached back to rub his sore cheeks, she put a hand on his shoulder and bent down to smack his red cheeks with a fast and furious barrage that had him pulling away from her hand, though he liked the unexpected suddenness of it.
“Thank you, Miss!” when she stopped.
“I’ve got a better way for you to show me your gratitude! Lay on the bed face up!” she commanded, and when he delayed, she spanked him again, harder, faster, and longer than the last. “Lay on the bed! Now!” He winced when his freshly spanked bottom hit the mattress. “Hurts, doesn’t it? I’ll turn you over and make it hurt more if you stall again!”
“Yes, Miss! Sorry, Miss!”
“I want you stretched out with arms and legs together.” Pulling the bench away from the end of the bed, she reached for something underneath and held a pair of leather cuffs up for him to see. “I have another set for your arms!” she said watching his face for a reaction, adding, “It won’t hurt. I promise.” She didn’t like that she had to make that promise and saw it as another compromise to what she really wanted.
He said it was okay without much enthusiasm and watched as both sets of cuffs were attached and the chains pulled tight. Though he couldn’t imagine what she could do to hurt him in this position short of beating his body, he was still apprehensive about his helpless position.
Monica climbed on the bed with a devilish smile and immediately sat on his face. With his head effectively immobilized, she had to do the work; he was merely a toy she could play with. And play she did, grinding his face into the mattress as his face sawed through her gash. She took hold of his head again and punched it into her crotch.
After cumming the first time, she continued her assault on his face, but before the next climax, she moved down his body to ride his cock, faithfully standing up tall and proud. Bouncing energetically, she fucked herself until she came.
Simon enjoyed the continuous stimulation but would have preferred to be an active part of it, not just something for her to rub her pussy on. With her silky sheath still enveloping his cock, he hoped she’d start again until he came, but that wasn’t her plan.
“Aww, did you think I was going to let you cum in my pussy?” she said as she rose off his staff and leaned forward to smack his face with her dangling tits. “This is all for me!”
For half an hour, she moved between sitting on his face and his cock while she came countless times. She’d reverse her position on his face, giving him a faceful of her ass, and then ride him in a reverse cowgirl until she came again. She was always careful to be very close to a climax before fucking him, so while she came, he didn’t.
Eventually, she’d had enough and bent down to kiss him before sitting on his aching cock. Releasing his hands from the cuffs, she encouraged him to play with her tits, and this time her ride extended through three orgasms; two for her and one for him.
Releasing his ankle cuffs as well, she pulled him into a hug as he got off the bed. Pulling back, she smiled affectionately before asking, “That was better, wasn’t it?”
“Yes, Miss,” he said in a less than convincing voice. He couldn’t help thinking that some of the magic they’d had originally was gone, and whether that was his doing or hers didn’t matter.
The night was over more quickly than previous times, and they headed for the foyer for him to get dressed and say goodbye, but not before Simon noticed his clothes lying on the chair. He thought he’d left them on the floor, but without anyone else in the house to move them, he decided he must be mistaken.
He left her home after a gentle kiss and looked back several times as he headed for his car, assessing his future with Monica. In his car, he sat in thought for a few minutes more and, finally, backed out of her driveway. As he pulled away, he was so lost in his thoughts he didn’t see the car behind him, whose headlights had just come on and followed him out of the neighborhood.
--===<<<O>>>===--
Will Monica find a way to get what she wants from Simon without driving him away? And where will Cindy fit in? No one seems to know what will come next, but you might in the next chapter coming soon! Please don't forget to 'Like' and/or 'Favorite' my story if you enjoyed it and ... THANKS FOR READING!!
