Monica woke the following day feeling like a hangover would be an improvement and glad she didn’t have to go to work. With a healthy dose of self-recrimination, she reviewed her actions from the prior night and drew several conclusions.
The side of her that didn’t want to take any blame argued that he’d happily accepted all she’d done until the strap, so it wasn’t like she’d been torturing him shamelessly all night. He seemed uncertain about having the strap-on stuffed in his ass but, ‘in the end,’ he had definitely enjoyed it.
The ‘special’ feature she’d sought in the spanking bench turned out to be not-so-special after all, or at least the way she’d set it up wasn’t. Maybe she shouldn’t have strapped his body quite so close to allow him more movement. Another idea that came to mind was that perhaps she should put another pair of arm/leg rests on that end to put her feet on, as her position was awkward at best. Insofar as Simon is concerned, it didn’t contribute to his ultimate condemnation, but it certainly didn’t help either.
The real mistake was in her use of the strap. She shouldn’t have pushed him to twice the number of lashes he’d reluctantly asked for to begin. Twenty vs. forty lashes didn’t seem like such a big difference to her, but then she’d never experienced even a playful spanking, let alone something as severe as the leather strap. Everything she’d read said that subs want to be pushed past their limit, but she’d forgotten that Simon wasn’t really a sub yet and overdid it. Now, she had to figure out how to undo it.
Simon’s morning was different than Monica’s in one respect in that he had lasting remnants of their scene, his still-sore butt. He was shocked when he looked in the mirror and saw the blue/black bruises across both cheeks. He was further surprised to find it didn’t hurt to sit on it as much as he expected and was reminded of threats from his favorite spanking porn about getting it so hard ‘You won’t be able to sit for a week!’ Was that just the typical exaggeration of porn films, or was it possible to hurt someone so badly that they’d have to stand or lie on their stomach for several days or even a week? He wasn’t about to try and prove it one way or the other.
Apart from that, his morning was quite similar to Monica’s. He felt bad about the way he’d reacted as he knew she didn’t do it intentionally. No Domme would apologize as profusely as she had if she were disappointed in his ability to take the pain she wanted to dish out. Yes, she went too far when he’d given ample indications not to exceed the limit he felt he reached, but she didn’t do so malevolently. He wanted to believe she did it because she genuinely thought he’d like it.
He worried that he’d burned a bridge behind him and that Monica would not want anything to do with him now. He considered calling her or writing an email to explain what happened, but decided his reasons would best be presented in person; but when? Would she even see him now that he didn’t measure up as a suitable sub?
Each went to work the next day, unsure how the other would act. They both wanted to continue but feared the other might not. Half the day had gone by, yet they hadn’t yet crossed paths, and they wondered if they were being avoided.
It was less than an hour till the usual quitting time when they saw each other in the hall at a short distance. They stopped in their tracks to read facial expressions. Monica’s was as neutral as she could manage, while Simon’s slight smile and puppy dog eyes convinced Monica to smile in return, and the presumed deadlock was broken.
‘See me in my office at 6!’ she texted at the first chance she got.
At a quarter to six, the customer service manager came to see Monica, asking if she’d come see something on his computer.
“Can it wait till tomorrow, Dean? I have an appointment,” she asked, not wanting to miss Simon.
“It may not show up tomorrow if I log off now. C’mon, it’ll only take a minute.”
As is usually the case with IT issues, it didn’t take a minute, and Monica returned to her office well after six, hoping Simon had waited. Finding her office empty, she pulled out her phone to call and see if he was still in the office.
“Simon! I’m sorry, someone held me up. Are you still here?” she asked, keeping her voice down lest she be heard.
“Yes, I’m still here, and it sounds like you are too. Do you want me to come now?”
Hearing the voice both on her phone and coming from under her desk, she smiled at what she guessed was a peace offering.
“No! Stay right where you are!” she laughed as she closed the door. She took a step toward her desk but decided to surprise him as he had her. Reaching under her skirt, she tugged her panties off, threw them on the desk, and sat in her chair, rolling it up under the desk.
She reclined in her chair when she felt his hands sliding up the back of her calves to her knees, feeling that familiar quiver between her legs when he pulled them apart. She pulled her skirt up and slid to the edge of the chair, laying it out for him to see.
“Mmm, are you being naughty, Miss? Going out in public without panties?” he accused as his hands slid up the tops of her thighs.
“Ohhh,” she sighed when his fingers touched her dampening lips. “Do you think I should get spanked?” she offered, and though she didn’t think he’d take her up on it, she was prepared to let him if ‘getting even’ was important to him.
“No. Not yet, anyway. I like it when you’re naughty!” he replied and smiled when she gasped at the touch of his tongue.
“Oh, yeah! Do it, Simon! Be a good boy and eat my cunt!” she said in a hushed voice.
Slipping and sliding between her moistening lips, he realized this was the first time she hadn’t already been wet when he started licking. She’d expected a discussion with Simon that would be either confrontational or conciliatory but not sensual. He relished the opportunity to be the one to take her from dry to dripping as her musky aroma filled his nostrils.
“Oh fuck, Simon!” she yelped when several fingers slipped inside and curled upward while a single finger tried to squeeze in between her ass and the seat cushion to reach the other opening. With her elbows on the chair’s arms, she lifted her hips, not only allowing that finger to tease her puckered star but to push her pussy into his face. “C’mon, Simon! Make me cum in your face now, or you may end up over my knee getting another spanking!”
He didn’t really need the encouragement, but he didn’t expect the threat of a spanking to further arouse him, especially when his bottom was still a bit sore, made more so by his confined position. Licking with abandon, he pictured himself across her knee with just the smack of her hand lighting him up, though they could hardly do something so noisy in Monica’s office.
“Oh God! Yes! Yes! Ye – Yesss!” she cried as her juices flowed into his mouth, attached to her pussy like a remora for mutual benefit.
Collapsing back onto the seat of the chair, her body shook and shivered with one of Simon’s trademark orgasms. Another aspect of his unique style was not letting up for a moment after she came, which prolonged the sensory overload of the first climax while building toward a second.
“Mmm, you do that so good, Simon! Oh! Ohh! Hoh!” she gasped when his lips and tongue concentrated on her protruding clit.
Charging toward another peak that she knew would eclipse the first, she was reduced to grunts and moans, the volume of which she tried to control, suddenly cognizant of the risky location they’d agreed never to use again.
Her voice rose in pitch, if not volume, and her body stiffened as he mashed his face into her seething crotch to push her over the edge again. Her body was limp from exertion, apart from the electrifying jolts that radiated out from her pussy.
Simon sat cross-legged beneath the desk and congratulated himself on not only another admirable performance with his fingers and tongue but on the way he managed to break the ice on what could have been a difficult discussion.
“Would you put these back on for me, please?” she asked, her panties dangling from a finger beneath the desk’s surface.
Simon took them from her and got up on his knees, holding the baby blue silk panties open for her near floor level. She stepped into the openings, rolled her chair back, and stood up while raising her skirt around her waist. Simon slipped them slowly up her shapely legs, gradually standing himself and watching as the swell of her thighs filled the elasticized openings. Pulling them up in back first, his palms caressed her perfect cheeks, and he was reminded briefly of her suggestion that maybe she should be spanked. Moving to the front, he pulled them up tight against her bare pussy, smoothing the shiny silk over the other lips he loved to kiss, and which he did kiss before standing.

“What a lovely surprise!” she said, taking him in her arms for a comforting hug. “I’m so sorry about Sunday, Simon! I took it too far and really hurt you! I hope this welcoming gesture is a sign that you forgive me?” she added, holding him by his shoulders at arm’s length.
“I suppose I do,” he started, “… if there really was anything to forgive. I could have been … I don’t know, more forceful? … when I wanted you to stop?”
“That’s certainly not your fault! The first time I strapped you, I let you pick the number. This time, the number you picked was almost double the lashes you picked before, but that wasn’t enough for me, and I ended up doubling that, leaving you badly bruised. I’m sorry I didn’t listen to you.”
“So where does that leave us? This time seemed more like that first time, only worse and I don’t know if I want to continue if I’m going to be surprised every time by the severity of our play. Especially when I’m strapped to a bench, unable to do anything about it if it gets too much.”
“Early on, I suggested you have a safeword. That’s usually the way to stop everything without question,” she suggested. His reluctance to be ‘surprised every time by the severity’ renewed her concern that perhaps he wasn’t a good sub candidate after all, as she thought most would accept being pushed past their limits even if not actually wanting it.
“I know, but … I don’t really want to stop everything, just what’s happening at that moment. I love giving you all I can offer, and I get immense satisfaction from seeing you cum as a result, even if I’m being ordered to do it rather than doing it on my own. As for pain, I love it when you take me over your knee and spank me with your hand. I feel like I could take that all night, and I like some escalations, like the hairbrush and even the strap, but within limits. I guess what I’m saying is I’d love to continue within those guidelines, and who knows? Maybe my limits will increase over time, but if you’re looking for someone to take anything you want to dish out, I’m not the guy for you. In the beginning, I thought I was, but I now know I’m not.”
Monica was stone-faced, giving no indication of how she felt about what he’d said. She’d have to admit she was more than a little disappointed at this last statement, but she remembered that her prior attempts to turn a lover into her sub were dismal failures, and why? Because she’d taken it too far, too fast. Maybe she just had to take it slower and read his needs and limits better, and maybe … just maybe, they’d get to the dom/sub relationship she ultimately wanted to have.
“I suppose I can accept that, Simon,” she offered, her disappointment showing. “We’ll take it easier, and we’ll both try to communicate better about what we need, okay?” she finished, and though he nodded with a smile, she wasn’t entirely sure this would work. “Would you like to come over tonight? Sort of a reset? Nothing painful, just pleasure?”
“I’d like that, but I’d really like another OTK spanking, and I don’t think my butt’s quite ready for that. Can we do it Wednesday? I should be okay by then?”
“I’ll have to let you know about that. I’ll be with a customer that afternoon, which may go into the evening. Can I let you know last minute?
“Sure. Thank you, Monica,” he offered as he reached for a hug that turned into a long but gentle kiss.
Cindy logged out of the computer she pretended to work on in the office next to Monica’s and quickly left the room with a big smile and wet panties. She’d had a suspicion about her Help Desk colleague and Monica, but she never dreamed what she’d learn from eavesdropping on their conversation.
She’d seen his face light up after receiving a text, and she stayed late on some pretext of needing to complete a task while keeping an eye on the fidgeting Simon. When he got up very suddenly and left his cubicle, she waited a moment and followed. She smiled when he entered Moncia’s empty office and, keeping her back to the wall to avoid being seen, slipped into the adjacent office that shared a back wall with Monica’s, faking her work on the computer in case she was discovered.
She could only guess what was happening behind Monica’s now-closed door when she heard praise for whatever Simon was doing. His voice was muffled for some reason, and she almost gave it up, but then they both started talking. The quiet of the after-hours office, with no ringing phones, copy machines, or people talking, allowed her to make out most of their conversation, which was far more than she’d expected, leaving her in this agitated state.
All the way home, she replayed all she’d heard in her head, wondering how she could live up to his expectations after being with the strikingly gorgeous Monica. A shy girl, she pictured herself as the ‘girl next door’ described so often in the stories she read on the Lush Stories site. ‘How can a plain girl like me compete with someone like her?’ she questioned herself.
She tried to devise a plan for letting Simon know she was interested, not only in him but his apparently very naughty bottom, but her mind was constantly tugged back to what she’d heard of their conversation. She’d suspected that something was going on with him and the CIO when he’d insisted on always being the one to work on her computer, but she hadn’t any idea what. Now she knew, and it would feed the masturbatory fantasy she promised herself as soon as she got home.
She closed the door of her tiny apartment, dropped her bag and keys on the kitchen table, and headed for her bedroom, opening clothes along the way. Sitting on the edge of the bed, she imagined Simon’s body draped across her knee, with his handsome face pleading for the spanking he wanted and the cute bottom she’d lusted after squirming with anticipation.
Standing up suddenly, she retrieved her favorite vibe from her bedside table, pausing briefly to consider the bottle of lube, but decided she was so wet, she wouldn’t need it. She tossed the vibe on the bed, quickly stripped off her clothes, and climbed on with one hand on her smallish tits and the other between her legs as she replayed the best parts of the conversation her spying had yielded.
“The first time I strapped you …”
“… when I’m strapped to a bench, unable to get up.”
“I love it when you take me over your knee and spank me with your hand …”
“ … but I’d really like another OTK spanking!”
Her fingers worked on automatic as they alternately swiped furiously at her clit and finger-fucked her sopping wet pussy, while her fantasy played in her head.
“Pull your pants down and get over my knee, Simon! I’m gonna spank your bare bottom!” she said aloud, taking her arousal to new heights. “A naughty boy needs to have his hiney spanked good and hard!” she continued. When she was close, she grabbed the vibe, shoved it into her pussy, crying, “C’mon, Simon! Fuck me! Fuck my tight, wet pussy!” Stabbing the purring vibe into her tunnel at an impossible pace, she finally came, crying his name out loud.
She lay on the bed as her body gradually stopped shaking, apart from a stray jerking shock. With the added stimulus of this knowledge about Simon, her new fantasy had produced one of the best self-induced orgasms she’d ever experienced. She tried to imagine what it would be like if somehow she could make her dream a reality, and the arousal it produced drove her fingers between her legs once again, triggering an incredible climax. With just the thought of Simon inspiring two unbelievable orgasms, she could hardly imagine what the reality would be like and promised herself she would use this intel in some way to try to make this fantasy with him a reality.
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Simon and Monica seem to be on shaky ground, and it may get worse once they find out that Cindy knows more than she should! More coming soon! I very much appreciate 'Like's, 'Favorites,' and comments! THANKS FOR READING!