Cindy and Simon couldn’t be happier and went to bed Sunday night, looking forward to just seeing each other the following morning. The only challenge in their minds was keeping their quickly growing relationship under wraps at the office. There were no rules against nepotism, but they could be separated or even fired if their work suffered as a result. They’d talked about it during their lie-in last night and agreed they could steal a kiss when no one was looking but not touch each other in any other way. They’d also agreed that would be very difficult!

Monica’s near-term future wasn’t quite so clear. Sure, Derek offered the possibility of becoming the kind of sub she’d always imagined, but doubts about whether she really wanted that bothered her still, though much less doggedly.

She still saw Simon as a young (nearly half her age), immature, and inexperienced candidate who himself didn’t seem to know what he wanted. It was almost as though he was teasing her, making her believe they wanted the same things, but then objecting when it got too intense for him. Judging by what she saw online, they were nowhere near as extreme as most BDSM relationships were. Still, she had enjoyed and still looked fondly on his boyish charm, his desire to please her with a tongue that would give Derek a run for his money, and his youthful enthusiasm for doing so.

She still couldn’t make up her mind about just how far down the Dom/sub rabbit hole she wanted to go. Reacting with extreme sympathy when Simon accused her of going too far wasn’t what a real Domme would do. She’d either castigate him for his weakness or toss him aside as unworthy, so, again, was she really Domme material? And did that matter if she wanted a tamer arrangement with an almost-sub?

She decided that she couldn’t answer those questions with the information she had. She had a date with Derek tonight where she’d push them both beyond what they’d done their one time together and see what happens. That she hadn’t heard from Simon in a week now was a bit disconcerting. Though she was the one who initiated contact, she half expected him to need her more than his silence would suggest. Still, it fit better into her current plans, avoiding conflict with Derek while she sussed him out.

During the workday Monday, she saw Simon a few times in the hallways, but he didn’t see her. Was that by design? Was he avoiding her? In the past, though they’d done nothing to attract the gaze of the other when such close encounters occurred, somehow, their eyes would meet regardless of the distance between them. It made her a little sad when she assumed the worst.

“Derek Johnson from WebCom Devices on the phone, Monica?” her admin said over the intercom, waking her from another thoughtful reverie. Startled at the intrusion, she thought she heard her say, ‘Big Johnson.’

“I’ll take it. Close the door, Cheri. Derek! How are you!” she said for her admin’s ears before the door was closed, then lowered her voice, “You shouldn’t be calling me here, but I’ll deal with that tonight! What was so important that you had to speak to me now?”

“I’m sorry, Miss, but I have a very full afternoon and won’t be able to call before eight tonight. I just wanted to know if I should bring anything.”

“Bring the paddle and expect to feel it rather more severely than you did on Saturday!” she said and hung up the phone.

“Are you okay, Monica?” her admin asked, standing at the door. “I heard the phone crash down and …”

“I’m fine!” she said aloud and again, ‘I’m fine’ to herself as she realized how easily that exchange came to her.

Her admin returned to her desk, confused about the satisfied look on Monica’s face after such a short call. She was sure that was the guy she’d been chided about making the appointment for.

Monica was suddenly looking forward to tonight more than before. She decided to modify her plan slightly and sent Derek a text.

‘When you arrive tonight, come right in. The door will be open, and instructions waiting. Don’t be late!’

Derek grinned broadly at the text he’d read while attending an incredibly dull meeting. He’d planned to be intentionally late to provoke his favorite ‘ramification,’ but after the phone call, he thought better about testing her like that.

Walking up the steps to her door, his anticipation, as well as expectations, were running high. He’d loved how she’d spoken to him with the call and text, raising his hopes higher still. He tried the door and smiled when it opened. Closing the door behind him, his eyes cast about the high ceiling of the foyer before seeing the small round table with a note card on it.

‘Whenever you walk in my door, whether I’m there to meet you or not, the first thing you will do is remove ALL of your clothes and place them on the chair. If I’m there to meet you, or if there are no further instructions, you will stand in the middle of the foyer with your arms folded behind you and wait. I will join you today when you have completed the first instruction.’

Derek smiled, thinking, ‘This just keeps getting better!’ He removed his clothes efficiently without rushing to avoid seeming too eager in case he was being watched. He placed the paddle on the table beneath the note and assumed his stance.

In fact, Monica was watching to see how he reacted to the note and was pleased with his smile and his following of her instructions. She hesitated a few minutes once he stood as directed, just to make him wait, though her arousal was already running rampant.

“Hello, Big!” she called from the top of the stairs and descended slowly, enjoying the look on his face when he saw her in the purple corset that had had a similar effect on Simon when she wore it. His eyes were glued to her body as she finally appeared before him. “I’m glad to see you can follow instructions now. Unfortunately for you, when it came to my telling you not to call me at the office, you evidently weren’t listening!” she accused, her hand resting on the paddle’s handle. “Bend over!”

“I’m sorry, Miss! It won’t happen again!” he apologized as he bent, placing his hands on his knees.

“Another thing you need to learn about me,” she said, tapping the paddle on his proffered ass. “Remorse and gratitude are shown with actions, not words. I’ll only add five swats for this infraction since you weren’t aware, but it’ll be ten in the future! Twenty-five, now! Count them!”

“Yeow!” he yelped. The first is always startling, but this was considerably harder than he was used to. “One, Miss! Two, Miss! Three … OW! … four, Miss!”

She hadn’t commented on the color of his cheeks, still showing some remnants of the paddling he received just two days ago, but thankfully, the pain was all but gone. He relished this paddling even more for the sudden timing and the sight of her gorgeous ass he couldn’t keep his eyes off of except when wincing from the painful swats.

“Twenty-five, Miss!” he panted and almost thanked her but remembered her warning just in time.

“Stand up! You can thank me for dealing with you upstairs,” she said as she led him by his dick to the stairs, where he had to stay right behind her when climbing them to keep her from pulling too hard on it.

His eyes opened wide when he entered her playroom with its dark atmosphere, dim lighting, and color scheme coordinated with her corset. The spanking bench, arranged as it was the last time she’d used it with Simon, caught his eye next. He’d only been on one once, but that was with a Domme he’d paid for the pleasure of his pain. All of it spoke of the experience he assumed she had.

Monica allowed him a few moments to take it all in, hoping he saw it as both threatening and promising. Noticing that ‘Big’ had returned to full measure, confirmed that he did.

“Kneel with your hands behind your back!” she commanded. She stepped forward till her crotch was just an inch or two from his mouth and stopped, testing him to see if he’d try to start without being told to; a test for her as well since her pussy was wet enough to have stained the front of her panties. “Good boy! Now show me how much you appreciated your paddling!” she said, pulling his face into her crotch with both hands.

He remembered her intoxicating scent, and his nostrils flared to savor it again while she pushed the moist gusset of her panties into his face. He tried to get his tongue involved, but her mashing of the wet satin into his face made it ineffective until she pulled the fabric aside.

“Put your hands on my ass!”

She loved this position, but was physically taxing, especially in her heels, but his hands supporting her helped. Having taken another step forward, she was now above his face, squatting to punish him with her pussy. Minutes later, she was cumming, and with the support of his hands, she wiped his face with her milky nectar.

“I assume you know how to mount a spanking bench?”

“Yes, Miss. Would you like me to?” he asked, unsure if that was an instruction or not.

“What did I tell you last time about repeating myself?” she asked, punctuating words with ten swats of the paddle.

He almost apologized but again remembered the rule he thought was strange. ‘Thank you’ and ‘I’m sorry’ seemed to be stock phrases he’d be expected to repeat frequently in his subservient role. Instead, he went to the bench and got on, finding that the arm and knee rests fit his frame quite well, though he had to rock back a bit to get his torso to lie on the padded top. His anticipation rose as she fastened all the straps, leaving him unable to move any part of his body except his head.

Monica could feel drips of her arousal running down her leg from sitting on his face, but she wasn’t going to compliment or congratulate him on his performance; instead, she’d demand more with consequences for failure. She removed her panties and stood at his side, running her fingers disarmingly through his hair while he salivated over the sight of her shiny wet pussy.

“Want another taste, Big? Hm?” she asked as she climbed on the bed and slid toward him. Her spread legs fell over the end as she placed her pussy just out of reach of his tongue. “You want to eat my cunt?”

“Yes, Miss! Please!?” he pled.

“Please, what?”

“Please let me eat your cunt and make you cum in my face!”

“Hm,” she pondered, “See, I wasn’t all that impressed with your prior performance, so I think you need some training!” She waited for a reaction, but getting none, continued. “I’m going to give you three minutes,” she started, holding up a kitchen timer and her leather strap, “to make me cum. If I do, you get a reward, but if you don’t, you get five lashes of the strap. Then I’ll give you another chance with ten lashes as the penalty. Each time you try and fail, I add five lashes and we keep going until you’re successful! Understand?”

“Yes, Miss!” he cried eagerly, promising himself to fail at least twice as he loved the feel of a strap but hadn’t had the pleasure for quite some time.

“We begin!” she said after moving forward and starting the timer.

She didn’t want him to succeed right away either and wondered how many times it would take, though he was doing a pretty good job already. As the three-minute mark approached, she barely felt something coming and wondered if she’d made the task too hard to accomplish.

“Nice try, Big!” she said as she slid off the end of the bed with the strap in her hand.

Derek watched as the flexible leather band flew with a full wind-up, and, “Oh God!” as it whipped across his ass with a sting that grew in intensity until the next one added to it. “Oh fuck!” He managed to survive the five, leaving his bottom on fire with the lasting sting he remembered, and soon, his face was in her crotch again for his second attempt.

With renewed vigor, his tongue worked furiously, and she could feel a climax approaching, hoping she could hold out another thirty seconds till the timer ran out again. She congratulated him on a better attempt but was eager to lay into his bottom with the strap again.

“Oh my God!” he cried on the fourth lash, as much in pleasure as pain, and by the tenth stroke, he wished he could have more but didn’t think he’d be able to take the promised fifteen. With her juicy fruit back in his mouth, he quickly knew he’d make it this time.

She knew he’d make it this time as well, as it started building quickly from the outset, evident in her body language. Writhing under his tongue, she moved with it, exaggerating its effect, and, this time, she went off at the same time as the timer, her fingers clutching at it to shut the damn thing off so she could enjoy the orgasmic rush. Her legs came off the floor as her thighs trembled, Derek doing his best to prolong her ecstasy until she pulled away from his mouth.

“Oh, very good, Big!” she offered a rare compliment as she sat up on the end of the bed.

He smiled as his tired neck lay his head on its side to look at her, happy to have pleased her so.

“You might need a little more training next time,” she said, noting how he smiled, looking forward to it as much as she did.

He followed her with his eyes as far as he could and assumed she was heading for the bathroom. He heard the tinkling sound of something metallic that was unfamiliar. It stopped, and moments later, he felt a cool liquid dripping into the cleft between his angry red cheeks, which he assumed was lube, and he expected to feel her pushing another butt plug into his ass.

“I believe I owe you a reward,” she said, standing behind him with the strap-on dildo well-lubed and pointed at his bumhole. Twisting her middle finger in his crack, she coated it with the slick liquid and then stuffed it quickly into his ass feeling little resistance, but that would likely change.

He was still expecting a plug to follow, but as his sphincter stretched to allow the violation, it didn’t close up as it would when the wide end popped in, and he gasped with the deeper penetration.

“Oh, fuck, Miss!” he cried when she pulled out a bit for more lube.

“Yeah! Oh fuck is right, Big! Ever had your ass fucked?”

Grunting as it probed even deeper, he couldn’t decide if he liked the wholly unfamiliar feeling of being so full. He felt it recede again, only an inch or so, squirming in his hole to get him used to it.

“Oh God, Miss!” he cried when she pulled back slowly and rammed the relatively small, compared to ‘Big,’ phallus back in. “Oh yeah! Fuck me, Miss!’ he cried, having concluded he liked it after all.

“Are you telling me what to do!?” she yelled at him and spanked him with both hands on each exit.

“No, Miss! Please fuck me, Miss!” he pled, straining at his bonds.

Feeling the rubber shaft gliding smoothly in and out of his tight hole, he felt the restraining strap across his back released, and he immediately rose up off the cushion and pushed back against her thrusts. The pace quickened with shorter strokes as she bent over him and reached around to take his cock in hand.

“Oh, Miss! Oh my God!” he cried, the pitch of his voice rising with each combined thrust and stroke of his cock.

Her hand was a blur as she jerked it as fast as she could, while her lunges became short, punching stabs until he spewed several strings of semen over the padded surface of the bench. She stayed inside him as his body slowly calmed and then pulled out quickly, triggering another shuddering gasp on the exit.

Not wanting to lie in his cum, he held himself elevated above the christened cushion as he heard those same metallic sounds, this time removing the strap-on and hearing it drop to the floor. She went to each of his restrained limbs and released them, but he waited till she said it was okay to get off, which thankfully was shortly after the last strap was opened.

He got up and stretched his arms and legs, unable to reach the high ceiling as he would his own, and quickly adopted the official stance with his arms folded behind his back. Only now did he see that she was as naked as he and about three inches shorter, having abandoned the heels, too.

“Did you enjoy that, Big?”

“I did, Miss. Thank …” he started and caught himself again.

“Don’t expect to be shown such consideration on a regular basis. I only let you cum because it served my purpose for you to do so,” she explained with surprising honesty. She was going to ride him again, and she didn’t want him cumming too soon. “Lie on the bed with your arms and legs stretched to the ends!”

She held the leather cuffs up for him to see but didn’t offer him the chance to decline them as she had with Simon. That memory got her thinking about how different everything had been with Derek. She was in complete control, with no challenges to her authority. The only mistake he almost made a few times was thanking her verbally, and she wondered if that rule she’d conceived should be changed as gratitude and apologies were voiced frequently in the videos she watched. Still, her rule gave her a chance to catch him on something since he was nearly flawless in accepting her dominion over him otherwise.

“I’m going to give you a choice,” she said as she fastened the second set of cuffs on his wrists. “You can take five with the strap now or ten with the paddle before you leave. Before you answer, know that all will be harder than before!”

“I’ll take the strap, Miss!”

“Turn over,” she instructed. He looked confused at first, but realized that even with the cuffs fastened, his arms and legs were together, and he could twist his body in place. “Lift up!” she said, smacking his bare cheek, and stuffed a firm, wedge-shaped cushion underneath, his torso resting on the downward slant, leaving his ass vulnerably perched on the top edge.

He was happy to be getting the strap again, and not the fifteen he’d have gotten had he failed a third time before. His face was pressed into the mattress, between his outstretched arms, and he couldn’t see her standing at his side, so he closed his eyes to just feel the strap with no clues as to when or how hard it might descend upon his raised bottom.

Monica was happy he’d chosen the strap as well, but noted that these five would make a total of twenty, the same number she should have given Simon last time. Just to tease him, she lifted the strap, made a grunting sound as though exerting much effort, and slashed the strap down on the bed, laughing devilishly when he jumped.

“Ready, Big?” she asked as she was already raising the strap and arcing it down to its target as he replied.

“Yes, Miss! Yeow! Holy shit, that hurts!” he complained pointlessly. “Fuck!” he cried with the second lash that came from the other side of the bed so that the strap’s whipping end treated both cheeks equally.

Each was harder than the last, and the excruciating fifth had him gasping and squirming in pain. Still, he was glad he’d been able to take it and that there’d be no more tonight.

“Turn over again!”

Turning the opposite way, he was once again face up, wincing with the pain of his freshly lashed cheeks against the bed.

“Maybe that wasn’t a good choice,” she suggested deviously, the pain he felt evident in his facial expressions.

“It was worth it to please you, Miss!” he said, surprised to see an empathetic smile flash quickly across her face.

“Well, now you’re going to get a chance to please me again, and all you have to do is lie there!” she said as she climbed on the bed and sat on his face. Rocking fore and aft, his nose and mouth slid easily through her slippery slit, and when he extended his tongue, she made sure it touched her in all the right places.

Staying on his face until she came, she moved down to toy with his cock, splaying her lips over it as she stroked it with her pussy, her fingers pressing it into her sloppy slit. Before moving back to his face, she filled her dripping hole with his long, thick shaft, but before he’d progressed beyond the delight of being encased in her sheath, she got off and moved back to his face.

Turning around, she smothered him between the cheeks of her ass briefly before feeding him her juicy cunt again. Taking ‘Big’ in her mouth, she got him a little further down the road before pulling him out and concentrating on his tongue until she came again.

Back and forth she went, getting her satisfaction while edging him mercilessly for what felt like hours but was, in fact, about forty minutes. When she was finally going to let him cum too, she rode him hard, bouncing as he tried to push up and meet her halfway. Bending over his prone body, she stuffed her tits in his face as her hips kept his cock on the boil until he couldn’t hold it any longer and filled her with his payload. She came shortly after and lay on his chest with him still inside her until their breathing normalized.

Lifting her head off his chest, she smiled and kissed him gently, offering her brief thanks before reaching up to undo the cuffs on his wrists. Climbing off the bed, she released his ankles as well, struggling to maintain her dominant persona when she really wanted to lie in bed with his comforting arms wrapped around her.

It was another of those ‘Domme or not’ quandaries that she hadn’t come to terms with yet. More than anything now, she wanted his gentle touch and kisses, but that would mean relinquishing her authority, and she didn’t know if he’d like that or not. He had been an obedient and willing sub, yielding to her control at every turn, so did he want to see her weaker side?

Her face had changed, devoid now of the demanding attitude she’d employed all night, and he imagined an internal argument taking place in her mind. The devil on her shoulder wanted her to resume her Domme demeanor, while the angel sought comfort.

“May I hug you, Miss?” he asked with a touching smile that melted her heart, and she fell into his arms. Tilting her head back with a finger under her chin, he kissed her with all the passion he had left, and she melted into his embrace.

“Are you sure you’re okay with this?” she asked when their lips parted.

“Much more than okay,” he replied in a quiet voice.

“But I’m not a Domme when we do this.”

“Don’t get me wrong, I love you as a Domme to my sub, but I’m not planning on adopting it as a lifestyle. I hope we’ll do this and more again, many times, but that doesn’t mean I don’t also want some tenderness and to give to you because I want to, not because you’re telling me to.”

Another long but gentle kiss ensued, and finally, she seemed to be sorting out what she really wanted. She’d found a person in Derek who was that last piece of the puzzle that brought the picture of her life back into focus. She felt like all her doubts were gone, and she was more sure of the future than ever.

As she lay alone in bed later, more settled than she’d been in years, she thought of Simon. Sweet, young, immature Simon, who’d played his part in helping her find what she didn’t know she wanted, but now she’d have to tell him she’d found someone else, and it pained her to think of the rejection he’d likely feel.

“Simon, I’m pushing you because I know how hard it will be to tell Monica, but it’s not going to get any easier and will likely get more difficult the longer you wait,” Cindy said as they were having lunch together later in the week after their fantastic weekend together. “Would it help if I threatened you with a spanking?” she said with laughing eyes.

“I’d probably delay it further then!” he replied, laughing as well. “I think I know what to say, but I don’t know where or when I should do it! I’m not supposed to talk about this stuff in the office, but I don’t want to go to her house to tell her, either. I’ll figure it out, Cindy,” he said, quieting her concern for the moment.

They’d talked about it a couple of times now, and it had a dampening effect on the time they spent together, but they were both concerned about their jobs, as Monica could easily fire them both in a fit of anger at their perceived betrayal. While she didn’t know about Cindy specifically, they knew that the best-kept romantic secrets were rarely kept long in a gossip-prone office.

Monica also struggled with picking a time and place to speak with Simon. Her home would be the safest, but she worried he’d overreact in that setting as memories of their times together might overwhelm him. She’d been putting it off all week, wondering what he was thinking, perhaps why she wasn’t calling to set up another date.

By Friday afternoon she decided she had to do it, not wanting it still hanging over her head during the coming weekend with Derek. She picked up the phone and dialed his extension.

“Help Desk, Simon speaking,” he answered as usual, though he began shaking inside upon seeing the caller ID.

“Hello, Simon. I’d like to see you in my office, please,” she said, and before he could reply, she hung up. He took it as another display of her dominance and knew he had to tell her before she tried to schedule another evening with him.

“Monica’s called me to her office!” he whispered to Cindy.

“Uh-oh! Good luck, Simon. I’ll be thinking of you!” she added as a way of telling him he had to do it now.

“Come in, Simon. Close the door, please,” she said in her typical role as his chain-of-command boss. “Have a seat,” she said as she walked around her desk to take the seat next to his.

“Miss, I have something I need to tell you,” he said, wanting to get the upper hand before she invited him over again.

“Call me Monica,” she said in a friendly tone. “I have something I need to tell you as well. May I go first?” she asked, which he saw as her taking control again, though she was asking, not telling.

“Yes, Miss … um, Monica,” he corrected, a little confused at this change of title.

“We’ve had some really good times together, haven’t we?

“Yes, we have.”

“But there have been some rough times, too, and I’m not sure either of us really knew what we wanted.” She paused, looking for a response, but he wasn’t sure what to say as it didn’t sound like she was leading up to another invitation.

“Yes, I think you’re right, but I have a much better idea now,” he said, hoping she would ask him to explain.

“Yeah? Well, I don’t know, Simon,” she said, stalling for something to say but deciding to bite the bullet and tell him. “You see, I don’t think we really belong together. We don’t seem to want the same thing anymore.”

“I agree,” he replied and decided to let her finish her thoughts.

“And I’ve … I’ve found someone who does want the same things I do,” she finally blurted out, surprised by the slowly growing smile on his face. “Simon? Why are you smiling” she asked, almost disappointed that he wasn’t shattered by her news.

“I found someone, too, Monica! You’re right. I thought I wanted what you were offering, but each time, it got harder to take, and … well, you know how I reacted. I don’t want to be someone’s submissive anymore. I still want to give and give … and give till it hurts!” he said, chuckling at his double meaning, “but I need someone who shows appreciation for my gifts. I’m sorry, that sounded mean.”

“No, you’re right. We’re both right! Oh, Simon, I’m so glad you found someone. I was so afraid to tell you …”

“Me too! I was shaking on my way here, knowing I had to tell you! You’re guy … he wants to be a submissive?”

“Yes and no,” she replied, smiling but not wanting to go into details. “Simon, I want you to know that your job was never threatened in any way, regardless of how this worked out.”

“That’s good to hear. We were worried about that!”

“We? Is it someone here?”

He wondered if he should tell her. She’d find out eventually anyway, and now that there was no danger of them losing their jobs, he may as well.

“It’s Cindy. She’s wonderful, Monica! Likes all the same things I do. She’s cute and sexy, and we’ve just spent an amazing weekend together.”

Monica picked up the phone and dialed her extension. “Cindy? I’d like to see you in my office, please. Yes, come straight up.”

A minute later, there was a hesitant knock on the door, and she was invited in. Her face showed how nervous she was when she walked in, not knowing how their discussion had led to her being summoned, but her fears ebbed somewhat when she saw Simon smiling and offering his hand to her.

“Monica’s found someone too, Cindy!” he said exuberantly.

“Hello, Cindy,” Monica said with a warm smile. “Simon’s just been gushing about how wonderful you are, and I can’t be happier for you two. I was telling Simon that your jobs were never in jeopardy, regardless of how this turned out, and now I don’t see any reason why you can’t continue working side by side as you have,” she said and paused thoughtfully, “as long as you can keep your hands off each other here in the office,” she added with a laugh.

Seeing them standing together, holding hands, Monica had a sudden maternal urge to hug them both and stood to gather them in her arms.

“You look so good together! I wish you all the happiness you deserve!”

“Thank you, Monica,” Cindy said.

“Yes, thank you, Monica. For all you’ve done, and I wish you the same happiness, too!” he said, getting choked up and when Monica offered her open arms, he fell gratefully into them.

“You’re a wonderful person too, Simon, and I couldn’t have found my happiness if it weren’t for you, so … thank you for all you’ve done too!” she said softly and gave him back to Cindy.

Again, Monica felt like a mother, sending her young man off to handle life on his own, and the way the two left her office, arm-in-arm, she knew they’d do just fine.

--===<<<O>>>===--

Seems like everyone found what they were looking for whether they knew they wanted it or not! I hope you found the end of this series satisfying. Look for a spin-off series about Simon and Cindy in the future. In the meantime, please remember to 'Like', 'Favorite' and/or comment on my story if you enjoyed it and ... THANKS FOR READING!!