You have no idea how much courage it's taking to send you this

this was never supposed to see the light of day

Asher sat in his office chair, spinning around in it as he thought about investments and allocation. He had a meeting in a few minutes with his boss and other big figures in the company, and being him and wanting to impress his boss and colleagues, he had been refining his speech and thinking of new things to add since he was told about the meeting. He walked down the hallway, suddenly flushing as he walked in to see his boss along with two other men.
"Oh, hello, Mr.Stirling, come in, come in." Maia Halloway, his boss, said as she waved for him to enter.
"Hello, Sir. How are you?" He asked, shuffling in, tucking loose strands of hair behind his ear.
"Everything's alright, thank you Stirling." Maia smiled at him kindly before organizing the papers in front of her.
Asher would never admit it, but he did find his boss just a little bit attractive. He liked how her eyes displayed emotions, or lack thereof sometimes. She could show exactly what she was feeling or hide it away with just her eyes. She also had a muscular frame, compared to his own small, almost scrawny frame.
But, he would never admit any of this, especially to the woman herself, because what did he want to do, loose his job? He snapped back to the present when two more people walked in.
"Gentlemen, now that we're all here, we can get this meeting started." Maia clapped her hands once firmly. Asher sometimes wondered what it would feel like to just hold those hands, aside from a handshake.
He listened attentively, taking note of everything his boss said through her presentation.
"Does anyone have any input?" He asked, voice laced with authority.
"Y-Yes, ma'am." Asher broke the silence she left with nerves evident.
"Alright, Stirling, let's hear it."
"Well, t-to start off, I think it would benefit us to invest in that company because they have..."
He was talking through his viewpoint while stuttering every time he made eye contact with his boss. He figured it was one of those, 'I'm-not-showing-my-emotions' days, not being able to keep eye contact long enough to see what she thought about his speech.
"And this is why I-I b-believe investing in this new, rising company would later become an asset to us." He concluded.
"Very nice, Mr.Stirling. Anyone else?" Maia asked, looking around the table. She was met with silence. "Then it's settled. Thank you gentlemen for your time" she declared. All the men hastily got up to leave the room, seeming bored out of their minds. Alex was the last one going out, but he was stopped.
"Stirling?" Maia called out quietly, only loud enough for him to hear. Asher spun around to look at her.
"Yes, ma'am?" He asked, trying to sound confident.
"May we have a word?"
'Oh no,' he thought. 'I screwed something up. I definitely screwed something up.'
Asher blankly turned towards Maia, but she held her hand out, stopping him, "Close the door.". Asher complied, closing it before setting his things down on the wide, circular table and taking a seat. "Yes, m-ma'am?" He asked again, shrinking down a bit.
"Are you alright?" She questioned, concern now evident in her eyes.
"I'm sorry?" Asher said slowly.
"You can't seem to string your sentences along properly, is there something making you nervous I should be concerned about"
"N-no, I'm n-not scared of anything in particular, ma'am." He stammered, putting his hands flat on the table.
"Then is there a reason you're stuttering so much?" She asked, almost sweetly. She put her hand on top of Asher's. Either she had meant it in a comforting manner or it was a reflex and she hadn't realised she'd done it.
"N-no, ma'am." He said quietly, squirming in his seat.
"Are you uncomfortable, Asher?"
Asher. She had never called him by his first name.
"I mean, I guess you could put it that way." He mumbled what he thought was quiet enough for his boss not to hear. He assumed wrong.
"What do you mean by that? Why are you uncomfortable?" Maia asked.
"I-just, it's n-nothing, ma'am." He stammered.
"Well it's obviously something since it's rendering you to this state." She seemed to wander into thought. After a couple minutes, she seemed to collect some ideas.
"Are you overworking yourself?"
"I'm underworking myself if anything." Asher almost laughed. He still felt the heat of his boss's hand on his.
"Bullshit, but I know that it's not the reason." Maia mumbled. "Any of your colleagues?" She asked.
"N-no, they've all been nice for the most part."
"No, I mean do you like any of them?" She seemed to suppress a smirk.
"What makes you say that I like any of you?" Asher said defensively, though he was already blushing.
"Don't think that it's a secret to me, Asher. You always eye up the girls around. I've also noticed that you've been looking in my relative direction lately." She now let herself smirk as Asher sunk in his seat.
"I-I don't think I k-know what you mean, ma'am." He stuttered, looking down at the table in front of him.
"Answer me straight, Stirling, do you like someone in the office and it's making you act fidgety?" Maia asked, face going back to its neutral resting bitch expression.
'Fuck fuck fuck,' he thought. 'I'm going to loose my fucking job.'
"No, ma'am." He mumbled.
"You're blatantly lying to my face, Asher." She almost chuckled.
"N-no I'm not, ma'am." He stammered looking at the ground. He heard a small laugh before Maia fully took his hand.
"Ma'am..." Asher sputtered.
"Stand up." She told him. He reluctantly stood up as his boss stepped closer, much too close. They were nearly touching at that point.
Maia held the taller boy's hips and pressed their bodies against each other. "S-sir!" Alex exclaimed as he felt her hip being pressed against his crotch. She quickly pressed her lips against his as he was pulled into a heated kiss. "Was it me the entire time, Asher?" She asked, slowly nipping at his jaw and down to the sensitive spot on his neck.
"Ah- yes ma'am~" he groaned, trying to subtly rub himself against his boss's leg. He felt himself growing harder and quickly becoming uncomfortable because he was strained against his pants.
"I suggest you go lock that door." Maia said. Asher jumped up and complied, speed walking over it the door and turning the lock.
"Good, now come here." She held her arms out. Asher walked over, looking down at how distraught he already looked, bulge evident in his pants.
"Mmmh, I know, sweet boy, let me take care of you~" she pulled him in and purred into his ear. He inched closer, hearing her breathe into his ear
"Mmmh~" he groaned.
"Look at you, aroused in front of your boss. Ready to do as she says, you're adorable." Maia whispered to him, sending a chill down his spine. Asher felt the humiliation of being in this state in front of the woman who controlled his job, but he was too lust filled for the humiliation to not be kinky.
He rubbed against his boss, making the smaller woman start to succumb to her own arousal. He whimpered as he felt small hands grab his hips and roughly thrust against him.
"Maia, p-please, oh fuck, please don't s-stop." He begged. His boss altered between long, agonising thrusts, and quick, rough pounds.
"Do you like this, Asher?" He asked, moving his hips slowly.
"Y-yes, ma'am. Please, it feels so good~" his boss continued to grind their clothed bodies together, holding the limp boy in her arms.
"please, I'm- aah-" Asher couldn't get his words out of his mouth after a couple minutes, leaving himself to cum in his pants. His boss slowed down as she felt his pants becoming wet and he lost all ability to stand on his own.
"Did you just cum in your pants, you little slut?"
"I-im s-so sorry, ma'am, I didn't mean to~" he said breathily. Maia noticed tears slide down her face. She immediately stopped her teasing, and held Asher up by his shoulders.
"Am I going too rough on you, sweetheart?" She asked the man in her arms in a serious tone, worried she hurt him.
"No, I'm en-enjoying this a l-lot"Asher hummed after pulling Maia in for a kiss. She replied cupping the man's face gazing into his eyes as she sat him on the desk, noticing him squirm uncomfortably, It took a second for her to put together why, but once she did her expression softened, "why don't I take those pants off you now." She asked, lightly pulling on the waist of his pants, subtly asking for permission, He nodded, groaning, his body sensitive against the fabric sliding down.
"Such a cute boy~" his boss purred, throwing his pants to the side, "Not to mention gorgeous". She put one hand on the desk to stabilize herself and used the other to lightly drag her nails up his thigh. "Hmm please~" he gripped onto her shoulders. He was already hard again. The woman kept running her nails against his skin, teasing his cock after feeling like she'd teased him enough. Asher was already whimpering, wanting her to stop teasing him already. "Why don't we get my clothes off before I make you mine" Asher quickly complied, taking off anything that got in between him and Maia. "Good boy~" she praised. He just nuzzled into her chest, quietly whimpering as he nipped at her skin. She grabbed a fistful of his hair and pulled him up to face her "over the table." She ordered, "but ma'am-" "do as you're told, slut" Asher turned and quickly laid on the table, feeling his chest
on the cold wood. A drawer was opened beside him before he heard the sound of something clip into place. He turned around, "ma'am, why do you have a strap on in your office?" He teased. "I said don't ask questions".
"Hmmm~" Asher suppressed his moans as he felt a finger prod at him. It slowly opened him up and made its way in, pressing against all his walls.
A second one was added, and he clenched around them. Once the third one was added and slowly moving in and out, he was starting to grow even more horny and impatient. "Maia, please~" he begged as she slowly rubbed inside of him. "Aah, I-I'm ready, p-please~" he groaned out, his body heating up, he was already becoming overly sensitive. "Alright, Asher" she breathed into his ear before lining herself up. She slowly pushed in, not wanting to hurt her best worker. She gave him time to adjust, moving slowly in and out after he gave the signal.
"More~" he groaned after a few minutes. Maia immediately complied, moving quicker. She grabbed his hips, pounding so hard his cock rubbed harshly against the desk. Not done teasing, she pulled out abruptly, turning Asher around so he was facing her. She looked at his body, red from all the stimulation. "Such a good boy~" she purred, kissing him lightly and pulling him close. "Let me ride you?~" she whispered. Asher nodded quickly, moaning to himself at the thought. Maia guided him to sit down in her chair, climbing on top of him, grinding against him before sinking down onto his cock slowly. Asher grabbed her hips, guiding her as her voice broke into moans, "Oh, you're just as much of a slut as I am-" Asher teased her, starting to rock his hips deeper into her. Maia grabbed his hands and pinned them to each armrest of her chair, "Such a good boy, fucking me so deep~" "I'm about to cum-" he moaned breathily. "No" Maia said harshly, slowing her movements and guiding one of Asher's hands to her clit. He traced circles that quickly turned into harsh ones as Maia started to move again, grinding her hips in between thrusts. "I- ma'am, can I please- ahh, cum? please~" he groaned at the overwhelming stimulation. His entire body felt like it was pulsing. "Yes, ahh, cum for me-" he didn't need to be told twice. He came all over himself and his boss, only pumping out more as he felt his boss come against thigh. "Such a good boy~" she praised.
"Did you enjoy that?" Asher blushed, feeling embarrassed at how much he liked it and how blissed out he was. "T-Thank you, that was really amazing." He said quietly. "So quiet now~" Maia teased, standing up so he could stand too. "It's okay," she cupped his face. "I would go for a round two with you but it seems that you've depleted yourself." She smirked, "We can go for round two some other time in a better location." She picked up Asher's clothes, handing them to him. He cleaned himself off with tissues before putting them on, trying to make himself look presentable. "You may go home early if you'd like, to recover." She offered. "I think I will, thank you." Maia nodded before letting him leave. "I'd better see you well rested tomorrow, Stirling"