The Office Boss [22F/38M] [Noncon] [Age Gap] [Humiliation]

*All characters are over the age of 18*

*This is The Book of Florence Volume II: The Office Boss. If you liked this, please consider checking out the full series on GumRoad or Amazon Kindle.*

I had started a new position as Secretary to the CEO of a prestigious financial company and was excited to receive my welcome email. But the instructions said I needed to wear the uniform they sent me. I held up the sheer white blouse and tight pencil skirt, confused.

My grades from high school hadn’t been great and I had barely passed college – despite letting Mr. Miller take my regular and anal virginity, I had still just managed to scrape by. My parents always said I made up for what I lacked in academics with buckets of enthusiasm and I guess they were right. In the job interview, I felt sure I had mucked up every question but my eagerness to do a good job must have come through. That, and the look the CEO gave me was the same as Mr. Miller. I briefly wondered if I should worry about that but quickly put it aside; this was a fresh start and I didn’t want to get on anyone’s bad side by making assumptions.

When Monday came, I put on the uniform given to me, including the sheer tights with a black seam running up the back and stiletto heels, determined to make a good impression.

I wobbled into the reception area, not used to the height of my new heels, and introduced myself as the new secretary. To my surprise, she scowled at me.

“You’re not the new secretary, you’re the other secretary,” she narrowed her eyes at me. She was about my age, maybe a year or two older, and was dressed immaculately. Her uniform was the exact same as mine, to my relief, but unlike me, she wasn’t wearing a bra. The blouse was sheer enough to show the outline of her breasts and nipples, and I immediately panicked that I had done the wrong thing by wearing my bra.

“I-I’m sorry,” I stammered. “My name’s Florence.”

“Penelope,” she sniffed, turning away from me.

“Ah! There she is,” we were interrupted by a loud male voice.

The CEO came through, dressed in a sharp suit. He grinned at me, his eyes roaming. I extended my hand, which he clasped heartily.

“Zack Colby,” he informed me, his eyes stuck to my chest. “We’ll need you to get rid of that as soon as – against dress code,” he winked at me. I blushed furiously.

“I’m so sorry, sir. I’ll do that right away.”

“Attagirl,” he casually slapped my ass hard enough to sting. I gave a small gasp in surprise but saw Penelope watching me carefully so pretended I had barely even noticed. “We’ll need to get your induction done this morning, make sure you’re all up-to-speed on how we work around here. I have a feeling you’ll fit right in.”

“Thank you, sir.”

“Penny, make sure the girl is prepped. And for God’s sake, get rid of that bra. Hate the sight of them.”

“Yes, sir, right away, sir,” Penelope immediately stood up and grabbed me by the arm. She dragged me to the bathroom as Zack retreated into his office.

The bathroom was sparkling white, with large spotless mirrors. The taps, hand towels and soap were all automatic – I’d never seen a bathroom so fancy.

“Right, get that off before you put him in a bad mood.”

“Oh, r-right,” I felt myself getting warm again, embarrassed that I had made a faux-pas already. I unbuttoned my blouse and unclipped my bra, under the critical eye of Penelope.

“Right, that’s better,” she whipped my bra from my hands and promptly put it in the bin. My cheeks burned – I would need to walk home like this – but I stayed silent, wanting desperately to get on her good side. “Don’t tell me you’re wearing panties as well?”

“Um…”

“Ugh,” she rolled her eyes. “From now on, no bra and no panties, okay? Zack likes easy access.”

“For what?”

She gave me a look I couldn’t decipher, but I stayed silent, not wanting her to think I was stupid.

“Zack will go through his rules for you, they might be different than the ones for me, but the important thing is that you just do whatever he says. Got it?”

I nodded eagerly.

“Go on, then,” she jerked her head towards the door. I nervously skittered out and across to Zack’s office.

The door and walls were solid wood, at odds with the rest of the office which had clear glass walls. I gently knocked and waited for him to call me in.

“Ah, Florence,” he beamed as I tentatively stepped inside. The automatically closed behind me and I thought I heard the subtle click of it locking itself but was sure I imagined it.

“Hello, sir,” I stood in front of his desk, hands clasped demurely in front of me. The back wall of his office was floor-to-ceiling glass, looking out over the city. I noticed a few other office blocks in close proximity that could likely see in.

“Come here then and say a proper hello,” he swivelled towards me in his large, cushiony chair and patted his knee. After a moment’s hesitation, I obliged and perched myself on one of his legs. I tried to remain upright, but as soon as I sat, he had curled an arm around my waist and pulled me towards him.

“Oh!” I gasped.

“That’s better, isn’t it?” he grinned, his other hand running up my thigh. I could smell his cologne, musky but pleasant, and felt the hardness of his muscles under his suit. I realised as soon as he pulled me in, he was much, much stronger than me.

“Yes, sir,” I swallowed, unsure what to do with myself. I was painfully aware of my breasts pushing through the see-through fabric of my blouse and my tight skirt riding up.

“Now, then, let’s go over some rules,” Zack continued as if my obvious uncomfortableness was a non-issue. His hand slipped between my thighs and stroked the nylon stretched over my skin. “Penny has probably already told you but no bra or panties in this office. I can see you’ve fixed yourself so I’ll forgive you for this one.”

“T-thank you, sir,” I stammered, my heart rate spiking at how high his hand was travelling.

We were interrupted by a knock at the door.

“Come in,” Zack called to my horror.

There was the electronic buzz of a key card and the door unlocked itself. An older man in a similar suit to Zack walked in. I immediately tried to dislodge myself from Zack’s lap but he held me with an iron grip.

“Don’t move unless I tell you to,” he growled in my ear, his earlier jovial tone evaporated.

I stayed where I was, but he didn’t loosen his grip, his fingers digging into the skin on my waist and inner thigh.

“Good to see you, Richard,” Zack resumed his handsome grin.

“Zack,” he other man greeted. “I see you’ve hired another secretary?”

“Isn’t she a beauty?” Zack replied, as if I wasn’t even there. “I was just performing her induction.”

“Ah,” Richard clapped his hands. “Fantastic. I’ll sit in if you don’t mind?”

“Be my guest.”

Richard sat himself in one of the other chairs lining the walls and watched.

“She’s been a bit of trouble so far,” Zack informed him before turning to me. “Haven’t you?”

“N-no, sir,” I wriggled under his grip.

“Came in wearing a bra, hasn’t been sitting still,” he shook his head as Richard tutted.

“Maybe she’s not cut out for the job.”

I froze at his words, devastated. I heard Mr. Miller’s cruel words echo in my mind.

I don’t think you’d make a good wife.

“No! Please, I want to be a good worker,” I told them. “Please, I’ll do what you say.”

The two men exchanged a look and I almost changed my mind, a small stab of fear in my chest.

“Alright, I’ll give you a chance to prove yourself,” Zack eventually said, to my relief. “Come into the meeting this afternoon.”

“Yes, of course, sir,” I nodded, smiling.

“I already shot a load into Penny this morning anyway,” he said to Richard. “Should give me enough time to recover.”

I looked between them, not sure what he meant, but smiling anyway to show my enthusiasm.

Zack released me and dismissed me from his office with another slap on my ass.

I bumped into Penelope outside, who shot me a sour look. I wasn’t sure what I had done to offend her but I was determined to make friends. However, as I was about to open my mouth, another man in a suit popped his head out of his office.

“Penny,” he barked. “Get in here, sweetheart.”

“Have you got permission from Zack?”

The man waved a paper slip at her.

“It’s my birthday,” he grinned.

Penelope straightened her skirt and strode over, not making eye contact with me, the door closing and locking behind her.

That afternoon, I made my way over to the board room, checking my appearance as I went. I wasn’t sure why it was important but I somehow knew that it was.

Zack and four other men, including Richard, were in the meeting room when I arrived. I heard the door lock behind me.

“There she is,” Zack smiled at me. “Right on time.”

I felt the other men’s eyes on me as I walked over, trying to channel Penelope’s confident walk, and sat on Zack’s lap. He pulled me in, like earlier, and seemed pleased.

“Well done, darling,” his hand swam up my inner thigh. “You ready to be a team player?”

“Yes, anything for you, sir,” I breathed, trying to calm my nerves. I didn’t want to be groped this way in front of all these strange men but I didn’t want to displease them.

Zack began unbuttoning my blouse until the cool air hit my breasts, stiffening my nipples. He squeezed them roughly while his other hand moved further up my inner thigh until it was resting on my vulva. Suddenly, he stiffened.

“What have you got on under those tights, Florence?” he asked, his voice low.

Fear constricted my chest as I realised I was still wearing my panties. I had forgotten to take them off.

“I-I’m sorry, sir, I’m so sorry,” I gasped but he only gave me a hard look.

“She’s broken the dress code,” Zack announced to the room. “You’ll need to be punished for this, you understand me?”

I nodded miserably.

“Get up and bend over the table.”

Obediently, I stood from his lap and walked to the large, polished oak table in the middle of the room. With my heels on, it was just the right height for me to bend over and remain pressed to the table. The way the chairs were angled, I would be bending over directly in front of all the men. I hesitated at this briefly before obliging, hinging myself at the hips, my legs straight.

My skirt had hitched up with the movement, barely covering my ass. This was made worse by a sudden kick to the inside of my left foot, forcing me to spread my legs. I knew everything was on show and I fought back tears, humiliated.

“Normally, I’d rip these open,” I heard Zack behind me as he fingered the nylon fabric. “However, you’ve broken a vital rule and worn panties underneath. So, I’ll need to pull everything down. I’m a busy man, Florence, so I need easy access. Wasting my time just means you’ll need to make it up to me.”

“I’m sorry, sir,” I whispered, my cheek against the cold wood.

“You will be.”

Zack forcefully yanked down my tights and panties and I couldn’t fight the tears anymore. I sobbed into the table as the air hit my bare pussy, my legs spread for all these strange men to ogle.

“Who wants a go?” Zack called to the room. The men cheered and I heard chairs being scraped back as they stood. My tears slipped uselessly onto the table.

I jolted at the first feel of fingers on my lips and felt my cheeks burn with humiliation as the men laughed at my wetness.

“She loves it, look,” one of them said and ran another finger down my pussy. I couldn’t help it; I felt the same arousal as when Mr. Miller forced himself on me and body responded by getting wetter.

One after the other, they explored me with their hands, rubbing my clit for a torturously short time before dipping a finger into hole. A few of them toyed with my asshole but Zack firmly told them that belonged to him. I could do nothing but wait until they had finished, my arousal growing deeper.

“Right, it’s time to see what she can really handle,” I heard Zack laugh and clenched my hands, feeling my fear climb. There was the sound of the other men cheering and laughing and a zipper being pulled down. “Now, Florence, normally I would make sure you were all ready for me because I’m a generous boss and I care about your well-being. But, well… you broke the rules, so you’ll need to face the consequences.”

Fresh tears poured out as I nodded, my eyes squeezed shut.

“Attagirl,” he slapped my ass one last time before I felt his head at my entrance.

He was not gentle as he pushed, and I realised how big he was. I cried out as he sank himself in me, my arousal doing almost nothing to ease the movement. There was a scattered applause from the other men as he buried his full length in my pussy.

“Well done, sweetheart,” Zack sounded slightly out of breath as his hands gripped fiercely onto my hips. He left a few seconds for me to adjust before pulling out and slamming back into me. He kept up a steady pace, using his iron grip to hold me in place while he pleasured himself. Despite myself, I felt myself getting wetter and the room was soon filled the sloppy sound of his cock in my tender pussy.

In my haze, I realised he was bareback.

“C-condom?” I whispered.

“What’s that, sweetheart?”

“Condom?” I said, slightly louder, still wincing at his cock as he sawed it in and out of me.

My question was met with more laughter from Zack and the rest of them.

“You love it raw, don’t you?” he replied, not breaking rhythm. “Look how wet the bitch is. She’s soaking.”

This returned yet more laughter.

“Please,” I begged. “Please don’t cum in me.”

I hadn’t started birth control since Mr. Miller abandoned me and I didn’t want to get pregnant. But my begging only spurred Zack on and he picked up the pace.

“Please,” I tried one last time but it was too late.

He buried himself in me with a moan, his cum spurting deep inside me. He remained that way for a few minutes before withdrawing. I felt his cum leak down my thigh.

“Don’t move,” he warned as I made to stand. I stayed where I was, terrified by the tone in his voice. There were a few moments of muttering between the men before I heard the tell-tale sound of a camera going off. I started to cry again as I realised they were taking pictures of my cum-filled pussy while I was bent over their table. I felt dirty and humiliated at the idea of their photographic evidence of my violation.

“Alright, get up.”

Miserably, I stood, pulling my tights and panties up. Zack’s cum was already leaking through. The men began to file out, giving me either a spank or a rub on the ass as they left. Defeated, I let them.

“I think you’ve been adequately punished, Florence,” Zack told me, tucking himself back in. “But don’t ever tell me not to cum in you again. This is your job so take what I give you, got it?”

“Yes, sir,” I bowed my head.

“Good,” he leaned forward and placed a hand on my shoulder, pulling me towards him. To my surprise, he dropped a gentle kiss on my forehead. Butterflies sprang up in my stomach and I swallowed hard; I knew then that I’d be back. That morsel of affection was enough for me to crave more of it.

Zack turned to leave as I stood there, my heart swelling and his cum soaking through my tights.

“I’ll see you tomorrow, bright and early.”

Source: reddit.com/r/Erotica/comments/xx1i5p/the_office_boss_22f38m_noncon_age_gap_humiliation