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Her Boss: A Dark Mafia Age Gap Romance by Trent Evans – Extended Preview

The last thing I expected an hour later was for Geneva to come bursting through my door, red-faced and enraged.

“I-I’m sorry, sir,” Chloe said, right behind her. “I tried to stop her. She… she says she has to talk to you.”

I suspected I knew exactly what the girl wanted to speak to me about. “It’s okay, Chloe. It’s all right. You can leave her with me. It’ll be fine.”

Reluctantly, she retreated, the door closing behind her with a soft snick.

“What the hell is this?” Geneva paced in front of my desk, the piece of paper I’d given her clenched in one fist. “I show up at this place, this dump, and the bitch running it tells me to take my rags off. Rags? What the fuck?”

I laced my fingers behind my head, plastering my best shit-eating grin on my face. I knew exactly what treatment Geneva would have received from Brooke, the proprietress of Unmentionables, the store I’d sent Geneva to for her work-appropriate clothes. “Yes, and what seems to be the problem?”

Problem? The bitch basically said I needed to strip naked so she could”—Geneva held up air quotes—“‘see what I’m working with here.’”

I sighed long and loud, leveling a glare at her. “What did I tell you?”

“This cunt seems to think that dressing me in slutty lingerie and revealing street walker chic was what was needed for this j—”

“I said, what did I tell you? Answer the question, Geneva.”

Her mouth opened and closed silently, her eyes fluttering, the girl apparently losing the power of speech for a moment.

Answer me!” I snapped.

“I-I don’t know.” She glanced down. “To do as I’m… told? I guess?” She flashed a defiant glare at me though. “But that doesn’t mean she has any right to—”

“Shut that mouth,” I said quietly, meeting her gaze.

“—tell me to take all my shit off and… uh, what?”

“Stop talking.” I rose from my chair, walking slowly around my desk, the tips of the fingers of my right hand posed upon the desktop as I moved. “And listen to me.”


“That isn’t being quiet.” I walked up to her, placing my hand across her mouth. My big palm covered the entirety of the lower half of her face. Her skin was impossibly soft and smooth. “Shhhh.”

Wisely, she simply nodded, her pretty blue eyes big and bright as they peered up at me. The fright, confusion, and something else much, much more embarrassing for her swirled in those gorgeous liquid depths.

“You don’t seem to understand your position here, Geneva. So, I’m going to explain it for you. But you don’t get to reply until I think you finally have learned how to behave. How long it takes for me to be satisfied on that front is entirely up to you. Got me?”

She nodded, her cheeks suffusing with a deep red.

“Good. That’s a start. Now, I’m going to take my hand away, but don’t for one fucking second think that that means I want to hear anything coming out of that smart mouth of yours. Not one little thing, you hear me?”

Another nod.

I removed my hand and sat down on the desk in front of her, crossing my ankles. “First. Don’t you come bursting into my office ever again. I could have had a client in here, or I could have been on an important call. Or I could have been doing nothing more important than having an afternoon fucking snooze. The point is, any and all of those possibilities are more important than your perceived right to come barging into a room where you haven’t been given express prior permission to enter. Am I making myself perfectly clear?”

Her slender throat worked, her plump lips showing just a hint of trembling. Her quick nod, pregnant with reluctance, was so subtle, I almost missed it.

“Now, you’re finally getting it.”

I stood once more, strolling around her in a long, lazy circle, certain her fear and embarrassment at having been called on the carpet would keep her rooted to her spot.

She didn’t disappoint. The only part of her that moved was her head, as she watched my every step, her eyes following me as I paced around her.

“Second. When I give you an order, and you disobey, there will be no repeating of that order again. It’ll be assumed that you just didn’t feel like following those orders. So, there will be consequences. We’ll be taking care of those now, right here in this office.”

Her lashes fluttered, her lips forming silent words, as if she meant to speak. My raised finger stopped her in her tracks though. “You want to keep digging that hole? Go ahead and talk. Say anything you like. If not, keep quiet.”

She snapped her mouth shut, looking down at the floor. Geneva had never looked more adorable than she did in that very moment.

But I’d be damned if I was going to tell her that. Because she needed to learn.

The hard way.

I pointed at the desk. “Bend over the front of that.”


“Do you have trouble hearing me?” I stood close to her, towering over her petite, and now clearly quivering, form. “Over the desk. Cheek to the desktop. And wait.

Be careful, Rick. This is Chester’s niece here.

But it wasn’t going to stop me. Not in the least. I needed to test her, to see what she’d accept.

I waited patiently for Geneva to either comply or flee the room. If she did the latter, we both knew her internship would be over.

For a moment, I considered the possibility that I’d pushed her too far, that she would indeed balk and take flight out of there.

Then, her intake of breath panicked and shallow, she advanced to the desk and laid herself down upon it. She was wearing the same navy blouse with the diamond-shaped cut-out over the chest that hinted at her cleavage. But I wouldn’t be afforded a view of that in her current predicament.

I would, however, take consolation in the mouthwatering sight of her black skirt stretched tight over a surprisingly broad, heart-shaped bottom instead.

My God, she’s going to wish she hadn’t been born with that gorgeous ass when I’m done with it this afternoon.

Even better, I’d noted her nipples while I was scolding her. Either she’d decided to go sans bra, or she was so turned on by my verbal dressing down of her that her steel-hard nipples were visible even through the fabric of a bra. I’d question her about that in due time.

First, there were other pressing questions that needed answering.

Let’s see where this goes.

It was then that I realized our interaction, and my treatment of her, had taken on a whiff of a paternal feel. It wasn’t blatant, but it was there.

Whatever one wanted to call it, there was indeed a subtle, but very real, sexual buzz in the office.

Perhaps it was my imagination—we’d find out soon enough either way—but if I were a betting man, I’d have placed good money that some of what had just transpired comported at least roughly with one or more things the young woman fantasized about. It wasn’t the first time I’d seen such a thing, but I hadn’t expected to observe it in someone like Geneva.

Her body’s reaction would help confirm or refute my little supposition.

Which filled me with both eagerness and a twisted, dark-hearted anticipation for what was going to come next.

What surprised me even more though was my own reaction. I’d never have thought I’d be into such a thing, but judging by the aching hardness of my cock, I’d been dead wrong about that, too.

I wanted to push her still further though. Much as Brooke had apparently told the headstrong girl, I too needed to see exactly what I was working with.

For an entirely different reason.

I wasn’t doing it solely out of prurience though. I really did need to determine what the girl was made of. If she would actually be a good fit working for me.

It wasn’t as if this would be the last time she’d be compelled to surrender her body in some way or another, as long as she was my employee. I’d rather figure out if she was into it, or completely wrong for it right up front though.

Chances were greater than zero that she’d stomp out and go tell Chester I was a controlling asshole—which her uncle already knew. If that were to happen, she’d actually be helping me, in a way. It would finally give me the cover to just say she was a troublemaker and wasn’t going to work out. Which wouldn’t be a lie, either.

Really, I had nothing to lose. I stood there in silence, watching her, and shockingly though she was clearly very embarrassed, she finally bent herself over my desk.

I strolled around the desk a couple of times just taking her in, focusing on the incredible sight of her ass. She was gorgeous. The skirt she was wearing was black and tight, clearly intended to show off her body.

And what a body it was.

It was actually an interesting contrast with the almost staid top she’d chosen, which was anything but scandalous. More than that, I was pleased at the breadth and roundness of her hips, the generous, soft curves of her ass. That was a part of a woman’s body that I could scarcely resist.

“From now on, Geneva, when you screw up, there are going to be consequences. This is just to show you that I’m serious when I say this. Do you understand me?”

“Yes… I think so. Sir.”

I allowed myself a silent smile about her seeming willingness to obey. It spoke volumes about her and encouraged me to both keep going, but to also perhaps be a bit less cruel with her than I had initially intended to be.

Something else I realized was that when I was talking to her and scolding her, telling her that there were going to be stricter measures taken with her… it was obvious that it was turning her on. The scent of her arousal had become detectable, her lips had swelled, the pace of her breathing increased—all of it signaling her true feelings about what was happening. I hadn’t encountered anything like that before with someone who worked for me.

Very interesting.

What was more, the fact that it turned her on, turned me on too. It was like a twisted, vicious circle.

“You will obey me, Geneva. So, get used to that now. You will do as you’re told. And if you don’t think you can do that, this is your chance, your one last opportunity to get that cute little ass out of my office. Have I made myself clear?”

Her head turned just a little bit, her eyes darting to the exit, then looking back up at me. Was she going to actually fail at the last jump? Or was her youthful eagerness and curious, hungry lust going to get the best of her? I knew what I hoped, but the truth was that the next few seconds would determine the entirety of our future together.

Future? You sound like a lovesick idiot right now. You sure you know what you’re doing here?

Finally, she took a deep breath, pressing her face directly to her folded arms beneath her. “Yes, sir.”

My cock got even harder at the sound of her trembling voice. I was so aroused I wasn’t sure what to do next, as if I were paralyzed by the tantalizing possibilities before me.

What the hell is going on?

But I decided to just go with it, see where it went. I had nothing to lose. If it went wrong, well, then I could say I at least tried, and I’d only be out an intern—and I might possibly have a new strained relationship with one of my best clients. For a while, anyway.

I placed a hand on the small of her back and her body tensed, but she made no move to get away or protest. “That’s good, just stay still. You’re okay now.”

Her hips shifted slightly, her quick shallow breathing the only sounds she made.

Finding the zip high up her hip, I drew it down slowly, until the skirt loosened and dropped to the floor at her feet. I was pleased to see that underneath she’d worn a sexy white lace thong.

“A thong to avoid panty lines?”

“Th-that’s not the only reason to—”

“You’re not fooling me.” I clasped her left bottom cheek, stroking it gently. “You didn’t want a panty line to mar the look of this slutty little skirt showing off your ass. Who were you hoping to impress, hmm?”

She made a frustrated noise, but didn’t reply.

“I think you wanted your ass to look as good as possible.” I patted her right buttock, giving the under curve a little pinch that made her tense. “While you are just a petite little thing, you do have a nice, round juicy bottom. And I’d be lying if I said I wasn’t very much looking forward to spanking it.”

She said nothing, her trim, but soft thighs just beginning to quiver the tiniest bit. I thrilled at the sight—and it only spurred me on to push her still further.

“Right.” I smacked her bottom gently. “Take down these panties for me.”

“W-what? Why?”

“Why do you think?”

Her hair flipped over as she turned her head toward me. “N-no, I’m not doing that.”

I clasped her hip in warning. “Yes, you will—or you’re out of here. No more internship. No more anything.”

It was the moment where she was most likely to balk and run. And I had no intention of stopping her if she did.

I would encourage her to submit to her discipline, but I would never force it. That wasn’t how I operated—and it never would be.

“I’m waiting, Geneva.” I squeezed her hip firmly. “Do as you’re told, right now—or get out. Last chance.”

“Fuck… fuck. Okay.” Hesitantly, she reached back with clearly shaking hands.

Though I wasn’t sure why, I took them in my own, and gave them a squeeze I hoped was reassuring. “It’s okay. I’m not going to hurt you, girl.”

“Y-you’re going to spank me. How is that not going… to hurt?”

“Yes, I am—and it will. But it’s not going to be anything you can’t handle. This is for teaching you a lesson, and ensuring you understand your place here. But you won’t be truly hurt. I’m not a brute.” I lowered her hands to her ass, pressing them there for a moment under my palms. “Not quite, anyway.”

Her hands didn’t move for a moment.

I patted her bottom. “Let’s get on with it. Panties down now.”

Fortunately, she decided to obey, and I cheered inside as her fingers hooked into the lace, drawing it out from the cleft of her ass, then down her trembling legs.

“All the way now. Drop them to your feet.”

Finally, she did, her hands hovering for a heartbeat.

“Fold your arms on the desk—and you’ll keep them there until I tell you otherwise. Move them, and this will be worse for you.”

In moments, her head was posed upon her forearms, and I beheld the beauty of her flawless bottom. On a lark, I spread her cheeks apart slightly, just enough to reveal clearly the dark whorl of her anus.

She mewled softly.

“Just need to inspect these holes, girl. Be still and quiet now.”

Geneva needed to learn that discipline from me meant submitting her bottom in every way, including being displayed, fondled, and inspected. Spankings weren’t only about punishment, after all. Gentle humbling and forced exhibition were essential to getting into the psyche of the penitent female receiving a correction. The pain was only part of it; reaching her mind and her emotional core, those places where she felt the most vulnerable, was as important, if not more so, than properly reddening her buttocks.

I wanted to see how she’d react to being inspected, to realizing that part of submitting to this arrangement meant allowing me to touch her anywhere and everywhere. In my experience, the process of humbling a woman meant steadily peeling away the layers of her defenses. That experience would generally do one of two things—either progressively reveal her for what she truly was, or illustrate in stark relief that she was indeed not the kind of woman prepared to genuinely surrender.

I touched the delicate circlet of her anus, tracing its outline with my fingertips, her tight hole clenching slightly. Rather than protest though, Geneva buried her face in her arms, her body staying very still.

A very promising sign indeed.

Even more encouraging was the strong scent on the air as I slipped two fingers between her legs, easing the delicate petals of her pussy open, revealing the tender blush rose of her exposed sex. “Mm, someone likes this, I think…”

“It’s… it’s not like that…” But there was no conviction in her whispered words.

I knew the truth. We both did.

Drawing close to her, clasping her upper hip, enabling me to pin her down firmly to the desktop, I pressed the bulge of my erection against the side of her bottom.

She gasped softly.

“Yes, this is part of it, too. Does it horrify you? That a man punishing you is excited by it?” I leaned over her, ensuring she felt the full length of my arousal against her. “Or is it quite something else? Is it that you’ve discovered the type of man who’s always appeared in your dreams? The sort of male mean enough to do to you what it is you really need?”

Her breathing was almost a pant. “No… it’s… I don’t like this…”

“But I don’t believe you. Not at all.” I patted the plump purse of her cunt, displayed as it was below the broad rounds of her buttocks. “This betrays the true you, Geneva. And I have a secret for you. I love that about you. Good girls don’t get wet and excited at being punished by a man, do they? What does that say about you? That your little pussy gets so wet and fragrant at the thought of how it’s going to feel having your bottom roasted under my hard hand. That you’re slick and hot down there knowing my cock is hard as steel as I look upon your perfect bottom laid bare and helpless before me to do whatever I want with it.” I pinched her left buttock, hard, until she squeaked. “And I will, bad girl. I intend to do just that.”

Not giving her so much as a second to reconsider, I smacked the upper curve of her right buttock, leaving my hand there for a heartbeat for the sting to sink in fully.

She clenched her cheeks tight.

“No. I want them soft. No clenching. The punishment does its best work on a soft, surrendered bottom.” I massaged her buttocks, cooing at her. “Come on, bad girl. Relax them. We won’t continue until you do. The sooner you give in, the sooner we can get through this.”

“I… please, I… don’t know what’s happening to me.” Her words held a poignant note of desperation, as if the last vestiges of her defenses were crumbling by the second.

“Shh, it’s okay. The only thing happening here is your surrender, and me showing you the error of your ways. When we’re done, and you’ve got a nice, stinging, red-hot bottom, and your pretty tears are streaming down your sweet face, all will be right with the world again. I promise.” I knew I shouldn’t do it, but her breathtaking vulnerability was already wearing down my own resolve, and I pressed a soft kiss to the silky hair at her temple.

Her hand shot out, grasping my arm, but it wasn’t to push me away. Rather, it was a frantic bid for comfort, for reassurance, that I wouldn’t abuse the power I had over her in that moment.

“It’s okay. Just relax. Let it take you under.” I smoothed a palm over her head. “I want you to accept all of it. I’ll be here at the end. You’ll see, beautiful.”

With that, I began her spanking. I believed that all spankings, to be the most effective, needed to start quite firmly, and not relent from that until the very end. There was no warming up her bottom, there was no easing her into things. If this had a possibility of going anywhere, then she had to know, in no uncertain terms, that I was that type of man who would hold her to account. The sort of man who would discipline her with the strictness, the consistency, and the determination that she truly needed—even if she didn’t quite know it yet.

I started with great slaps all across both her buttocks, judging by only the color of her flesh rather than her mewls, cries, and pained outbursts whether or not she’d received a sufficient dose. It wasn’t until the whole of her pretty bottom glowed a solid pink that I concentrated on the lower third of her buttocks, giving them harsh, steadily applied smacks, like pistol shots, that had her crying out at each one within minutes.

“Be still. Obey,” I admonished softly, pressing upon the small of her back, pinning her down completely as I laid another great smack across the lower curve of her right cheek. I concentrated there, slapping harder and harder, her bottom wobbling and bouncing with ever more abandon as her discipline went on.

At one point, she tried to slide sideways upon the desk, my hand slapping her upper thighs in quick, alternating succession. I took a handful of bottom cheek, squeezing it fiercely hard. “What do you think you’re doing?”

“I… it hurts! I’ve… had enough… I won’t do it again.”

“Oh, I know you won’t.” I laid down another whistling slap, catching her bottom under both cheeks, sending them bounding upward, the blow rippling through her soft, crimson flesh, her cry a piercing note signaling that the pain had begun to do its work upon her willfulness.

“Felt that one, bad girl?”

“Ah! Yes… ah, it’s so… hot! Stings!

“Then it’s working like it’s supposed to.” I gave her two quick ones, right on top of each along the outside of her left hip.

She bit off a scream at that.

“Surrender, girl. Give in. Let go of this silly willfulness.” I spanked her hard and fast the whole time as I spoke the words. Pulling up each buttock in turn, I laid down particularly harsh spanks upon the tender crease between bottom and thigh.

At the second one, she cried out, her voice breaking, then she burst into tears.

Her body sagged then, her head lolling upon her arms as she sobbed, tears pooling upon the worn, battered wood of the desktop. I gave her a few more spanks, searching for any further tiny sections of unreddened flesh. Then I held her there, my big hand spanning the breadth of her entire ass, just holding her there, protectively, my touch proprietorial. “It’s all done, Geneva. All done, sweet girl.”

Shocking me, she burst up from the desk, but rather than run from me, she wrapped her arms about me, the pitiful tears flooding down her red, blotchy face in twin streams, her crimson lips open, trembling, locks of her hair stuck to her wet forehead and cheek.

I bundled her into my arms, lifting her from the floor, and when I did, she cried even harder. She sobbed in my embrace like that for long minutes, and I remained silent, the tableau moving to me in a way I couldn’t quite explain, and with the instinctive knowledge that there was nothing to be said, that her flood of emotion was profound far beyond the pitiful reach of any mere words.

Instead, I simply rocked her, stroking her heated, sodden hair, kissing the crown of her head now and then. She burrowed even closer to me each time, until her head was wedged under my right jaw, her body curled up against mine, utterly vulnerable, utterly beautiful.

I didn’t want that moment to ever end.

Then, as quickly as it happened, she seemed to snap back to herself, her head raising from my chest, her bloodshot, bleary gaze upon me. “I… I don’t know why I did that. I’m… sorry, Rick. I mean… sir.”

“It’s all right,” I said, my voice thick. I cleared my throat, speaking the words in a gentle tone. “It’s all over, girl. All’s forgiven.”

Her smile at me, her breathtakingly beautiful tears still staining her cheeks, was a sight that I knew in that moment I’d never, ever forget.

“Yes, sir.”

But before I completely lost my head, the temptation to kiss the silly woman suddenly so strong it took Herculean will to resist it, I gently dropped her to her feet.

Geneva’s panties were still tangled around her shoes, the open-toed sandals a playful and pretty counterpart to the sultry skirt, highlighting her slim, toned legs. She moved to pull them up, but I stopped her with a hand under her chin.

“No, you leave them there. Those stay with me today.”

“B-but… I have to work… don’t I?” A deep crease formed between her gorgeous dark brows, her lips formed into an O.

“You do—and I expect you to try your best to learn the ropes as soon as possible, too.” I crouched down, helping her extract one foot, then the other from the tangle of lace.

I rose, holding up the thong and bundling it into a ball before stuffing it unhurriedly into my breast pocket, as if it were some sort of lurid handkerchief. The scent of her was strong on the fabric, and it made my mouth water. “Put your hands behind your back.”


“Do it.” I frowned at her. “Perhaps you need more?”

Her eyes went wide, her mouth dropping open. “N-no, sir!”

I dropped my gaze down to her sex, careful to let her see me doing so. The dark delta of her pubic hair was just visible under the front hem of her blouse. “Pull that up, girl. I want to see your cunt.”

Swallowing audibly, a deep blush suffusing her face, she nonetheless obeyed, the fingers of her hands trembling like leaves in a storm, drawing the hem up, revealing her sex in all its beauty.

“Now, that is very pretty,” I said, smiling at her. “I like this nice thick bush you have here. It’s refreshing. So many of you young women nowadays seem to have this pathological need to just shave everything off. This is much better.”

The bald cunt thing was a look I’d never warmed to, and I was quite certain I never would.

“I want you to keep that nice and trim, of course, but I much prefer the look of your pubic hair. Do not shave it off. Understand me?”

She nodded, her mortification coloring her face almost scarlet, her gaze locked to the floor.

I placed a finger against her slit, just holding it there, her flesh hot and slick to the touch. “I wonder something about you. Why did you let me do this? It’s not as if you need this job—you aren’t even being paid.”

Her white teeth worried the corner of her bottom lip, her glance up at me one purely of embarrassment. Her gaze dropped right back to the floor as soon as she caught my eye.

“So, why is that? Hmm, I’ll have to think about that one, I suppose.” I let her go then, moving back around my desk, and dropping into my chair. My cock was so hard, it was an angry ache at my groin. I unbuttoned my suitcoat. “You’re dismissed, Geneva.”

In a heartbeat, she dashed for the exit, yanking up her skirt as she went, zipping frantically, her back to me.

Then she fled my office, the door closing softly behind her.

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