Finding Out Who’s The Boss
Life was good. I had a great job doing what I liked, and unbeknownst to me, things were going to get a lot better excitingly.
The day my life would be entirely changed was a late Friday evening. I returned to the office as I realized I had forgotten something. The office space wasn’t massive as our company was small, consisting of 15 people, so the walk to my desk was relatively short. It also meant that sound often carried clearly throughout the office walls.
And on that night, the sounds I heard were unusual. I could hear the distinct sounds of slapping and muffled voices. Curious about the noise, I cautiously made my way to the source, leading me to my boss’s office.
The door was closed hence why the noises were so muffled, and the blinds to the windows were also closed, preventing me from looking in. My curiosity was peaked at this point, and to better understand what was going on, I placed my ear against the door, trying to listen in.
WHAP! WHAP! WHAP! I thought it almost sounded like someone was getting whipped by a leather crop.
“You like that… punished… Slave? Yes, Mistress, thank you!” I only caught these few words, but I could tell there were two people, one man, and one woman.
While I couldn’t quite make out everything that was said, from what I heard, I had a good idea of what was going on behind the door. It was something straight out of one of the femdom erotica I read or the porn I watch; my boss was being dominated sexually.
This can’t be real; this only happens in erotic fantasies, but I found myself getting turned on at the thought of my boss being dominated by his mistress in his office, no less.
I’ve always had submissive fantasies, fantasizing about a strong dominant woman humiliating, controlling, and using me sexually. So to find me in a situation where someone else was living that fantasy with only a door separating us, I couldn’t resist. Slowly and carefully, I cracked open the door to peek in. I was met with the stunning sight of Robert, my boss, kneeling naked except for a blindfold and a collar around his neck that said “SUBBY” in metal letters.
To see Robert in this position was shocking, to say the least, as he is a caucasian man in his early 40s with salt and peppered hair, 6’0 and relatively muscular. Combined with the fact that he usually comes across as an alpha male, seeing him so submissive was highly erotic and shocking. However, the surprises continued as I continued observing.
“Look at you, my pathetic little Subby Hubby. Your tiny slave dick is hard for me. Maybe I should dominate you in your office more often.” Whap, she punctuates her point with a strike to his chest with her riding crop.
“Whatever will please you, Mistress!” Robert’s boss responds to her.
As I watch this woman, apparently my boss’s wife, circle and deliver strikes with her crop, I digest the information I’ve learned.
My alpha boss is a submissive slave to his wife, and this doesn’t seem new to them.
Before I can ponder further, I realize that Robert is now kneeling alone, his wife entirely out of sight, but I quickly find out where she went as the door is yanked open, and she’s standing in front of me.
“Well, hello there, you naughty little boy. Enjoying the show?” She asks threateningly as she places her crop right at my crotch, ready to strike.
Stunned, I can only mutter, “I’m sorry, I didn’t mean to. I just came back for some things I forgot.”
She laughs at my response and then flashes a menacing look at me. “Your sorry, you say, and you didn’t mean to. What a lame, sorry ass fucking excuse.”
At this point, she’s now standing just inches away from me, and I can’t help but look her over.
She’s a beautiful Asian woman who looks like she could be in her late twenties but based on conversations with my boss. I heard she’s only a few years younger than him. While she seems to be about 5’6, I estimate that the thigh-high leather boots she’s wearing give her an extra 4 inches, making her usually 5’2. As my gaze moves up from her boots, I notice her exposed hips, as she’s wearing some latex corset leotard with a zipper leading up to her nice B-cup breasts. Her sexy dominatrix outfit is completed with latex gloves covering her arms up to her elbows.
I’m brought out of my lustful gazing, though, by a light strike from her crop to my crotch area, which brings my attention to her soft, delicate face, which has an angry scowl.
“I hope you’ve finished staring at me, you naughty boy. Take one more look at my body, and I’ll give you much more than a warning strike, am I understood?” she says it with such authority that I know it’s a command and not a question.
“Yes, ma’am,” I answer right away.
“Good, now come with me,” she says, pulling me by my arm with surprising strength but not enough where I couldn’t easily overpower. Yet I can’t help but obey, and I’m now standing over my still-naked boss, who has remained silent this whole time. Once positioned where this beautiful Asian goddess wants, she moves behind Robert, her cropless hand on his blindfold.
“Well, Hubby, it’s time for us to see which one of your employees were spying on us.” She then rips Roberts’s blindfold off, revealing me to him. I stand there awkwardly, seeing the surprise, embarrassment, and submission in his eyes as he looks at me.
“That’s Mike, my love. He’s the young man I recently told you about that I hired straight out of college.” Seemingly satisfied with his answer, she moves away from Robert and begins circling me like a shark.
“So Mike is it, not bad. You’re an attractive specimen. Now, Subby, tell Mike the nature of our relationship and why you’re kneeling there naked.” She doesn’t look away from me nor cease her circling as she orders Robert.
“Please, Mistress, he’s my employee. Don’t make me tell him.” I’m shocked at how submissive my boss sounds as he begs her. she doesn’t say anything until, during her circling, she delivers a firm strike to his cock and ball area. This brings out a yelp of pain from him, but she ignores it and keeps circling me, never breaking her stride.
“Mike, this beautiful, dominant woman you see here is May, my wife and my Mistress,” he says, his voice full of pain. He continues.
“We’ve had this Mistress Slave relationship for the past five years, starting when I confessed my submissive desires. Since then, she has dominated our sex life; she controls my household while I run the business.”
Before Robert can continue, though, May ceases her circling, standing right in front of me while her back faces her husband.
“You see, Mike, I’ve found that I like dominating men, controlling them, and putting them in their proper place. however, I’m also a private person, so I’m content letting Robert maintain the public perception that he’s an alpha male.” She then turns sideways so that I can look at Robert, and Robert can look at me. She also points her crop directly at his crotch.
“I mean, just look at him, boy, look at the REAL Robert and tell me who you think runs this relationship. I’ll give you a hint it certainly isn’t the one kneeling naked with their little dick hard.”
Taking the hint, I look down at my naked boss. This successful businessman who gave off every impression of being a dominant alpha male was kneeling naked in his own office. What’s more, with his larger, more muscular body, he could easily overpower his small petite wife, but instead, it was evident that this was what he wanted. Despite his expressions or reluctant tone, his rock-hard erection betrayed him. I also realized why she kept insulting his dick size; despite his large frame, his dick was tiny. Even from where I stood, I could tell it was rock hard, but it looked like it only measured a measly 3.5 inches.
Robert must have seen that I noticed his under endowment as he bowed his head in shame, but the twitch of his dick betrayed him. It was apparent that the humiliation he felt from being exposed was turning him on.
I don’t know how long I spent looking at Robert, but I knew that I wanted this. I wanted a strong dominant woman like May to put me in this position, to dominate and control me sexually, using me for her pleasure. My erection was growing in my pants as I thought more and more about it until the silence was broken by May.
She made a coughing sound which brought my attention to her, and I saw a knowing smirk on her face. She then moves to the side of me, staring down at Robert as he now looks up at May and me.
“I take it that you need another hint then. Robert, be a dear, and tell Mike what you are.”
I can see the despair on Robert’s face as he seems to understand what he was just asked to do.
“I am Mistress Mays little dick Subby Hubby; I live to serve and meet my Mistress Wife’s every sexual need!” Silence fills the room until May whispers in my ear.
“There should be no doubts now about who is in control of the situation and my relationship with my husband. The only thing that’s left for you now, though, is to decide between three different options. You can either walk out of this room and expose us, of course, no one will believe you, and well sue your ass into the ground for defamation. You could just walk out of here and pretend that nothing happened. Or you can choose the option you and I both know you’ll pick. You can stay and submit to me. I’ll train and make you just as obedient as my husband, plus you’ll get the chance to earn the right to serve a gorgeous mistress like myself.”
Once May has laid out my options, she walks over to Robert and stares at me, waiting with that all-knowing look on her face. I knew what I would choose as soon as she said it, so I immediately started to answer, but she stopped me.
“I don’t want a verbal answer, Mike. If your choice is one of the first two options, just leave. But if you choose the third option, you’ll need to strip naked, crawl to me, and kneel at my feet.”
My heart races as wordlessly I start stripping. I see the satisfied look on May’s face as she watches me closely. I’m standing in nothing but my underwear when May stops me.
“Wait, I want to admire the view a bit; give me a twirl, boy.”
I obey, turning in place as I see May taking in my entire 5’10, lean muscle, naturally tan Hispanic body. After turning, I noticed she was also staring at the prominent bulge in my underwear.
“Not bad. Looks like I’ve found myself a nice hot submissive stud. Now take off that last bit of clothing and crawl to me like a good little boy.” She says, pointing at her feet.
Nervously I pull my underwear down, my heart racing at having my deepest fantasies about to be fulfilled. When I pull down underwear, it causes my rock-hard 8-inch cock to flop out, which May gets a chuckle out of. Fully naked, I lower myself to my knees, and then as instructed, I crawl to kneel at May’s feet. My eyes go up from the bottom of her thigh-high boots to her face; she smirks at me.
“Well, isn’t this a lovely sight, a hot young stud ready to be trained and earn their place as my new slave? And take a look, Robert. He has a real cock, not some worthless little nub like yours.” I can’t help but look at my boss to see his reaction to hearing his wife talk about the difference between our cock sizes.
He looks embarrassed as he stares at my cock, noticing our apparent differences. Where his is short and skinny, mine is long and thick. However, before I can feel too proud of myself, I feel the flat of her boot pressing against my dick and pushing it against my stomach. While May isn’t pressing hard enough to hurt me, it does an excellent job warning me that she could easily make it hurt.
This brings my attention back to her as she looks down on me with a wicked grin.
“Don’t go getting full of yourself, boy, you might have an impressive endowment, but that means nothing to me. You are a naughty untrained submissive little boy, which means that you and that massive cock are beneath me.” she punctuates this point by rubbing my cock with the flat of her boots, then continues.
“You will soon learn that your purpose is to serve me and my sexual needs. Am I understood, boy?”
“Yes, Mist…” before I can finish, May strikes me with her riding crop, which doesn’t hurt but comes as such a surprise that it causes me to yelp at the strike.
“You haven’t earned the right to call me Mistress yet, boy. Only those I’ve taken in as my slaves may refer to me as Mistress. As far as I’m concerned, you are just an untrained submissive welp who wants to become my slave stud. Don’t worry; that might happen if you do well during your training. Until I deem you worthy of being my slave though you will refer to me simply as Miss, Miss May, or Ma’am, am I understood?”
“Yes, Miss May,” I answer, admittedly feeling slightly sad that Miss May doesn’t consider me her newest slave but as just some boy she might reject. Miss May must have noticed my disappointment as she took her boot off my cock so she could squat down and look me directly in the eyes.
“Don’t look so sad, boy. If you behave and do as I say, you will earn the right to be my new slave boy. And I have a feeling you won’t disappoint me.” she gives me a light slap on the cheek before standing back up and walking to Robert’s desk behind her.
I can’t see exactly what she’s doing, but from what I can tell, she’s rummaging through a bag on the desk. Robert and I look at one another, seemingly feeling equally awkward and embarrassed, before looking away from one another. I’m thankful that it isn’t long before Miss May returns. She left her riding crop on the desk and exchanged it for two sets of leather cuffs. She is standing between Robert and me with the cuffs in her hand, the two of us wondering what she has in store for us.
The anticipation is excruciating as we wait for her to break the silence when finally, she does. She looks down directly at me.
“Stand up, boy.” confused, I immediately do so, and before I can wonder what she has in store for me, she guides me to a chair in front of Robert’s desk. She then pushes me down onto it. Without a word to me, she uses the cuffs to restrain each of my arms to one of the arms of the chair.
Miss May takes a step back and leans on the desk so that her ass is resting on it, but her feet are still firmly planted on the floor.
“Now, boy, you interrupted me and my husband’s fun, and while I would like to start your training immediately, I have some unfinished business with my Subby Hubby to attend to. So you be a good boy and just enjoy the show. This will also be a great opportunity for you to get a little preview of what being my submissive slave will entail.”
She then looks away from me and turns her attention toward her husband, who hasn’t moved from his kneeling position on the floor.
“Come here, Subby, crawl to your Goddess wife. I want you on your best behavior so that you can set a good example for your employee.”
Instantly Robert crawls towards Miss May’s feet with zero hesitation. I also notice Robert’s posture; he’s kneeling without his butt resting on his feet, his back completely straight, and his hands behind his back. I can’t help but wonder if this is how Miss May expects her submissives to kneel at her feet. Before I can think about this further, I see Miss May place the flat of her boot on Robert’s dick, much as she did to me earlier. However, I notice that, unlike with me, her boot entirely covers his 3.5-inch dick. Miss May must have thought the same thing as she smirks at this and begins degrading him for it.
“Look at that, my little Subby Hubby. My boot covers your little dick completely, but did you notice when I did this to Mike’s cock that it wasn’t completely covered?”
“Yes, Mistress, I noticed that his dick is significantly bigger than mine,” he says with his head down, unable to look at his wife.
“Oh, there’s no doubt about that. If I had to guess, I’d say his dick is at least twice as big as yours. Then again, we both already know how pathetic your little dick is, but you like it when I tell you how small and pathetic you are.” Miss May starts to rub her boot on Robert’s dick before continuing. “Especially when compared to men with a proper dick. I bet this is turning you on so much that you are starting to leak, aren’t you?”
“Yes, my Goddess wife, I love when you degrade my inferior dick, especially when you compare me to other men… And yes, Mistress, I am leaking.” Miss May smirks at that statement and then lifts her boot, rubbing Robert’s dick toward his face.
Even bound from where I am, I can still clearly see the precum that has gathered on the bottom of Miss May’s leather boot.
“Clean up your mess, you filthy pervert!” I watch in awe as, with zero hesitation, my once alpha male boss begins devouring his precum from his wife’s boot.
I watch as he vigorously licks it all up; I’m slightly impressed and turned on, as while I’ve always fantasized about being made to eat my cum I can never go through with it. Miss May notices me looking at this display with great lust, and for the first time since binding me to the chair, she acknowledges my presence.
“Do you like what you see, boy? Take note of just what a good obedient slave my husband is. With no hesitation, he devours and eats his cum. He knows that if he makes a mess, he must clean it up, or any other messes I tell him to.” she says this last part with a slight wink.
Her attention is directed back to Robert, who has cleaned up the precum from Miss May’s boot. With her free foot, she pushes Robert away obediently he backs away.
“I’m sure by now that you’ve adequately cleaned up your mess, haven’t you, Subby.”
“Yes, Mistress, it is all cleaned up.”
“Good boy, now tell me, you ready for the main event?”
“Yes, Goddess May, please. I’ve been looking forward to this all week!” An evil smirk forms across Miss May’s lips as she looks down at Robert.
“Tell Mistress what you want then, Subby, tell me loud and proud what you’ve been looking forward to all week.”
With zero hesitation, Robert loudly proclaims, “Please, my beautiful, gorgeous Mistress Wife, please peg your obedient Subby Hubby. I beg you. Please fuck me in my own office with your strap-on, fuck me away in my place of power!”
Miss May laughs at Robert’s statement, and I see her reach for the bag next to her on the desk. She rummages in there until she finds what she’s looking for. It’s a strap-on harness with a flesh-colored rubber dildo the size of my cock attached to it. I look at it wide-eyed, shocked that she will use such a large strap-on to peg Robert.
The look on Robert’s face, though, as Miss May brandishes that enormous cock in front of him, is ecstasy and desire. She hands the harness over to Robert and then tells him, “Put it on me, Subby.”
“Yes, Goddess May.” Eagerly he begins putting the harness on Miss May, placing it at her feet to step between the straps, and then slowly slides it up her body.
As Robert sinks back to his kneeling position waiting for Miss May’s following orders, I can’t help but be stunned at sight before me. I didn’t think Miss May could look any more dominating, but as she stands there in her dominatrix outfit, now brandishing a strapon dildo the size of my cock she has accomplished precisely that.
Not wasting any time now that she is wielding a massive cock of her own. She grabs a handful of Robert’s hair and begins cock slapping Robert across the face with the dildo. Each slap makes a resounding thud while Robert kneels there, taking it.
“Open that slutty little mouth of yours, Subby!” she commands; Robert instantly obeys, opening his mouth wide, and without any delay, Miss May shoves that rubber dick down Robert’s throat.
I assume that this isn’t the first time Miss May has used this size of dildo on Robert before, as he can take 5 inches of that thick monster before he starts choking and gagging on it.
“What a cock hungry slut you are, Subby. It’s easy for you to take over half of this cock in your mouth. Seeing you be such a capable slut just fills Mistress with pride, but remember you need to be a good boy and slobber all over this cock so you can get it nice and lubed up.” There is a sadistic grin on Miss May’s face as, without warning, she pulls Robert by his hair and forces him to take another inch of her rubber cock.
I can hear him sputter and gag on it, seemingly only urging Miss May on to further fuck his throat. Then, suddenly she pulls out of his mouth, but before Robert can respond, she’s pulling him up by the hair, barking orders at him.
“time to see how good of a job you did lubing me up, Subby. Stand up and bend over! Now spread that pretty ass for me!”
Miss May pushes Robert so that he’s bent over the desk. I can tell he still hasn’t fully recovered from the throat fucking as he looks like he’s in a trance. He collapses his upper body onto his desk, face turned to the side, but he obeys Miss May’s command as he spreads his ass wide. When he does this, I notice a black rubber hook-looking thing protruding from his ass hole that I hadn’t seen until now.
Before I can debate it, Miss May places one hand on Robert’s ass and the other on the hook. She then pulled on it hard, revealing that it was an anal bead plug. Once fully pulled out, Robert lets out a loud moan of pleasure, his head and back arching backward.
Entirely pulled out, though, I looked at the anal bead plug. Eight beads looked to have been spaced out an inch apart from one another.
Not wasting any time, though, Miss May quickly tossed the beads aside and grabbed some lube from her bag. She squirted a decent amount on the strap-on before shoving it in Robert’s stretched ass. This brings another loud moan out of him as Miss May thrust just half of the 8-inch dildo into his ass.
“That’s it, Subby, take my cock. I know your bitch ass can handle this!” Miss May then delivers a hard slap to Robert’s ass as she continues taunting him. “You know most bosses would love to fuck their wives in their empty offices, but not you, my Subby Hubby. No, you’d much rather get fucked by your Mistress Wife!” she punctuates each word with a hard thrust that has Robert moaning.
I can’t believe my eyes as I watch this erotic scene of dominance; my cock is rock hard at watching this scene unfold. It aches to be touched as I imagine myself in Robert’s place. My imagination is interrupted by a loud moan of submission as I watch Miss May shove all 8 inches of the strap-on into Robert’s ass.
“Ooooooh fuck, Mistress! Pl-please ah m-more!” Robert can barely form coherent thoughts as Miss May has begun to pound her husband’s ass.
“That’s right; Hubby, take my cock! This is how you fuck someone into submission! This is what happens to pathetic submissive little dick losers like you, Subby! They get fucked by their Mistress wives by a cock that dwarfs them!”
“Uh ah, y-yes Mistress, I’m a pathetic small dick lo- loser who loves the taste of your strap-on! Ooooh, please, my beautiful God-Goddess wife, I’m going to cum! P-please, I beg of you, t-touch my insignificant little dick, Mistress!”
I look on with great desire, noticing that Roberts rock hard 3.5-inch dick is leaking precum profusely; it’s incredible to watch as this entire time, Miss May hasn’t touched it once.
“Oh, what’s wrong, my Subby Hubby? Is a prostate orgasm not good enough for you tonight?”
As Miss May waits for an answer, I notice that she reaches down between Robert’s legs with one of her latex-gloved fingers and begins sliding her finger along his dick. She slides one finger along his short shaft; typically, this might be nothing more than teasing, but in Robert’s current state, it must be heaven. I would kill to have that latex-covered finger sliding on me like that.
“Oh, Mistress May, that feels so good! It’s not that it’s not good enough, just please, I haven’t felt your touch on my dick in so long. And I’m so close right now!” Miss May slows down her pounding of Robert’s ass, content to let it fill him up as she debates.
I can tell this must be torturing Robert as he fights the urge to squirm on it for stimulation. After finishing her debate, Miss May breaks the silence.
“I’ll make you a deal, Subby. I’ll jerk you off until you cum, but you’ll have to cum all over your face, and you won’t get to watch me ride Mike’s cock to orgasm.”
Oh my god, I think to myself. She wants to ride my cock! It twitches with anticipation at the thought of having this beautiful Asian Goddess riding me, filling up her pussy in front of her husband, who just so happens to be my boss.
“I-I accept those terms, Goddess May….”
“I knew you would, my pathetic little Subby Hubby. Get into position then!” Miss May pulls her strap-on out of her husband’s ass, which brings a groan out of him.
I watch as Robert positions himself in a way I’ve seen many times from watching self-facial CEI clips. He’s now resting his shoulders and neck on the floor, with his legs flipped over him. This puts his dick directly over his face, and I can’t help but think that because his dick is significantly smaller than mine, it’s not directly over his face.
Once settled in this position, I watch as Miss May moves behind him in awe as she reinserts her strapon into her husband’s ass, so she’s now piledriving him. Quickly she takes his dick into her latex-gloved hand and begins pumping it.
“Mmmm, that’s it, my little slave Hubby. I hope you didn’t think I’d let you cum without having your ass filled with my cock. Your a little submissive bitch, so you are going to cum like a submissive little bitch. Only now you get your tiny little dicklette played with, and you will have to paint your face with your pathetic seed.”
Miss May picks up the pace of her thrusting and pumping. I can tell that Robert won’t last much longer like this as his moans start growing in volume. Then suddenly, he lets out a roar.
“Oh please, Goddess May, please may I cum!?”
“Not just yet, Subby Hubby.”
“Oh please, I-I can’t!”
“You can, and you will bitch, or you’ll suffer!”
“Ah uh, oh god, Mistress!”
Miss May waits another 5 seconds, and still, Robert holds and then, “Fucking cum, my pathetic Subby Hubby, paint your pathetic face with your pathetic seed from your pathetic little dick. And keep your mouth closed. You don’t deserve to eat your cum tonight!”
At Miss May’s permission, Robert instantly explodes all over his face, blasting himself with ropes and cum. I don’t know how many ropes he shot out, but it was enough to paint most of his face, and Miss May ensured that as she directed every shot.
Miss May has a sinisterly satisfied smile as she starts undoing the harness. Once she undoes the harness from herself, she proceeds to strap the harness to Robert so that the strap-on is still inserted in his ass. She then leaves her husband there in a heap with his dick deflating and his face covered in his cum.
I watch as Miss May walks over to me, where I’m still bound in the chair. She then sits on my lap, crossing her legs over one another and wrapping an arm around me. Her eyes stare directly into my very soul as she has a delighted look on her face.
“So boy, how’d you like the show?”
To Be Continued…?
*This story has been edited to fix spelling, punctuation, formatting errors, & basic grammar, but the narrative and plot have remained the same. Remember, even with the limited editing we do, it doesn’t mean any possible major flaws in this story were fixed (That’s the author’s job). The opinions/views expressed in this story (and in any comments) are those of the author and do not represent this site. We support freedom of speech.