My day had started badly. First, I’d hit the snooze button one too many times, which meant that I could either shave or not be late for work. I’d chosen the latter for fear of being chewed out by my boss. Sleeping in also meant that I didn’t have time to put on a pot of coffee for me and my wife, who was already in the shower. I hoped she’d understand as I rushed out the door to catch my train. I’m useless without caffeine so I grabbed a coffee at the deli near the station. Of course, the train was packed so I had to stand, and half of my morning joe ended up on my shirt and tie.
Shit, I thought as I snuck into my cubicle, hoping to sort things out before my boss arrived. Her strictness is legendary in our office, and as her personal assistant, I often receive sympathetic looks and comments from my coworkers. If they only knew the half of it. I sighed to myself as I scrubbed my shirt with a tissue, which only made things worse.
I was so intent on what I was doing that I didn’t notice Stephanie’s arrival yet another strike against me. When the intercom on my desk buzzed I was startled, and my trepidation grew when she barked through the tiny speaker, “Get in here, now!” which, to me, sounded as though it had been loudly announced over the PA. I jumped up and buttoned my jacket, hoping that my imperious boss wouldn’t notice the stains.
Unfortunately, that was not the case. “I can see you’ve had your coffee,” she said coolly, and a chill ran up my spine. “But for some reason, you didn’t care about looking professional enough to shave.” My pulse raced as her eyes swept over me and, as often happens, my cock began to stiffen. This didn’t escape her exacting inspection: She looked vexed when her gaze reached my crotch. I just stared at the floor and waited, marveling to myself for the millionth time that such a small display of female power could make me so fucking hard.
“Look at me when I’m talking to you!” my boss snapped, and as I raised my head, I hoped the lawyer in the neighboring office hadn’t heard the reprimand. “Go get me a cappuccino while I figure out what I’m going to do with you.”
I rushed down to the lobby caf and ordered my boss’s drink the way she likes it: dry, with an extra shot of espresso. I paid for it out of my own pocket, not wanting to risk pushing her buttons any further by handing her a receipt. My dick throbbed while I ran my errand despite or perhaps because of whatever disciplinary action I was about to receive. Returning to the office as quickly as possible, I handed Stephanie her beverage.
“At least you can do something right,” she said with a snide grin before taking her first sip. “Now go home and clean yourself up, but don’t bother coming back until you’ve heard from me. I need to decide whether you’re still worthy of being my assistant.
My voice cracked as I responded, “Yes, ma’am.” Then I left her office, grabbed my things and headed home. I didn’t know how I was going to tell my wife that I might have lost my job.
After a trip to the cleaners, I spent the rest of the day scrubbing the house, wanting to temper Caroline’s inevitable anger. I even cleaned the gutters, hoping that would somehow soften the blow that I might be unemployed. My wife can be as demanding as my boss, sometimes even more so, and as much as that usually aroused me, I wasn’t sure about pissing off two tough chicks in one day.
Six o’clock arrived much too soon and with it, the sound of Caroline’s key at the door. I met her in the foyer with a freshly shaken martini in my hand, and she seemed a little wary as she took the drink and proffered her cheek for a kiss. “You’re home early,” she said, looking around, and I hoped she was taking note of the gleaming tiles in the hallway and the newly shiny brass banisters. Summoning all the nerve that I could, I started telling her about the day’s events, but she cut me off. “We’ll talk later,” she announced, before saying she was glad that at least the house was clean because we would be having company for dinner.
Something about the way she spoke to me told me that she already knew about my situation. I was ordered to retrieve the groceries from her car, which I then endeavored to turn into the best meal I could in the little time I had before our mystery guest arrived. I could only wonder who it was as I cut up vegetables and marinated steaks, because Caroline had gone to change her clothes without telling me anything, so I was totally unprepared when the doorbell rang.
I opened the door with my eyes already cast downward, so my first image of Mistress Stephanie, as I quickly learned to call her, was of the tips of her pointy black boots. Her look was a far cry from the staid businesswoman who had sent me home from work that morning. Her black hair was still pulled back in a severe bun, but she now wore sheer black stockings and a hip hugging leather miniskirt that barely concealed her ass, instead of gray flannel trousers.
The rest of her suit had been replaced by a silky black garment that highlighted her cleavage it was the merry widow that Caroline had given her for Christmas last year. Their friendship was how I had gotten my job. My wife had been dominating me since early in our relationship, and she felt that I needed to be watched even or maybe especially when we were apart. Her friend, who was a high powered lawyer as well as a domme, needed an assistant, which provided the perfect solution for everyone.
So there I was, counting the floor tiles while my hard on tented the jeans I guessed I wouldn’t be wearing much longer. Then I heard the sound of heels approaching from behind. “Don’t be rude!” I was admonished by my wife with a smack to my ass. “Take Mistress Stephanie’s things and invite her in.” She then addressed my boss. “I don’t know what we’re going to do with him. He can’t seem to obey either of us.”
“I have a few ideas,” Stephanie said with a wink as I took her bag and put it in the bedroom like I was told. Then, after I’d served the two dommes their dinner in the dining room, I ate standing at the kitchen counter, ready to put down my plate and be at their service at a moment’s notice. What I really wanted to do was peek through the door, getting even a quick glimpse of the two gorgeous women as they plotted my discipline.
My wife was wearing a PVC catsuit, her fair hair in sharp contrast to her friend’s dark tresses, and I was overcome with lust for them both. Being topped by two women was a new situation for me, and I wondered how to best serve a duo of dommes. My mind wandered, inevitably, to an image of them together, naked and embracing, their breasts pressed close as I moved between the moist petals of their pussies, licking voraciously. This possibility, while unlikely, was not out of the question because I knew they had a history, although details had never been divulged and I knew better than to ask questions.
I was so lost in my fantasies that I didn’t hear my name being called from the next room. Suddenly, the door swung open and my wife was standing in front of me. “We’re ready for dessert,” she said, obviously peeved at my inattention, and I knew I’d fucked up again when she glanced over at the coffeemaker sitting on the counter, cold and empty. “Really?” she asked icily, and I knew for certain that I was in hot water, especially when she told me that she’d take care of it and I should wait for them in the bedroom. “Naked, of course,” she called after me as I retreated upstairs.
After I’d stripped, I stood by myself in the bedroom for what felt like many hours. I couldn’t hear them, so I didn’t know if they were still plotting or simply wiling away the time talking about old friends or the latest episode of “American Idol.” My erection had deflated by that point the thought that they might just leave me there a definite possibility was too distracting. In fact, I was so overcome by worry that when the dommes finally pitied me enough to join me, my dick didn’t spring back to life it didn’t even give a tiny jerk or twitch.
“Look at that poor little thing,” Stephanie taunted at the sight of my flaccid member. This was the first time she’d seen me naked. I was embarrassed, but I felt a tiny rush of arousal when my boss reached out like she was going to touch me, however it subsided when she stopped short. I almost groaned with the frustration but luckily checked myself, because my wife said, “Go ahead it’s cool,” completing my fantasy.
Well, almost completing, and I knew that I was an idiot for expecting anything more than what happened next. The tall domme wrapped her fingers around my shaft and stroked me until I was once again turgid. My balls throbbed as she pumped my rejuvenated rod a few times, and I had to do multiplication tables in my head to hold back the orgasm threatening to burst loose. I assumed that it wasn’t her intention to let me come, at least that easily and without permission, and I also knew that was the quickest way to annoy both women further. Still, the handjob felt so good, so I shut my eyes and let the sensations wash over me.
I was still struggling not to come when I felt something constrictive being wrapped around my ball sac and the base of my dick. That was followed by a snapping sound and then the warm grip of Stephanie’s fingers disappeared. When I opened my eyes, both women were looking at the cockring that was holding me erect. “Now you’re ours to do with as we please, and for as long as we please,” my wife teased as she ran a finger over the band of leather holding me captive. This wasn’t a toy from our collection I figured it was from my boss’s bag of tricks, and I wondered what other naughty implements she’d brought.
I got my answer a moment later when I felt the sting of leather against one asscheek. I’d been too busy contemplating the cockring to notice the whistle of the riding crop slashing through the air. Mistress Stephanie was still in front of me so I knew that my wife was wielding the instrument, and I smiled at the thought of my petite, ladylike blonde laying into me like that.
“What’s so funny, slave?” snapped Stephanie, mistaking my pleasure for mirth. Her reprimand was followed by another sharp swat of the crop, and the resulting sting wiped the grin right off my face. A series of blows followed, raining down on my butt cheeks in quick succession, and I shut my mouth tightly, struggling not to make any noise. The slapping continued for a few minutes, cutting across my buttocks until both were warm, tender and, I guessed, a glowing, dark pink hue.
As the whipping intensified, I wanted to beg my wife to stop. It wasn’t because of any pain. No, it was because with each subsequent lash of the crop, the pressure in my cock and balls was ratcheted up another notch, until they strained at the band that restricted them. A droplet of pre come oozed from my crown, and I prayed that it wouldn’t drip off and soil the carpet. However, Mistress Stephanie noticed it first and, giving a little sigh of disgust, wiped off the offending moisture with a tissue.
I didn’t know how I was going to face her in the office after this, and then I remembered that I might not even have a job. If I was going to be unemployed, though, a night with two dommes was better than severance, especially now that one had laid down her crop and was tenderly rubbing my heated buttocks. I relaxed slightly, thinking that the worst was over, and was immediately forced back to attention by Stephanie, who didn’t miss a thing.
“On your knees!” she commanded, and I sank to the carpet with haste. “Do you realize how lucky you are to have a wife who cares about you enough to train you properly?” I nodded my head enthusiastically. Not a day goes by that I don’t count my blessings for Caroline, because a sub without a domme to serve is nothing. “Then thank her,” she instructed, reaching for my wife’s hand and pulling her toward me.
Caroline’s catsuit had a zipper that ran along its front, and Stephanie lowered it slowly, making my blood boil, which I’m certain was her intention. There was something about the way she looked at my wife’s tits as they spilled out that led me to believe that her blood was boiling, too. The zipper soon cleared Caroline’s pussy and her scent, musky and familiar, wafted over to me. I stuck out my tongue, eager to dive in, but she stopped me mere millimeters before I made contact with her fragrant slit.
“Where are your manners?” my wife asked, embarrassed by my behavior. “A good slave always attends to the needs of his mistress’s friends first.”
Thus directed, I turned back to Stephanie and waited as my wife returned her friend’s favor and hiked up Stephanie’s short skirt. Like my wife, she wore no underwear, and the only difference between them was that she was clean shaven. She spread her legs a little as Caroline took hold of the back of my head and guided me forward until my tongue made contact with her moist pink flesh.
My boss groaned as I licked up and down her labia, and my mouth filled with her nectar. I swallowed down the salty juices as I found her clitoris, which was as hard as a button, and zeroed in on it. First, I nipped it lightly with my front teeth, and then I toggled it with my tongue for a bit. Her body responded immediately, giving a quiver, so I continued my ministrations until she was quaking hard. Soon, she was shaking so violently that Caroline had to increase her hold on my head to keep me from being knocked over. Despite the difficulty, I persevered, and my lips grew slippery with her juices. The sound of panting from above me, as well as the fingers pressing into my scalp, urged me to work even harder.
I hoped that bringing my boss to climax would help me redeem myself after that morning’s blunders, but regardless, nothing would have pleased me more. That’s why, when she finally came, crying out, “Oh, yes fuck!” I probably would have come, too, but my cock was still cinched tightly at the root. She grabbed at my head, practically tearing out my hair, and her hips rocked back and forth to grind her cunt against my mouth. Meanwhile, Caroline increased her grip to ensure I wasn’t knocked over so that her friend received as much pleasure as possible. She only let go when Stephanie’s pussy became too sensitive and I was ordered to stop.
I waited for my next instruction. By now, my dick was throbbing so hard that it hurt, making me desperate for relief. However, my wife hadn’t come yet, so the cockring remained in place, my dick untouched, as I was ordered to the floor so that I lay prone with my erection sticking up straight, like a flagpole.
Caroline got on her knees and swung one leg over my body, spreading her cunt lips wide. They were shiny with dew, and she positioned herself over my crown, and then lowered herself to envelop my velvety knob with ease. Next, she slid down my length slowly, no doubt to torment me even further, before rising up again, dragging her labia along my shaft. She began riding my hard on at a lazy pace, using it like a dildo, until my frustration reached a point where I thought I might burst regardless of the cockring.
From my position on the floor, I saw my wife’s breasts hovering above me. I knew she was as turned on from the games we were playing as she was by the sex, so I struggled to remain in character and not come until I’d received permission. In order to play the good slave, I closed my eyes and gritted my teeth, trying to hold back the inevitable geyser. This grew more difficult as Caroline’s arousal mounted, and she was soon gasping and moaning above me, the walls of her pussy spasming around my stiff rod. She seemed more excited than normal so I looked up and saw my other mistress straddling my legs behind her, squeezing and pinching the erect tips of my wife’s heaving tits.
If that didn’t test my willpower, nothing would, and aware of that, the two women put on quite a show. In addition to the breast play, Stephanie nuzzled the nape of my wife’s neck and ground her pussy against her back, as much for my benefit as her own. I clenched my fists and looked away, knowing from Caroline’s familiar noises that she wouldn’t be able to hold on much longer anyway. She soon began bouncing on me fast and hard, her ass slapping against my thighs as Stephanie urged her on. Finally, she let loose with a loud cry, her cunt constricting around my shaft with a series of forceful spasms as she crashed down on my body and slumped over.
No time was wasted after that. Quickly, Stephanie helped her off me. Then she reached for the band of leather around my overly sensitized dick and yanked it off. Without any warning, my floodgates opened immediately, sending the churning contents of my balls rushing through the slit in my crown. My cock pulsed furiously as my load spurted onto my quivering stomach, and there was so much of the sticky goo that what didn’t pool in my pubic hair dripped onto the carpet on both sides of my torso.
“Would you look at that?” Stephanie commented to Caroline as they stepped away from where I was lying and straightened their clothes. “He still doesn’t know how to avoid making a mess.” She gave me one last look so filled with obvious disdain that my cock once again started to rise, and then they left and my wife accompanied her friend to the door. As I got up and started cleaning the wet spots from our carpeting, I realized that I still didn’t know if I’d been fired. Not that I really cared spending an evening in the thrall of my two mistresses had been so rewarding that nothing else mattered.