My 5 Bosses

by Penny Wylder

  I giggle as I walk up the stairs toward my room. I have the biggest bed so that’s where we’re going. Jason comes up behind me and grabs me by the waist, stopping my ascent so Trey can pull my panties off. They go flying through the air. I have no idea where they land.

  Trey bends me over and spanks my ass. I yelp at the sudden sting of it. Then he kisses the hand print to soothe the redness and says, “Get your ass onto the bed before I tear it up right here on the steps.”

  I hurry to the room and throw open my door, the clamor of heavy footfall from my guys close behind.

  Trey sticks his tongue out and gives me a wolfish grin. “I’m going to destroy that ass tonight. But first I want you to get on your knees and suck my dick.”

  I love the way he bosses me around and takes charge. He’s not at all like that in our day to day lives, and I don’t think I would like him that way, but in the bedroom it’s sexy as hell.

  I kneel before him. He pulls out his dick and grabs a handful of my hair, forcing his cock down my throat. I lap it up, my mouth watering, drool running down my chin as I guzzle his cock.

  “Yeah, fuck that beautiful face,” Jason says as he strokes himself. The others strip out of their clothes and come over to watch as well. They stand in a circle around me, each taking their turn. I have to practically split my face open to suck Winston, barely able to get the head past my lips.

  Derrick says, “Lube?”

  My mouth is full so I point to the nightstand next to the bed. Inside is the lube along with all of my sex toys. He pulls out a butt plug and holds it up. “Hey, look at this.”

  “Bring that over here,” Beck says.

  Beck takes the plug and slathers it with lube then works it into my asshole. I wince a little as it enters, but once it’s in place it gets more comfortable. I bought it right after the first night I had sex with all of my bosses. Having five men with impressively large cocks, all wanting to fuck my various holes, I figured my ass could use the practice, so I’ve been using it every night to get comfortable with it. It’s only uncomfortable for the first few minutes, but after that, having something in my ass is heaven.

  “Bend over, let me taste that pussy,” Beck says.

  I get on my hands and knees, my ass in the air. He licks me from behind and tugs at the butt plug, but doesn’t pull it out. He adds two fingers inside of me, and it’s all starting to be familiar with them, but still exciting. The more we’re all together, the more they learn my body and know what I like. They are becoming experts in the subject of me, and the fact that they always seem to want to learn more, just makes my heart fuller each time I’m with them.

  Winston holds my hair like reins and continues to plunge into my open mouth. The others grow restless.

  “Pull that thing out of her ass,” Trey insists. “I want a turn.”

  Someone pulls my ass cheeks apart and the plug comes out.

  “That’s one gorgeous ass,” Derrick says while someone, I’m guessing Trey, spanks it.

  Winston pulls out of my mouth and I turn to see Beck waiting for me, naked on the bed. He sits up against the headboard, his legs splayed open, his dick on alert.

  “Bring that pussy over here,” he says.

  I crawl across the bed and lower myself onto his lap, sinking down on him until I’m fully impaled. He holds my hips and starts to rock his own. He always watches me during sex. I don’t know if I’ve ever seen him close his eyes, not even during climax. His gaze is just as penetrating as anything else on his body. It’s intimate and intrusive, and I think it makes me love him even more because it’s like he can see through me. He knows me. It’s not just about sex, it’s about me, and no one has ever made me feel the way Beck does. His love for me is deep and personal and I trust him more than I’ve ever trusted anyone. I will get there with the others but I’m already there with him, and because of that there’s a connection that I can’t deny. When we come together, it’s not just sex; we’re making love. Even when there are four other men stacked on top of me, writhing in ecstasy, and Beck is commanding me to look into his eyes while sticking his dick down my throat. It’s always something just a little bit more with Beck than it appears on the outside.

  He pulls me against his chest and kisses my cheek, then whispers in my ear, “You’re so beautiful.”

  He holds me tight as if he’s afraid I’ll disappear if he lets go. He rocks into me, slow and steady. No one seems to be in any kind of rush to get theirs the way they had been when they formed a train in the communal room the other night. They seem very content to watch Beck make love to me. In a subdued, almost casual fashion, the others lounge across the bed, stroking themselves to keep hard, but not to get off, and rubbing various parts of my body.

  I close my eyes and lay my head on Beck’s shoulder, enjoying the attention. Then someone breaks into my euphoria with a thumb at my back entrance. It’s lathered generously with lube, and due to my readiness from the butt plug earlier, slips right in. There’s something about ass play that turns things up a notch. It turns my guys’ subtle groans into animal noises. They come alive suddenly, poking and prodding like scientists trying to figure out how to break into me and see how I tick.

  They hover around, a dick at my cheek, one in my hand, but Beck holds me to him, not allowing me to rise. His eyes are closed and he’s not quite ready to share me fully just yet. He’s the alpha of this pack and what he says goes, so the others adjust their expectations and use what’s available to them, which for now is my hands and my ass.

  I have two cocks in my hands and one rubbing my cheek. I don’t know who is who, or what is what. My eyes are closed and I just feel. Then something quite a bit bigger pushes up against my asshole and my eyes spring open. I look at Beck. He rubs my back in soft circles.

  “Just relax,” he says.

  A light comes on, showering the room in a dusty glow. My eyes take some time to adjust.

  “I can’t see what I’m doing,” Trey says, he has his phone out, recording.

  I look around, at all the different mirrors still up on my walls. Depending on which ones I look at, I can see everything going on. Winston stands behind me, aiming his giant member at my backside. He puts his weight into it as he presses against my unwilling entrance.

  I squeeze my eyes closed as pain trickles through my backside. “It’s too tight, it won’t fit,” I say.

  “I thought you said you could handle anything we give to you,” Trey says in a teasing voice.

  I thought I could but I’m not sure about this. If it were one of the others, maybe, but having both Winston and Beck (two of the biggest dicks in a group of men who are way above average in size) I don’t think it’s going to work. I’ll need a lot more stretching than just a plug.

  Winston starts to back off, but I say, “No, stay,” because Trey is giving me an I-told-you- so look and I’m not a quitter. “I can take it.”

  Beck gives me a concerned look. I’m not sure I can handle it, but I want this. The thought of being double penetrated by two of my men is just about the sexiest thing I can imagine. I’ve fantasized about it. And now it’s actually going to happen. I’m determined.

  I kiss Beck. Kissing him always gets me in the mood and now is no exception. I grind onto his cock, pressing my clit hard against him, but making sure not to move too much while Winston tries to enter my stubborn asshole.

  “Fuck, you’re tight,” Winston says. Normally that wouldn’t be a bad thing, but right now he’s frustrated.

  Just when we’re all thinking it’s not going to happen, the head pops in and I let out a scream that fills the room. My body quivers from the sudden intrusion and the pain is both livid and lovely.

  They all gather, concerned, but I assure them it’s okay. I just need to adjust to this new, very full sensation. Once I’ve caught my breath, the pain starts to subside and the pleasure it leaves behind is both familiar and completely foreign. It’s almost as if there’s nothing to separate the sensations. When Winston
moves, I feel it in my pussy, and when Beck does, I feel it in my ass. And when they move together the world explodes into the most intense pleasure I’ve ever experienced in my life.

  I’m too dumb to talk. My brain is useless at the moment. All I can do is make noises that will wake the neighbors and scare small children. I sit up, letting go of the dicks in my hands, and press my now hands against Beck’s chest. Beck and Winston push in and out of me. It isn’t long before my body starts to convulse. Here comes the ringing in my ears again, the temporary blindness. But this time it all seems amplified.

  Trey laughs somewhere in the distance. I barely hear him when he says, “Holy shit this is better than porn.”

  I barely register anything as I’m thrown into the abyss of one cataclysmic orgasm after another. I don’t know how long it lasts. Hell, I hardly know where or even who I am, but I feel a stupid smile on my face as I finally come down from what I fear might be the best orgasm of my life. Can anything get better? Is there hope for future orgasms, or will that always be the one I strive to reach again?

  Somewhere in the peripheral of my mind, I realize I’m covered in cum. The boys must have unleashed their loads on me while I was in the throes of my orgasm, but I don’t remember any of it. Now Beck is cleaning me up. He’s found makeup wipes in my vanity drawer and is taking care of me.

  “Let’s get you in the shower,” Beck says.

  The others start to put their boxers on. “Stay with me tonight,” I tell them. I have a king sized bed. It’s big enough to fit everyone, maybe not comfortably, but we will fit. “I want to sleep with my guys,” I say.

  “Of course, baby. Anything our girl wants, she gets,” Jason says and kisses me. The others kiss me too then race each other to the showers.

  Beck and I stay behind to wait for another shower to open up. “That was a lot to take,” he says. I’m still naked, exposed without a hint of modesty. I spread out on the bed. He lies next to me and kisses my breasts, almost absentmindedly. It’s not meant to arouse, just something loving he does to be close to me. It feels good. His gentleness is a welcome juxtaposition to all the hardness I’d just experienced earlier.

  I smile lazily. “My body is wrecked. I’m not going to be able to sit right for a week.”

  He laughs quietly. “Get used to it cause there’s going to be a lot of those days. I’m sure you’ve noticed by now that Winston is obsessed with your ass.”

  “You seem pretty preoccupied by it yourself.”

  “I’m obsessed with all of you.”

  I brush the hair out his eyes and try to mold it back into its perfect coif. It doesn’t want to stay and keeps falling to the side. “I’m so happy right now. In fact, I don’t think I can possibly be any happier.”

  “I think you could,” he says.

  “How?”

  “It’s a surprise.”

  “Should I be worried about my ass?”

  His laughter shakes the bed. “Not that kind of surprise. But trust me, you’ll love it.”

  “I’m sure I will because I love you.”

  “I love you too, pretty girl.”

  I snuggle up to his side and try not to fall asleep while I wait for the showers to open.

  Nine

  It’s been several weeks and Beck still hasn’t told me what my surprise is. Whenever I ask, he just smiles and says, “You’ll see. A surprise like this takes time.”

  I glare at him, but don’t push too hard. Besides, they’ve done plenty to distract me as of late. The first week after the app sold, the boys whisked me off on a romantic trip to the Bahamas, and let’s just say there were a lot of deliciously sore nights after that. No time to think much about big surprises. But now that we’re back to work and we’ve come up with a new idea for an app, it’s business as usual and now I want to know.

  Normally I have all the patience in the world, but I see the boys huddled in corners throughout the day without me. They hush and scatter whenever they see me coming. And there’s a man who keeps showing up at the office to talk to only them. I’ve never seen him before, but I don’t like the way he looks. I try not to let it hurt my feelings because Beck assures me it’s all part of the surprise. I’m starting to really hate surprises.

  At lunch we sit in the breakroom. I’ve barely touched my salad, picking at it and moving lettuce around with my fork.

  “What’s wrong, babe?” Jason asks.

  They all stare me down.

  I put on a weak smile. “Nothing.”

  “No lying,” Trey says.

  I made the same deal with all of them about lying that I did with Beck. We swore to each other always to tell the truth, but since they’re keeping things from me, I’m entitled to keep my feelings to myself.

  “She’s upset about the surprise,” Beck says.

  “Wait, you don’t like it? I thought you—” Derrick clamps his hand around Trey’s mouth, shutting him up.

  I thought he was going to accidently spill the details, so I sat up and prepared myself, but now that he’s been silenced, I deflate back into my chair again.

  “Soon, Anya. I promise,” Beck says.

  “You’ve been saying that for almost a month.”

  He shrugs. “These things take time.”

  I roll my eyes. I’ve heard that before.

  “What do you guys want for dinner tonight?” Beck asks, changing the subject. Each of them throw out their orders. I pick up my lunch and toss what’s left of it in the trash before going back to my office.

  A few minutes later Beck walks up to my office door. He knocks, then walks in without waiting to be invited. I’m fooling around with a new graphics program I got, trying to figure out how it works. It’s like Photoshop on speed and so far, I love it. Burying myself in work is the best way I can think to not embarrass myself by acting like a brat around the guys right now.

  Beck sits on my desk, trapping my mouse next to the keyboard so I can’t work. I have no choice but to look up at him.

  “Can I help you with something?” I ask in a very professional, very cold manner.

  He smiles with all his brilliant white teeth, and now I can’t stay irritated with him because I adore that smile and it makes me happy just seeing it.

  I groan and put my head on his knee. “You guys are driving me mad.”

  He runs his hands through my hair and down my neck, giving me a one-handed massage that feels incredible right now. “I know I keep telling you soon, but we’ve hit a few bumps along the way. Let’s not think about it until it happens, okay? Why don’t we all go out to a nice dinner tonight and loosen up?”

  “That sounds good to me.”

  He continues to massage me for a good fifteen minutes before going back to his office. I feel much better and I’m able to get through the rest of my workday without giving anyone dirty looks.

  Just as we’re about to leave the office for the day and go out to dinner, that same man who’d been coming around is here again. Normally I try to enter Beck’s office with them, but Beck will give me that damn smile of his that melts my brain and says, “This will only take a minute; we’ll be right back,” and push me out the door in a way that somehow keeps it from being rude. Beck has a magical way about him. It’s not until I get home and start to rehash the day in my head that I realize that he literally pushed me out of his office and shut the door in my face.

  This time when they all meet up, I don’t try to enter. I don’t like the looks of the guy in there with them. He’s wearing a suit and there’s something about him that’s fake and snake-like. Maybe he’s a lawyer. Something curdles in my stomach and I start to think of every bad thing I can imagine. What if they regret making me a partner and they want to be done with me? What if that sleazy guy in there is making deals with them and Beck is masking it as a surprise to keep me out of the loop? He would definitely be right by calling it a surprise.

  I shake my head. That’s just my paranoia at play. Those men in there love me. I know they do and I
trust them enough to know they would never hurt me like that. I just have to learn to ignore these old feelings bubbling up. The boyfriends I’ve had in the past weren’t always honest with me. Some even cheated. I can’t compare my guys to them because they are nothing alike and I have to keep remembering that so I don’t get sad about being left out.

  Their laughter cuts through the quiet office building. I look around the partition into Beck’s office just in time to see the outsider slip something into Beck’s hand, but I can’t tell what it is. They all shake hands. Just as he’s leaving the office, he sees me and winks at me. I quickly look away, embarrassed for spying on them.

  Beck pokes his head into my office. “Ready for dinner, babe?”

  “Let me grab my coat.”

  I grab my coat and force myself not to ask questions as we leave.

  We decide on Thai as we’re driving. Beck says he wants to try a new place and the others agree. I don’t really care where we go. I didn’t eat lunch and now I’m starving.

  “Is Winston going to meet us there?” I ask.

  One of his first purchases with his new riches was a Tesla SUV. He usually rides with the rest of us when we’re going somewhere as a group, but today he decided to drive himself.

  “Yeah, I’ll text him with the directions,” Derrick says.

  We drive out of the city. Usually when we leave work, the sun is starting to set, but we cut out early today. The sun is still out and it’s an overcast, but beautiful day.

  “Where are we going?” I ask when we turn down a road that looks like it’s about to turn into a neighborhood rather than a business district. This doesn’t look like some place a Thai restaurant would be located.

  Beck takes another right and we come to a huge gate.

  “What are we doing here?” I ask.

  “I just need to make a quick stop before we eat,” he says.

  He types a number into the keypad but nothing happens. He turns to the others. “Are you sure this is the right number?”

  “You have to hit the pound sign after it,” Derrick says.