My 5 Bosses

by Penny Wylder

  I’ve always been a fan of bigger dogs myself. When I was young, my family had a border collie. His name was Turbo and he was the smartest dog ever. But because he was a herding dog, whenever I had friends over, he would chase us. When I asked my dad why Turbo did that, he said it was because that breed was born to herd. It’s part of his DNA. After that it became a game with me and my friends. We’d clump into a tight group at first, then we would try to scatter, screaming and laughing as my dog would gather us back together again …

  An idea hits me suddenly and I say, “Oh my god, that’s it!” so loudly the people sitting on the benches look in my direction. I ignore them, my brain abuzz with how I can turn this new idea into a graphic for the app. Then my mind flashes me the perfect logo for the company. A border collie. That’s exactly what this app is built for, to herd all the apps people use regularly into one space. It’s so perfect I can’t believe I hadn’t thought of it before now. It’s cute and fun and I’ll design it with bold, eye-catching colors. Like I told the guys, the big tech expo is coming up soon and the new app will be debut there. This idea couldn’t have come at a better time.

  I sit on a bench and sketch my idea on a note pad I pull out of my purse. I watch the dogs play for a while longer for inspiration as I compile a full mental preview of all the thing I have in mind for the app.

  It starts to hit me that once this app comes together and is sold, that means Derrick, Trey, Jason, Winston, Beck and I will all part ways. Maybe not completely. I’m sure we’ll still get together after this, but my job will be over and I’ll have to get a new one. Depending on where that is, I’ll probably have to move out of the apartment. What they pay me for my part of the app might be enough to buy that house I’ve always dreamed of, but I won’t have the five men in my life who have made me so happy these past few weeks. The thought of leaving them brings a physical pain to my stomach.

  I take a deep breath and try to calm down as I walk back. I’m several minutes early when I get back to the office. My guys are still sitting at the table eating lunch.

  “How was your walk?” Beck says. He sounds like he’s making casual conversation, but there’s concern in the way he looks at me, a gathering of the skin between his eyebrows. The others look just as troubled.

  “It was nice,” I say, struggling to muster a smile. I look at all of their beautiful faces, those strong jaws and powerful features that are unique to each of them, and feel pressure behind my eyes as tears build up. I can’t let them see me cry, so I force a smile onto my face and say, “I should get to work. I’m a little behind on what I need to get done today.”

  “Okay,” Beck says, still assessing me with those questioning eyes. A muscle in his jaw twitches like he wants to say more. I’m glad he doesn’t. The others nod and look at each other.

  I go into my office, close the door and cover my face, letting the tears fall and hoping no one comes in or walks by. Having glass doors is so inconvenient during an emotional breakdown.

  By the time I get home that evening, I’m able to pull myself together. I’m still broken up, but I’m better at hiding it. The guys want to have dinner together and I really want to spend time with them outside of the office. Some days it feels like I never really get to spend time with them even though we’re in the same office day in and day out.

  We each make a dish in our own apartment because the one thing we don’t have is a shared kitchen, and bring it down to the communal room. We have spaghetti and salad with bread and wine. When I’m stressed I drink too much and now I’m on my third glass.

  “You’re going to regret that later,” Beck says as I reach for the bottle again.

  He’s right. Wine gives me terrible headaches. But it makes my racing thoughts bearably numb.

  “Which is why I’ll worry about it later,” I say, pouring another glass. He slides his glass toward me and I fill it up.

  While the others laugh and chat, having their own conversations about the up-coming tech event, Beck leans in, talking quietly. “When are you going to finally tell me what’s wrong?”

  Why is he so good at reading me? I seem to have managed to hide my mood from everyone but him.

  “Nothing’s wrong,” I say.

  “Let’s make a deal, okay?”

  “Okay.”

  “You promise never to lie to me and I’ll promise never to lie to you,” he says.

  I swallow back the lump in my throat. “Deal,” I say.

  “So what’s wrong?” he asks.

  I’m not about to tell him the main reason I’m upset, but I’ll give him something. “This tech event is rushing at me and my graphic isn’t finished. I just don’t want to disappoint any of you.”

  He takes me by the hand and traces the length of my fingers. I love just sitting here holding his hand. Sometimes just that connection with someone is better than any kind of sexual act—well, maybe not better, but it still feels really good.

  “There’s no way you will disappoint us. I’ve seen what you can do. I have all the confidence in the world in you,” he says. He kisses the top of my hand, then up my bare arm until he reaches my lips.

  “Hey, I saw that,” Jason says.

  Beck and I look at the others. They’re all watching us.

  “You kiss one, you have to kiss us all,” Derrick says.

  I laugh. “All right. Who’s next?”

  Jason hops up eagerly, wanting to be first in line. The others gather around. I give them each a peck on the lips the same way I did with Beck. But then Beck comes in for another kiss. His lips linger on mine. They part and he slips his tongue in. He tastes like the red wine he’d been drinking. Our tongues tangle and dance before he breaks away from the kiss

  “You know the drill,” Jason says, giving Beck a grateful look when he comes over to be the first in line again for a deeper kiss.

  The wine has really gone to my head and I’m relaxed and wet with all this attention. Jason lifts me into his arms. I wrap my body around him. The hard bulge in his pants presses up against me as he carries me over to the couch in the corner of the room. The others follow. Our kiss becomes hot and heavy. I pull his shirt off, raking my nails down his smooth back until it looks as though he’s been whipped.

  Our lips part just long enough for him to say, “I’m going to fuck all that stress from your body.” He rubs my cunt on the outside of my jeans and I moan into his ready mouth.

  “That sounds incredible,” I say as he lowers me onto the couch. I unbutton my jeans in a frenzy.

  Jason pulls them down, and then reaches for the waistband of my panties to pull them down too. Once I’m naked from the waist down, I eagerly spread my legs and play with myself, giving them a little show.

  They cheer me on as I rub my clit and finger myself, but Jason has no patience. He puts his head between my legs and breathes in my scent the same way he inhaled the aroma of his wine when he first poured it into a glass. “You’re pussy smells even more delicious when you’re turned on.”

  “It tastes even better,” I say, licking my fingers clean. He groans and sucks on my inner thigh, giving me a hickey.

  I put my hand on the back of his head to bring him closer. His smile spreads from ear-to-ear as he reaches toward my clit with his tongue.

  His smooth tongue sends a shiver through me as he runs the tip of it along the wet, pink folds. When he dips it into my center, everything gets brighter. The lights seem to flare like the sun, colors seem more vibrant, everything feels exaggerated. Someone plays with my nipple and I almost get off right then and there.

  “Fuck, your tongue feels so good on my pussy,” I say. “Suck my clit. Yeah, just like that,” I tell him as he latches on.

  “Oh, yes,” I cry as I hump his face.

  Beck comes up beside me, fully naked, his erection dwarfing his hand. “Open that sexy mouth,” he says.

  My lips part for him and he eases the head in. “Look at me,” he says. My eyes flick up to meet his. “I want your eyes on m
e when my cock is in your mouth.” I nod obediently. He pushes into my mouth with slow, even thrusts. “I haven’t been able to stop thinking about your perfect pussy.” He pushes deeper. “It keeps me up at night.” And deeper still. “It makes it hard for me to concentrate at work.”

  He pulls all the way out and I swallow and take a deep breath. He leans over so our faces are only centimeters apart. He kisses me, just a peck, then licks my bottom lip. “You’re a good little cock sucker, aren’t you?”

  I nod.

  “Tell me how much you want it,” he says, his breath brushing against my lips.

  “I want it bad,” I say. “I want it in my mouth. I want to suck you dry.”

  He kisses me harder. “Beg for it.”

  What Jason does with my clit makes my eyes roll in the back of my head. Beck says, “Look at me, Anya.”

  His words snap my attention back in place.

  His voice becomes stern. Right now he’s the boss. “I said beg for it.”

  “Please give me your cock,” I beg.

  He stands over me and shoves his dick in my mouth, fucking my face.

  He pulls out suddenly and I gasp for hair just as Jason’s hard cock plunges into my pussy.

  Jason takes ahold of my hips and slams into me with enough force to move the couch a solid inch. “Deeper,” I beg, grabbing onto his muscular ass cheeks. “Fuck my pussy like you mean it.”

  He gets a wicked smile on his face and starts pounding me hard. I’ll be bruised when it’s over, but right now I don’t care. I love the way it hurts.

  My tits jiggle and bounce—actually, every part of my body jiggles and bounces—with his rapid-fire thrusts. Then he suddenly stops and tenses up. I feel his cum heating up my pussy as he unloads into me. He pulls out, a drop of semen on the tip of the head.

  Isn’t he afraid of getting me pregnant? Does he even care?

  Derrick is next, and I notice everyone is lined up like a train awaiting their turn with their hard dicks hanging out of their pants.

  I giggle and say, “I’ve always wanted to go on a dinner train.”

  “Careful what you wish for,” Trey says, rubbing himself. “You’re going to need crutches when we’re done with you.”

  My body shivers with excitement at the threat. Is this how it’s going to be every time? Me against all five of them? I’m going to have one busy pussy, that’s for sure, but I’m not complaining. Every boyfriend I’ve ever had could never last the full ride. Two-pump-chumps, all of them. Rarely would I ever get the chance to come before they got theirs, and I was left to my own devices. At least with five men someone is bound to get me to the finish line.

  I spread my legs wide and rub my clit. Derrick kneels between my legs and pushes into me. I wince and grunt as he bottoms out. “I love it when you shove that long dick inside of me,” I tell him.

  “It’s hot in here,” he says, talking about the inside of my pussy. “Jason really made a mess of you, didn’t he? It’s nice and lubed up for me.”

  I’m a little taken aback by the dirtiness of his words—which I shouldn’t be, because everything that comes out of our mouths during sex is dirty. But to acknowledge that I’m lubed up with another man’s cum and he’s enjoying it … well, that takes it to a whole different level and I’m so turned on right now because of it. The wet sounds it makes while he’s fucking me make it even more hot and dirty. I’m loving every second of it.

  After several more minutes of wet, sticky sex, he too tenses up and spills his seed inside of me.

  Derrick stands up and Trey quickly takes his place in front of me.

  “I hope you’re flexible,” he says with mischief in his voice.

  My heart starts to race. He pulls me up from my position on my back and maneuvers my body into an odd position so that I’m on my stomach, draped over the arm of the couch. My hands are on the ground, my ass in the air. Derrick and Jason hold my legs spread apart so I’m basically doing a spread-eagle hand stand on the side of the couch. Trey stands up on the cushions and starts drilling into me.

  I choke out a scream the moment he enters me from this position. I thought sitting on someone or getting it from behind was the only way to get someone in as deep as they can go, but this … this is mind-blowing. I cry out as he fucks me, coming so hard my entire body starts to spasm.

  “God damn, that pussy is strong,” he says as my muscles clamp down around his cock while my orgasm rages. Seconds later he lets out a roar as he too comes. Beck doesn’t give me time to come down from my orgasm, instead he immediately starts to fuck me so forcefully my arms threaten to buckle. The orgasm seems to just keep lingering, never getting the chance to subside, and I’m cursing and screaming and begging him not to stop.

  When he’s done, he switches places with Winston, and I’m not empty for long. Winston takes his turn and it feels like I’m being fucked by a bull. Holy shit, he’s powerful. The force with which he slams into me makes my skin ripple up to my neck. My ass cheeks clap together and I’ve forgotten to breathe. All the blood has rushed to my head and my vision starts to grey.

  “Oh god. Oh god,” I chant as the glorious pounding continues. I roll my hips, urging him on. He presses deep and hard, unrelenting until finally his body starts to shudder. He pulls out and my insides feel hollow.

  I’m flushed and tired and utterly satisfied when it’s all over. This is what it could be like every night if only this app didn’t get finished. But it has to. It’s all going to be over soon. Until then, I’m going to enjoy these men while I can.

  “Boys, I’m going to need a towel,” I say without moving. I can feel all the cum sloshing around inside of me.

  “Wait, hold on, let me get my phone,” Jason says.

  “Seriously?” I say. “You’re going to take pictures?”

  “Of course not. I’m going to film it.” I start to protest, but he says, “Don’t worry. No one but us will ever see it.”

  “Fine,” I grumble.

  Someone brings a towel and a bowl over to the couch. They put the bowl under me and gather around. I pull myself up and squat over it. As soon as I do, five massive loads of cum spill out of me. They guys all make varying sounds and comments. “Damn, that’s hot”, “Spread that pussy till it gapes,” and “That sweet cunt is all ours.”

  Exhausted, I get dressed and plop on the couch. They take turns kissing me, then sit down too. It’s strange how after what can be considered a gang bang, we fall into completely normal conversation. They talk mostly about the excitement of the app launch and all the different things that are going to be at the tech expo. They beg me to tell them about the graphic for the app, but I refuse because it’s not finished and I want it to be a surprise.

  We laugh and joke around, and it’s just so normal and comfortable and safe with them. Each man has their own individual thing that makes him special and makes me care about them. There’s no way I could possibly decide who I care about more. I guess I have to admit that Beck and I have the strongest connection. He’s in my head and can read my moods. Still, the others are just as important. I don’t want to live without any of them.

  While Winston puts on a movie, I put my head on Beck’s lap. He runs his fingers through my hair. We all lie together on the couch in a comfortable pile of arms and legs. I don’t even realize I’ve fallen asleep until I wake up in Winston’s arms and he’s carrying me up the stairs to my room. He lays me down in my bed. I’m too tired to open my eyes and tell him goodnight. He kisses me on the lips and I could swear I hear him say, “I love you” before he leaves the room.

  Six

  The night of the tech expo approaches fast. Only one more day. I sit in the office. It’s late. The others have already gone home for the day. All I have left to do is submit the graphic and I’m done. The app will be complete. It will sell and everything will be over. I have no doubt I’ll be able to get another job offer quickly. I’m sure other tech companies will be crawling over each other to get to me after this one
sells. It’s an impressive thing to have on my résumé. But I don’t want just any job. I want this one. With my guys. It sounds crazy, but I think I’m in love with them. All of them.

  Sitting in front of my computer, clicking my pen and bobbing my knee, I contemplate not updating the app with the new graphic. That would slow everything down. We would miss the deadline to show at the tech expo, but it wouldn’t hurt our chances of selling it. It’ll give us an extra month or two to be together before the next show. But then I’d let everyone down. They are so excited about the launch tomorrow. There will be some heavy hitters out of Silicon Valley there. The boys want to show everyone what they’re capable of in front of such an impressive audience, and I want that for them too. As much as I’d love to be selfish, I can’t do that to them.

  With a deep breath, I hit send and put my pen down before I throw it across the room. I need coffee.

  This place is kind of scary at night without the natural light coming through the large windows. It’s pretty boring too without the chatter of the others. It’s like any other office building. It’s my bosses that make this place comfortable and colorful.

  I head down the dark hallway to the breakroom and put water and grounds into the coffee maker and wait.

  “You’re here late,” a voice says behind me.

  I scream and turn to find Beck standing in the doorway. I grab my chest and let out a string of expletives. “Jesus fuck, you scared the shit out of me!”

  He smiles like he’s proud of himself, which makes me think scaring me was the point.

  “Sorry. I was driving by and the light in your office was still on, so I wanted to make sure everything was okay.”

  “Everything is fine,” I say, finally able to catch my breath. “I was just doing a few last minute tweaks on the graphics before I sent it. There’s an attachment in your inbox.”