My 5 Bosses

by Penny Wylder

  Jason, spent and out of breath, gets up off the bed and grabs his drink off the table and sits in the lounge chair next to a still fully clothed Winston. Jason doesn’t reach for his clothes or bother to cover his deflating cock. Just sits there, sipping on his drink, watching.

  Trey is quick to replace Jason at my side. He smiles down at me, his proud cock dripping. “Hey, sexy. Ready for another?”

  I give his cock a little tug, bringing him toward my eager mouth and say, “Give it to me.”

  As he aims for my mouth, I notice that he’s not circumcised. I’ve never been with anyone who hasn’t been cut before. I’m mesmerized by the way the skin folds over the head, then peels back as he gives it a quick stroke before entering my mouth. I’m surprised how much it turns me on. I wonder if it will feel different from the others when he’s inside of me. His slips between my lips with an appreciative moan. He tastes as delicious as he looks.

  Now there are three. Derrick is in my right hand while I suck off Trey, and Beck continues to impress me with his oral skills. I couldn’t possibly be any happier right now. Having Jason and Winston as an audience makes things even better. They call out instructions to the others the way they do when they all sit around playing video games: “play with her nipples” and “finger that pretty asshole.” And the boys oblige.

  Beck stops licking me long enough to reach for his jacket. Inside one of the inner pockets is a bottle of lube. It seems he came prepared. He drops a generous amount on his hand and starts to rub it on my asshole.

  “Don’t tense up, baby,” Beck says. “Just relax and enjoy the ride.”

  I do as he says and let my body turn to putty in his hands. There’s no pain at all when he slips his finger inside, just a strange, but wonderful fullness. It takes a bit for my body to warm up to this new sensation. I’ve had anal sex before, but I didn’t enjoy it. My boyfriend at the time just pushed into me without lube and without warning and it was painful enough to turn me off completely. I never thought I would even try it again, but I’m actually really excited about it. If the feeling of his finger inside of me is any indication of what a dick will feel like, than anal sex might be my new favorite thing.

  I moan loudly as Beck adds another finger in my ass. Derrick and Trey each take one of my ankles and hold them up in the air when Jason and Winston ask for a better view. I feel my own juices spilling down my ass crack, making entry even slicker.

  Trey groans long and loud. “Shoot it on her asshole,” Jason says.

  Trey, on the edge of losing it, pulls out of my mouth with a pop. Beck pulls his fingers out of me and spreads my ass apart, giving Trey the perfect shot. His hot cum hits the bullseye. It tickles a bit as each spurt hits its target.

  Just as he finishes, Derrick quickly pulls out of my hand and starts stroking himself at a furious pace. “My turn,” he says. Trey steps out of the way to give him room. He’s not as solid with his aim. One rope hits my ass cheek, another the entrance of my pussy, but the last one hits true to its mark.

  Now it’s just me and Beck. He climbs on top of me kissing each of my breasts before sucking a nipple into his mouth. Once he gives the other a little attention, he kisses his way up my chest and to my mouth. He breaks the kiss and looks me in the eyes. The look he gives me is so sweet and gentle and loving that I feel a tightness in my chest.

  “How do you feel?” he asks, genuinely concerned.

  I’m quick to reply, “I feel better than I ever have.”

  And it’s true. I feel special to have been chosen by all five of these men, to be the center of their lust and attention. I don’t ever want it to end.

  He kisses me long and deep. He must be able to taste the others on my lips, but he doesn’t seem bothered by it as his tongue tangles with mine. He reaches between his legs, grabs his thick cock and guides himself into me.

  I moan into his open mouth and run my fingers down the soft skin of his back as he slowly pushes into me. I’m a little sore from being stretched out with their fingers, but I don’t mind it at all. In fact, I enjoy a little pain with my pleasure. It makes me feel alive. Makes me aware of every single pleasure that comes along with it.

  Beck fucks me fast and hard, making my tits jiggle and bounce. His pubic bone crashes against my clit, the slap of our skin like applause. He lifts my legs, bringing my knees to my chest. This new angle causes him to drive into me as deep as my body will allow. I scream as my first orgasm rips through me. He pounds me until I see nothing but stars in front of my eyes and keeps at it until I hear ringing in my ears.

  “Your pussy feels so good clenched around my cock,” he says, breathless.

  Just when I start to think Beck is superhuman and can last forever, he lets out a loud grunt and pulls out, spraying his load on my asshole. I start to wonder if that’s something they choreographed before we arrived at the bar when they were planning this whole tryst, or if they were all just following each other’s lead. Either way, they all seem preoccupied with my ass.

  Proving my observation further, Beck starts to finger my asshole using his own cum. I suppose he’s using everyone else’s too since there was no time to clean up between climaxes.

  After my orgasm, I’d started to come down off the high, spent and tired, but as Beck works his fingers in and out of me, adding a third one, my body starts to wake up again. Beck doesn’t have small fingers, and I’m definitely noticing the tightness. But as he continues to work me over, I relax more and my opening becomes pliant.

  “God, yes, just like that,” I say, rocking into him.

  I notice movement beside me and see Winston stand up. He pulls his jeans down and takes his massive cock out of his boxers and again, I’m stunned by the size of him.

  Jason lets out a giddy laugh and says, “Time to bring out the big guns.”

  Beck winks at me and pulls his fingers out of my ass. “I think your ass is finally prepared.”

  My eyes grow wide and I stare up at Winston. He stands in front of me with a crooked smile. “You plan to fuck my ass with that?” I say, glancing at the monster between his legs.

  “I promise you’re going to love every second.”

  I swallow hard, but I trust him. I nod.

  He takes me by the hand and leads me over to the table. The others get up off their lounge chairs and follow.

  “Bend over the table, now,” Winston demands.

  I do what I’m told and bend over, exposing myself to him. My breath comes out in hard bursts. I’m nervous, but excited, too.

  “Look at all that jizz. You’re a filthy girl,” he says and starts fingering my asshole, making a squelching sound. The smell of sex sits heavy in the air and lingers. By now I’m loosened up and there’s no longer the feeling of pressure when his fingers enter me. It feels so dirty knowing there are three loads of cum on my ass while he’s doing it.

  I look over my shoulder and watch Beck hand him the bottle of lube. He slathers it on his dick and presses the massive head against my opening, gently pushing until it breaks through the tight barrier. I squeeze my eyes closed making sure to keep breathing. It’s painful at first despite all the fingering, but I know it won’t stay that way, so I keep breathing through the pain until he’s all the way in. The others play with my tits, and someone rubs my clit, making sure this is the most pleasurable experience it can be for me.

  Winston doesn’t move, allowing my body to adjust to his size.

  “Damn, that ass feels good,” he says, then slowly starts to work his way in and out of me. At first, it’s a strange, sort of an uncomfortable feeling for me, but after a few seconds, I crave more.

  “Harder,” I say.

  He doesn’t hesitate to oblige, plunging deep inside of me.

  I cry out. Holy shit. How am I almost ready to come when he hasn’t even really done anything yet? Being fucked in the ass is such a different experience when I’m comfortable and prepared. It’s almost better than having my pussy nailed. Everything is more sensitive, more reactiv
e. The orgasm building feels supercharged. When it happens, it’s going to be epic. I know it and I’m so excited my knees start to shake with anticipation. But I don’t want to come just yet. I want to enjoy the ride first.

  “Wait, slow down, I don’t want to come just yet,” I say.

  “You close, baby?” he says, slowing his pace to a mere crawl.

  “Right on the verge.”

  He chuckles. “You like my big cock in your ass?”

  “I love it.”

  He rubs my back and I take slow, even breaths to calm down and force back the orgasm clawing at the surface. It wants to break through, wants to incapacitate me, debilitate me. I want that too, but I want to make this incredible feeling last longer. I’m not ready for my time with my bosses to be over just yet.

  After a minute, Winston starts to move his hips again in a fluid rhythm that’s comfortable and pleasurable. My body has grown accustomed to his size by now and I just relax and enjoy it.

  The others continue to play with my tits and rub my clit. Jason, Trey, and Derrick leisurely rub their semi-hard cocks again, content to watch the scene in front of them, but Beck is ready to go again. I smile at him and say, “Come here with that thing,” and open my mouth for him.

  His dick twitches as it slips between my lips. It smells like my pussy and tastes sweet. I swallow him down, turned on that he reeks of me.

  He runs his fingers through my hair and holds me behind the ears as if they were handlebars, and pushes deeper into my throat.

  “I didn’t think you could get any more beautiful, but damn, you look good with my cock in your mouth,” he says, watching intently as each inch of him slips past the barrier of my lips.

  “Think you can take more?” he says.

  I give a slight nod. I can take it all. And he gives it, pushing his entire length into my mouth. I gag slightly and he pulls out, giving me a chance to breathe.

  “Come in my mouth,” I tell him. “I want to taste you.”

  He smiles and slips back in.

  Watching Beck fuck my mouth seems to bring out the beast in Winston, and now I’m getting drilled at both ends.

  “I’m going to fuck that ass so good you’ll need us to carry you home,” Winston says as our skin slaps together at a furious beat.

  This next orgasm is going to destroy me. I feel the intensity of it in my pores, my hair, my fingernails. It starts in my core and radiates up my spine and down my arms, into my legs until it reaches my fingers and toes. My entire body starts to quake.

  The sounds Beck and Winston make become more animalistic, grunting and growling as they come closer to release.

  “Oh, fuck,” Beck roars as his seed spills into my mouth.

  When he pulls out, my throat is full of his cum and the scream tearing out of me is gargled.

  With one more desperate thrust, Winston digs his fingers into my ass cheeks and releases his load inside of me.

  “You’re incredible,” he says with an exhausted laugh. He gives my ass a playful slap and pulls out.

  My body has definitely been pushed beyond its limits and now everything is numb. Beck catches me as I stumble backwards.

  “Let’s get you cleaned up so we can go home,” he says, kissing my cheek.

  I nod, unable to form a coherent sentence.

  “You were incredible, babe,” Jason says, and he also kisses my cheek while Beck uses the napkins on the table to wipe the sweat and cum from by body.

  I can’t help but laugh as they each give me some kind of compliment and kiss me. I’m spent, but they bounce around, playful, teasing each other like a team that just won a game. The others had taken an Uber to the bar, but now they ride in the SUV with Beck and me. They fight over who gets to sit next to me on the ride home, then play a game of rock/paper/scissors to determine the winner.

  “She’s riding up front with me,” Beck says, flashing me a grin. He always seems to get the final say. They grumble and take their seats in the car and we go home.

  First thing I do when I get home is take a steaming hot shower. The water feels amazing on my skin as I wash the stickiness and sweat away. I’m just about to wash my hair when Beck walks in with a towel around his waist.

  I smile at him, no longer shy about nudity. He’s seen me in every conceivable position. “I don’t think my body can handle another round if that’s what you’re here for.”

  “As tempting as it sounds, I’m just here because this shower has two heads and I figured we can share.”

  “Come on in. The water is scorching hot. Don’t burn yourself.”

  He drops his towel and gets under the showerhead opposite me, but doesn’t stay there long. Before I know it, his arms wrap around my waist and he’s looking me in the eye with an affectionate look on his face. My heart melts at the sight of it, and I put my arms around his neck. I love the way our wet bodies feel up against each other, especially when he looks at me like that.

  “How are you feeling?” he asks.

  How am I feeling? Sore, exhausted, bursting at the seams with happiness, but I don’t tell him all that. Instead I sum it up with, “I feel good.”

  “You know tonight wasn’t just about sex, right?” he says.

  “What was it about then?”

  He pours out some of the shampoo from the bottle in my hands and starts to massage it into my scalp. The clean scent of lemon fills the room. I close my eyes, reveling in the way his fingers knead my skin.

  “We care about you. I care about you. The five of us rarely agree on anything but we agree on you. We want you to ourselves. Exclusively.”

  My eyebrows raise in surprise. “All of you?”

  “Yes, all of us.”

  “Has this ever happened before?”

  “Never. You would be our first communal girlfriend.”

  We both laugh at his wording, but that’s exactly what I would be. The exclusive girlfriend of five different men.

  “How would this work?” I ask.

  He shrugs. “I guess we just figure it out as we go. As long as no one tries to keep you to themselves, we should be good—but I have to admit having you all to myself is tempting.”

  He gives me a soft kiss on the lips. “So what do you say?”

  I don’t even have to think about it. The arrangement sounds perfect. “I’m all in,” I say.

  We finish our showers and kiss goodnight before heading to our separate rooms. I crawl into bed, exhausted and elated at the same time. I play back the details of my amazing night over and over in my head until I finally fall asleep.

  Five

  The next morning everyone is up early and waiting for me downstairs. Winston has a donut for me from the bakery down the street. The others give him shit for not getting them one, too.

  “If you had an ass like Anya, I’d get you one too,” he says, goading the others.

  “What are you talking about?” Jason says. “I have an incredible ass, look at this thing.” He pulls his pants down, mooning us as he runs to the car.

  Trey puts his arm around my shoulder and says, “How does it feel to date five giant children?”

  I laugh. “Creepy when you put it like that, but there’s never a dull moment.”

  Everyone piles into the SUV. I have a permanent spot in the front seat. There are perks to being the only girl. But before I can open my door and get in, Beck takes me by the hand pulls me to the side away from the others. “How are you feeling this morning?” He keeps asking me that. Is he worried about me?

  I face him, stand up on my tip-toes and give him a soft peck on the lip. “I feel wonderful.”

  His smile glows from within. “Good. I’m glad we didn’t scare you off. I love having you around.”

  “Not a chance. I don’t scare that easily.”

  He lets out a quiet chuckle and says, “I noticed.”

  “You don’t have to worry about me, Beck. I love being with you guys.”

  He seems to relax and looks as if a two-hundred-pound we
ight has just been lifted off his shoulders.

  Beck and I get into the car and head to the office.

  Once we’re there, it’s business as usual, but things have definitely changed. Each of my new boyfriends will sneak into my office from time to time to steal a kiss or just to say hi. They have completely given up on pretenses. I love it, but it does make it difficult to focus on my job sometimes. I still haven’t come up with the logo for the app yet. All of my ideas feel lackluster. This app will be huge and it needs a special graphic. That’s why these men chose me. They saw my portfolio and decided I was the right person for the job. Even Winston, who was skeptical about having an outsider on his team at first, has put all his confidence in me. Now I need to prove I’m worth the hire.

  On my lunch break, I decide to go for a walk to clear my head instead of eating with the others like I normally do. They sit in the break room at the table. I come in to grab my purse off the hook where I keep my things.

  “You’re not eating with us today?” Derrick asks.

  They give me an odd, almost worried look, and glance at each other. We always eat together.

  “Not today, guys. I’m going to take a walk and clear my head.” I hope they don’t think that my wanting to be alone has anything to do with what happened between us last night. To make them feel better I add, “This tech expo we’re supposed to show the app at is coming up quick and I’m just a little nervous. The pressure is making me kind of jumpy. I’m going to go walk off some of this energy.”

  They nod, but they don’t look all that convinced. “Be safe,” Trey says.

  I nod and leave.

  There’s not much of a breeze today. Smog blurs everything with its yellow-grey cast. Traffic is hectic as usual in the city at this time of day, but I like all the noise. It blends into a hum and I’m able to tune out my racing thoughts—the ones that get in the way when I’m trying to concentrate. As I stroll down the street, racking my brain for ideas that just aren’t coming to me, I see a dog park. It’s a good-sized area, fenced off from the sidewalk with signs that say Dog X-ing. Inside the fence there are benches all around and fountains for the dogs to drink. One side of the park is designated for little and old dogs, while the other is wide open for the bigger breeds.