Page 9 of My 5 Bosses


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I reply by sucking him harder. He smiles and brushes the hair off my forehead. “That’s my girl.”

He sends the length of his dick deep into my throat until my nose is up against his dark curls. Two more deep thrusts into my mouth and he explodes. Rope after rope of hot cum hits the back of my throat until he’s empty. I swallow every drop. He pulls out and I gasp in a deep breath. He leans over and kisses me long and deep. I find it kind of hot that he doesn’t mind kissing me after he shot in my mouth. None of my exes would’ve done that. They were always prudish and boring in bed. I have a feeling I won’t have to worry about that with any of my bosses.

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.

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