Pregnant By My Boss: A Bad Boy Secret Baby Romance Compilation

by Cassandra Dee

  And I began running my finger in and out, slowly at first, gently testing her back door before edging another finger in to join the first, stretching out that sweetness, preparing her for me.

  “That’s right, honey,” I growled, pressing my lips to her ass. “I’m big and you’re small back here, so I want to stretch you out, I want you to be ready for me.”

  And she mewled again, wordless, in the thralls of pleasure. Her ass contracted against my fingers before relaxing once more and I could tell Katy was consciously trying to let go, to let her body enjoy the sweet slide of my digits.

  “That’s it,” I complimented again. “Give yourself up because it feels good, doesn’t it, little butt slut? You’ve never been touched here before, never had a man slide his fingers deep into your anus.”

  And with that the girl’s moans crescendoed into a full-on whine of pure ecstasy, unable to hold back anymore. Because Katy came full force then, her ass clamping around my fingers once, hard, before letting go in a shower of tremors, each more vivid than the last, her plump body shaking, shivering with each spasm.

  “Oh god!” she shrieked, lifting that perfect profile to the skies, lips slightly parted, eyes squeezed shut with ecstasy. “Oh god!”

  And I kissed her haunches as I tunneled my fingers in deep, the hefty flesh squeezing me again and again as she shattered, gasping and screaming, those big boobs swaying to and fro as she struggled to maintain her balance, gripping the headboard, elbows locked.

  “Umph,” I grunted, lapping her butt cheeks once more. “That’s it baby girl, let it all out, let it all out.”

  And she threw her head back once more and shrieked again, loud, before dissolving into a series of small shudders.

  “Oh god Jase, oh god oh god,” she panted, head dropping between her shoulders, haunches quivering and jerking. “Oh god!”

  And finally, things calmed a bit, her breathing growing more even, stilling, that sweet, sleek form glistening with a sheen of sweat. It was only then that the pretty brunette looked over her shoulder, shy despite what had happened, with my digits still locked deep in her body.

  “Jason,” she murmured. “That was amazing … but there’s more right? I mean,” and here she colored, “fingers don’t count right?”

  And my cock popped out like a fucking jack in the box, ready to take, to own, to control. Because Katy was right, a finger fucking doesn’t count, and I was more than ready to do my duty.

  CHAPTER SIX

  Katy

  It was so illicit, I could hardly believe what was happening. On the one hand, I’d given up my pussy cherry a mere twenty-four hours ago to Brent, a man I lived with. And now I was giving up my ass cherry to Jason, a man I’d adored for the last year. How did life get so complicated?

  But the thing is that it wasn’t complicated at all because somehow things felt right. I was confused at first, my emotions tugging me this way and that because I felt like I had to choose. I felt I could only have either Brent or Jason, and that being with both was something that only trashy girls did.

  But during fifth period, I’d looked it up on my phone. There were so many sites on “multiple love,” “polyamory,” and even teen magazines dispensing advice to girls who liked more than one boy. I chuckled at that one. Sure, I was still in high school so I guess I fit their demographic, but this was more than a passing phase, more than just a fling. I was in love with two men, couldn’t wait to have them both, and the question was how exactly we were going to work this out.

  Because I desperately wanted it to work out. I wanted to have both men with me, separately or together I wasn’t sure, but there had to be some combination that would make sense for all three of us. I wasn’t sure what it was yet, the articles on-line seemed to harp on a lot of therapy, a lot of “open-hearted talking,” and at this moment, we hadn’t had a serious discussion. In fact, Brent didn’t even know about Jason yet, putting us at square one, if not square zero.

  So I stepped into our trailer after school thinking that maybe we’d chat a little, maybe Jason and I had some more talking to do after our impassioned discussion this morning. I was totally prepared to sit down with him and brainstorm a little. But he’s an alpha male with something to prove, namely that Brent isn’t the only man in my life. So we started exploring almost immediately, our bodies hot and hungry for one another, not a second to lose.

  But Jason, as much as I love him, pulled back. Again, it’s this male ego thing and I almost cried when he asked, “What did you do with Brent yesterday?”

  I flopped around like a fish gasping for air because what good would it do if he knew? How would that help?

  “Nothing,” I murmured, head down before looking straight at him again. Because being a shy pansy wasn’t going to get anything done, I needed to be direct. “What I did with Brent yesterday has no bearing on what we’re about to do,” I said seriously.

  But again, male egos run strong especially with alphas, and Jason wouldn’t let it go.

  “I have to know,” he growled, shaking his head. “I have to know.”

  So instead, I detoured.

  “Well,” I murmured, “I shaved myself yesterday, you know … like down there,” I said, demonstrating a little, parting my thighs and running an imaginary razor through my pink folds.

  And that was enough. I didn’t have to say anything about how Brent shaved me, how he pulled my labia back with big, gentle fingers, and traced the razor carefully over my sensitive skin before dropping a kiss on my clit, lapping lightly at his work.

  Instead, Jason was fixated on my pink pussy, how it creamed wetly, how I opened it for him, letting him look inside, and I breathed a sigh of relief. Thank god, I’d been able to lead away from that dangerous train of thought and we could get back to our love play.

  And oh god, but it was amazing. He shaved my back pucker, running his finger around the tight pleats before penetrating me, making me shiver, scream, the feel of those blunt digits in my ass so dirty and delicious. And incredibly, I came from the ass play. I couldn’t help it, I’d never done it before and the shock, the taboo aspect was so strong, so overwhelming, that I creamed hard, my butt and pussy spasming as electricity ran through my body, making me moan and cry out his name.

  The big man was pleased, there was no doubt about that. He leaned forward to kiss my back, press his lips against the sinuous S of my waist.

  “That, honey, was a damn good butt fuck,” he growled.

  And I turned to look at him over my shoulder. The dirty words should have made me angry, should have made my skin crawl with disgust but instead they just turned me on, made my temp begin to rise once again.

  “But Jason,” I murmured coyly, still panting. “What about you? You haven’t put it in yet,” I said, nodding towards his pole. His staff was so big, so aroused, that veins pulsed wetly along the top and bottom, the tip dripping like a leaky faucet, a steady stream of cum oozing off to form a pool on the floor.

  And he grinned at me then.

  “I know, baby girl,” he said smoothly. “And here’s where we’re gonna use the reinforced bed.”

  My breath caught. Jason is good with his hands, he has a real talent for working with raw materials, and he built this bed himself. I remember when he hauled it into the trailer in parts, there’d been so much sturdy oak that I’d laughed, sure it wasn’t going to fit. But once he set it up, I ate my words because it was marvelous. A giant California King, it was big enough to romp freely in, with a huge, ornate headboard he’d carved with a geometric design, hard-edged trapezoids and triangles.

  I’d teased him about it.

  “So what are you gonna do with this?” I asked. “You got a girl you want to bring home for some sassy play?”

  Back then, there had been no indication that he was interested, so it was just friendly banter, although my heart twinged at the thought of Jason with another woman.

  But his eyes clouded over, the blue suddenly mysterious and shuttered.


  “Naw,” he said, not looking at me. “Just wanted a bigger bed to sleep in.”

  And I looked over him appreciatively because yeah, my housemate had filled out a lot in the last year and was truly a man now, tall, huge, filling up all the space in the small trailer. My heart beat faster, body growing soft at the thought of Jason naked between the sheets, his muscled chest bare, long legs hidden only by thin cotton. But this was back then and my cheeks colored at the illicit daydreams.

  “Oh okay,” I murmured. “Yeah, bigger is better.”

  And now that refrain danced in my head as I looked at the alpha. Because oh god, his dick was huge. Ten inches at least, pulsing with power, and oh god, he was going to put it so hard in me that I’d be clenching my teeth, gripping the headboard in agony and ecstasy. Oh my god, oh my god … yes.

  So I climbed up onto the soft mattress, wiggling my ass at him, throwing my curls over my back while looking coyly over my shoulder.

  “Let’s use the bed then,” I purred. “Let’s try this baby out.”

  And Jason growled low in his throat, on me in an instant, his big body covering mine from behind, like a blanket, my back pressed to his chest as he nibbled my neck.

  “That’s right, baby girl,” he whispered against my skin. “I’ll be making you scream and shout so loud, feel so good, that we’re gonna break this fucking thing.”

  And I shivered deep then, my insides running wet once more, desperately delicious, wanting him, tilting my head back to savor his touch, his mouth locking with mine.

  “Mmm,” I murmured. “I can’t wait, big boy,” and with that it was on. I perched on my hands and knees as Jason ravished my body. He was all over me, stroking me everywhere, kissing me everywhere, loving me with every fiber of his being.

  “Oh god,” I cried out, panting breathily as the big man bit into my soft haunches, leaving a half-moon circle of teeth marks. “Oh god.”

  But that was only the beginning because Jason crouched behind me then and slipped his tongue against my snatch, running that wetness all the way from clit to asshole, dipping his tongue in at the top, savoring my rusty star once more.

  “Oh god!” I screamed, eyes squeezed shut with ecstasy, throwing my head back, elbows locked to keep myself upright. “Oh god!”

  And Jason chuckled low in his throat.

  “Looks like my little girl likes her cunt play,” he rasped throatily. “Good thing because I love sucking pussy. Part your legs more, baby girl,” he commanded. “Give it to Daddy.”

  And I obeyed, head dropping to the coverlet, forehead pressed against the mattress as the most delicious sensations overcame me. Because Jason had flipped onto his back with his head between my legs and was holding my steamy folds open, running his fingers through the wetness, inspecting my swollen channel of pink.

  “God you’re beautiful,” he muttered before lifting his head and placing an open-mouthed kiss against my twat. “And you taste good too.”

  And I lost it then, burrowing my face against the mattress as he licked and licked and licked, kissing my clit before tracing circles around it with his tongue, sampling my folds, sucking the cream out of my hole.

  “Ohhh!” I moaned, desperate, body shaking, nips hard and achy, grinding my pussy into his face. “Oh fuck!”

  The big man didn’t let up at all, pressing his tongue up my passageway, burrowing into the pink, drinking the ambrosia that flowed from my insides, gulping it like he couldn’t get enough.

  And just when I thought it couldn’t get any better, I felt the faint brush of his finger against my asshole. My body clenched violently, I’d just been breached there. Was he going in again?

  But Jason chuckled, his deep rumbles muffled by my cunt, he was so far inside.

  “That’s right, baby girl, I’m gonna push myself in here because I gotta keep you stretched out, who knows, maybe you’ve shrunk in the last five minutes,” he growled, stuffing his finger in, feeling up my musty channel. “Fuck, you’re so tight.”

  And I lost it then, everything we were doing was so deliciously nasty that I careened over the edge, screaming, gripping the sheets to keep myself from levitating off the bed.

  “Ohhh!” I shrieked, body jerking and spasming uncontrollably as I mashed my pussy harder onto his face. “Oh!”

  And the big man opened his mouth to take it all in, lapping and licking my folds, letting me take however much I needed to come.

  “Yeah, face-fuck me, do it,” he rumbled, voice muffled, as he pushed his finger in harder up my ass, this time slipping a second one in with the first, pulling slightly before scissoring them, the jolts in my ass magnified by his mouth. I felt like my pussy and ass were going to shake right off, I was coming so hard that I jerked like a marionette, unable to control my body.

  But Jason rode me through the storm, fingering my butt while mouthing my cunt, the big man was with me every second of the way and I collapsed onto the bed, exhausted, a sheen of sweat on my haunches as he pulled himself out from under me.

  “That was good,” he growled, wiping his chin with his hand. And oh god, but the lower half of his face was completely drenched from my sopping juices, his chin shiny and wet.

  But the big man just grinned.

  “You taste delicious baby girl, now back on your knees,” he commanded.

  My eyes flew open. He’d just treated me to another amazing orgasm and I was wrung out, limp as a rag doll on the bed, heaving, panting, my sweet folds swollen and wet still. But that was his point exactly.

  “I haven’t had you on my dick honey, and it’s time to take that ass cherry.”

  I gasped then, turning to look at him over my shoulder.

  “Jason, now?” I panted. “But … but … but I’m so fucked already.”

  And he just rumbled deep in his throat, laughing.

  “That’s right baby girl, and you’re gonna be even more fucked when I’m through,” he ground out. “Now hands and knees, upsy-daisy.”

  And slowly, I obeyed. My limbs were so weak and shivery that I could hardly manage, slowly dragging myself up, my head dropping from my shoulders like a flower too heavy for its stalk. I was so spent, so exhausted, small residual tingles still running through my frame.

  But Jason growled approvingly, gazing at my pussy, because I knew how it looked. Pink, swollen, creamy, and begging for his touch, my slit was open and all his. But instead of fingering it, he got behind me, doggy style, and spit into his hand, lubing up his dick.

  “That’s right baby girl, I’m getting myself wet for you,” he ground out. And then he began lifting my torso, helping me up so that I knelt on my knees facing away from him. “Come on baby girl,” he murmured against my skin, “Come on, sit down on Daddy’s dick.”

  My eyes flew open then, every sense on alert, my body jolted back to life with electricity. Me sit on his dick? He wasn’t gonna push it in slow, breach my pucker with a couple of expert strokes? I was gonna have to impale myself, push myself down on that massive cock? With my ass, no less?

  And he chuckled deeply into my ear, confirming it.

  “That’s right, baby girl,” he rumbled. “Not your pussy, honey. I want to see you break your ass cherry on my pole, I want to see that sweet anus take me deep, shove itself onto my shaft.”

  I shook my head furiously, struggling for a moment. My ass? No, I couldn’t! No, it wasn’t possible, wasn’t physically possible.

  “I can’t Daddy,” I gasped, wrenching around to meet his gaze. “I can’t, I’m too tight and you’re so big!”

  But Jason wouldn’t let me go, my small body helpless against his. In fact, I could feel his huge head poking against my dark star already, and my abs immediately tightened, my butt clenching reflexively.

  “Baby girl, you’re gonna be fine,” he ground out into my ear. “Now relax,” he commanded.

  And helpless before him, I tried to do as told. I closed my eyes and let myself breathe for a moment, inhaling deep of the sex smells in the air, the scent of my f
ragrant cunt wafting. I inhaled again, focusing my mind while letting my body go limp, letting the heat of his big frame seep into me from behind.

  “That’s right,” he growled encouragingly in my ear. “Let go and your ass will take it naturally.”

  And with that, he angled me so that I was just above his cock, my dark star kissing his dick tip. I whined a little, shifting my butt against him, letting his cock brush against my tight pleats, feeling the shiny wetness, how he’d lubed himself up for me.

  “That’s right,” he groaned again into my ear. “Get yourself comfortable.”

  And with a small exhale, a small sigh, I pushed my butt down slightly, taking him about a half inch into my channel.

  “Oh!” I gasped. The invasion was huge, stretching me although I’d barely done anything.

  “That’s right,” he rasped again, holding completely still as my butt adjusted. “Keep going.”

  And taking another deep breath, I humped my ass down again, this time his pole sliding in two or three inches into my musty channel.

  “Oh god,” I squealed. “Oh god!” My tight ring clenched reflexively around him, gripping the massive shaft before relaxing, pulsing again and again as my small hole adjusted.

  Jason groaned deeply then, his chest vibrating against my back as his cock got fucked.

  “Oh fuck, baby,” was all he could manage, rasping deeply in his throat. “Fuck you feel good.”

  And with one last heave, one last push, I slid down him all the way, his balls pressed against my wetly creaming cunt, my ass flush with his pelvic bone. Oh my god, it felt so good, I was so stretched, so tight, so fucked, with a man’s cock deep in my anus, my rectal walls gripping him like they’d never let go.

  “Jason!” I mewled, my head lolling against his shoulder. “Oh god!”

  And the alpha male paused, breathing hard for a moment, his hands wrapped around my waist as we sat, letting our bodies savor one another, the closeness, the deep intimacy.