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

by Cassandra Dee

I was so floored that I couldn’t speak. Hot tears trickled down my cheeks as I looked down at the floor. My daddy, the one I’d thought was amazing, handsome, charismatic, who cared about me, was now with another woman? I was hurt, devastated although I told myself I shouldn’t be.

  “Oh I see,” I said quietly.

  “That’s it, honey, buck up,” said my mom. “Try to make a good life for yourself. It’s not that we don’t care about you. But life is complicated, you know? With the baby on the way and everything ….”

  Lorena’s voice trailed off but I couldn’t believe she was so callous about it all. I mean, she should have been doubly threatened with a new woman and a baby living under her nose. So trembling, I asked, “But what about you? Aren’t you afraid that Drake’s going to ask you to leave too?”

  And Lorena laughed at that, her voice tinkling with amusement.

  “Honey, I was never under any illusion that I was anything but a convenience to your stepdad. I was the maid originally, remember? Someone to vacuum his floors and suck his dick when he felt like it. So cheer up, honey,” she encouraged again. “Drake’s going to fund your apartment for two years while you get on your feet, and I had sex with those dolts at the Donkey Club so they’d give you a job. It was all part of the plan, okay baby? Don’t worry about me, I’m going to be fine, just worry about you.”

  And choking back sobs, I hung up the phone. This was some fucking twisted turn of events. My mom and step-dad, they’d propelled me into a den of sin, encouraging me to bare my body, even sell it to the highest bidder. But I was determined to find my own way here on out … Drake’s money be damned.

  CHAPTER TWELVE

  Drake

  I kept thinking that Cleo would come home. Lorena’s proclamations that Cleo was going to be a famous model were overblown sure, but even if she did become famous, the little girl should come home to see her parents, right? Especially a daddy who loved her.

  I missed her more than I cared to admit. I’ve been a playboy all these years, even after my marriage. My general approach to life is that pussy is there to be fucked, so why not me? I’m pretty indiscriminate so long as she’s attractive, voluptuous, and doesn’t talk too much.

  But something changed with Cleo. Suddenly I found it difficult to get excited about other women. Of course, my little girl and I had never promised to be exclusive, after all we’d only slept together for two weeks. But the memories were overwhelming. Cleo at sixteen, all long legs and an innocent expression. Cleo at seventeen, beginning to fill out, her body developing curves. And finally at eighteen … ripe for the picking.

  Lorena tried to comfort me. Knowing that I was no longer interested in her sassy curves, she offered Marie, our dog-walker. Because yeah, there was no pretense that we were even interested in each other anymore, Lorena stays with Carlos in the pool house now while I’m holed up in the mansion.

  But my wife knows her place and never neglects me for too long, instead looking for substitutes, replacements for the beautiful Cleo. What was wrong with subbing her daughter? Oh right, she’s my step, we’re technically related.

  “Drake, you’ve got to let Cleo go,” Lorena purred. “Cleo’s got her own life, she wants to explore the world as a model, fly around and see places, meet new people. She’s young, she’s not going to stick around with us old fogies forever.”

  I snorted. Lorena and I were hardly old fogies, and I shook my head disgusted.

  But the woman could read my mind.

  “To her, we’re old fogies,” she reprimanded gently. “Anyone over thirty is ancient to Cleo, so let her spread her wings a little, see what the world has to offer. Besides, what about Marie? She’s perfect,” she purred. “An athletic blonde will be good for you.”

  I thought about Marie. She was cute, sure, in a wholesome, All-American way, tanned with freckles, a strong build. Our dogs loved her, but I just couldn’t get Mr. Happy to bite.

  “Nah,” I said dismissively. “I’m not feeling it.”

  Lorena gave me a disbelieving look, startled because I was turning down free pussy. But she smiled slyly.

  “How about this then?” she asked, slipping the strap of her sundress off her shoulder, baring a big jug that jumped and swayed.

  I have to admit, I was tempted. I’ve always been a titty man and Lorena had a nice pair, bronzed with dark nipples, often leaking from some kind of hormonal imbalance. I should have figured something was up. The innocent sundress wasn’t really her style, she was more of a body-hugging cocktail dress woman. But even the promise of a good suckle couldn’t tempt me. I wanted pale, creamy flesh, not the brown gazongas Lorena was offering.

  As if reading my mind, she tucked herself back in, hiding her boobies once again. With a flip of her hair, she sashayed away, no doubt to look for Carlos. But whatever, I wasn’t interested in my own wife anymore, I just wanted her daughter to come back.

  “I’m not done yet,” Lorena called over her shoulder. “You can’t be celibate forever.”

  But with the way I was missing Cleo at the moment, it sure seemed like I was destined for the life of a monk.

  That night, I ate dinner alone before retreating to my study. I was looking forward to a glass or two of port, contemplating the flames of the fire, maybe beating myself off while thinking of Cleo’s fine, sassy form. Heck, I could see her in my mind’s eye, that creamy white pussy, the lips wrapped around my dick, throwing her head back while panting my name. Fuck yeah, I’d start a search for her tomorrow. It wouldn’t be hard, there’s only so far an eighteen year-old can go.

  But when I opened the door to my study, there was a woman waiting on my leather lounger … completely nude, wearing high heels only.

  “Mr. Markham,” she giggled. “It’s so nice to see you again. Lorena asked me to wait for you here.”

  What the fuck? Who was this blonde? Did I know her from somewhere? What was my wife up to?

  The woman giggled, cupping a breast and jiggling it at me, seeing my confused expression.

  “Don’t you recognize me?” she asked. “I’m Marie.”

  Holy shit! Lorena must have done some kind of black magic on the girl because Marie had been transformed from All-American blonde to vamped-up vixen. She was wearing a crapload of make-up so as to be almost unrecognizable, her hair teased like a Pamela Anderson clone.

  Her body though, was tempting. Big round jugs with ruby red nipples narrowed to a tiny waist before flaring out into wide hips and chunky thighs. I have a thing for big girls, and Marie was larger than I’d previously thought. There was plenty of flesh for the loving.

  “Mr. Markham,” she giggled again. “Come closer.”

  I approached stealthily like a cat, but wasn’t about to make a move. My dear Cleo was still on my mind, her chestnut tresses and sweet smile a remembrance of days past.

  “Mr. Markham,” she repeated sweetly. “I have a gift for you.”

  I was expecting her to do something vulgar like spread her legs and show me her pussy, or maybe get on her hands and knees and wiggle her bare ass. But instead, she reached below the chaise lounge and pulled out a manila folder. Oh fuck. I’ve been in business a long time and know what unmarked folders usually mean. Bad news.

  Suddenly angry, I strode over to the blonde and ripped the folder out of her hands, not bothering to say anything as I tore it open.

  Oh fuck, it was worse than I expected. I’d been expecting Lorena to do something outrageous, maybe slip some condoms into the envelope, or some nasty sex pics. But instead, she’d doubled down.

  Somehow, she’d known that I hadn’t given up on Cleo, far from it, and was determined to find the redhead. So Lorena had done the worst possible thing. The photos inside … they were of Cleo, totally nude, her assets flying, on display for men to see.

  There was one where she was dancing, wearing nothing but stripper heels, her hair whirling as she gyrated on a pole. She looked gorgeous as attested by the male faces in the background, practically drooling at her lusc
ious body.

  The other photos were even more explicit. Cleo squatting, nude, baring her cunt to some guy, and then backing up to shake her rump in his face. Then bending over and showing off her breasts, her nips perky and tight, that creamy flesh ready to be devoured. There were dollar bills everywhere on the stage, littering the floor, making my little girl rich.

  What the fuck? How could Cleo have turned so dirty, so fast? She’d been a virgin when I took her, and it was unbelievable that a mere two weeks later, she was taking her clothes off for money, getting dollars for shaking her tits, wiggling that ass.

  But it only got worse. As I flipped through the files, there were more and more photos, and they just got more explicit. The shots were blurry in some cases, but otherwise unmistakable. Cleo’s legs spread, her cunny stuffed full with a massive dildo on stage. Cleo bent over, her ass being violated by a toy mounted on a wall. Over and over again, cream trailing from her thighs, juices running from the holes of her body.

  I closed the file slowly, unable to look anymore. My little girl was working it, probably making thousands by baring body. Why? What the fuck? There was no reason, I would have provided for her. Sure, we hadn’t talked about our living situation, college, anything, but I figured that it was just a matter of time. There was absolutely no reason for Cleo to be dancing, to put that beautiful body on display for cash.

  But evidently, this was what she wanted, to move out and live her own life, and Lorena wanted to drive the point home. She’d urged me to move on, resume my playboy ways, hinting that Cleo had a “modeling career,” even offering me another woman. I hadn’t believed any of that shit until I saw these photos, and it was like a stake to the heart, chest pains literally making me double over in agony.

  Fuck this. Resolutely, I stiffened my back. My heart hurt and my libido was crushed, shredded to smithereens but I was an alpha male and wouldn’t let emotion control me. Betrayal hurts, but I’d get over it.

  “Marie,” I ground out, my voice gravelly. “Get up and bend over.”

  The blonde giggled, shifting her curvaceous form so that she teetered in high heels, doubled over the couch. As an enticement, she reached behind to hold herself open, pulling her cheeks apart so that I could look into that deep pink channel.

  It smelled different, it looked different, and it was going to feel different than my beautiful girl. Reaching into my desk drawer, I pulled out a black, twelve-inch dildo that Cleo and I had experimented with right before she left. I hadn’t cleaned it afterwards, taking it out to sniff sometimes when I was working, that aromatic pussy scent still heavy, embedded in the rubber, rubbing it against my cock as a tantalizing treat. But the best way to get over one girl is to get right back into the saddle with another, and I was going to fuck the memory of Cleo right out of my mind.

  CHAPTER THIRTEEN

  Drake

  Did I fuck Marie the dog-walker? Surprisingly … no. I’d planned on giving it to her good, taking out my rage on the blonde’s unsuspecting body.

  And she’d been all for it.

  “Please mister,” she’d pleaded, spreading her legs, holding her pussy lips apart. I could see straight up that channel, the pink walls pulsing, creaming with lust already. “I need it bad, put that big toy in my cunt!”

  But disgusted, I’d tossed aside the dildo. I couldn’t bear to touch the blonde because of all the memories circulating in my head of a certain gorgeous redhead, ripe, willing, so tight that my pole got stiff just thinking about it. I didn’t want some random blonde chick wrapped around my cock, I just wanted Cleo’s sweet, tart pussy, in all ways, all places, creaming hard.

  So I’d dismissed Marie curtly, kicking her out of the office before turning to my rolodex. Not caring that it was close to midnight, I’d called my private investigator and instructed him to get on it, to look for my little lost lamb. But as fate would have it, I beat him to the punch. The next evening, I’d been looking out the window of my chauffeured car in Manhattan when a taxi drove by, Cleo’s face smiling from the billboard up top. What the fuck? It’d only been two weeks! Doesn’t it take at least a month to buy advertising space, not to mention hire a photographer and schedule shoots?

  But evidently Cleo was so beautiful that her new bosses had juiced the process. The Donkey Club, as the fucking joint was called, must have realized that she was a honeypot and had pasted her face on the ad, her eyes half-lidded, smoldering, while holding a finger up to her lips in a dirty shhh!

  Holy fucking shit. Judging from the open mouths of other dudes looking at the ad it was fucking working, there’d be some very interested new patrons gracing the Donkey with their presence very soon. And it was bound to be bad. After all, any joint called the Donkey was going to be bottom of the barrel, seedy and unsanitary.

  So I’d whipped out my cell and called off my client dinner, instead directing the driver to go straight to Cleo’s workplace. It was only eight, so the club obviously wasn’t packed, but I managed to slip in unnoticed, just another guy in a suit.

  It was dark and disgusting. Sawdust rose in gusts off the floor and the space was a far cry from the velvet rope treatment of premiere gentlemen’s clubs. Instead, the counters were sticky, dudes in cowboy hats chewed on straw as they watched girls gyrate, and there was a live horse in the back that night for whatever reason.

  But I saw what I’d come to see. There was my little redhead, shimmying on stage, her assets luscious and bouncy. Mr. Happy rose to attention at that one glimpse, watching raptly as she swung and shook, her pale creamy flesh almost incandescent in the low lights, a spattering of freckles barely visible just above her bosom. I watched, entranced, my heart in my throat. Cleo looked delicious, ripe and juicy, and I could barely breathe, I wanted to jerk her off that stage and smother her with kisses.

  But another dude beat me to it. Some old farmer went up there waving dollar bills, and Cleo bent over, presumably to let him stuff the bills into her g-string. But instead the dude whisked her off her feet so that she came to rest in his lap, bouncing and laughing.

  I couldn’t hear what she said but the old farmer slobbered over her shoulders and breasts, and Cleo threw her head back in mock ecstasy, reveling in the attention, loving the gentle tugs and nips. She managed to score even more money, the guy literally getting out his wallet and giving her all of its contents.

  I stood, my back stiff, and began to make my way out of the club. As a businessman, I knew my logic was flawed. Cleo was a professional actress in many ways, she smiled and blew kisses to make money. But my heart was thundering, feeling betrayed and lost, torn apart by her shocking departure. I wanted my little girl to be mine only, and it killed me that she was giving it away to other men, selling herself, baring it all for others to see.

  Shaking my head resolutely, I got back into the car.

  “Home,” I barked. I would forget the brat no matter what it took.

  CHAPTER FOURTEEN

  Cleo

  Four years later …

  I miss my stepdad. I think about my old life sometimes, and it makes me sad. It’s like when you’re all grown up, and you realize that your childhood is gone now, the sweetness, the purity, the innocence. Okay maybe I’d been none of those things, but definitely the two weeks I’d had with Drake had been amazing. Not just the sex, but his reassuring presence in me, surrounding me all the time.

  Because things have really changed. I’m a working girl now, on stage every night, serving customers right and left. I don’t know how I got here exactly.

  When I first came to New York, Lorena helped me find a really nice apartment.

  “Don’t worry, Daddy’s going to pay for it,” she reassured me. We’d signed a lease for five thousand a month. But after two months in the rental, Lorena canceled my lease and put me into a shared apartment with five other dancers. It was awful -- some of the girls were crackheads, smoking whenever they were off duty, stoned and dazed all the time. Not to mention that the place was a fucking sty, cockroaches and mice scr
abbling at night.

  But Lorena was adamant.

  “You can’t live off Daddy’s money forever,” she admonished. “You’re eighteen now and Drake won’t support you forever. The rent here’s only $900, you can afford it by working hard at the Donkey Club.”

  And it was true. I made about $500 a night dancing, all cash, so covering my rent wasn’t an issue. It was more the knowledge that Drake didn’t care anymore. I felt like a ghost now. He never called, he never visited, was too busy with his new girl … and the baby on the way. I was bitter, and the tang in my mouth sour and hurtful. It was so painful to think that our connection was completely forgotten, that I was a piece of trash, used and discarded already. The agony made me throw myself into work, trying to forget.

  And so I danced with a frenzy. The customers at the Donkey Club had never seen a girl hustle so hard, baring everything, breaking down all walls. I held nothing back, pushing all the boundaries, working every night, showing everything, holding nothing back. I can’t say I’m proud of it, but I wanted to be the best, even if it was just being the best in a seedy strip club.

  And my efforts paid off. Since I first set foot in the Donkey Club four years ago, I’ve seen my star rise. Okay, maybe I’m not a world famous model, but I am a world famous erotic actress and dancer. The Club uses my face in its advertisements so you can see my visage whiz by on the tops of taxi cabs, the sides of buses, and even a small billboard in Times Square, pointing the way to the Donkey Club.

  Plus, I’ve been able to build an on-line empire. Men log-on to watch me do all sorts of things, and wow, the subscription service turns a pretty penny. Guys pay fifty bucks a month to chat on the computer, to watch me dance on camera, to live out their fantasies with a girl they’ll never meet in person. There are t-shirts, dolls, branded sex toys, and even a rubber mold of my pussy, can you believe it? The business is called “CleoWorld,” and other strippers are asking to join now, to be profiled on my site. Why not? I might as well keep the smut bucks rolling in.