Double Dare: A Fake Fiancee MMF Romance

by Cassandra Dee

  “Ma!” I gasped. “What are you doing?” I mean, my mom looked fantastic, don’t get me wrong, but what the fuck?

  “Cleo honey,” purred my mom, “you’ll see. Come on,” she commanded, sashaying to the VIP area.

  I trembled. The Donkey Club was filled with rednecks, dudes who looked like they worked on farms, which was pretty incredible given that we were in the middle of Manhattan. Some were literally chewing stalks of hay, and I didn’t want to get undressed in front of them but I felt like I had no choice. Slowly, I eased off my overalls and shrugged out of the crop top, leaving nothing but my lingerie and a pair of stilettos. On trembling legs, I followed my mom, my ass swaying and boobs bouncing.

  It was so uncomfortable walking through the crowded tables filled with men, not a few letting out cat-calls, hooting at us as we passed.

  “There ya go, little girl,” cawed one. “Lookin’ fresh, lookin’ juicy.”

  Another one went so far as to grope my ass as I snuck by, taking the opportunity to give my peach a solid smack.

  “Ripe and plump, just like we like ‘em,” he cackled. And despite myself, I shivered a bit inside, my nips tingling as my cunny moistened. Could it really be happening? Were these disgusting guys, this dirty place, turning me on?

  But I didn’t get a chance to think about it because as we neared a table filled with men, my mom pinched my ass cheek, making me jump.

  “Mom, what the?” I gasped. “What was that for?”

  But Lorena ignored me, instead turning to two men sitting in the booth.

  “Robert, Lester,” she purred to two seedy-looking guys. “How are you? Long time no see.”

  The two men looked up, oily and dressed in cheap suits.

  “Well, well, what have we here?” growled the greasier of the two. “Our prodigal girl returns.”

  “Yeah,” grunted the other. “Where the fuck you been?”

  “Oh here and there,” replied Lorena airily, cocking a hip to the side. “You know I wanted to better my situation, and I got a housekeeping job with Drake Markham in Long Island.”

  “The Drake Markham?” remarked the first dude, cocking an eyebrow. “The owner of the New York Jets?”

  “Yep, that one,” smirked Lorena. “It was the best decision I ever made. Lonely older man, hot housekeeper? Check out my ring, boys,” she said, extending her left hand.

  And both men’s eyebrows almost popped off their foreheads, the ten carat diamond sparkling madly even in the low light of the club. I’d seen that diamond before – one night, when spying on my stepdad, I’d watched amazed as he inserted it into Lorena’s cunt, stirring it a bit before pulling it out dripping wetly, sucking it, growling with pleasure.

  “Tastes like nasty-ass woman,” he’d rumbled, eyeing my mom’s bod lasciviously.

  And Lorena hadn’t let him down. Twisting sinuously, she’d parted her legs, revealing that pink slit, looking up at him through half-lidded eyes.

  “Fuck me,” she breathed, “fuck me good with that ring.”

  And of course, my step-dad had gone at it like an alpha male, stuffing the diamond back in her before burying himself to the balls in my mom’s ass, both of them panting and heaving like dogs gone wild. But that had been in the good ole days. I hadn’t seen something nasty and hot happen between them in ages now, and it wouldn’t happen anymore, not with me in Daddy’s bed.

  But now the gem had reappeared, gleaming on my mom’s hand, giving no hint as to where it’d previously been.

  “That’s a fuckin’ whopper alright,” marveled Lester. “Good for you.” Actually, come to think of it, the dude wasn’t terrible looking. Seedy, with a wifebeater under his pin-striped suit, but overall he was well-built with nice features.

  “We always knew you were sharp,” added the second. “Glad you found a sugar-daddy.” Actually this guy wasn’t terrible looking either. I was just turned off by the guys’ overall presentation as Jersey guidos with slicked back hair and cheesy accents.

  Besides this whole interchange was eye-opening. How did Lorena know these people? Why were we even here? But before I could butt in, my mom answered my questions.

  “Lester,” said Lorena abruptly. “I’m here because I want to repay my debts. I left the Donkey Club hanging, but I don’t forget people who were good to me,” she said smoothly.

  “Oh yeah, how?” said Les. For the first time, his gaze slid over to me appraisingly, like I was a piece of meat. “This your offering?” he grunted, nodding my way. I shrank back a bit, intimidated by the way his eyes assessed my curves.

  “Yes indeed,” said my mom. “Cleo, come here.”

  Nervously, I teetered over to the group. I’d been hiding in the back hoping no one would notice me, halfway behind a velvet drape.

  “This is Cleo,” she said. “Turned eighteen two weeks ago, dances like a ballerina. Perfect material for the Donkey Club if you ask me,” she said conspiratorially.

  I colored. I couldn’t dance at all, I had two left feet and had been a wallflower at my high school prom, literally sitting the entire night on the bleachers watching everyone else get jiggy. Why was my mom singing my praises?

  But the guys didn’t say anything, merely looking me over, taking a swig of their beers.

  “Boys, she’s a natural,” promised my mom. “Just give her a try, you’ll enjoy it,” she said suggestively, wiggling her eyebrows.

  Give her a try? WTF, these guys better not touch me. My mom wasn’t pimping me out to these two losers, even if they had decent builds under their cheap suits.

  But the men said nothing, instead appraising my curves, letting their eyes trail over my assets, lingering on my flat belly and big boobs.

  Finally, Les replied.

  “Ya think?” he said to the second guy.

  “Sure, why not?” his friend replied.

  I flushed. They were talking about me with me right there, and it made me feel like a speck of dust. But Jimmy turned to the girl spiraling on the stage in front of them and ran a finger in a line across his throat. The signal was unmistakable. The girl abruptly stopped dancing and slunk off, grabbing as many dollars as she could on her way out.

  “What do you say, Red?” Jimmy addressed me abruptly. “Here now’s your chance.”

  I gawped. He expected me to get up there and dance? Right now, in the middle of someone else’s set? I didn’t even recognize the music, it was some grinding heavy metal stuff and I usually liked Top 40 hits. But my mom shoved me into the spotlight, hissing, “Go!” fiercely.

  “No Mom!” I gasped, trying to hide behind a chair even as my mom pried my fingers off the back. “No, what are you thinking?”

  My mom just glared at me, her eyes fierce, her breathing coming hard.

  “I’ve sacrificed so much for you, can’t you do one thing for me?” she hissed again. “Get out there! Make the most of what you have!” she commanded, glaring at me, hands on her hips.

  And I almost cried then, hot tears rising to my eyes. But at the same time, I felt ashamed. My mom had done so much for me, worked as a cleaning lady as we tried to get by. And what had I done for her? Seduced my stepdad, that’s what.

  And so I forced myself to get on the pedestal, hoisting myself up before looking around, unsure what to do. I looked at the two other girls still dancing and basically just tried to do what they did. I swayed my hips in small wiggles, kicked a foot out and tried to smile, still blindly looking out into the audience for my mom. I couldn’t see her, the light was too bright but I could hear her voice, hissing still.

  “Dance!” she said. “Dance like you mean it!”

  Like I meant it? Trembling, I tried to do a little more, swiveling a little, gyrating my hips, running my hands up and down my waist.

  “Stop acting like you’re so innocent,” came Lorena’s hiss again. “Dance like your stepfather’s watching!” she commanded, and I almost passed out right there. Lorena knew? She knew about me and Drake? Oh god, oh no. But if she knew, then I might as we
ll make the most of it. I closed my eyes, pretending that Drake was in the room with me, that it was just the two of us, his dark blue eyes leaving hot trails over my body. I blocked everything out and began dancing, just for him.

  It was as if a light clicked on in my head, channeling the dirtiest moves I’d only ever seen on my laptop. Suggestively, I licked the pole once, and squatted, showing off my toned glutes, highlighting my calf muscles.

  I noticed that the other girls were completely nude, and I toyed with my bra straps, softly stroking my shoulders, unsure about next steps. But my mom interjected again, her voice like a harpy, intruding into my dream.

  “Take it off,” she hissed loudly from the sidelines. “Every single piece.”

  Ugh, that didn’t sound good. But I turned back to imagining Drake. He’d told me that I needed experience, right? Well, I was going to get some right here, right now. So slowly, I slid the straps off my shoulders, and then unsnapped the clasp in the back, gripping the lace cups to my torso as a last ditch effort at modesty. But seeing my mom’s glare from the sidelines, I let the cups drop, exposing my Double Ds.

  They were glorious, pale and creamy, jiggling and swaying as I continued to dance. The deep pink areola swung like hard candy, my nips stiff in the chill air of the club. I tugged one hesitantly and it lengthened immediately, protruding like a bullet.

  Oh god, Daddy would love this and I closed my eyes, pretending that we were back in his study, just the two of us, me dancing under his heated gaze. I don’t know what made me start, but suddenly my eyes flipped open and my dreams of Drake went crashing into the ground, bringing me with a thud back to reality.

  Because the two pit bosses, Robert and Lester, had their dicks out and were stroking the shafts, lovingly tracing each bulging vein with male fingers as they stared at me, my nubile, sinuous form. Oh god, oh god. Where was my mom? I wanted to get out of here.

  But I gasped because my eyes had adjusted to the gloom and I caught a glimpse of movement under the table. I watched, shocked, as my mom, now completely nude, got on her knees in front of Lester and took his monster into her mouth. He threw his head back, groaning so loudly that I could hear it even above the pounding music as my mom massaged that staff with her mouth like a champion, her head bucking furiously as she laved it up and down, popping it in and out of her mouth like a delicious lollipop.

  I kept dancing as a shield, trying not to stare at the scene before me, but the most incredible things just kept happening. The dude she was sucking off reached down and grabbed her by the waist, slowly rotating her until her thighs were propped over his shoulders and they were in a vertical sixty-nine. Her mouth never left his dick, indeed she was sucking him off still, upside down in his lap, making moaning noises deep in her throat, her eyes closed as she savored the man meat.

  And the dude made good of the opportunity. He paused for a moment, his gaze focused on the steaming cunt before him.

  “Rob, get in here and help me for a sec,” he commanded his friend.

  The little weasel stopped beating his dick for a moment and stood up, positioning himself behind Les so that he had a perfect view of my mom’s vagina. Like a trooper, she hadn’t stopped sucking this entire time, the slurping noises loud and resonant.

  “Pull her apart will ya?” asked Lester, and Rob obliged. With two hands, he reached over his friend’s head and tugged my mom’s cunny lips apart, revealing that deep pink interior, moist and glistening with vaginal juices.

  “Man, she’s just as beautiful as the day we met her,” Robert reminisced. “What was she then, eighteen, nineteen?”

  Now I completely stopped dancing, taken aback by the stunning revelations before me. Not only had my mom known these guys at a tender young age, but she’d evidently been showing her cunny for over twenty years! I knew I shouldn’t have been blindsided, but I was. It’s always a shocker to realize that the woman who gave birth to you is a tramp, even if the evidence is unmistakable. She’d probably been sucking and fucking at the Donkey as soon as she hit adolescence.

  Shaking my head, I started to sway my hips again, trying to let the music take over, desperate to get back to my dream of Drake, but it barely seemed to matter given that neither of the guys was watching anymore. Instead, as Robert held Lorena’s pussy lips open, Lester tasted Lorena’s cunt, causing her to squeal around his dick, her body shivering, her pussy twitching visibly. The man was gross, but he knew how to lick a vagina. His tongue went flat first, covering as much area as possible, tracing every nook and cranny of my mom’s darkly pink snatch. He then contracted it into a sharp spear and tongue-fucked her hole, moving his head in and out, jabbing it again and again into her sensitive spot before licking and sucking her clit, loving that tender bundle of nerves.

  Just when I thought I couldn’t be surprised anymore, my mom came, a low moan emanating from down below, her breasts squashed against Les’s torso, an earthquake overtaking her body so that her pussy literally shook itself free of the man’s mouth. And I watched, astounded, as a fountain of female ejaculate spurted over both men, hitting Lester and Robert in the face as she orgasmed, like a lawn sprinkler gone out of control, jetting creamy white drops everywhere.

  “Awww, fuck,” groaned Les, throwing his head back, neck muscles strained, a look of ecstasy in his face. Judging from the choking sounds emanating from his groin area, he’d just creamed into Lorena’s mouth, filling her with his cum, spurting that jism down her throat.

  And the other dude erupted as well, his hand like a piston at his waist, palming himself until his dong exploded in a shower, droplets spraying in Lorena’s hair, coating her with a sticky film of white.

  “Ahhh, fuck fuck fuck!” he panted, his wrist still moving up and down that fuckpole, the jism dripping off the tip of his dick. “Fuck!” he said once more for good measure.

  And with a sigh, the trio relaxed, all of them sated and satisfied from the dirty encounter. My mom went limp, the tension gone from her body as she slithered downwards, only to be cradled in Les’s lap.

  She smiled flirtatiously at the men, purring deep in her throat.

  “Still as good as when I was eighteen, hmmm?” she said slyly.

  And both men grinned like Cheshire cats.

  “After that star performance, I think we can guarantee your daughter a job, right Les?” rumbled Robert, cleaning off his dick. He shook his snake, white droplets spattering everywhere on the floor. No wonder this place had sticky floorboards, it probably had all sorts of sex fluid in every nook and cranny.

  And Lester was no better. This dude literally squeezed his own ball sacs, grunting a bit as the last drops of semen erupted from his dickhead, pearling at the tip before dribbling to the floor, joining the expanding pool of jizz before him.

  “Yep, after that star performance, we can guarantee your daughter a job, no problem,” rumbled Les, his dick still erect despite his efforts. A trail of white slime ran down from the tip, and Lorena swiped it lazily with her finger, bringing it up to her mouth for a taste.

  “Thank you,” she smiled slyly. “I promise Cleo’s just as talented as me. Now gentlemen, shall we move to part two? You know I haven’t taken you inside yet,” she purred, teasingly stroking Robert’s cock with one hand while reaching for Lester’s shaft with her other.

  Holy shit, there was a part two? Where the dudes would put their shafts in my mom’s tight cunt? Evidently so because my mom seized Robert’s cock in her mouth again, her cunny trembling as Les shoved two fingers inside, making her squeal and squirm. Holy shit! I needed to get out of here, and I ran to the coat check, seizing my jacket before stumbling outside. Where was Drake? my heart cried. I needed my Daddy now, more than ever.

  CHAPTER TEN

  Drake

  I haven’t seen Cleo in ages. She disappeared after that “girls’ night out” with Lorena and never came back.

  The morning after, I’d expected to wake and find Cleo snuggled against me, hopefully nude, willing and wet, the way I loved my
little girl. But instead I’d woken up alone, stumbling downstairs to find Lorena waiting for me, slinkily sexy in a silk robe.

  “Where’s Cleo?” I ground out. At this point, I still had no idea that Lorena knew everything.

  “She’s in the city,” said Lorena airily, sliding a plate of scrambled eggs and bacon before me. Now I knew this was a trap. Lorena never cooks because we have a personal chef and yet she’d gotten up early to put something on the grill.

  “What do you mean, in the city? She has school on Monday and needs to study,” I ground out. “Cleo’s going to college and needs to make a last ditch effort to bring up her grades.” Both of us knew that our daughter was terrible at academics but my connections could probably get her into some small private college. When you have unlimited funds, even the most elite, snobbish schools throw open their doors.

  Plus, I’d been doing some planning of my own. I was seriously contemplating buying a condo near wherever she matriculated. Hey, if I wanted to see my little girl, what was wrong with having a love nest nearby where I could fuck that little pussy to my heart’s content?

  But Lorena rudely interrupted my reverie.

  “Oh college,” she sighed, waving her hands vaguely. “Cleo’s decided not to go. We stopped by a modeling agency in the city and they loved her Drake! They signed her immediately and she’s boarding with some other girls until she gets her first job. Just wait,” bragged Lorena. “You’ll see her face in all the magazines!”

  I frowned. Okay, my little step was definitely beautiful enough to model, but I thought fashion types were six feet tall and thin as whips. My little girl was about five four, and luscious everywhere … especially in the places that mattered.

  “There’s a revolution going on in the fashion industry,” rushed Lorena. “They like girls with personalities even if they’re not skinny and Cleo was the perfect fit, just so photogenic with that glorious hair. You know,” she added helpfully, “redheads are especially in demand right now.”