Double Dare: A Fake Fiancee MMF Romance

by Cassandra Dee

  “Come in,” I sang out. I half-expected it to be Drake again, but it was my mom, slinking in, her curvy form squeezed into a skintight red dress. She probably had a date with Carlos tonight, who knew where they were going, but the scarlet dress was sure to see the floor at some point.

  “Mom, I didn’t expect you,” I said, turning to look at her, keeping my voice even. “Where are you headed?” I said indicating the dress.

  “Oh nowhere,” said my mom breezily. “Nowhere you’d know.”

  I rolled my eyes.

  “Okay, fine,” I said deadpan. “It’s up to you.”

  “Well, since you’ve asked,” she pouted. “I’ve been thinking of visiting Mr. Jennings on the North Shore.”

  Oh my god. The same Mr. Jennings who’d kicked her out stark naked? Oh god.

  “Lorena, get a grip,” I said tightly. “This guy is no good, don’t you remember? He treated you like shit, made you do the walk of shame naked, and threw his dog’s crap at you too. Why? Why would you visit him?”

  Because that was what I hadn’t told Drake. Not only had Lorena been ejected in her birthday suit, but she’d been covered with dog crap Jennings had hurled at her, his epithets ringing as she strode down the walkway. The rags I’d run to her with had been to wipe that stuff off, to protect her.

  But Lorena just looked at me slyly.

  “Honey, you’ll never understand,” she said. “I’ve had a lot of experience with men, sometimes they just need to let the bad vibes out, you know? Jennings needed to let loose that day, vent some steam, and if I helped him do it? All the better, he appreciates me that much more.”

  This was some messed-up reasoning, but I wasn’t about to argue with her.

  “Fine Mom, have it your way,” I said tightly, turning back to the mirror. “Just don’t expect me to pick up the pieces like I usually do.” And a shiver ran down my spine as I remembered the sight of my mom walking down the walkway covered in shit. I almost cried again, it made me so sad for a woman who didn’t even seem to feel it.

  But Lorena had come in to say something.

  “Honey, I understand that you’ve been talking with Drake?”

  My pupils dilated with shock, but I kept my expression impassive, fighting the instinct to turn in my seat and pin her with a glare.

  “What do you mean?” I managed smoothly, continuing to brush, giving nothing away. Oh god. She must have seen me go into his office, but I hoped she hadn’t figured out what had gone on in there, that she hadn’t pressed her ear to the door. So I tried to play it off.

  “Yeah, Daddy and I chatted a little. Why what did he say?”

  And Lorena merely smiled again.

  “He said you were growing up to be so beautiful, that’s all,” she purred.

  Oh thank god, Drake hadn’t said anything and I let out a sigh of relief.

  “Oh okay, great,” I said, as nonchalantly as I could manage. “Mom, I’m going out tonight, if you’ll excuse me?” I said, eyeing the door, my hint obvious. Of course, I was going nowhere. I just wanted to lie in bed and replay my conversation with Drake in my head, the way he’d been so manly, so amazing, so unbelievably caring.

  But Lorena had come in for a purpose.

  “Honey, it’s time for you to pick up on family traditions,” she said, serious for once in her life. “We’re vixens and even if you look like an Irish lass, you still have my hot Spanish blood coursing through you.”

  I rolled my eyes.

  “What does that mean, Mom?” I asked, exasperated. I really wanted her to leave, I wanted to get back to my daydreams of my hot stepdad again.

  “It means, honey, that it’s time for you to see the Donkey Club,” she said, shooting me a sly smile. “To learn about men, we always start at the Donkey.”

  What? What was that? It sounded like some kind of lame kids’ playhouse with Mickey Mouse as its leader.

  Seeing my befuddled expression, my mom laughed.

  “No baby, the Donkey Club is a gentlemen’s club in the City. I’ll take you. Some of my old contacts might still be around.”

  Internally I lurched back in horror but tried not to show it, instead keeping my expression frozen.

  “Um, Mom, I’m not the right girl,” I said tightly. “A gentlemen’s club? In the city? It’s just not me, I like it here on Long Island with the trees and birds and big lawns. Besides, why? Why a gentlemen’s club?”

  “Oh honey, lighten up,” scolded my mom. “Drake’s comment about you being so beautiful made me think, that’s all,” she said nonchalantly. “It’s time for you to come out to the City with me, girls’ night and all that. You’ll like it, I promise.”

  I hesitated. I’m ashamed to admit but after everything that’s happened, I still craved Lorena’s love. Even knowing that my mom was the champion of bad decision-making, that she always prioritized herself above anybody else, when I heard the words “girls’ night,” I immediately thought that maybe, just maybe, Lorena wanted to spend quality time together.

  “You mean, like you and me, together, for a night?” I asked tentatively. I hated the slightly begging tone in my voice, hated myself even as I felt my heart lurch faster. Maybe this could be an opportunity for us to bond a little, develop some mother-daughter kinship.

  “Of course baby, it’ll be you and me like best friends,” purred Lorena. “It’ll be fun. You’ll see.”

  And so it was set. I had a date to explore the City with my mom … at a place called the Donkey.

  CHAPTER SIX

  Cleo

  The sexual tension between Drake and I was thick as a knife, although I hadn’t talked him since our interlude in his office. But I could feel his eyes glued to my body whenever we passed each other in the hallway, whenever I happened to brush up against him walking by. He’d grow hard, his body stiffening, streaks of color slashed across his cheeks, but he never stopped to talk.

  Meanwhile, I was getting desperate, my body on fire, dying for the big man. I twisted and turned in my bed at night, re-living our conversation in the den. How did he know I wasn’t ready? How could Daddy make that decision for me?

  One night when I was feeling especially frustrated, I got up and stormed into the study where Drake sat at his desk, his head snapping up when I banged open the door.

  “Daddy, I’m ready,” I said. No further explanation was needed, he knew exactly what I was talking about. But Drake didn’t move a muscle.

  “Shut the door Cleo,” he said calmly, his big body giving nothing away.

  Once the door was shut, he turned to me.

  “What do you want, Cleo?” he rumbled, looking at me, his eyes running up and down my curves. And I blushed then because I was wearing just the thinnest whispers of cotton, a tiny tank and bootie shorts, the tank so sheer that my luscious curves were on full display, my nipples poking out. And the sleep shorts were so short that you could see the bottom curves of my ass hanging out, jouncing this way and that.

  “Daddy, I want you!” I said petulantly. “I want you, I want you in my body!”

  Drake didn’t react immediately, instead looking at me calmly, those cool blue eyes assessing, in total control.

  “You want it, little girl?” he asked. “How bad?”

  I was stumped for a second. What to say to this? All of a sudden, inspiration hit.

  “So bad Daddy, that I’ll let you take my pussy cherry and my ass cherry,” I said coyly, causing Drake to hiss slightly, a hard gleam coming into his eyes.

  “I see,” he rumbled, still not moving although I could see a tent at his crotch now, the fabric of his pants straining, his cock dying to get out. “And which one would you like popped first?”

  First? I thought dumbly. But suddenly I was elated with joy. If Drake was asking me which one I wanted first, then it meant he was going to take me, I was going to feel his huge penis inside, my virginity gone.

  And slowly, oh so slowly, I sauntered over to his chair. Cocking a hip sassily, I stood between the vee of hi
s legs before running my fingers through that ink-black hair, bending down to whisper against his lips.

  “Daddy, it doesn’t matter which cherry you pop first. Just as you long as you take them both,” I mewled, and suddenly found myself sprawled across his lap face down, my boobs and stomach mashed against his legs, my butt hanging off the edge.

  “Oof!” I squealed. “What the?”

  But a smack descended on my left cheek, leaving it red and stinging.

  “Ouch, what’d you do that for?” I shrieked, turning halfway to look at the big man. “Why’d you do that?”

  But Drake frowned at me, pinning me down.

  “You do as Daddy says,” he rumbled. “And you’ve been a bad, bad girl, Cleo, not answering Daddy’s question. Now which one do you want popped first?” he asked again.

  “Daddy, I thought the question was just rhetorical,” I squealed, trying to explain myself. But without further ado, another slap rang out, this time on my right cheek.

  “Which one?” he ground out harshly.

  And my body flooded with sensation because Drake was now pulling my shorts down so that they were mid-thigh, my peachy orbs on display, my pink slit running wetly.

  “Daddy,” I tried again, “I want …” but my sentence ended in a languorous moan as Daddy trailed his finger over my slit, dipping in the wetness, touching my little nub for a moment, caressing it before moving to my ass.

  But I still hadn’t answered his question and this time Drake was fast. He flipped me over so that I was face forward on his lap and when he slapped me again, it was on my pussy.

  “Ohhh!” I whined. It felt so good, my little clit vibrating from the touch, the way his fingers immediately smoothed over the sting, running through my folds. “Ohhh!”

  “Baby girl,” whispered Drake harshly, his eyes never leaving my face. “Once more. Which cherry do you want Daddy to pop first?”

  And without even thinking about it, I blurted, “Pussy! Pop my pussy cherry first, please Daddy!”

  And Drake finally dropped a kiss on my clit, flicking it with his tongue, murmuring against my cunt.

  “That’s right baby girl, when Daddy asks you a question, you answer right away,” he rumbled, lapping at my pussy. I heaved and gasped on his lap, my voice becoming a whine of pleasure as he licked my pinkness, pulling my labia apart to sample my clit, tease me a bit before settling into a deep suckle.

  “Oh,” I moaned, writhing on his lap, “Yes, Daddy, please!”

  By now, my tits had fallen out of my tank and I was playing with my nipples, pulling and twisting them, rolling the hard pebbles between my fingers.

  But suddenly Drake slapped my pussy again, making me jerk up with a shocked gasp before melting again into a puddle, every nerve on fire.

  “Daddy,” I panted, “what’d I do this time?”

  “You don’t touch yourself until I tell you to,” he ground out, eyeing my breasts possessively. “Those tits, that ass, that cunny, they belong to me,” he said coolly. “No one touches them until I say so, and that includes you.”

  My face colored. Oh god, Drake was so possessive but it made me feel fantastic inside, I wanted it so badly, wanted to sample him, feel him in me even more. And suddenly I had an idea.

  Slowly lifting a knee I looked him in the eye, baring my cunt to him, the pink pulsing and slick.

  “Daddy, you know I’m a virgin still,” I reminded him coyly, holding my pussy lips apart, giving him a view up my pulsing channel. “I just have one request. Will you lick my hymen before it breaks?”

  CHAPTER SEVEN

  Drake

  She was so dirty and I loved it. Cleo was my dirty virgin and I loved every second of it, the way she was laid out on my lap now, her tits falling out of her tank top, her pussy bare, those little shorts a heap on the floor.

  And I loved how she was so bold even though I’d just spanked her. Asking me to lick her hymen? Oh shit, yes.

  But I wanted to do just more than just lick. I lifted Cleo so that her cunny was poised above me and slowly trailed my fingers over her lower lips, her snatch bare and smooth like a baby’s. She whined, her eyes closed, her hips gyrating against my hand.

  “Does that feel good, little girl?” I whispered. “Does it feel good when Daddy massages your twat?”

  “Yes,” she gasped. “Yes! Yes! More, please,” she panted in my ear as her vagina ran heavily, drenching my fingers in her juice. I would have been happy to touch her forever, fingering her, exploring her hole, except that I’d promised to taste her hymen. I picked her up as she clung to my large frame and strode over to the couch, placing her on her feet in front of it. She wobbled like a newborn colt, turning to look at me with a hungry, questioning air.

  “Now baby,” I said, spinning her around so that she faced the armchair. “Brace your hands against the sofa and lift your ass.”

  She looked at me over her shoulder, not sure what came next. Except I knew exactly how I wanted to taste my baby. I pushed her back down so that her snatch was on display and spread her labia wide, baring that beautiful pink pussy.

  “Oh!” she squealed in shock. Because Cleo was about to feel a man’s tongue for the first time.

  With any hesitation, I pressed my face into her bottom from the back, running my tongue deeply all the way from her clit to her anus, giving her a thorough lick. I paused at her dark star, inhaling her perfume, letting myself breathe in her musky ass scent before turning back to her twat. I nudged her legs wider so that the folds were on display and pulled them apart so I could look deep into that steaming pink channel. Ahhh perfect. She was so tiny, her hole so tight that it was just the merest opening, the tiniest bit of darkness peeking out between those juicy flaps. Slowly, I traced my tongue along every crevice, every nook of her cunt, letting myself savor her female juice.

  “Aieee!” she shrieked, knees buckling, legs unsteady as I drank from her vagina. I stroked the back of her thighs, pausing for a moment, murmuring encouragement as I lifted and squeezed her butt cheeks.

  “Shhh, shhh,” I rumbled, “that’s my good little girl,” I said before helping myself to another heap of tasty twat.

  This time I suckled her clit, alternately licking and sucking that hardened nub, teasing it with my tongue as her juices slid down my throat.

  “Ah fuck, little girl you taste so good,” I moaned into her folds, pushing my tongue into her hole before trailing up and down between her labia again. By now, my mouth and nose were soaked in her femaleness, and I needed to bury myself in her stet.

  I stood, popping my dick out of my pants. Like a fucking sword, it sprang out at ninety degrees, hard, hot and heavy, ten inches long, dribbling like a fucking faucet, I was so horny.

  “Daddy,” she breathed, her eyes huge as she eyed it from over her shoulder. “Is it going to fit?”

  “I don’t know baby, but we’re going to find out,” I rumbled.

  I ran my dick up and down between her pussy lips, coating the shaft, letting myself bask in the heat running from her cunt. Cleo contracted and pulsed against me, her pussy instinctively knowing its mate, gushing a bit as I lubed myself up in her juices.

  “Ohhhh,” she moaned, tilting her hips back, instinctively trying to catch me in her hole. I chuckled and lubed up some more, letting her feel each throbbing vein along my pole, dragging my glans across those puffy lips, teasing her a bit.

  With a swift arch of her back, she caught me in her, wriggling slightly so that I was buried about an inch.

  “Mmm, Daddy like that,” she said saucily. Oh fuck. The sight of her teen twat with my pole sticking out made me shudder, and I reflexively pushed in more, Cleo crying out and arching her back.

  “Oh it’s so tight!” she cried. “Slow Daddy slow!”

  “Mmm baby, I will,” I promised, running my hand up and down her haunches. Her buttocks were smooth and gleaming, pearly white in the low lights, and I stroked them before running a hand up to grip at her breasts, squeezing those mounds, pulling at
her nipples, stimulating her from another angle.

  “Ready for more?” I murmured into her neck. Without bothering to wait for a reply, I pushed forwards again, pressing against the resistance, burrowing my way into those fleshy pink folds. She was so tight that when her pussy convulsed reflexively, it almost pushed my dick out, the rolling of her muscles like a giant wave. But I braced myself against her hips and held her down, my dick still in her cunny.

  “There’s more honey, we’re not done yet,” I husked. This time, I shoved my hips forward all the way, breaking through a barrier within, making her shriek and spasm with pain and hurt.

  “Oh!” she gasped, her breasts heaving, a sweat breaking out on those smooth haunches, tantalizing me, titillating me as I stood completely still inside her, letting that little cunt taste its first dick.

  “You like?” I growled, reaching beneath to stimulate her clit. It helped a bit and within a few seconds, I could feel her grinding back with her hips, her pussy loosening slightly, beginning to pulse and flex on my fuckpole. “Yeah, you like, don’t you?” I growled again, this time straightening up and grabbing her by the waist to begin a deep fuck.

  And I didn’t hold back. I fucked that virgin pussy like it was a mature one. She was so tight, so hot, so wet that I almost lost my nut immediately. But I took a deep breath, instead reaming her again and again, pushing my dick deep, hitting my tip against that rubbery cervix. And when the time came, I didn’t hold back. With a mighty roar, I erupted in her, my man milk showering her insides, coating her ovaries with sperm, spraying her fertile fields.

  As I pumped, the little girl came too, her first man-made orgasm. She shrieked loudly, her breasts swaying beneath her as her cunny spasmed around me, gripping my cock with wave after wave of pleasure, the folds vibrating and trembling as they clenched down hard. Her spasms were so violent they almost forced me out of her body but I resisted, grabbing her butt cheeks and planting my dick firmly inside.