Double Dare: A Fake Fiancee MMF Romance

by Cassandra Dee

  I was immediately suspicious. What did my looks have anything to do with anything? My brows immediately lowered but the man didn’t notice and pressed on.

  “I’m a successful guy, I’ve got means,” he said meaningfully, lowering his voice to a whisper, “and you’re a little lady who needs some help.”

  That only made things worse.

  “Right, but we don’t know each other,” I said pointedly. “What can I do for you?”

  And he tossed his head back and laughed.

  “Oh you’re a smart one, aren’t you? I was thinking along the lines of a set-up that would benefit us both. Horizontal working,” he intimated with a sly smile.

  What the fuck was horizontal working? I was nonplussed.

  “And that would be …?” I asked, eyebrows raised, the question lingering in the air. But the guy just leaned in even closer.

  “Something comfortable for both of us, something where I’d get what I need and you’d get what you need.”

  By now, I was exhausted and no longer wanted to play games. It was too early to beat around the bush and I had chemistry to get back to.

  “No thanks,” I said, turning back to my textbook. “I’ve already got a job.”

  “Well, I think I can do better than what you’ve got,” he said, still pressing his case. “You’re on the bus every morning, working full time while going to school and I can make things a little easier for you. How about five hundred a pop?”

  I closed my book then, turning to look at him straight in the eye.

  “But for what?” I asked, shaking my head, bewildered still. “Do you need an assistant with you on sales calls? Someone to carry your suitcase, lug around the medical samples? I’m happy to consider it, but you need to be more specific.”

  And that’s when the stranger threw back his head and laughed, the raucous sound ringing out in the silent bus, causing a few of our fellow passengers to glare our way.

  “No, I don’t need help with sales, I want to go on a date with you,” he clarified, his voice still lowered. “Five hundred a pop.”

  I sat back, perplexed. Why would he pay for a date? I was confused. Sure, the guy on a date usually picks up expenses like the dinner bill, flowers, the movie tickets, but it sounded like something else was going on. Plus, five hundred dollars was a lot to spend. I’d been on a couple dates and the boys had spent thirty bucks max, taking me out to places like Pizza Shack and Burgers a Go Go.

  “I don’t get it,” I said. “Why would you pay me to go on a date with you?”

  And here, the man shot me a glance.

  “You really are naïve aren’t you?”

  I flushed at that one because he’d hit close to home. The fact is that even though I’m eighteen with a bodacious bod I’m really, really inexperienced when it comes to men. I’ve only been out a couple times with some gangly teenage boys, and hadn’t even done that in the past few months. With my impossible schedule, there was no way to meet up with anyone for anything, much less something as frivolous as a date. I figured I’d wait until I graduated, until I had a normal schedule, to get my romantic life going.

  But that wasn’t for the middle-aged man to know and I wasn’t going to let on.

  “I’m young,” I said stiffly, “but I’m not clueless.”

  “Yes, you are,” he corrected gently, “because I’m paying you to come to a hotel room with me. Get it? We’ll have the type of date where there’s no food, no drink, no conversation. Just some horizontal action with our clothes off, my dick buried in your cunt.”

  And that’s when my cheeks flamed. I realized what a dunce I was, how stupid I’d been. When I’d sat down next to the man, I’d seen the gleam of a gold band on his left index finger and immediately assumed that he was a married man, that his intentions were honorable.

  “But … but you’re married,” I gasped, horrified, forgetting to keep my voice down. Looking around, I was mortified. Oh my god, I was being propositioned at 6 a.m. on the Midtown Express by a married man. Oh god, oh god.

  But the dude just laughed.

  “So what? Yeah, I’m married and I have three kids too. Doesn’t mean that you and I can’t get it on,” he said, waggling his eyebrows.

  But now I was just completely disgusted. It’s not that I think people are angels, I’d just never had this happen to me, never had a married man proposition me, openly offer me money for sex.

  Immediately, I started stuffing things back into my bag, shoving papers hurriedly, not caring if they were crumpled. Without wasting a second, I jumped up and ran to the back of the bus.

  “Excuse me, excuse me,” I huffed as I made my way down the aisle, losing my balance a couple times, clipping people’s knees, almost knocking over one woman’s laptop. But fortunately, my old seat was still open and I collapsed into it with a relieved sigh, not caring how I landed. Better to be carsick than have to sit next to that sleazy dude for one more second.

  But once the ride ended, he was waiting for me on the sidewalk outside the bus as the sun dawned in Manhattan, our fellow passengers streaming around us.

  “If you change your mind, let me know,” he smirked, briefcase in hand. God, he really was a smarmy bastard with the greasy hair and cheesy pin-striped suit. “I’m Barry,” he added with a knowing smile and quick pat on my butt. “See ya tomorrow, little lady.”

  And I turned and ran to work, flying those last few blocks, my feet pounding the pavement, footsteps heavy, not caring if anyone saw. I just wanted to get away, get away from this nightmare. With a relieved sigh, I let myself into Luxor Corp., taking a deep breath once the massive door closed after me. The silence was deafening, the whir of the machines a soothing hum and I’d never been so happy to be alone, to catch my breath and calm down.

  Gratefully, I settled myself at my computer, making a cup of instant coffee, trying to calm down. But my concentration was lost, I couldn’t focus, the numbers of the screen blurring in front of me, melting into dizzy figures. Because the proposition had tickled my fancy. Heck no, I didn’t want to be Barry’s convenient hook-up, his paid-for easy lay. The middle-aged man was way too gross, his skin slicked with oil, out of shape with a significant paunch. It was more the fantasy of sex that beckoned. Yes, I was lusting for a man. A handsome man, one commanding and alpha who’d take my nubile body with expert hands and a big dick, make me sigh, scream and moan with ecstasy.

  And the thought made me shiver in my desk chair, my body on high once more. There were no men in sight, heck, there were no other people even in the basement. And so I turned to the next best option … a sex toy rumbling against my cunt, making me scream with pleasure.

  CHAPTER THREE

  Tammy

  Slowly, I got out the key to my secret drawer, slipping it into the lock with a snick. The drawer rolled open on its own, hissing on the metal wheels, and a shiver ran through my body at the contents.

  Because I’ve been keeping a drawer full of sex toys at work. It’s crazy, I know. Like I mentioned, I’ve been wicked, very, very wicked, and this went beyond the pale, beyond my wildest dreams. I’d been so embarrassed when I bought my first one … and now I was keeping a stash at the office.

  I remembered my first time in a sex shop. I was mortified to be standing in the Pink Cherry at midnight, perusing the section called “Female Fun.” But things were getting desperate. Not only was I a virgin, but I had no conceivable romantic life to speak of and my body was dying for a man’s touch, to explore the secret unknown, to explode somehow, somewhere, with a man’s help.

  Except that there was no one with a Y chromosome in sight. So I’d taken myself to the Pink Cherry to browse in a grey sweatshirt, the hood up, trying to conceal my identity. Although it wasn’t possible, not really. The sex shop was brightly lit, more like a food emporium than a seedy den, and it was decorated with all sorts of bright pink banners and signs saying “His Pleasure,” “Her Pleasure,” helpful tidbits like that. It actually felt like a normal store, I could alm
ost pretend I was grocery shopping or browsing for books.

  But I was still embarrassed and when a friendly associate accosted me, I tried to shrink into myself, to disappear. No such luck.

  “Hi, I’m Marie,” she chirped. “Anything I can help you find?”

  “Um … um … what is that?” I said, gesturing vaguely to my right. I was too embarrassed to even pick up any of toys, my shyness overwhelming. But the clerk was really nice, a clean-cut blonde about my age with glasses and a friendly smile.

  “Oh that!” she said merrily. “That’s a pocket rocket, perfect for a woman’s pleasure. You put this part on you,” she said, picking up the toy, “and then flick this little switch, and ta-da! Feels like heaven!”

  I flushed again but was intrigued. Reaching out a tentative hand, I took the rocket from her and closed my palm around it, feeling its weight, its heft, the soft, sculpted rubber.

  “And see, you can turn up the speed,” added Marie helpfully as her finger twitched on the controls. And just like that the pocket rocket went from a gentle hum to throbbing vibrations. Holy cow! That would feel amazing against my pussy and with a flaming red face, I mumbled, “I’ll take it.”

  “Sure!” chirped Marie cheerfully. “Anything else? Let me ring this up for you.”

  And just like that, it was done. Marie packed up my purchase in a brown paper bag, logo-less, totally discreet, and I hid it in my book bag, eager to get home and try it out.

  And it was pure heaven. I loved it, coming on my own over and over again, moaning, squealing and gasping as I played with the controls, rubbing my clit with the little vibrator. But that experience lit a fire in me, opened up a yawning chasm and I found myself back at the Pink Cherry again and again, becoming friendly with Marie.

  “How about this one?” the sales associate asked, holding up a glass shaft. Oh my god, it was so big, so commanding, and I’d never be able to use it, I was a virgin still and too scared to pop my own cherry. But I nodded wordlessly and the glass rod joined my growing collection, ten and then twenty sex toys, at my disposal for lonely nights at home.

  It’s just that I’m rarely at home now. I work so much and then go to school, only dropping into bed at eleven p.m., dead tired from the combination of work, school, and commute. So I’ve moved most of my toy collection from home to work. Sitting alone in the basement of Luxor Corp. with nothing to do and no one around, I figure I’m not hurting anyone and no one will ever know. It’s my wicked little secret and the toys have provided me with some much-needed entertainment and relief. I use the Women’s Restroom a couple times a day now, exploring myself, playing with myself, and it’s been amazing. The hours go so much faster and I’m able to concentrate on my chemistry homework after it’s done, the orgasms clearing my mind, my body relaxed and sated.

  And now, after Barry’s disgusting interlude in the bus, I found myself curiously horny. Oh no, it wasn’t the thought of Barry, no way. It was the thought of sex with a handsome man, his hands touching me, stroking my folds, making me wet, and letting me touch him in return. And oh god … but I was hungry.

  CHAPTER FOUR

  Nick

  It’s another day at Luxor Corp. Or, to be more precise, another busy, jam-packed day managing my real estate empire. I’m a mogul on par with none other in New York City, at the helm of a company that has controlling stakes in the Empire State Building, Madison Square Garden, and countless office buildings all over Manhattan. Construction and development, not to mention building management, is my forte and at the grand old age of forty-five I’m literally worth billions, my portfolio is enough to make a lesser man gasp and go green with envy.

  But it’s not like the money makes itself. I’m still up at 6 a.m. every morning working like a madman, whether going over spreadsheets, reviewing proposals, or touring the buildings themselves.

  That’s right, even though I’ve got thousands of people working for me, there’s nothing like walking the site itself, evaluating the construction, the maintenance, making sure the crews are using the right screws, the right type of window frames, keeping everything gleaming and in tip-top shape. Because when they know the boss is going to do a random drop-in, they’re on their toes and do a better job. I’m not just an invisible figure at the top, I’m the man himself come to life, with encyclopedic knowledge of this industry and a sharp eye that can pick up the smallest details, nothing gets by me.

  So this morning I headed over to 666 Madison Ave., a new office tower that I’d acquired a couple months ago. Seeing that it was 6:30 a.m., no one in my entourage was with me, I’d be walking the halls alone. Pulling the Maserati into the garage, I slid slowly, smoothly into my appointed parking space. Even in crowded Manhattan, there was always a spot for the boss, just one of the perks of being me.

  I clicked my badge at the back entrance and made my way into the sub-basement. This is how I like to do it sometimes. If you give them notice that you’re coming, they prep everything in advance, scrubbing and buffing, making sure everything gleams. But if you do a surprise visit, then you see how things really are, what the average person sees.

  So I let myself into the back and proceeded down a deserted hallway. Okay, it wasn’t exactly fancy down here but that’s not the point. The basement is a place where supplies are kept, equipment stored, that kind of thing. Maintenance comes by once in a while to make sure everything’s in working order but for the most part, no one’s down here.

  And everything looked kosher. The hallways were narrow, lit with fluorescent lights, the floors a shiny vinyl. I could hear the hum of the boiler, the bellows of the heating/cooling system, and the crank of the elevator as it was called up to a floor above.

  But I was surprised to find a door open with a lamp on inside, casting a wedge of light onto the polished walkway. What the hell? Who was here this early?

  With a nudge, I opened the door and peered in. There wasn’t much, just a desk, a chair, and a file cabinet, a couple papers strewn here and there, a stapler and paper weight lying carelessly on the desk. The computer was on though, humming away and I took a look at the monitor. Hmm, the screen was locked. That was in accordance with company policy, we tell employees not to leave their work stations unattended because you never know who’s going to come by and see privileged materials. Even if in this case, it was me.

  I retreated, continuing with long strides down the hallway. I’d have to get Jones to look into who was in the solitary office but it was probably just the super running some figures, calculating the cost of cleaning supplies or rejiggering the maintenance schedule. No worries.

  But then I heard it. A low hum, and then a sigh. What the heck? I glanced at my watch. Yep, 6:45 a.m., far before most people got into work. I strained my ears and the noises came again. This time there was a breathy gasp and then a slight whine, ending in another deep sigh. These were definitely not the sounds of a workplace environment. In fact, I’d have to say that someone was getting it on down here, before the day got started, before anyone would notice.

  And so following the sounds, I came to a halt before the women’s restroom. Pushing the swinging door open gently, I glanced inside. Was there a couple making out in one of the stalls? Maybe getting down right against the wall?

  But instead, the most beautiful girl came into view. Curvy, luscious, with brown hair hanging down her back, she had her skirt hiked up and panties pulled down and was touching herself, moaning and gasping with pleasure.

  CHAPTER FIVE

  Nick

  I watched amazed at the scene before me. After all it’s not every day that you get to work, doing your rounds as usual only to find a beautiful girl pleasuring herself in the public restroom. Careful not to make a sound, I continued staring at the show before me, my dick growing rock hard.

  Because the girl was luscious, curvy in all the right spots, totally wanton and completely into it. She’d pulled her blouse apart baring two beautiful, perfectly-shaped DD tits and was playing with them at the moment, r
olling her nipples between her fingers, squeezing and pulling at those hard nubs.

  “Oh!” she sighed, throwing her head back, eyes closed. “Oh god!”

  And I watched entranced as her jugs bounced up and down, the soft white flesh pendulous and creamy, mashed between her hands as she squeezed herself. With a sly smile, the brunette brought one up to her mouth, licking the nipple lasciviously before bringing the other one up as well, sucking lightly before stuffing both tips into her mouth while moaning deep in her throat.

  And a deep growl escaped me then, a throaty rasp. Because I love big boobs, I’m a breast man and seeing these luscious curves on display, squeezed, caressed, licked and sucked made my cock pop out to full mast, a stiff tent in my crotch.

  But the girl didn’t notice, she was too caught up in her fun. Leaving her breasts for a moment, she pulled up her skirt, struggling to get it over thick thighs. And my mouth hung open at the sight of those legs because they were heavy, meaty, like ham hocks you can bite into deep, get a good mouthful of juicy flesh. She jiggled this way and that, struggling with the fabric, only to finally have it pop, sending a button flying. But the girl just wiggled her ass temptingly and scrunched the material around her waist before slyly dipping her fingers between her legs.

  Moaning, she lightly rubbed herself through her panties, the lacy pink fabric dark with her fluids.

  “Mmm,” she moaned. “Mmm.”

  And I almost creamed at the beguiling sight. Because her panties were tight up against that cunt, the soaking material coating her lips making the outline of her labia visible. And as I watched, the girl gushed even more, her crotch positively dripping now, drenched with nectar.

  But the girl wanted to take her time playing. Instead of going straight for her clit and rubbing one out, she pulled the fabric of her underwear taut so that it was a string bisecting her pussy libs, right up against her clit. And slowly, she pulled the material back and forth, rubbing that little bud with the wet fabric, rocking her hips slightly, enjoying the friction on her sensitive spot.