Friends with Benefits

by Amy Brent

  “Oh, come on!” She complained. “The night is still young! I know – let’s get something to eat! That’ll make you happy, at least!”

  Yes, it would. I immediately agreed, and found myself swept off to a nearby restaurant, one that Veronica promised would be excellent. I was surprised to find that it was actually part of this ritzy hotel, The Clifton. It was the kind of place with doormen, a million managers, and single-night room prices that would probably pay our rent for a month.

  “Are you sure?” I asked hesitantly. “It looks expensive.”

  “Bitch, everything in New York is expensive,” Veronica shot back, and, before I could protest any more, ushered the pair of us inside.

  Even though it was so late, the place was still really crowded, and I was immediately impressed by how great of a place it would be to work. A hotel and a restaurant, right in the center of New York City? Imagine all the possibilities! Still, I knew that it would be way out of my league, at least for now, so I contented myself instead to gush about it to Veronica as we sat down.

  “Oh, work, work, work! Is that all you ever talk about?” She mocked, ordering herself another drink.

  “Uh, Veronica,” I murmured quietly. “Are you sure you should be having another one? Remember that time on spring-break, when you – ”

  “Aw, shut up, Danielle. You’re such a mom.”

  I winced. It was not the first time I’d been called that before. You try raising four little brothers and not being motherly, alright?

  Her drink came. A whiskey sour. Probably the worst idea she could have had. She plucked it from the waiter’s hand with a scowl, so I thanked him instead before ordering a pair of water for the two of us, and some bread. Veronica snarled that she did not like bread – too many carbs – before downing two thirds of her cocktail.

  At which point she turned, glared at the waiter, and vomited all over his shoes.

  Chapter 3

  Roger

  I was really worried about Maggie. Stayed up half the night thinking about her, and how to make things better.

  “Victoria would know what to do,” I muttered, taking a swig of scotch as I glared at a small scratch in my expensive, mahogany desk. Her photo was sitting right beside it, and it seemed strange that there could be such an imperfection in such close proximity to perfection. I made to reach for the photo, an old habit, and then stopped myself. I needed to focus.

  “You manage a multi-billion dollar business, and yet you’re confused by a little girl.” I scolded myself. I knew I was a little drunk, but responsibly so. Fortunately, I had the next few days off, as was usual this time of year. My staff knew better than to expect my attendance now, not on the anniversary of…

  “Focus, Roger! Focus, damn you!”

  I blinked, put my drink aside, and slammed my computer shut. I’d been researching common problems associated with bereaved children, but none of them seemed to fit. Why now did her grades take this sudden nose dive? What had happened?

  Since the internet had failed me, I turned my attention to something that had been drawing my gaze all night: a pamphlet, which had arrived to our mailbox ages ago, to Brookdale Heights, one of the most prestigious and exclusive private schools in all of New York. When Maggie had turned eight, we had automatically received an acceptance letter without even applying. Most would have thought this was because of my money, but I knew it had been her grades and obvious talent.

  Now, though, that her grades were so poor, it would need my money to get her in. If I decided to send her.

  “She’d hate me forever.” I muttered, grimacing at the bitterness of my scotch. I knew she didn’t want to go. It would mean leaving all of her friends and favorite places, for it was a boarding school that required total dedication.

  It would also mean leaving me.

  When Victoria died, Maggie and I – our eyes still puffy with tears – had opened up the discussion about Brookdale Heights again. Initially, Victoria had insisted we turn the invitation down because she wanted Maggie to grow up with her family, but, once she was dead…

  Let’s just say, it was important to bring up again.

  Maggie, however, had protested immediately. She’d cried on my shoulder, saying that she wanted to be with me, not at some stupid prep-school. And I’d agreed, because I didn’t want to lose my wife and my daughter in less than a month. Part of me had worried that I was being selfish. Brookdale was of course a great school, but Maggie had been doing so well in her current school that it didn’t seem likely to be a problem.

  Until now.

  I gazed at the pictures of pretty, engaged students on the front of the pamphlet and scowled. They looked so vapid, so disconnected from the terrible world of reality.

  “No,” I said. “There has to be another way. There must.”

  Then it occurred to me: I have all the money in the world. I don’t need to send Maggie to a fancy private school to make sure she behaves. I can hire somebody to do that! What did they call those people nowadays? Governesses? No. Mentors? No.

  Nannies! That’s right: nannies.

  I smiled and took a sip to celebrate.

  Hiring a nanny of course had its downsides. Some stranger, coming into the grief-stricken and complicated world of my and my daughter’s private lives. Adjusting to our household, and ‘airing out the dirty laundry for her to see.’

  Now that was an old phrase, dug up from what my mother used to say when I was a child. Back before I had money.

  It was also important that Maggie like her. I did not want to stick her with a stranger she hated. But, I realized, she can’t like her too much! Otherwise Maggie will walk all over her. Maggie was a clever, charismatic girl – whatever her current grades said – and would surely be able to manipulate anyone who wasn’t clever and tough as nails. But also likeable.

  “Christ.” I muttered, rubbing my temples in frustration. I swear, having a board meeting with my shareholders was less stressful than this, sitting there and listening to all their concerns…

  At this point, a great, and in retrospect obvious idea occurred to me: I did not have to decide this alone. I should talk to Maggie!

  I glanced at the clock. Two a.m. Would she be asleep? Yeah, but who cared!

  Excited, I leapt to my feet (wobbling only slightly from the scotch) and jogged to Maggie’s bedroom. It had been “pony” themed, but her stuffed animals and pictures of horses were slowly being eclipsed by band posters and piles of clothes. I realized how old she was getting, and fought back a wave of depressed nostalgia.

  “Maggie, honey, wake up!” I whispered, shaking her shoulder gently. She stretched, opened her eyes, and blinked several times, half asleep and unfocused.

  “Whassamatter, daddy?” She mumbled, her eyes already closing again.

  “Nothing, Mags, listen. I want to ask you something: would you like a new nanny, or would you rather go to that boarding school, Brookdale Heights?”

  Just like that, her eyes snapped into focus.

  “Brookdale Heights?” She demanded. “What are you talking about?”

  “I’m worried about your grades,” I explained. “I thought that, at Brookdale, maybe you’d be less distracted – ”

  “Oh, no, dad, please! I don’t want to go there! Don’t send me away!”

  “But, sweetie – ”

  “What was the other option? A nanny? Yes! Get me a nanny! Just let me stay with you!”

  She seemed so earnest, half in tears and half savage with outrage, that I immediately agreed.

  “Of course, my dear, of course. I’ll get you a nanny, and then will your grades get better?”

  She bit her lip in thought, as if she was on the cusp of a difficult decision. “We’ll see, daddy,” she murmured. “I’ll do my best.”

  “Okay, honey. Please do.”

  She must have seen how eager I was, how important this was to me, for as she settled back down for sleep and opened her eyes one last time and looked at me. “When will the nan
ny start?”

  She looked so beautiful, young and innocent and full of dreams – despite those horrible teen-goth band posters – that my heart melted.

  “Tomorrow, my dear,” I murmured. “She’ll start tomorrow.”

  * * *

  “Are you serious, Roger?” It was the startled, angry, and yet sleepy voice of Rita, the manager for my New York hotel. Usually, my staff did not call me by my first name, but I let it slide with Rita. She’d been working for me for years. And there was also that fact that I’d just woken her up to a 2:30 a.m. phone call.

  “Yes, Rita,” I said patiently. “I need a nanny. A good one. By tomorrow, 9 o’clock sharp.”

  I heard her sigh all the way across the phone. “Alright, sir. But I’ll never understand how you’ve become as successful as you have, being this crazy.”

  “Please, Rita,” I chuckled. “Craziness is a key ingredient of success.”

  “Yeah, yeah, yeah,” she grumbled. “I’m on it. Now try to get some sleep, boss. And lay off the scotch, you hear?”

  I scowled. I hadn’t realized that my voice sounded slurred. Still, if anyone had the right to rebuke me, it was Rita.

  “Thanks, Rita,” I said. “It means the world to me.”

  I hung up.

  Though it was late, I felt jazzed and excited. I took another sip of my drink, clicked a few useless links on my computer, and realized that I needed to do something exciting, or else I would go stir crazy.

  Since my wife’s death, I rarely rewarded myself with “Something exciting.”

  A thought occurred to me: You are the wealthy owner of this amazing hotel. Take advantage of it.

  So I did something I hadn’t done in months: I donned an expensive suit, dabbed on some cologne, and went downstairs, to the hotel bar.

  By this point, most of the people had already left. Distantly, I heard to the sounds of some annoyance coming from the restaurant area, so I steered clear of it, and headed directly to the bar itself. I was here for some excitement, not to work.

  I sat down, ordered our highest class scotch (which of course the bartender gave me for free) and waited.

  I don’t know what it is, but I never have to wait long. Within minutes, a beautiful, buxom brunette wandered over, standing suspiciously close to me as she ordered her drink and pressing her tits up so I was sure to see them.

  I smiled. I already knew I was in.

  I was fairly certain that women found me very attractive. Victoria had been a stunner, of course, and then there were the women I’d dated before I met her. Supermodels. Showgirls. All legs and tits and little brains. That what was so great about Victoria: beautiful and brilliant. For most of my life, I was tired and bored with the way so many women threw themselves at me. I knew they liked the five o'clock shadow that formed around my strong jawline, and how rich and silky my dark hair was. Even now, as it slowly shifted to a salt-and-pepper, woman loved to run their hands through it. The one sitting before me, too. I could tell by the way her eyes shifted from my eyes, to my hair, and then, fleetingly, down to the bulge between my legs.

  The woman introduced herself. Christina. I filed it instantly into my brain. It was good manners to remember their names. Common courtesy.

  It was also common courtesy that led me to buy her a drink, and too soon slip my hand onto her thigh. Her dress was so short, that I figured it must be freezing!

  She inhaled sharply, then looked up at me with glittering eyes.

  “Is it true you’re Roger Clifton?” She asked, dewy lips parted and round, so that it seemed she wanted to suck on the words themselves.

  I smiled, nodded, and ordered another pair of hundred dollar scotches.

  Twenty minutes later we had rented out one of the luxury suits, and were alone inside. I stripped her of her clothing, tossed her down on the bed, and gave her a long, appraising look.

  She was lovely. Her tits were the color of caramel, and perky as scoops of ice cream. She had curvy hips and a flat stomach – she was a little diminutive for my taste, but I wasn’t about to complain. Not with her little swirl of chocolate pussy opened up before me.

  Normally, I would take some time to warm a woman up. I also viewed this as good manners. Eat her out a little. Suck those tits. Slip my fingers into warm, wet places, making sure she was ready for my girth. My plentiful sexual experience had warned me that I was in fact very well hung. While this of course tickled my pride, I took it more as a sense of caution. If I didn’t get a woman streaming wet and ready for it, I could hurt her with the size of my dick.

  But tonight wasn’t about her. It was about me, and “finding something exciting.”

  So I turned to another option.

  “Lube it up,” I ordered her, retrieving from a cabinet an unopened bottle and tossing it to her. (I made sure that all of my VIP rooms had such amenities.) She giggled, squirted the liquid into her hands, and waited while I undressed.

  I heard her gasp, and saw her eyes widen in that surprise and wonderment that had become so familiar to me, when I woman finally sees my cock. Grinning, she reached out and began massaging the lube onto my cock, eventually leaning in to spread it further with her lips.

  I gritted my teeth with pleasure. She was an expert, who obviously knew what she was doing, and was familiar with big dick.

  Which meant that she ought to be ready to take it.

  I shoved her back, roughly, watching her tits bounce and her eyes widen in surprise. Then, I mounted her, wasting no time and thrusting myself instantly inside. She gasped, and I felt her nails dig right into the flesh of my back, but I didn’t care. I was too busy pounding her, watching her whole body shake with it.

  She screamed and moaned with pleasure. I grunted and gritted my teeth, sweat breaking out on my brow as I made sure to pound her as hard and as long I could. I was impressed with her: there’s not that many women who can take it so long and so deep.

  Finally, as her eyes rolled up into the back of her head, I felt the pleasure in my dick building. The cumshot was coming, and I was ready to explode all over her. I wanted to paint her with my pleasure, show her that, tonight at least, her body was mine.

  The ecstasy grew. My grunts grew into growls, and I long last I wrenched my dick out of her pussy.

  And came all over those lovely, caramel tits.

  * * *

  Afterwards, I thanked her, making sure to call her Christina, to show that I had paid attention. I then told her that the room was hers until morning, and that she should help herself to anything in the minibar or through room service, on me.

  Then, quietly and with a kiss to her forehead, I left, and returned to my penthouse apartment.

  Maggie was asleep, thank god. On the very rare occasions that I hooked up with someone, I didn’t want her to know. I was worried she’d be mad at me, finding out I was with a woman other than her mother.

  In the immediate wake of that thought, I felt desperately sad again.

  “No more,” I muttered, meaning no more one-night stands. Sure, they were fun, and sure, my dick felt good, but I always felt so sad and lonely afterwards. It’s like someone in desperate need of sleep only drinking coffee to get by. Quick fixes wouldn’t do it for me anymore. I needed a long rest, between comfy sheets and with a woman I admired.

  I sighed, stepping into the shower and staring without caring as the water flowed down my muscled body and into the drain. Victoria had been that sweet sleep. She was the only one who had been able to give it to me. And now, she was gone.

  “Focus on Maggie,” I told myself. “She’s the woman in your life that matters most right now.”

  I trudged from the shower, and still dripping wet and miserable, I toppled into bed.

  Chapter 4

  Danielle

  “Oh, no,” I thought, as I heard the sickly splatter of Veronica’s mess, all over that poor guy’s shoes. And let me remind you that this was an upper-class restaurant, so even the waiter’s shoes were more expensive than any pair I
had ever owned.

  He stared at the mess, gaping in horror, then looked up at me, his eyes wide with astonishment. I knew, in seconds, I would see anger there.

  Which meant I only had seconds to react.

  Immediately, I snapped into action.

  “I am so sorry, sir!” I exclaimed, leaping from my seat and taking his tray from him. “We will clean this up right away!”

  “Y…you?” He said, still baffled.

  “Yes, sir,” I stated back, so matter-of-fact and businesslike that it brooked no argument. “It is our mess, and we will clean it up. A mop, please. And leave those shoes here. I’ll clean them off, too.”

  I’m not sure if he was just a placid fellow, or if my self-assuredness got to him, but he nodded, kicked off his shoes, and then marched off. In the meantime, I pulled Veronica upright, thrust a glass of water in her hand, and ordered her to sit still.

  Moments later, the water returned with a mop, towels, and a bucket of soapy water. I plucked a towel from his hand, bent, and began scrubbing at his shoes. Within ten seconds, they were cleaner than when he’d started his shift.

  Trust me. When you’ve raised four little brothers practically yourself, you learn not to be afraid of a little sick. And you get awfully good at cleaning it.