Boss Me, Daddy: An Older Man Younger Woman Romance Read online

  Table of Contents

  Boss Me, Daddy

  Chapter One

  Chapter Two

  Chapter Three

  Chapter Four

  Chapter Five

  Chapter Six

  Chapter Seven

  Chapter Eight

  Chapter Nine

  Chapter Ten

  Epilogue

  Contents

  Boss Me, Daddy

  Chapter One

  Chapter Two

  Chapter Three

  Chapter Four

  Chapter Five

  Chapter Six

  Chapter Seven

  Chapter Eight

  Chapter Nine

  Chapter Ten

  Epilogue

  Boss Me, Daddy

  Boss Me, Daddy

  Penny Grey

  Copyright 2017 Penny Grey

  All rights are reserved.

  This is a work intended for adults.

  Enjoy! <3

  Previously under Charli Childs

  Chapter One

  Willow

  This is supposed to be punishment. Light boring paperwork and clerical stuff, what a drab.

  But it isn’t.

  It’s a dream come true. Well sort of…

  If only my boss would come out here and punish me the way I’d like to be punished, then I would be able to say all my dreams have come true. But he hasn’t. Yet.

  Every day, at my desk positioned neatly outside his ornate gold trimmed office, I think of all the degrading ways he could and should treat me. How I wish he’d bend me over his lap and spank me. Or better yet, over the desk and fuck me till his cock couldn’t take it anymore. I bet an older man could definitely last longer than these super horny young ones.

  Mr. Ryan Gold. The name matches him to a tee. All the things he wears on his wrists are nothing but gold this and gold that. And not to mention his office which is also decked in gold. Not to mention the whole damn house.

  My boss is a kingly man. And the very man I want to break my virgin wall and fuck me all through his home. Sometimes I feel guilty, since he’s my daddy’s friend, and my best friend’s father. However, the love and lust still remains so heavy in my core.

  My desk side intercom crackles to life and I sit up straight, eager to hear his voice.

  “Good morning, Willow,” he says, his voice deep with authority, “I was wondering if you could get me a glass of cold water.”

  Ohhh, cold water. Maybe to pour down my shirt to make my nipples hard and poke out? Every little request from my boss makes me wetter than melted ice.

  “Yes, Boss,” I chirp, love swelling into my chest. Anything for him!

  “Oh, and one more thing. Could you make sure it’s in my favorite glass? I always need a nice little hit of good luck.”

  “Yes, Boss,” I sing again, feeling my body respond to the sheer sound of his voice with naughty abandon. Like, how could nipples get so hard from a voice? Other guys my age never make me feel this way. They don’t thrill me like Mr. Gold does. All they’re concerned about is a fast fuck then leave you high and dry.

  “Thank you so much, Willow.” The intercom hangs up and I pop out of my desk as if this was some sort of race to the finish line. I hear my stilettos clack into the kitchen and catch a glimpse of my body in the reflection of the stainless steel appliances. Sexy as hell. How can he resist for so long? Turning around, I double-check to make sure my ass looks nice in this black pencil dress I’m wearing. Check, check, check.

  I reach up into the cabinet to get his favorite glass cup that I’ve secretly kissed on a few times before and fill it up with fresh filtered water and no ice. He may’ve left it out, but I will never forget his aversion to ice.

  Though… I could be naughty and put some ice in there just to irk him. Nothing like an angry, sexy man.

  Maybe I could even go the extra mile and bring him hot coffee in a different cup to make him want to punish me very hard.

  But no, I decide to be the angel and bring him just what he asked for. No need in stressing him out more. After all, he is a multi-billion dollar man. He owns banks and tech companies. The last thing he needs is some twenty-year old girl making things harder on him. The switch of my hips gets a little bit more obvious as I near his door with his cup of cold water in hand.

  Knock knock.

  “Come in, Willow.”

  He knows it’s me and I can’t help but feel dampness in between my thighs. I knew I should have worn something other than a lacy thong. I push the door open and sashay inside, making sure my hips catch his eyes. The whole office smells like him. A hint of cologne and a whiff of whiskey. Mr. Gold is at his desk staring down his screen that I bet is filled with great secrets and important bank matters and stops to lock his eyes on me and crack a smile. Fuck, all he needs to do is speak and I’d be dripping all over his floor.

  Right as I smile, my body decides to fuck up and I trip on my own damn heels. My own heels!

  “Agh!” I yelp out, falling head first. The cup flies out of my hand, and even though I don’t see it, I hear it crack into a million pieces. Shards of crystal land not too far from me.

  “Willow!” Ryan gets up and comes to my side as I struggle to recover as quick as I can from such an embarrassing fall.

  If I wasn’t feeling so horny as I walked to him, I am pretty sure I wouldn’t have fallen like some dumb bimbo.

  Ugh.

  “I’m fine. I’m so, so sorry!” I say, wobbling to get back up. Ryan helps me up and sighs. And it sounds so delicious.

  “That was a five-thousand dollar glass, Willow,” he says in a disappointed voice.

  Brace yourself, Willow, this isn’t the exact punishment you’re looking for.

  “That will have to be added onto the debt of thirty-thousand you already owe me for the vase you knocked over. Let’s call that an extra five weeks at the office, shall we?”

  I blush, feeling my pussy come alive again. “Yes, Boss.” I look at all the mess and water spilled everywhere and turn to go get some napkins. “I’ll be right back. I’ll just get some napkins so I can clean up—”

  “No, no,” he says, turning my help down, “there is glass here and that is much too dangerous. I’ll get the housekeeper down here to do it. She has a way with cleaning up broken glass. Just return to your desk. I’ll call if I need anything. Except water of course.”

  “Yes, Boss.” I smile and sprint out of the office, making sure my hips still sway. God, I was on all fours in front of him just a minute ago. I hope my ass looked good.

  I sit back down at my office chair and look at the blank computer screen. I don’t even bother to turn it on. I am focusing on turning myself off. My mind is swirling. I wanted to beg him to spank me so badly. My virginity is worth way over thirty-five thousand dollars.

  Not only that.

  But I can swear that I saw… That Mr. Gold, my Boss’s crotch area was a little… it was bulging a bit more than usual?

  Wishful thinking! But the thought alone sends my body into a wanton mode of pulsing and squirming around. At this rate, I am going to create a puddle of juice right here in my chair. I bite my lip and squish my thighs together to hold myself from running into his office and yelling ‘fuck me’ into the air.

  Oh, the life of a virgin.

  It’s even worse when your boss is hot as fuck and he’s a gentleman instead of a pervert.

  ***

  About an hour or two later, Mr. Gold calls to tell me that I have the rest of the day off. He says something about meeting a private client and I have a mind not to ask since he’s already a man of so little words.
r />   Private means private.

  I want to be on his kinky side, not his irritated bad side.

  Jealousy bubbles up inside me. What if it’s some skanky woman coming to claim him all to herself. I take my early leave and whip out my phone. As soon as I’m bouncing down the front door’s steps I hit my speed dial button programmed for Bella, Mr. Gold’s daughter and my bestie. If she knows, she’ll tell me. We tell each other every damn thing.

  “Hey, Willow. What’s up?” she asks, cheerful as ever.

  “Bella, what’s up with this private client at three today?”

  “Hmm, I don’t know. Daddy didn’t say anything about it. But I don’t like secrets, I’ll ask him and let you know.”

  “No, don’t ask like that! I’m sure I wasn’t supposed to say anything at all!”

  “Don’t worry, I’m as slick as a snake. Call you back soon, ciao!”

  I hang up and saunter up the stairs to my daddy’s home. Luckily, my house was just a few blocks down. My daddy was still at the office, meaning I had the house all to myself for a few hours. There is only one thing I can focus on, and that’s pleasuring myself to get rid of this restless, aroused feeling pulsing at my cunt.

  Inside my room I throw off my dress and flop down into my bed. A huge dildo would have been so damn great about now, but I am saving my virginity for him… my boss and best friend’s daughter, Ryan Gold. Even though it seems like a stretch, unless I meet someone better, then this pussy belongs to him and him only.

  I plunge my fingers deep into my flooding core and jerk them around as I close my eyes and envision Ryan bending me over to ram his thick cut cock deep down inside me. My clit slips around as I give it the attention it needs. In a roar of passion and fluid, I come to the final image of Ryan coating my face with his seed.

  “Oh, Ryan, yes!” I holler.

  Can it get better than this?

  Chapter Two

  Ryan

  I wait as I watch Willow walk up the street from my office. I'm tenting in my pants as I watch her hips sway side to side in that form fitting dress of hers. She's twenty, I'm forty two. There's no way such a succulent young girl like her would for an old man like me. Sure I have money, but Willow is so pure.

  The way she looks at me isn't because I'm rich, it's because she's a sweet soul. Images of her on all fours on my floor causes my cock to strain and pulse against the confinement of my slacks.

  If I could have my way with her, I'd do the nastiest things I could to her. I can already feel her tightness gripping me, begging me for more.

  I want her badly. And I really don't know how long I can last without touching her and ultimately causing a shit storm.

  Grabbing my cock through my pants, I stroke it once to see if I can't cool down the monster. Willow has me all hot and bothered to the point I feel twenty years younger myself. I've been without a wife for ten years, and ever since then, most women don't appeal to me.

  But Willow does. She awakens my dormant dragon.

  Awakens my dark desires.

  Dark fantasies that I think about on a daily basis.

  There's a damp spot on my pants now. I have a meeting very soon, I need to take care of this.

  ***

  "Hey, daddy!" my daughter says, flying through the doors without knocking. My meeting is in ten minutes and even my daughter isn't supposed to be here.

  "Hello, Bella, dear. Daddy is busy, come back in another two hours?"

  "Trying to shoo me off quickly, aren't you?” she points out, hopping onto the corner of my desk. She kicks her legs up and down and stares me down.

  "Of course!" I chuckle. "Daddy has a very important client coming and lots of private business to discuss."

  That was another reason Willow and I couldn't work. My daughter. They are the best of friends. And Willow's father is a friend of my own.

  Pray tell, my desires are always the most dangerous ones.

  "Oh? Private, huh?" she repeats, giving me a side stare.

  "Yes, I even let Willow go home early. As a matter of fact, why don't you go and hang out with your friend?"

  "Because now there's some mystery person creeping around our house. I wanna know! Ohh, are you dipping into the man pool, dad? Tell, tell!"

  I sigh and rub my head.

  “Honey, daddy isn’t dating anyone right now. And if I were to, you’d be the very first one to know.”

  “Really keeping this one a secret aren’t you?” Bella brings her face closer to mine, searching my eyes for the truth.

  “Bella, dear. I am expecting them soon—”

  “Nope, not going anywhere.”

  Bella isn’t usually so persistent on being rebellious. That’s Willow’s style. I guess with them being friends it was bound to rub off on her at some point. Though, the rebellion looks better on Willow.

  “Poor Willow,” Bella begins, “she’d be so heartbroken if she finds out you’re dating some other women,” Bella bends back with her arm over her head as if she’s going to faint. Though this sudden news piques my interest. “She has the biggest crush on you, and this is how you do her?”

  My heart leaps. All the dirty fantasies in my head seem to throb closer and closer to reality. The taste of possibility sizzles on my tongue. I could dominate her like no other, have her scream my name. Is Bella joking?

  It would be too risky to ask. Though it is worth investigating.

  My client knocks on the door and Bella’s face turns to the direction of the door as it slowly opens. Everyone seems to like coming into my office without permission today, don’t they?

  “Mr. Goldblocks!” a lady chimes, breezing into my office. She isn’t just a client, but an employee as well.

  “You’re so totally dating!” Bella cries out, pointing at Ms. Chevelle.

  “Bella, darling—”

  “Oh my, what have I walked into?” Ms. Chevelle says, placing a hand over her mouth.

  “If you’d wait after knocking you wouldn’t have to find out. And it’s Mr. Gold, Ms. Chevelle.”

  Bella pouts in my direction. “This isn’t worth being a secret!”

  “Secret?” Ms. Chevelle echoes.

  “You’re dating my father aren’t you?” she asks with brute honesty.

  “Why of course not! Men aren’t even my thing,” she says, flipping her hair back. Ms. Chevelle is quite the animated character.

  The look on Bella’s face is a mix of surprise and confusion.

  “Bella, I need you to go hang out with your friend. Ms. Chevelle and I have business to discuss. Or do you want me to cancel your credit cards?”

  Bella gulps and scoots off my desk.

  When she closes the door Ms. Chevelle sits down at my desk and we begin to discuss a matter that has been weighing over my head for a while.

  “Any news?”

  “Yes, we found out where all that missing money might be going to. But we’ll need to track that person for a while. Which is why I’m here. It’s going to cost some extra money. I wanted to get this approved by you to find out quickly if it’s who I think it is stealing some of the company’s hard earned green.”

  Ms. Chevelle tosses a lock of her wavy blond hair to the side. My mind wanders off and I think about Willow’s short red hair cut neatly in a bob with Betty Page bangs.

  “Goldblocks!”

  “Huh? I’m sorry. I was deep in thought.”

  Ms. Chevelle grins. I know what that wicked grin means.

  “Ohh, thinking about a girl aren’t you? I mean, a wealthy man like you needs to—”

  “Ms. Chevelle, not this again,” I groan.

  “Of course, this again! Tell me all about her.”

  I sigh heavily and lean back in my chair, lacing my fingers together on my lap. The longer I keep this from her the longer she’ll nag me. Then everyone will find out that I’m eyeing someone.

  “She’s dangerous to touch.”

  “Isn’t that what makes it worthwhile?” she asks, her green eyes sparkling w
ith delight.

  “Yes and no. As far as funds for this investigation, they are approved. Just keep receipts and let me know the progress.”

  “Hmph, always dodging my questions, you devil you. Okay, I’ll let my team know. But just tell me one more thing about this mystery girl. What is it about her that makes her dangerous?”

  “Her…” I pause, trying to figure out how to say it without making it too obvious about who it was. “Her existence. Now, if you’ll excuse me.”

  I smile at Ms. Chevelle, an attempt to get my mind off the verge of aroused demand. The mere thought of Willow sends me into a hard on without warning.

  “Hmph, okay then. I’ll keep you informed.” Ms. Chevelle rises gracefully like a swan out of her seat and walks to the door. Looking back at me once more before leaving, she says, “It’s nice to see you all in love again. Keep it up, it looks good on you.”

  Then she leaves, making me feel awkward.

  Love?

  Images of Willow’s sultry ass and beautiful walk go across my mind, giving me a bullet proof hard on. I rip open my pants and sigh with relief as my cock pops out and drips onto the ground. The veins pulse with lust, with the need to bury down to the root inside Willow’s sweet cunt. I grab it near the head and stroke down hard and slow as I close my eyes and imagine punishing her the best way I know how.

  The moment she broke my vase and cup, I should have ordered her into my special room and punished her. Her arms tied, eyes covered, mouth gagged. Yes, metal handcuffs would look splendid on her.

  Without much of my conscious notice, my hand begins to jerk off my cock faster and harder as I see myself plunging into her wet pussy hard and unprotected. When I come, I feel myself buried inside her, coming against her cervix. Ropes of cum slide down my fist and plop down onto my carpet. This is something I’d have to clean up myself.

  Gasping, I open my eyes and allow myself to breathe again.

  I’m nearing my breaking point.

  One day soon, she’ll do something naughty.