Blackmailed

Constructive criticism is welcome!

At forty-three years old I was nearing late adulthood and while I enjoyed the company of various women in my life, I enjoyed my single status and bachelorhood even more. That was until the partners at my firm made it abundantly clear that they respected and upheld family values. Simply put: if I were to ever advance any further than where I was in my career, I needed to get married. Fast.

They were all hypocrites. I knew of three of them who were cheating on their spouses and the other one flirted openly with anything in a skirt. They had the nerve to talk to me about family values. But suggestions were suggestions and I found myself increasing the age range on my dating app from twenty-eight to a whopping thirty-nine. I scrolled through a few matches on the way home and by the time I let myself into my penthouse apartment uptown, I had three dinner dates with three different yet equally gorgeous women.

Katie Georges was a redhead with a light smattering of freckles across her nose and cheeks. Her eyes were a deep green, and her hands were soft. According to her profile, she liked long walks on the beach, romance novels and intelligent conversation. We made idle chitchat but by the end of the hour, I knew she wasn't the one for me.

Scarlett Shaw was a blonde-haired blue-eyed sex kitten. She had full lips and a heart shaped face. There was a twinkle in her eyes that promised fun and mischief. We hit it off immediately, but being a widow, she was only interested in casual sex and vacation getaways. I said my goodbyes and copped a feel of her phenomenal double D tits on my way out. She blushed and swatted my arm with no serious objections. I saved her number. If my last date was a bust, I knew where I'd be headed at the end of the night.

Finally, Nadine Franklin walked into the bar. She was a vision. Jet black hair, startling gray eyes. She was almost as tall as I was with legs that went on for miles. Fifteen minutes later, we deduced that we wanted the same things. She was a wedding planner who had begun to lose clients due to her unmarried status. She was going into debt trying to keep her business afloat and she had a young daughter to take care of and send to college in a matter of months. She was the one.

Things move relatively quickly after that. Nadine and I went on a variety of dates all over the city and by the end of the week we were practically inseparable. There was just one more obstacle to overcome. That of her eighteen-year-old daughter.

"She's very protective of me." Nadine confessed as we pulled up to her modest one-story clapboard house on the outskirts of town. "She has managed to chase away almost every guy she's seen me with." I turned the engine off and stared up at the house. "I don't know how she does it, but one day we're a perfectly fine couple and then the next, I never hear from them again."

"Very curious..." I wanted to frown. How was she pulling this off? Did she do background checks on all of her mom's boyfriends and then blackmail them into ghosting? It would be interesting to find out. "I hope she knows I'm in this for the long run."

"We'll see." I stepped out first to open the door for Nadine and we walked up to the house hand in hand. Something was cooking and it smelled divine. I couldn't help but inhale deeply as I walked through their front door.

"I left something special in the slow cooker. Seems like it's almost done." Nadine dropped her coat, scarf and gloves by to door and led me to the kitchen. Nadine's daughter was seated at the small kitchen table.

Natalie Franklin was almost a carbon copy of her mother. She was considerably shorter, but the same jet-black hair, same gray eyes. She was scribbling furiously in a notebook and barely spared me a look as we walked in.

"Nat, this is my friend, Daniel, that I was telling you about." Nadine began tentatively. "He's here to have dinner with us." Natalie kept her eyes on her book but waved halfheartedly.

"Hi."

"Hi." I answered. I took a seat opposite her. "What are you writing?" She lifted her eyes to mine, and I saw nothing but annoyance. I liked a challenge. "Something for school?"

"It's a report." She shut the notebook firmly. "Not that it's any of your business."

"Natalie!" Nadine scolded. "I know you're upset about the party but that's no excuse to be rude to our guest." Natalie rolled her eyes and stood up. "Go get ready for dinner." The second she was out of the room, Nadine heaved a sigh and explained. "There was some kind of pool party at the neighbors' to celebrate the end of senior year."

"You should have let her go." I told her. "This dinner could have easily been rescheduled." Nadine shook her head, glancing at the slow cooker pensively.

"Her grades were awful! She only just scraped the required GPA for graduation."

"Ah."

"She has a lot of growing up to do this summer." We heard the shower turn on. Nadine sighed again and stood up to push open the kitchen window. "I'm going to go freshen up. Please, make yourself at home."

She left the kitchen and ducked into what I presumed was her bedroom. The door clicked shut. I glanced out of the window. This was a wonderful neighborhood. The air was certainly cleaner than that of the city. If we did indeed get married, I wondered if Nadine would insist on staying here.

I was so lost in my thoughts that I didn't even notice that I was no longer alone.

Natalie cleared her throat and I looked up in surprise. She was clad in nothing but her towel. I gaped, wondering what game she was trying to play.

"You need to get up and leave this house or I am going to drop this towel and scream so loud your ears pop." I narrowed my eyes and instead of getting up, I leaned back in my chair. She shuffled her feet, suddenly uncomfortable.

"I suppose this is the same old trick you've been pulling on all your mom's ex boyfriends." I wanted to laugh. "Very interesting." I was genuinely impressed. Who knew there were coherent thoughts behind her eyes? I crossed my legs leisurely. "You're forgetting one thing though."

"Oh yeah?" She sounded smug. "And what is that?"

"Back then, there was that handy fact of you being a minor." I grinned as realization dawned in her eyes. "Now, you're an adult and this..." I couldn't help but savor the look on her face. "Technically qualifies as sexual harassment." Reaching over, I yanked the towel away, balled it up and tossed it out of the open window.

I was allowed a full second of openly staring--nay appreciating--her pert breasts and shaven pussy before she brought her arms up to cover herself. I smiled widely and took a deep breath.

"Natalie, what on earth are you doing?" My voice was loud enough to be heard on the street outside much less Nadine's bedroom. Natalie gave me a horrified look before she dashed away, presumably into her own bedroom.

Nadine was understandably curious about what had gone on in the kitchen and I knew my vague answers were not going to satisfy her for long, but we went through dinner with no incidents. Natalie was quiet and withdrawn. She spoke only when spoken to and was no longer openly hostile to me.

To my satisfaction, Nadine and I got married at City Hall two weeks later. By then, Natalie hadn't quite warmed up to me, but she understood that not only did I make her mother happy, but my considerable funds made life easier for both of them. I also had the handy leverage of her "exposing herself" to me. Indecent exposure was a crime and Natalie knew that.

I helped Nadine get a business loan and set her up with a few of my friends and acquaintances that I knew were looking for event planners. Slowly, her business began to take over her days and weekends.

It was on one such weekend that I found Natalie sitting on the floor in the living room pouring over fashion magazines.

"I haven't forgotten." I told her simply. She froze where she was and didn't answer. I admired her round ass, currently clad in leggings. "I just thought you should know that." She was still frozen, but I knew she was listening. "You might be enjoying this house and this life that I have pulled you and your mother into but with a few words whispered in her ear, I could have you shipped away to some boarding school for troubled children."

"You wouldn't." Her voice was trembling. She was right, I wouldn't. I'd looked into those boarding schools and they usually capped off at seventeen, but she didn't need to know that.

"I might." I shrugged and sat down on my armchair. "I mean, what kind of twisted little girl uses her body to scare off her mother's boyfriends?" Natalie pulled herself off the floor and sat down, knees to her chest. She was wearing a cropped t-shirt so I could see her belly button. "That is bordering on psychopathic behavior."

"I wasn't..." She gasped. "That wasn't my intention." She tried to argue, but I knew I had her exactly where I wanted her. "You can't tell my mom any of that."

"I'm still debating it." I placed a hand on my chin looking thoughtful. "Of course, I might change my mind if I felt like you were truly sorry." Her eyes were wide, tears spilling down her cheeks. She nodded furiously. "How sorry are you Natalie?" I asked. "Sorry enough to sit on daddy's lap?"

"What?"

"You heard me." I leaned back, practically lounging. She gaped at my lap, or more specifically, the bulge in my pants. "Prove that you deserve to live here and benefit from my hard work." She looked positively hopeless as she stood up, but I tutted under my breath. "On your knees."

She could listen to instruction, I reflected as I watched her crawl across the floor to me. I could see right down her top. She wasn't wearing a bra and her tits were just as sensational as the last time I saw them. They would fit perfectly in my hands.

She was hating every second of it, but it made it all the more satisfying. She deposited herself in my lap and opened her legs without me telling her to. I put one hand around her tiny waist and the other on her knee.

"Good girl." With light fingers, I climbed my way up her torso until I was cupping one breast in my hand. I heard her sharp intake of breath and her light moan as my fingers slid across her nipple. My other hand began to slide up her leg but, with frustration, I realized her leggings would get in the way. "Stand up." I commanded and she scrambled up. I pulled her so she was standing in front of me and, using both hands, ripped the leggings at the crotch.

"What the fuck is your problem!" She yelled, jumping away, "What I did is nothing compared to this." Her voice was shaking, and she leaned down, grabbing her cellphone from the floor. "I'm telling my mom that your forty-year-old ass wants to fuck her eighteen-year-old daughter." She unlocked her phone, smiling smugly. "Then we'll see who gets shipped away." She was dialing when she noticed that I wasn't fazed at all. "What?" She demanded and I shrugged.

"You really think your mom is going to believe that I...what?" I gestured to her. "Tried to fuck you?" I scoffed. "Not only is your mother concerned about the way you dress with those crop tops and tight leggings you prance around in but..." And here, I pulled out my own phone, dialing my office on speaker. My assistant Isaac answered the phone.

"Mr. Greenwood's Office."

"Good afternoon, Isaac," I smiled at Natalie's confused look. "Where am I right now?"

"Mr. Greenwood is in a meeting." He answered simply, ever the professional. "I'm afraid he's asked me to hold his calls, but I can take a message and he will get back to you as soon as possible."

"What meeting is it?"

"The partners have a mandatory biweekly lunch meeting, and it's ran a little longer than usual."

"Thank you Isaac." The man hung up the phone and I grinned at a terrified looking Natalie. "You see, I've been in meetings all day. And when your mother confronts me about these--quite frankly--disturbing allegations, I will have no choice but to ask her to get rid of you." My smile never left my face. "I wouldn't feel comfortable having someone who tells such dangerous lies around my home."

Natalie was out of her league when it came to deception. Every single partner would corroborate my story. There was indeed a twice weekly lunch meeting, but it wasn't mandatory and provided a very nice cover story for the three, now four, partners who were engaged in extramarital activities. I stood up so I was towering over her.

"Your mother is going to be home at five which means I have..." I glanced at my watch. "...three hours." She stepped back and I followed her. "Do you know what I plan to do for those three hours?" I didn't wait for her to answer me, I used both hands and ripped her t-shirt to shreds, exposing her for my pleasure.

"Please... don't do this."

"But I really want to." She stepped back again practically tripping over the other armchair, but I steadied her with one arm. Pulling her to me, I enveloped her in a hug. "I might love control but it's no fun if you're actively resisting." I muttered in her ear. "So, here's the deal. I can tell your mom that you've thrown yourself at me twice." Her mouth popped open and I entertained a brief fantasy of shoving my cock so hard down her throat she puked. "But the happier I am, the more likely I am to keep it to myself." I pulled away from her and smiled. "Now your mom is wonderful in bed. Positively delightful. But she is also thirty-nine years old." I tugged her nipples and she, unbidden, thrusted her chest out, practically begging for more. "You are young, vibrant, relatively inexperienced." I continued palming her breasts until she was breathing heavily. Her eyes were shut, and her face was positively euphoric. "I could show you the world, all you have to do is say yes."

I waited patiently. And finally, she nodded. I didn't need any more prompting. I pulled her up and deposited her onto the sofa. I left her clothes as they were. Fucking through ripped clothing was a bit of a turn on for me and I lowered my head between her thighs. I spread her lips apart with my fingers and flicked her clit, sucking and probing as I wanted. She let out a string of profanities, unintelligible words and moans and I pleased her. And right when she was about to come, I stuck a finger inside of her, making the all too famous come-hither motion. She came gloriously, leaving my face dripping wet.

"My turn." And this was the only warning she got before I made my way up the couch and positioned myself right over her mouth. She opened up, as obedient as ever and I began fucking her face with renewed vigor. She was a novice for sure, but she made up for it with zeal. Moaning and salivating and coughing and gagging until she took my entire length down her throat. I had to stop many times before she puked but I did it again and again, shoving my hard cock deeper and deeper into the young girl's throat. When I knew I was close, I ignored her protests of not being able to breathe in favor of holding her head as I emptied myself into her throat. She coughed, sputtered and gasped trying to catch her breath but I didn't let up until I was done, and every drop had slid down her throat. When I pulled myself off of her, she threw herself onto the floor, doubled over, coughing.

"I'm not done with you yet." I told her and she looked up at me, eyes red and tearing up. I grinned and yanked her up by her torn leggings. "I'm going to f..." I trailed off, my ears picking up a distinct sound. Keys unlocking the front door. Instead of bending her over the couch like I wanted, I pulled Natalie in for a breathtaking kiss. "Leave your bedroom door unlocked." I told her. She nodded up at me, eyes wide. "I can't wait to have that pussy of yours wrapped around my dick.

I strolled out of the living room and ducked into my study. I heard when Natalie ran up the stairs and when Nadine dropped her keys, bag, and shoes in the foyer. She peeked into my study on her way upstairs.

"How was your afternoon?" She asked, coming inside and closing the door behind her. I was sitting at my desk, innocently reading case files. "My client had some kind of emergency so I figured I could come catch up on some of the sleep I've been missing out on."

"My afternoon was good. Quiet." We waited a beat and listened as Natalie stomped around her bedroom. Nadine and I locked eyes and a slow smile spread across her features.

"I hope that means everything has gone according to plan."

"Well, I didn't quite get around to fucking her senseless." I pursed my lips. "But I hope to change that tonight." She grinned widely, letting out a disbelieving laugh

"And?"

"And I will write you a check tonight matching your loan amount."

"Excellent!" Her smile was beatific. "I hope you won't think less of me for selling Natalie to you like this." I shook my head. For a hundred thousand dollars I had bought myself a live in fuckdoll. Who was complaining? Nadine was still talking. "When my bitch sister drained my bank account and left me that rugrat, I knew someone would have to pay. I gave the best years of my life to Natalie only for her to repay me with insubordination and downright disrespect." I nodded along, barely listening. My mind was on the eighteen-year-old girl upstairs. I wanted to leap up and run to her, but I knew I could wait.

Smiling, I sat back in my chair. Natalie had barely graduated high school, she hadn't been accepted to any colleges, she had no prospects and with a mother/aunt who was willing to shove her off onto the highest bidder, she had no one in the world looking out for her. I had the rest of my life to do whatever I wanted with her. It was a thought that made me smile.